Compound and organic light-emitting element comprising same

Abstract

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

Description

Technical Field

[0001] The present specification relates to a compound and an organic light-emitting device including the same.

[0002] This application claims priority to and the benefit of Korean Patent Application Nos. 10-2023-0036948 and 10-2024-0038563 filed on March 21, 2023 and March 20, 2024, respectively, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Background Art

[0003] The organic light-emitting phenomenon generally refers to the phenomenon of converting electrical energy into light energy using organic materials. An organic light-emitting device utilizing the organic light-emitting phenomenon generally has a structure including a positive electrode, a negative electrode, and an organic material layer therebetween. Here, in many cases, the organic material layer has a multilayer structure composed of different materials to improve the efficiency and stability of the organic light-emitting device, and for example, the organic material layer may be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light-emitting device, if a voltage is applied between the two electrodes, holes are injected into the organic material layer from the positive electrode and electrons are injected into the organic material layer from the negative electrode, and when the injected holes and electrons meet each other, excitons are formed, and light is emitted when the excitons fall back to the ground state again.

[0004] There is a continuing need to develop new materials for the aforementioned organic light-emitting devices.

[0005] [Citation List]

[0006] [Patent Document]

[0007] (Patent Document 1) Korean Patent Application Publication No. 10-2020-129990 Summary of the invention

[0008] Technical issues

[0009] The present specification provides a compound and an organic light-emitting device including the same.

[0010] Technical Solution

[0011] An exemplary embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[0012] [Chemical formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] X is NR, O or S,

[0016] Y is O or S,

[0017] Ar1, Ar2 and Ar3 are the same as or different from each other and are each independently a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring, provided that at least one of Ar1, Ar2 and Ar3 comprises a heterocyclic ring; or a substituted or unsubstituted aliphatic hydrocarbon ring, and further, when X is NR, at least one of R, Ar1, Ar2 and Ar3 comprises a ring to which a substituted or unsubstituted aliphatic hydrocarbon ring is fused,

[0018] When X is NR, at least one of Ar1 and Ar3 may be bonded to R to form a ring, and Ar2 and Ar3 may be bonded to each other to form a ring, and

[0019] R is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0020] In addition, an exemplary embodiment of the present specification provides an organic light-emitting device, which includes: a positive electrode; a negative electrode; and an organic material layer having one or more layers arranged between the positive electrode and the negative electrode, wherein one or more layers in the organic material layer contain the above-mentioned compound.

[0021] Beneficial Effects

[0022] The compounds described in this specification can be used as materials for an organic material layer of an organic light-emitting device. The compounds according to at least one exemplary embodiment of the present specification can have a narrow half-maximum full width, improve efficiency, achieve low driving voltage, and / or improve service life characteristics in an organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 An example of an organic light emitting device in which a substrate 1, a positive electrode 2, a light emitting layer 6, and a negative electrode 10 are sequentially stacked is shown.

[0024] Figure 2 An example of an organic light-emitting device is shown in which a substrate 1, a positive electrode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a first electron transport layer 7, a second electron transport layer 8, an electron injection layer 9 and a negative electrode 10 are sequentially stacked. DETAILED DESCRIPTION

[0025] Hereinafter, the present specification will be described in more detail.

[0026] In the present specification, when a part “comprises” a constituent element, unless otherwise specifically described, this does not mean excluding another constituent element but means that another constituent element may further be included.

[0027] In this specification, when one member is disposed “on” another member, this includes not only a case where one member is in contact with the other member but also a case where another member is present between the two members.

[0028] In the present specification, "*" means a position bonding to a formula or a compound.

[0029] Examples of the substituent in the present specification will be described below, but are not limited thereto.

[0030] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed into another substituent, and the position to be substituted 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 substitutions are made, the two or more substituents may be the same or different from each other.

[0031] In the present invention, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from the following: deuterium; halogen group; nitrile group (-CN); nitro group; hydroxyl group; alkyl group; cycloalkyl group; alkoxy group; phosphine oxide group; aryloxy group; alkylthio group; arylthio group; alkylsulfonyl group; arylsulfonyl group; alkenyl group; silyl group; boron group; amine group; aryl group; or heterocyclic group, substituted with a substituent in which two or more substituents are linked together among the exemplified substituents, or having no substituent. For example, "a substituent in which two or more substituents are linked together" can be a biphenyl group. That is, the biphenyl group can also be an aryl group, and can be interpreted as a substituent in which two phenyl groups are linked together.

[0032] In the present specification, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, an amino group, an alkoxy group, an aryloxy group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, and a heterocyclic group, substituted with a substituent in which two or more of the exemplified substituents are linked together, or having no substituent.

[0033] In the present specification, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, an alkyl group, an aryl group, and a heterocyclic group, substituted with a substituent in which two or more of the exemplified substituents are linked together, or having no substituent.

[0034] Examples of the substituent will be described below, however, the substituent is not limited thereto.

[0035] In the present specification, examples of the halogen group include fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0036] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to yet another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited thereto.

[0037] In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specific examples thereof include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but are not limited thereto.

[0038] Alkyl, alkoxy and other alkyl moiety-containing substituents described in this specification include both straight-chain and branched forms.

[0039] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another exemplary embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples thereof 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, stilbene, styryl, etc., but are not limited thereto.

[0040] In the present specification, as a substituent including a triple bond between carbon atoms, the alkynyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 40. According to one exemplary embodiment, the number of carbon atoms of the alkynyl group is 2 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkynyl group is 2 to 10.

[0041] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specific examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0042] In the present specification, the amine group is -NH2, and the amine group may be substituted by the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, combination thereof, etc. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to an exemplary embodiment, the number of carbon atoms of the amine group is 1 to 20. According to an exemplary embodiment, the number of carbon atoms of the amine group is 1 to 10. Specific examples of the substituted amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, 9,9-dimethylfluorenylphenylamine, pyridylphenylamine, diphenylamine, phenylpyridylamine, naphthylamine, biphenylamine, anthracenylamine, dibenzofuranylphenylamine, 9-methylanthrylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, diphenylamine, etc., but are not limited thereto.

[0043] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to an exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 20. Examples of monocyclic aryl groups include phenyl, biphenyl, terphenyl, quaterphenyl, etc., but are not limited thereto. Examples of polycyclic aryl groups include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, triphenylene, Here, the aryl group includes not only a structure consisting of only an aromatic hydrocarbon ring but also a structure in which an aromatic hydrocarbon ring is condensed with an aliphatic hydrocarbon ring.

[0044] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro ring structure. In this case, the spiro ring structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

[0045] When the fluorenyl group is substituted, the substituent may be a spirofluorenyl group such as and substituted fluorenyl groups such as (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) However, the fluorenyl group is not limited thereto.

[0046] In the present specification, the above description of the aryl group can be applied to the aryl group in the aryloxy group and the arylamine group.

[0047] In the present specification, the above description of the alkyl group can be applied to the alkyl group in the alkylthio group and the alkylsulfonyl group.

[0048] In the present specification, the above description of the aryl group can be applied to the aryl group in the arylthio group and the arylsulfonyl group.

[0049] In the present specification, the heterocyclic group is a cyclic group containing one or more of N, O, P, S, Si and Se as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of heterocyclic groups include pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarbazolyl, triazinyl, etc., but are not limited thereto. Here, the heterocyclic group includes not only a structure consisting only of a heterocyclic ring, but also a structure in which a heterocyclic ring is condensed with an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

[0050] In the present specification, the above description of the heterocyclic group can be applied to the heteroaryl group, except that the heteroaryl group is aromatic.

[0051] In the present specification, the description of the aryl group can be applied to the arylene group, except that the arylene group is divalent.

[0052] In the present specification, the description of the heteroaryl group can be applied to the heteroarylene group, except that the heteroarylene group is divalent.

[0053] In the present specification, the hydrocarbon ring includes an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring thereof.

[0054] In this specification, heterocycle includes aromatic heterocycle, aliphatic heterocycle, or condensed ring thereof. In the case of a ring in which two or more rings are condensed, when one or more of the rings are rings containing non-carbon heteroatoms as ring members, the entire ring may be referred to as a heterocycle. In this case, the ring that may be condensed with the ring containing heteroatoms as ring members may be a heterocycle or a hydrocarbon ring.

[0055] In the present specification, in a substituted or unsubstituted ring formed by bonding with an adjacent group, "ring" means a hydrocarbon ring; or a heterocyclic ring.

[0056] For example, when one group is bonded to an adjacent group to form a ring, a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a condensed ring thereof may be formed. A hydrocarbon ring means a ring consisting only of carbon atoms and hydrogen atoms. A heterocycle means a ring containing one or more selected from elements such as N, O, P, S, Si, and Se. In the present specification, an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aliphatic heterocycle, and an aromatic heterocycle may be monocyclic or polycyclic.

[0057] In the present specification, an aliphatic hydrocarbon ring means a ring consisting of only carbon atoms and hydrogen atoms, which is a ring that is not an aromatic group. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc., but are not limited thereto.

[0058] In the present specification, an aromatic hydrocarbon ring means an aromatic ring composed only of carbon atoms and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenanthene, pyrene, tetracene, Pentacene, fluorene, indene, acenaphthene, benzofluorene, spirofluorene, etc., but not limited thereto. In the present specification, the aromatic hydrocarbon ring may be interpreted as having the same meaning as the aryl group.

[0059] In the present specification, an aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms. Examples of the aliphatic heterocycle include ethylene oxide, tetrahydrofuran, 1,4-dihydrofuran, The present invention also includes, but is not limited to, oxane, pyrrolidine, piperidine, morpholine, oxepane, azocane, thiocane, and the like.

[0060] In the present specification, an aromatic heterocycle means an aromatic ring containing one or more of heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, Azoles, Isopropylamine Azoles, thiazoles, isothiazoles, triazoles, diazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazines, Azine, thiazine, di Indole, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, naphthyridine, triazaindene, indole, indolizine, benzothiazole, benzo azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phen Oxazine, indolecarbazole, indenocarbazole, etc., but not limited thereto.

[0061] Hereinafter, a preferred exemplary embodiment of the present invention will be described in detail. However, the exemplary embodiment of the present invention may be modified into various other forms, and the scope of the present invention is not limited to the exemplary embodiment to be described below.

[0062] Hereinafter, the compound of the following Chemical Formula 1 will be described in detail.

[0063] [Chemical formula 1]

[0064]

[0065] In Chemical Formula 1, the definitions of the substituents are the same as those described above.

[0066] According to an exemplary embodiment, Ar1, Ar2 and Ar3 are the same as or different from each other and are each independently a substituted or unsubstituted aromatic hydrocarbon ring; a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocyclic ring; a fused ring of a substituted or unsubstituted heterocyclic ring and an aromatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted heterocyclic ring, an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and at least one of Ar1, Ar2 and Ar3 is a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocyclic ring; a fused ring of a substituted or unsubstituted heterocyclic ring and an aromatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted heterocyclic ring, an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.

[0067] According to an exemplary embodiment, Ar1, Ar2 and Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring; a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocyclic ring containing O or S as a heteroelement; a fused ring of a substituted or unsubstituted heterocyclic ring containing O or S as a heteroelement and an aromatic hydrocarbon ring; or a substituted or unsubstituted fused ring of a heterocyclic ring, an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and at least one of Ar1, Ar2 and Ar3 is a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocyclic ring containing O or S as a heteroelement; a fused ring of a substituted or unsubstituted heterocyclic ring containing O or S as a heteroelement and an aromatic hydrocarbon ring; or a substituted or unsubstituted fused ring of a heterocyclic ring, an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.

[0068] According to an exemplary embodiment, Ar1, Ar2 and Ar3 are the same as or different from each other, and are each independently substituted or unsubstituted benzene, substituted or unsubstituted tetrahydronaphthalene, substituted or unsubstituted furan, substituted or unsubstituted benzofuran, substituted or unsubstituted dibenzofuran, substituted or unsubstituted tetrahydronaphthofuran, substituted or unsubstituted tetrahydrobenzonaphthofuran, substituted or unsubstituted thiophene, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted tetrahydronaphthothiophene, or substituted or unsubstituted tetrahydrobenzonaphthothiophene, and at least one of Ar1, Ar2 and Ar3 is substituted or unsubstituted tetrahydronaphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted furan, substituted or unsubstituted benzofuran, substituted or unsubstituted dibenzofuran, substituted or unsubstituted tetrahydronaphthofuran, substituted or unsubstituted tetrahydrobenzonaphthofuran, substituted or unsubstituted thiophene, substituted or unsubstituted benzothiophene, or substituted or unsubstituted dibenzothiophene, substituted or unsubstituted tetrahydrobenzonaphthothiophene, or substituted or unsubstituted tetrahydrobenzonaphthothiophene.

[0069] According to an exemplary embodiment, at least one of Ar1, Ar2, and Ar3 comprises substituted or unsubstituted tetralin, or X is NR and R comprises substituted or unsubstituted tetralin.

[0070] According to an exemplary embodiment, at least one of Ar1 and Ar2 is a substituted or unsubstituted tetralin, or X is NR and R is a substituted or unsubstituted tetralin, or at least one of Ar1 and Ar2 is a heterocyclic ring having a substituted or unsubstituted tetralin fused therein.

[0071] According to an exemplary embodiment, Chemical Formula 1 is represented by any one of the following Chemical Formulas 11 to 13:

[0072] [Chemical formula 11]

[0073]

[0074] [Chemical formula 12]

[0075]

[0076] [Chemical formula 13]

[0077]

[0078] In Chemical Formulas 11 to 13,

[0079] X and Y are the same as those defined in Chemical Formula 1, Z1 is CRxRy, O or S, and

[0080] Ra to Rc, Rx, Ry, R and R' are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl; or are connected with adjacent groups to form a substituted or unsubstituted ring, a and c are each an integer from 0 to 4, b is an integer from 0 to 3, a' and c' are each an integer from 0 to 2, and b' is 0 or 1.

[0081] According to an exemplary embodiment, Chemical Formula 1 is represented by any one of the following Chemical Formulas 21 to 23:

[0082] [Chemical formula 21]

[0083]

[0084] [Chemical formula 22]

[0085]

[0086] [Chemical formula 23]

[0087]

[0088] In Chemical Formulas 21 to 23,

[0089] X, Y, Z1, Ra to Rc, a, b, c, a', b' and c' are the same as those described above, and

[0090] Rd are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl; or adjacent groups are connected to form a substituted or unsubstituted ring, and d is an integer from 0 to 4.

[0091] According to an exemplary embodiment, Chemical Formula 1 is represented by any one of the following Chemical Formulas 31 to 34:

[0092] [Chemical formula 31]

[0093]

[0094] [Chemical formula 32]

[0095]

[0096] [Chemical formula 33]

[0097]

[0098] [Chemical formula 34]

[0099]

[0100] In Chemical Formulas 31 to 34,

[0101] X, Y, Z1, Ra to Rd, a, b, c, d, a', b' and c' are the same as those described above, and

[0102] Z2 and Z3 are the same as or different from each other and are each independently CRxRy, O or S, and Rx and Ry are the same as those described above.

[0103] According to an exemplary embodiment, Chemical Formula 1 is represented by any one of the following Chemical Formulas 41 to 43.

[0104] [Chemical formula 41]

[0105]

[0106] [Chemical formula 42]

[0107]

[0108] [Chemical formula 43]

[0109]

[0110] In Chemical Formulas 41 to 43,

[0111] X and Y are the same as those defined in Chemical Formula 1,

[0112] Z1 and Z2 are each independently CRxRy, O or S, and

[0113] Ra to Rc, Rx, Ry, R, R', R" and R'" are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl; or are connected with adjacent groups to form a substituted or unsubstituted ring, a and c are each an integer from 0 to 4, and b is an integer from 0 to 3.

[0114] According to an exemplary embodiment, R and R' of Chemical Formulas 41 to 43 are bonded to each other to form substituted or unsubstituted benzene, or substituted or unsubstituted tetralin.

[0115] According to an exemplary embodiment, R and R' of Chemical Formulas 41 to 43 are bonded to each other to form unsubstituted or alkyl-substituted benzene, or unsubstituted or alkyl-substituted tetralin.

[0116] According to an exemplary embodiment, Rb of Chemical Formulas 41 to 43 is hydrogen or deuterium, or forms a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocyclic ring.

[0117] According to an exemplary embodiment, Rb of Chemical Formulas 41 to 43 is hydrogen or deuterium, or forms an unsubstituted or deuterium or alkyl-substituted aliphatic ring, an unsubstituted or deuterium or alkyl-substituted aromatic ring, or an unsubstituted or deuterium or alkyl-substituted heterocyclic ring.

[0118] According to an exemplary embodiment, Rc of Chemical Formulas 41 to 43 is hydrogen or deuterium, or forms a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heterocyclic ring.

[0119] According to an exemplary embodiment, Rc of Chemical Formulas 41 to 43 is hydrogen or deuterium, or forms substituted or unsubstituted hexane, substituted or unsubstituted benzene, substituted or unsubstituted indene, substituted or unsubstituted benzofuran, or substituted or unsubstituted benzothiophene.

[0120] According to an exemplary embodiment, Rc of Chemical Formulas 41 to 43 is hydrogen or deuterium, or forms unsubstituted or deuterium- or alkyl-substituted hexane, unsubstituted or deuterium- or alkyl-substituted benzene, unsubstituted or deuterium- or alkyl-substituted indene, unsubstituted or deuterium- or alkyl-substituted benzofuran, or unsubstituted or deuterium- or alkyl-substituted benzothiophene.

[0121] According to an exemplary embodiment, Chemical Formula 1 includes a C1 to C6 linear or branched alkyl group or a cycloalkyl group.

[0122] According to an exemplary embodiment, Chemical Formula 1 includes an unsubstituted or alkyl-substituted arylamine group; or an unsubstituted or alkyl-substituted heteroarylamine group.

[0123] According to an exemplary embodiment, Rb is hydrogen, deuterium, a C1 to C6 straight chain or branched alkyl group, a cycloalkyl group, an unsubstituted or alkyl-substituted arylamine group; or an unsubstituted or alkyl-substituted heteroarylamine group.

[0124] According to an exemplary embodiment, Rc is hydrogen, deuterium, a C1 to C6 straight chain or branched alkyl group, a cycloalkyl group, an unsubstituted or alkyl-substituted arylamine group; or an unsubstituted or alkyl-substituted heteroarylamine group.

[0125] According to an exemplary embodiment, Rc is hydrogen, deuterium, or an unsubstituted or alkyl-substituted arylamine group.

[0126] According to an exemplary embodiment, X is NR, and R comprises a C1 to C6 straight chain or branched alkyl or cycloalkyl group.

[0127] According to an exemplary embodiment, X is NR, and R is phenyl substituted with a C1 to C6 straight chain or branched alkyl or cycloalkyl group, biphenyl substituted with a C1 to C6 straight chain or branched alkyl or cycloalkyl group, alkyl-substituted tetrahydronaphthyl, dibenzofuran, or dibenzothiophene.

[0128] According to an exemplary embodiment, X is NR, and Y is O.

[0129] According to an exemplary embodiment, X is NR, and Y is S.

[0130] According to an exemplary embodiment, X is O, and Y is O.

[0131] According to an exemplary embodiment, X is S, and Y is O.

[0132] According to an exemplary embodiment, X is O, and Y is S.

[0133] According to an exemplary embodiment, X is S, and Y is S.

[0134] According to an exemplary embodiment, the compound of Chemical Formula 1 may be represented by the following compound:

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

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[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246] The substituents of the compound represented by Chemical Formula 1 according to an exemplary embodiment of the present specification may be bonded by a method known in the art, and the type and position of the substituents or the number of the substituents may be changed according to techniques known in the art.

[0247] In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by Chemical Formula 1. In addition, in the present specification, by introducing various substituents into the core structure having the above structure, a narrow half-maximum full width can be achieved, and the HOMO energy level and LUMO energy level of the compound can also be adjusted.

[0248] In addition, the present specification provides an organic light-emitting device including the above compound.

[0249] The organic light-emitting device according to the present specification is an organic light-emitting device including: a positive electrode; a negative electrode; and an organic material layer having one or more layers disposed between the positive electrode and the negative electrode, wherein one or more layers of the organic material layer contain the compound represented by Chemical Formula 1 above.

[0250] The organic material layer of the organic light-emitting device of the present specification may be composed of a single-layer structure, but may also be composed of a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including one or more of the following layers as an organic material layer: a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer. However, the structure of the organic light-emitting device of the present specification is not limited thereto, and may include a smaller or larger number of organic material layers.

[0251] In the organic light-emitting device of the present specification, the organic light-emitting device includes a light-emitting layer, and the light-emitting layer may include the compound.

[0252] For example, the compound of Chemical Formula 1 may be included as a dopant for the light emitting layer. In this case, X in the compound may be NR.

[0253] In an exemplary embodiment of the present invention, the light emitting layer includes a dopant and a host.

[0254] In an exemplary embodiment of the present invention, the light emitting layer includes the dopant and the host in a mass ratio of 1:99 to 5:95.

[0255] In an exemplary embodiment of the present invention, the light emitting layer includes the compound of Chemical Formula 1 as a dopant.

[0256] In an exemplary embodiment of the present invention, the light emitting layer includes the compound of Chemical Formula 1 as a blue dopant.

[0257] In an exemplary embodiment of the present invention, the light-emitting layer includes a host.

[0258] An organic light emitting device according to an exemplary embodiment of the present specification includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1 and a compound represented by the following Chemical Formula H.

[0259] [Chemical formula H]

[0260]

[0261] In the chemical formula H,

[0262] L21 to L23 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0263] R21 to R27 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted silyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl,

[0264] Ar21 to Ar23 are the same as or different from each other and are each independently deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0265] k is 0 or 1.

[0266] In an exemplary embodiment of the present specification, when k is 0, hydrogen or deuterium is linked to the position of -L23-Ar23.

[0267] In an exemplary embodiment of the present specification, L21 to L23 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group containing N, O, or S.

[0268] In an exemplary embodiment of the present specification, L21 to L23 are the same as or different from each other, and are each independently a direct bond; a C6 to C30 arylene group; or a C2 to C30 heteroarylene group containing N, O, or S, and the arylene group or the heteroarylene group is unsubstituted or substituted with a C1 to C10 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group.

[0269] In an exemplary embodiment of the present specification, L21 to L23 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted divalent dibenzofuranyl group; or a substituted or unsubstituted divalent dibenzothienyl group.

[0270] In an exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and are each independently deuterium; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0271] In an exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and are each independently deuterium; an unsubstituted or deuterium-substituted C6 to C30 aryl group; or an unsubstituted or deuterium-substituted C2 to C30 heteroaryl group.

[0272] In an exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and are each independently deuterium; a substituted or unsubstituted monocyclic to tetracyclic aryl group; or a substituted or unsubstituted monocyclic to tetracyclic heteroaryl group.

[0273] In an exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and are each independently deuterium; an unsubstituted or deuterium-substituted monocyclic to tetracyclic aryl group; or an unsubstituted or deuterium-substituted monocyclic to tetracyclic heteroaryl group.

[0274] In an exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and are each independently deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted anthracenyl; substituted or unsubstituted phenanthrenyl; substituted or unsubstituted phenanthrenyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted benzofluorenyl; substituted or unsubstituted furanyl; substituted or unsubstituted thienyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted naphthobenzofuranyl; substituted or unsubstituted dibenzothienyl; or substituted or unsubstituted naphthobenzothienyl.

[0275] In an exemplary embodiment of the present specification, Ar21 and Ar22 are different from each other.

[0276] In an exemplary embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted aryl group.

[0277] In an exemplary embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted heteroaryl group.

[0278] In an exemplary embodiment of the present specification, Ar21 is an unsubstituted or deuterium-substituted aryl group, and Ar22 is an unsubstituted or deuterium-substituted aryl group.

[0279] In an exemplary embodiment of the present specification, Ar21 is an unsubstituted or deuterium-substituted aryl group, and Ar22 is an unsubstituted or deuterium-substituted heteroaryl group.

[0280] In an exemplary embodiment of the present specification, R21 to R27 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0281] In an exemplary embodiment of the present specification, R21 to R27 are hydrogen.

[0282] In an exemplary embodiment of the present specification, R21 to R27 are deuterium.

[0283] In an exemplary embodiment of the present specification, Chemical Formula H is represented by the following Chemical Formula H01.

[0284] [Chemical formula H01]

[0285]

[0286] In the chemical formula H01,

[0287] Definitions of L21, L22, Ar21 and Ar22 are the same as those defined in Chemical Formula H, D means deuterium, and k1 is 0-8.

[0288] In an exemplary embodiment of the present specification, the compound represented by Chemical Formula H is any one selected from the following compounds.

[0289]

[0290]

[0291]

[0292] The organic light-emitting device of the present specification may also include an organic material layer having one or more of the following layers: a hole transport layer, a hole injection layer, an electron blocking layer, an electron injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole injection and transport layer.

[0293] In an exemplary embodiment of the present specification, the organic light emitting device may be a normal type organic light emitting device in which a positive electrode, an organic material layer having one or more layers, and a negative electrode are sequentially stacked on a substrate.

[0294] In an exemplary embodiment of the present specification, the organic light emitting device may be an inverted organic light emitting device in which a negative electrode, one or more organic material layers, and a positive electrode are sequentially stacked on a substrate.

[0295] The structure of the organic light-emitting device of the present specification may have Figure 1 and Figure 2 The structure shown in, but not limited to this.

[0296] Figure 1 The structure of the organic light emitting device is illustrated in which a substrate 1, a positive electrode 2, a light emitting layer 6, and a negative electrode 10 are sequentially stacked. In the above structure, the compound may be contained in the light emitting layer 6.

[0297] Figure 2 The structure of an organic light-emitting device is illustrated in which a substrate 1, a positive electrode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a first electron transport layer 7, a second electron transport layer 8, an electron injection layer 9, and a negative electrode 10 are sequentially stacked. In the above structure, the compound may be contained in any one of the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light-emitting layer 6, the first electron transport layer 7, and the second electron transport layer 8, for example, in the light-emitting layer 6.

[0298] The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that one or more layers of the organic material layers contain the compound, ie, the compound represented by Chemical Formula 1.

[0299] When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0300] For example, the organic light-emitting device according to the present specification can be manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate to form a positive electrode by using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation, forming an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer on the positive electrode, and then depositing a material that can be used as a negative electrode on the organic material layer. In addition to the above method, the organic light-emitting device can also be manufactured by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate.

[0301] The positive electrode is an electrode for injecting holes, and as a positive electrode material, a material having a high work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of positive electrode materials that can be used in the present disclosure 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), polypyrrole and polyaniline, but are not limited thereto.

[0302] The negative electrode is an electrode that injects electrons, and as a negative electrode material, a material having a small work function is generally preferred so that electron injection into the organic material layer is smooth. Specific examples of negative electrode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; and the like, but are not limited thereto.

[0303] The hole injection layer is a layer for promoting the injection of holes from the positive electrode into the light-emitting layer, and the hole injection material is preferably a material that can well receive holes from the positive electrode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the positive electrode material and the HOMO of the adjacent organic material layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc., but are not limited thereto.

[0304] According to an exemplary embodiment of the present specification, the hole injection layer may include a compound represented by the following Chemical Formula HI-1, but is not limited thereto.

[0305] [Chemical formula HI-1]

[0306]

[0307] In the chemical formula HI-1,

[0308] X11 is any one of NR301; O; and S,

[0309] R301 is hydrogen; deuterium; or substituted or unsubstituted aryl,

[0310] R101 and R102 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl,

[0311] R201 and R202 are the same as or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted amino group; or a substituted or unsubstituted aryl group,

[0312] n101 and n102 are each an integer of 1 to 4, and when n101 and n102 are each 2 or more, R101 and R102 are each the same as or different from each other, and

[0313] n201 and n202 are each an integer of 1 to 8, and when n201 and n202 are each 2 or greater, R201 and R202 are each the same as or different from each other.

[0314] In an exemplary embodiment of the present specification, X11 is NR301.

[0315] In one embodiment of the present specification, R301 is hydrogen; deuterium; substituted or unsubstituted phenyl; or substituted or unsubstituted biphenyl.

[0316] In an exemplary embodiment of the present specification, R301 is hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0317] In an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted heteroaryl group.

[0318] In an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted benzofuranyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted benzothienyl group; a substituted or unsubstituted dibenzothienyl group; or a substituted or unsubstituted carbazolyl group.

[0319] In an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and are each independently hydrogen; deuterium; or an unsubstituted or deuterium-substituted carbazolyl group.

[0320] In an exemplary embodiment of the present specification, R201 and R202 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkylamine group; a substituted or unsubstituted C6 to C20 arylamine group; or a substituted or unsubstituted C6 to C20 aryl group.

[0321] In an exemplary embodiment of the present specification, R201 and R202 are the same as or different from each other, and are each independently hydrogen; deuterium; or an unsubstituted or deuterium-substituted C6 to C12 arylamine group.

[0322] In an exemplary embodiment of the present specification, the hole injection layer may include both the compound represented by Chemical Formula HI-1 and the hexanitrile hexaazatriphenylene-based organic material.

[0323] In an exemplary embodiment of the present specification, the hexanitrile hexaazatriphenylene-based organic material included in the hole injection layer may be hexanitrile hexaazatriphenylene (HAT-CN) in which a nitrile group is substituted.

[0324] The hole transport layer can play a role in smoothly transporting holes. The hole transport material is suitably a material having a high hole mobility that can receive holes from the positive electrode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers having both conjugated and non-conjugated parts, etc., but are not limited thereto.

[0325] In an exemplary embodiment of the present specification, the hole transport layer may include a compound represented by the following Chemical Formula HT-1, but is not limited thereto.

[0326] [Chemical formula HT-1]

[0327]

[0328] In the chemical formula HT-1,

[0329] R311 to R313 are the same as or different from each other, and are each independently selected from hydrogen; deuterium; substituted or unsubstituted amine; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; and any combination thereof,

[0330] r311 is an integer of 1 to 4, and when r311 is 2 or more, two or more R311 are the same as or different from each other, and

[0331] r312 is an integer of 1 to 4, and when r316 is 2 or more, two or more R312 are the same as or different from each other.

[0332] In an exemplary embodiment of the present specification, R311 may be hydrogen; deuterium; or a substituted or unsubstituted amine group.

[0333] In an exemplary embodiment of the present specification, R311 may be an amine group which is unsubstituted or substituted with one or more selected from hydrogen, deuterium, a phenyl group, a naphthyl group, a carbazole group, and a combination thereof.

[0334] In an exemplary embodiment of the present specification, R312 may be hydrogen; deuterium; or a substituted or unsubstituted heteroaryl group.

[0335] In an exemplary embodiment of the present specification, R312 may be hydrogen; deuterium; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothienyl group; or a substituted or unsubstituted carbazolyl group.

[0336] In an exemplary embodiment of the present specification, R312 may be a carbazole group.

[0337] In an exemplary embodiment of the present specification, R313 may be hydrogen; deuterium; or a substituted or unsubstituted aryl group.

[0338] In an exemplary embodiment of the present specification, R313 may be hydrogen; deuterium; a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

[0339] In an exemplary embodiment of the present specification, R313 may be a phenyl group.

[0340] The electron blocking layer may be disposed between the hole transport layer and the light emitting layer. The electron blocking layer is a layer that can improve the service life and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light emitting layer and entering the hole injection layer. The electron blocking layer may be formed between the light emitting layer and the hole injection layer, between the light emitting layer and the hole transport layer, or between the light emitting layer and a layer that simultaneously injects and transports holes, and known materials may be used without limitation.

[0341] In an exemplary embodiment of the present specification, the hole blocking material may include a compound represented by the following Chemical Formula HT-2, but is not limited thereto.

[0342] [Chemical formula HT-2]

[0343]

[0344] In the chemical formula HT-2,

[0345] R315 to R317 are the same as or different from each other, and are each independently selected from hydrogen; deuterium; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and any combination thereof, or bond with an adjacent group to form a substituted or unsubstituted ring,

[0346] r315 is an integer of 1 to 5, and when r315 is 2 or more, two or more R315 are the same as or different from each other, and

[0347] r316 is an integer of 1 to 5, and when r316 is 2 or more, two or more R316 are the same as or different from each other.

[0348] In an exemplary embodiment of the present specification, R317 may be any one selected from a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof.

[0349] In an exemplary embodiment of the present specification, R317 may be any one selected from a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted triphenylene group; and combinations thereof.

[0350] In an exemplary embodiment of the present specification, R317 may be a biphenyl group which is unsubstituted or substituted with one or more selected from hydrogen, deuterium, a phenyl group, and a carbazolyl group.

[0351] In an exemplary embodiment of the present specification, R315 and R316 are the same as or different from each other, and are each independently a substituted or unsubstituted amine group; or a substituted or unsubstituted aryl group, or may be bonded with an adjacent group to form a substituted or unsubstituted ring.

[0352] In an exemplary embodiment of the present specification, R315 and R316 are the same as or different from each other, and may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted alkylamine group; or a substituted or unsubstituted arylamine group.

[0353] In an exemplary embodiment of the present specification, R315 may be a phenyl group.

[0354] In an exemplary embodiment of the present specification, R316 may be a diphenylamine group.

[0355] The light-emitting layer may emit red, green or blue light, and may be composed of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine the holes and electrons to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. The compound of the above chemical formula 1 can be used as a material for the light-emitting layer, and specific examples thereof include: 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; diphenylethylene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo-based azoles, benzothiazole-based and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorenes; rubrene, and the like, but are not limited thereto.

[0356] Examples of host materials for the light-emitting layer include fused aromatic ring derivatives, heterocyclic compounds, etc. Specifically, examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but examples thereof are not limited thereto.

[0357] When the light-emitting layer emits red light, a phosphorescent material such as bis(1-phenylisoquinoline) iridium acetylacetonate (PIQIr(acac)), bis(1-phenylquinoline) iridium acetylacetonate (PQIr(acac)), tris(1-phenylquinoline) iridium (PQIr) or platinum octaethylporphyrin (PtOEP) or a fluorescent material such as tris(8-hydroxyquinoline) aluminum (Alq3) can be used as a light-emitting dopant, however, the light-emitting dopant is not limited thereto. When the light-emitting layer emits green light, a phosphorescent material such as planar tris(2-phenylpyridine) iridium (Ir(ppy)3) or a fluorescent material such as tris(8-hydroxyquinoline) aluminum (Alq3) can be used as a light-emitting dopant, but the light-emitting dopant is not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as (4,6-F2ppy)2Irpic or a fluorescent material such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), a PFO-based polymer or a PPV-based polymer can be used as a light-emitting dopant, however, the light-emitting dopant is not limited thereto.

[0358] A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.

[0359] The electron transport layer can play a role in smoothly transporting electrons. As the electron transport material, a material that can advantageously receive electrons from the negative electrode, move the electrons to the light-emitting layer, and has a high electron mobility is suitable. Specific examples thereof include: Al complexes of the above-mentioned compounds or 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavone-metal complexes; and the like, but are not limited thereto.

[0360] In an exemplary embodiment of the present specification, the electron transport material may include a compound represented by the following Chemical Formula ET-1 or Chemical Formula ET-2, but is not limited thereto.

[0361] [Chemical formula ET-1]

[0362]

[0363] In the chemical formula ET-1,

[0364] R601 to R607 are the same as or different from each other and are each independently hydrogen; or deuterium,

[0365] L601 to L603 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group,

[0366] Ar601 to Ar603 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0367] k603 is 0 or 1,

[0368] [Chemical formula ET-2]

[0369]

[0370] In the chemical formula ET-2,

[0371] Z11 to Z13 are the same as or different from each other and are each independently N or CH,

[0372] L701 to L703 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group,

[0373] Ar701 to Ar703 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0374] n701 to n703 are each an integer of 0 to 2, and when n701 to n703 are each 2, L701 to L703 are the same as or different from each other.

[0375] In an exemplary embodiment of the present specification, R601 to R607 are all hydrogen or all deuterium.

[0376] In an exemplary embodiment of the present specification, L601 to L603 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted phenylene group.

[0377] In an exemplary embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0378] In an exemplary embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.

[0379] In an exemplary embodiment of the present specification, Ar603 is a substituted or unsubstituted heteroaryl group.

[0380] In an exemplary embodiment of the present specification, Ar603 is a benzimidazolyl group which is unsubstituted or substituted with one or more selected from hydrogen, deuterium, and a phenyl group.

[0381] In an exemplary embodiment of the present specification, all of Z11 to Z13 are N.

[0382] In an exemplary embodiment of the present specification, L701 to L703 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0383] In an exemplary embodiment of the present specification, Ar701 to Ar703 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; or a substituted or unsubstituted carbazolyl group.

[0384] In an exemplary embodiment of the present specification, the electron transport layer may include a first electron transport layer and a second electron transport layer, and at least one of the first electron transport layer and the second electron transport layer may include a compound represented by Chemical Formula ET-1 or Chemical Formula ET-2.

[0385] In an exemplary embodiment of the present specification, the electron transport layer may include a first electron transport layer and a second electron transport layer, and the first electron transport layer may include a compound represented by Chemical Formula ET-1.

[0386] In an exemplary embodiment of the present specification, the electron transport layer may include a first electron transport layer and a second electron transport layer, and the second electron transport layer may include a compound represented by Chemical Formula ET-1.

[0387] In an exemplary embodiment of the present specification, the electron transport layer may include a first electron transport layer and a second electron transport layer, and the second electron transport layer may include a compound represented by Chemical Formula ET-1, and may further include lithium quinolate (Liq).

[0388] In an exemplary embodiment of the present specification, the electron transport layer may include a first electron transport layer and a second electron transport layer, the second electron transport layer may include a compound represented by the chemical formula ET-1 and lithium quinoline (Liq), and may include the compound represented by the chemical formula ET-1 and lithium quinoline (Liq) in a weight ratio of 1:1.

[0389] In an exemplary embodiment of the present specification, the electron transport layer may include a first electron transport layer and a second electron transport layer, and in this case, the first electron transport layer may be disposed between the light emitting layer and the second electron transport layer.

[0390] The electron injection layer can play a role in smoothly injecting electrons. The electron injection material is preferably a compound that has the ability to transport electrons, the effect of injecting electrons from the negative electrode, and the excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents the excitons generated by the light-emitting layer from moving to the hole injection layer, and is also excellent in the ability to form a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, etc., and derivatives thereof; metal complex compounds; nitrogen-containing 5-membered ring derivatives; etc., but not limited thereto.

[0391] The metal complex compounds include 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) chlorogallium, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0392] In an exemplary embodiment of the present specification, the electron injection material may include lithium quinolate (Liq), but is not limited thereto.

[0393] The hole blocking layer is a layer that blocks holes from reaching the negative electrode and can generally be formed under the same conditions as those of the hole injection layer. Specific examples thereof include Oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but not limited thereto.

[0394] The organic light emitting device according to the present disclosure may be a top emission type, a bottom emission type, or a dual emission type according to the materials used.

[0395] Embodiments of the invention

[0396] Hereinafter, this specification will be described in detail with reference to the embodiments for specifically describing this specification. However, the embodiments according to this specification can be modified into various forms, and are not to be construed as limiting the scope of this application to the embodiments described in detail below. The embodiments of this application are provided to more fully illustrate this specification to those of ordinary skill in the art.

[0397] Preparation Example of Compound 1 (F-1)

[0398]

[0399] Synthesis of I-1

[0400] After 30 g of 1-bromo-3-chlorobenzene, 61 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)amine, 1.6 g of [bis(tri-tert-butylphosphine)palladium(0)], 30 g of sodium tert-butoxide and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 57 g of I-1. (Yield 73%, mass [M+] = 501)

[0401] Synthesis of I-2

[0402] After 25 g of I-1, 12.5 g of (3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)boric acid, 21 g of K2CO3, 0.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 26 g of I-2. (Yield 72%, mass [M+] = 669)

[0403] Synthesis of F-1

[0404] After 20 g of I-2, 20 g of boron triiodide and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.5 g of F-1. (Yield 37%, mass [M+] = 677)

[0405] Preparation Example of Compound 2 (F-2)

[0406]

[0407] Synthesis of I-3

[0408] After 30 g of 1-bromo-3-chlorobenzene, 70 g of 5,5,8,8-tetramethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-amine, 1.6 g of [bis(tri-tert-butylphosphine)palladium(0)], 30 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 62 g of I-3. (Yield 71%, mass [M+] = 557)

[0409] Synthesis of I-4

[0410] After 25 g of I-3, 11.4 g of (2-hydroxy-9,9-dimethyl-9H-fluorene-3-yl)boric acid, 19 g of K2CO3, 0.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the residue in toluene, then treated with MgSO4 (anhydrous) and filtered. The filtered solution was recrystallized to obtain 23 g of I-4. (Yield 70%, mass [M+] = 731)

[0411] Synthesis of F-2

[0412] After 20 g of I-4, 18.2 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.2 g of F-2. (Yield 36%, mass [M+] = 739)

[0413] Preparation Example of Compound 3 (F-3)

[0414]

[0415] Synthesis of I-5

[0416] After 25 g of I-3, 11.2 g of (3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)boric acid, 19 g of K2CO3, 0.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the residue in toluene, then treated with MgSO4 (anhydrous) and filtered. The filtered solution was recrystallized to obtain 25 g of I-5. (yield 77%, quality [M+] = 725)

[0417] Synthesis of F-3

[0418] After 20 g of I-5, 18.4 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.3 g of F-3. (Yield 36%, mass [M+] = 733)

[0419] Preparation Example of Compound 4 (F-4)

[0420]

[0421] Synthesis of I-6

[0422] After 30 g of 1-bromo-3-chloro-5-methylbenzene, 65 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)amine, 1.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 28 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 55 g of I-6. (yield 73%, quality [M+] = 515)

[0423] Synthesis of I-7

[0424] After 25 g of I-6, 20.3 g of (4-(bis(4-(tert-butyl)phenyl)amino)-2-hydroxyphenyl)boric acid, 21 g of K2CO3, 0.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 30 g of I-7. (Yield 72%, mass [M+] = 852)

[0425] Synthesis of F-4

[0426] After 20 g of I-7, 15.6 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.4 g of F-4. (Yield 37%, mass [M+] = 860)

[0427] Preparation Example of Compound 5 (F-5)

[0428]

[0429] Synthesis of I-8

[0430] After 30 g of 1-(3-bromo-5-chlorophenyl)adamantane, 40 g of N-(4-(adamantan-1-yl)-2-methylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine, 0.9 g of [bis(tri-tert-butylphosphine)palladium(0)], 18 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 46 g of I-8. (Yield 74%, mass [M+] = 673)

[0431] Synthesis of I-9

[0432] After 25 g of I-8, 5.2 g of (2-hydroxyphenyl)boric acid, 16 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 21 g of I-9. (Yield 77%, mass [M+] = 731)

[0433] Synthesis of F-5

[0434] After 20 g of I-9, 18.3 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.5 g of F-5. (yield 37%, mass [M+] = 739)

[0435] Preparation Example of Compound 6 (F-6)

[0436]

[0437] Synthesis of I-10a

[0438] After 30 g of 1-(3-bromo-5-chlorophenyl)adamantane, 37.2 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)amine, 0.9 g of [bis(tri-tert-butylphosphine)palladium(0)], 18 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 43 g of I-10a. (Yield 72%, mass [M+] = 649)

[0439] Synthesis of I-10

[0440] After 25 g of I-10a, 9.9 g of (3-mercapto-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)boric acid, 16 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 23 g of I-10. (yield 74%, quality [M+] = 833)

[0441] Synthesis of F-6

[0442] After 20 g of I-10, 16 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.4 g of F-6. (Yield 37%, mass [M+] = 841)

[0443] Preparation Example of Compound 7 (F-7)

[0444]

[0445] Synthesis of I-11

[0446] After 30 g of 1-(3-bromo-5-chlorophenyl)adamantane, 41.1 g of 5,5,8,8-tetramethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-2-amine, 0.9 g of [bis(tri-tert-butylphosphine)palladium(0)], 18 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 45 g of I-11. (Yield 71%, mass [M+] = 691)

[0447] Synthesis of I-12

[0448] After 25 g of I-11, 8.3 g of (2-hydroxydibenzo[b, d]furan-3-yl)boric acid, 15 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 23 g of I-12. (Yield 76%, mass [M+] = 833)

[0449] Synthesis of F-7

[0450] After 20 g of I-12, 16 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.3 g of F-7. (yield 36%, mass [M+] = 847)

[0451] Preparation Example of Compound 8 (F-8)

[0452]

[0453] Synthesis of I-13

[0454] After 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 41.5 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)amine, 1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 46 g of I-13. (Yield 73%, mass [M+] = 591)

[0455] Synthesis of I-14

[0456] After 25 g of I-13, 10.5 g of (3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)boric acid, 18 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 24 g of I-14. (Yield 75%, mass [M+] = 759)

[0457] Synthesis of F-8

[0458] After 20 g of I-14, 18 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.4 g of F-8. (Yield 37%, mass [M+] = 767)

[0459] Preparation Example of Compound 9 (F-9)

[0460]

[0461] Synthesis of I-15

[0462] After 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 43 g of 3,5,5,8,8-pentamethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)-5,6,7,8-tetrahydronaphthalene-2-amine, 1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 46 g of I-15. (yield 71%, quality [M+] = 605)

[0463] Synthesis of I-16

[0464] After 25 g of I-15, 11.2 g of (2-mercapto-9,9-dimethyl-9H-fluorene-3-yl)boric acid, 18 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 25 g of I-16. (yield 76%, quality [M+] = 795)

[0465] Synthesis of F-9

[0466] After 20 g of I-16, 17 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.3 g of F-9. (Yield 36%, mass [M+] = 803)

[0467] Preparation Example of Compound 10 (F-10)

[0468]

[0469] Synthesis of I-17

[0470] After 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 52 g of N-(5-(adamantan-1-yl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine, 1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 52 g of I-17. (Yield 71%, mass [M+] = 691)

[0471] Synthesis of I-18

[0472] After 25 g of I-17, 9 g of (3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)boric acid, 15 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 24 g of I-18. (Yield 77%, mass [M+] = 860)

[0473] Synthesis of F-10

[0474] After 20 g of I-18, 15.5 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.4 g of F-10. (yield 37%, mass [M+] = 867)

[0475] Preparation Example of Compound 11 (F-11)

[0476]

[0477] Synthesis of I-19

[0478] After 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 31.4 g of 7,7,10,10-tetramethyl-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran-3-ol, 1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 38 g of I-19. (Yield 72%, mass [M+] = 496)

[0479] Synthesis of I-20

[0480] After 25 g of I-19, 12.5 g of (3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)boric acid, 21 g of K2CO3, 0.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 25 g of I-20. (yield 75%, quality [M+] = 664)

[0481] Synthesis of F-11

[0482] After 20 g of I-20, 20 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.3 g of F-11. (Yield 36%, mass [M+] = 672)

[0483] Preparation Example of Compound 12 (F-12)

[0484]

[0485] Synthesis of I-21a

[0486] After 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 43.9 g of N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20.5 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 50 g of I-21a. (Yield 77%, mass [M+] = 613)

[0487] Synthesis of I-21

[0488] After 25 g of I-21a, 9.4 g of (3-hydroxydibenzo[b, d]furan-2-yl)boric acid, 17 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 23 g of I-21. (Yield 74%, mass [M+] = 761)

[0489] Synthesis of F-12

[0490] After 20 g of I-21, 17.5 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.4 g of F-12. (Yield 37%, mass [M+] = 769)

[0491] Preparation Example of Compound 13 (F-13)

[0492]

[0493] Synthesis of I-22

[0494] After 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 40 g of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)dibenzo[b,d]furan-3-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 43 g of I-22. (Yield 71%, mass [M+] = 571)

[0495] Synthesis of I-23

[0496] After 25 g of I-22, 11.8 g of (3-mercapto-9,9-dimethyl-9H-fluorene-2-yl)boric acid, 19 g of K2CO3, 0.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 24 g of I-23. (Yield 72%, mass [M+] = 761)

[0497] Synthesis of F-13

[0498] After 20 g of I-23, 18 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.3 g of F-13. (Yield 36%, mass [M+] = 769)

[0499] Preparation Example of Compound 14 (F-14)

[0500]

[0501] Synthesis of I-24

[0502] After 25 g of I-13, 10 g of (3-hydroxydibenzo[b, d]thiophene-2-yl)boric acid, 17 g of K2CO3, 0.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 23 g of I-24. (Yield 75%, mass [M+] = 755)

[0503] Synthesis of F-14

[0504] After 20 g of I-24, 18 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.4 g of F-14. (Yield 37%, mass [M+] = 763)

[0505] Preparation Example of Compound 15 (F-15)

[0506]

[0507] Synthesis of I-25

[0508] After 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 29.5 g of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-thiol, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 36 g of I-25. (yield 71%, quality [M+] = 478)

[0509] Synthesis of I-26

[0510] After 25 g of I-25, 13.3 g of (2-hydroxy-9,9-dimethyl-9H-fluorene-3-yl)boric acid, 22 g of K2CO3, 0.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 26 g of I-26. (yield 76%, quality [M+] = 652)

[0511] Synthesis of F-15

[0512] After 20 g of I-26, 21 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.5 g of F-15. (yield 37%, mass [M+] = 660)

[0513] Preparation Example of Compound 16 (F-16)

[0514]

[0515] Synthesis of I-27

[0516] After 25 g of I-13, 10.8 g of (2-hydroxy-9,9-dimethyl-9H-fluorene-3-yl)boric acid, 18 g of K2CO3, 0.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 22 g of I-27. (Yield 68%, mass [M+] = 765)

[0517] Synthesis of F-16

[0518] After 20 g of I-27, 18 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.7 g of F-16. (Yield 38%, mass [M+] = 773)

[0519] Preparation Example of Compound 17 (F-17)

[0520]

[0521] Synthesis of I-28

[0522] After 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 47.5 g of 5,5,8,8-tetramethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 51 g of I-28. (Yield 74%, mass [M+] = 647)

[0523] Synthesis of I-29

[0524] After 25 g of I-28, 9.6 g of (3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)boric acid, 16 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 23 g of I-29. (yield 73%, quality [M+] = 815)

[0525] Synthesis of F-17

[0526] After 20 g of I-29, 17 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.2 g of F-17. (Yield 36%, mass [M+] = 823)

[0527] Preparation Example of Compound 18 (F-18)

[0528]

[0529] Synthesis of I-30

[0530] After 30 g of 4-bromo-2-chlorodibenzo[b,d]furan, 43.9 g of N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 50 g of I-30. (Yield 77%, mass [M+] = 613)

[0531] Synthesis of I-31

[0532] After 25 g of I-30, 9.3 g of (2-hydroxydibenzo[b, d]furan-3-yl)boric acid, 17 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 24 g of I-31. (Yield 77%, mass [M+] = 761)

[0533] Synthesis of F-18

[0534] After 20 g of I-31, 18 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.3 g of F-18. (Yield 36%, mass [M+] = 769)

[0535] Preparation Example of Compound 19 (F-19)

[0536]

[0537] Synthesis of I-32

[0538] After 30 g of 4-bromo-2-chlorodibenzo[b,d]furan, 53 g of 7,7,10,10-tetramethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-yl)-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran-2-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 52 g of I-32. (Yield 70%, mass [M+] = 695)

[0539] Synthesis of I-33

[0540] After 25 g of I-32, 8.8 g of (2-hydroxydibenzo[b, d]thiophene-3-yl)boric acid, 15 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 23 g of I-33. (Yield 74%, mass [M+] = 859)

[0541] Synthesis of F-19

[0542] After 20 g of I-33, 16 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.4 g of F-19. (Yield 37%, mass [M+] = 867)

[0543] Preparation Example of Compound 20 (F-20)

[0544]

[0545] Synthesis of I-34

[0546] After 30 g of 4-bromo-2-chlorodibenzo[b,d]furan, 43 g of 3,5,5,8,8-pentamethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)-5,6,7,8-tetrahydronaphthalene-2-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 46 g of I-34. (Yield 71%, mass [M+] = 605)

[0547] Synthesis of I-35

[0548] After 25 g of I-34, 11 g of (3-hydroxy-9,9-dimethyl-9H-fluorene-2-yl)boric acid, 18 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 25 g of I-35. (yield 75%, quality [M+] = 779)

[0549] Synthesis of F-20

[0550] After 20 g of I-35, 17 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.3 g of F-20. (yield 36%, mass [M+] = 787)

[0551] Preparation Example of Compound 21 (F-21)

[0552]

[0553] Synthesis of I-36

[0554] After 30 g of 4-bromo-2-chlorodibenzo[b,d]furan, 45 g of N-(4-(adamantan-1-yl)-2-methylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 49 g of I-36. (Yield 73%, mass [M+] = 629)

[0555] Synthesis of I-37

[0556] After 25 g of I-36, 10.4 g of (3-mercaptodibenzo[b,d]thiophene-2-yl)boric acid, 17 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 23 g of I-37. (Yield 72%, mass [M+] = 809)

[0557] Synthesis of F-21

[0558] After 20 g of I-37, 17 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.4 g of F-21. (Yield 37%, mass [M+] = 817)

[0559] Preparation Example of Compound 22 (F-22)

[0560]

[0561] Synthesis of I-38

[0562] After 30 g of 4-bromo-2-chlorodibenzo[b,d]furan, 33.1 g of 7,7,10,10-tetramethyl-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran-2-thiol, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 42 g of I-38. (Yield 77%, mass [M+] = 512)

[0563] Synthesis of I-39

[0564] After 25 g of I-38, 12.4 g of (2-hydroxy-9,9-dimethyl-9H-fluorene-3-yl)boric acid, 20.3 g of K2CO3, 0.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 25 g of I-39. (Yield 78%, mass [M+] = 686)

[0565] Synthesis of F-22

[0566] After 20 g of I-37, 19.5 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.2 g of F-22. (Yield 36%, mass [M+] = 694)

[0567] Preparation Example of Compound 23 (F-23)

[0568]

[0569] Synthesis of I-40

[0570] After 30 g of 2-bromo-4-chlorodibenzo[b,d]thiophene, 43.1 g of N-(4-(adamantan-1-yl)-2-methylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 46 g of I-40. (Yield 71%, mass [M+] = 645)

[0571] Synthesis of I-41

[0572] After 25 g of I-40, 10.3 g of (3-mercapto-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)boric acid, 16.1 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 24 g of I-41. (Yield 75%, mass [M+] = 829)

[0573] Synthesis of F-23

[0574] After 20 g of I-41, 16.1 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.3 g of F-23. (Yield 36%, mass [M+] = 837)

[0575] Preparation Example of Compound 24 (F-24)

[0576]

[0577] Synthesis of I-42

[0578] After 25 g of I-40, 8.9 g of (3-hydroxydibenzo[b, d]furan-2-yl)boric acid, 16.1 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 23 g of I-42. (Yield 75%, mass [M+] = 793)

[0579] Synthesis of F-24

[0580] After 20 g of I-42, 16.8 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.4 g of F-24. (Yield 37%, mass [M+] = 801)

[0581] Preparation Example of Compound 25 (F-25)

[0582]

[0583] Synthesis of I-43

[0584] After 30 g of 2-bromo-4-chlorodibenzo[b,d]thiophene, 26.3 g of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-ol, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 35 g of I-43. (Yield 73%, mass [M+] = 478)

[0585] Synthesis of I-44

[0586] After 25 g of I-43, 12 g of (3-hydroxydibenzo[b,d]furan-2-yl)boric acid, 22 g of K2CO3, 0.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 24 g of I-44. (Yield 73%, mass [M+] = 626)

[0587] Synthesis of F-25

[0588] After 20 g of I-44, 21.3 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.3 g of F-25. (yield 36%, mass [M+] = 634)

[0589] Preparation Example of Compound 26 (F-26)

[0590]

[0591] Synthesis of I-45

[0592] After 30 g of 4-bromo-2-chlorodibenzo[b,d]thiophene, 49.8 g of 7,7,10,10-tetramethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-yl)-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran-2-amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 55 g of I-45. (Yield 77%, mass [M+] = 711)

[0593] Synthesis of I-46

[0594] After 25 g of I-45, 8.6 g of (3-mercaptodibenzo[b,d]furan-2-yl)boric acid, 15 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 23 g of I-46. (Yield 75%, mass [M+] = 875)

[0595] Synthesis of F-26

[0596] After 20 g of I-46, 15.2 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.4 g of F-26. (Yield 37%, mass [M+] = 883)

[0597] Preparation Example of Compound 27 (F-27)

[0598]

[0599] Synthesis of I-47

[0600] After 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 29.5 g of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-thiol, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20.5 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 37 g of I-47. (Yield 73%, mass [M+] = 478)

[0601] Synthesis of I-48

[0602] After 25 g of I-47, 22.7 g of (4-(bis(4-(tert-butyl)phenyl)amino)-2-mercaptophenyl)boric acid, 21.7 g of K2CO3, 0.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 31 g of I-48. (Yield 71%, mass [M+] = 831)

[0603] Synthesis of F-27

[0604] After 20 g of I-48, 16 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.5 g of F-27. (Yield 37%, mass [M+] = 839)

[0605] Preparation Example of Compound 28 (F-28)

[0606]

[0607] Synthesis of I-49

[0608] After 25 g of I-28, 16.8 g of (4-(bis(4-(tert-butyl)phenyl)amino)-2-hydroxyphenyl)boric acid, 16 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 29 g of I-49. (Yield 76%, mass [M+] = 984)

[0609] Synthesis of F-28

[0610] After 20 g of I-49, 13.5 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.3 g of F-28. (Yield 36%, mass [M+] = 992)

[0611] Preparation Example of Compound 29 (F-29)

[0612]

[0613] Synthesis of I-50

[0614] After 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 23.5 g of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-thiol, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20.5 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 33 g of I-50. (yield 74%, quality [M+] = 422)

[0615] Synthesis of I-51

[0616] After 25 g of I-50, 25.7 g of (4-(bis(4-(tert-butyl)phenyl)amino)-2-hydroxyphenyl)boric acid, 24.6 g of K2CO3, 0.6 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 33 g of I-51. (Yield 73%, mass [M+] = 759)

[0617] Synthesis of F-29

[0618] After 20 g of I-51, 17.6 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.2 g of F-29. (Yield 36%, mass [M+] = 767)

[0619] Preparation Example of Compound 30 (F-30)

[0620]

[0621] Synthesis of I-52

[0622] After 25 g of I-19, 21.9 g of (4-(bis(4-(tert-butyl)phenyl)amino)-2-hydroxyphenyl)boric acid, 20.9 g of K2CO3, 0.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 32 g of I-52. (Yield 76%, mass [M+] = 833)

[0623] Synthesis of F-30

[0624] After 20 g of I-52, 16 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.2 g of F-30. (yield 36%, mass [M+] = 841)

[0625] Preparation Example of Compound 31 (F-31)

[0626]

[0627] Synthesis of I-53

[0628] After 25 g of I-13, 18.4 g of (4-(bis(4-(tert-butyl)phenyl)amino)-2-hydroxyphenyl)boric acid, 17.6 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 29 g of I-53. (Yield 74%, mass [M+] = 928)

[0629] Synthesis of F-31

[0630] After 20 g of I-53, 14.4 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.3 g of F-31. (Yield 36%, mass [M+] = 936)

[0631] Preparation Example of Compound 32 (F-32)

[0632]

[0633] Synthesis of I-54

[0634] After 25 g of I-13, 17.7 g of (5-(bis(4-(tert-butyl)phenyl)amino)-2-hydroxyphenyl)boric acid, 17.6 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 28 g of I-54. (Yield 71%, mass [M+] = 928)

[0635] Synthesis of F-32

[0636] After 20 g of I-54, 14.4 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.4 g of F-32. (Yield 37%, mass [M+] = 936)

[0637] Preparation Example of Compound 33 (F-33)

[0638]

[0639] Synthesis of I-55

[0640] After 30 g of 4-bromo-2-chlorodibenzo[b,d]furan, 41.5 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)amine, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20.5 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 44 g of I-55. (Yield 70%, mass [M+] = 591)

[0641] Synthesis of I-56

[0642] After 25 g of I-55, 18.4 g of (5-(bis(4-(tert-butyl)phenyl)amino)-2-mercaptophenyl)boric acid, 27.6 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 29 g of I-56. (Yield 73%, mass [M+] = 944)

[0643] Synthesis of F-33

[0644] After 20 g of I-56, 14.1 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.4 g of F-33. (Yield 37%, mass [M+] = 952)

[0645] Preparation Example of Compound 34 (F-34)

[0646]

[0647] Synthesis of I-57

[0648] After 30 g of 2-bromo-4-chlorodibenzo[b,d]furan, 27.8 g of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphtho[2,3-b]thiophene-3-ol, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 20.5 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 37 g of I-57. (Yield 75%, mass [M+] = 462)

[0649] Synthesis of I-58

[0650] After 25 g of I-57, 22.6 g of (4-(bis(4-(tert-butyl)phenyl)amino)-2-hydroxyphenyl)boric acid, 22.5 g of K2CO3, 0.6 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 32 g of I-58. (Yield 74%, mass [M+] = 799)

[0651] Synthesis of F-34

[0652] After 20 g of I-58, 16.7 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.4 g of F-34. (Yield 37%, mass [M+] = 807)

[0653] Preparation Example of Compound 35 (F-35)

[0654]

[0655] Synthesis of I-59

[0656] After 30 g of 1-(3-bromo-5-chlorophenyl)adamantane, 35.9 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)amine, 0.9 g of [bis(tri-tert-butylphosphine)palladium(0)], 17.7 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 41 g of I-59. (Yield 70%, mass [M+] = 635)

[0657] Synthesis of I-60

[0658] After 25 g of I-59, 17.1 g of (4-(bis(4-(tert-butyl)phenyl)amino)-2-mercaptophenyl)boric acid, 16.3 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 29 g of I-60. (Yield 75%, mass [M+] = 989)

[0659] Synthesis of F-35

[0660] After 20 g of I-50, 13.5 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.5 g of F-35. (yield 37%, mass [M+] = 996)

[0661] Preparation Example of Compound 36 (F-36)

[0662]

[0663] Synthesis of I-61

[0664] After 40 g of 3-bromo-5-chlorophenol, 75.1 g of bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)amine, 2 g of [bis(tri-tert-butylphosphine)palladium(0)], 37.1 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 72 g of I-61. (Yield 72%, mass [M+] = 517)

[0665] Synthesis of I-62

[0666] After 40 g of I-61, 35.1 g of 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride, 32.1 g of K2CO3, 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 3 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, then treated with MgSO4 (anhydrous) and filtered. The filtered solution was recrystallized to obtain 52 g of I-62. (yield 84%, quality [M+] = 799)

[0667] Synthesis of I-63

[0668] After 40 g of I-62, 12.4 g of (3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)boric acid, 20.8 g of K2CO3, 0.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 600 mL of tetrahydrofuran, and 300 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 25 g of I-63. (Yield 71%, mass [M+] = 989)

[0669]

[0670] Synthesis of I-64

[0671] After 20 g of I-63, 19 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.6 g of I-64. (Yield 38%, mass [M+] = 711)

[0672] Synthesis of F-36

[0673] After 7 g of I-64, 2.5 g of bis(4-(tert-butyl)phenyl)amine, 0.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 2 g of sodium tert-butoxide, and 100 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 6.7 g of F-36. (Yield 71%, mass [M+] = 956)

[0674] Preparation Example of Compound 37 (F-37)

[0675]

[0676] Synthesis of I-65

[0677] After 40 g of 3-bromo-5-chlorophenol, 77.8 g of 3,5,5,8,8-pentamethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-yl)-5,6,7,8-tetrahydronaphthalene-2-amine, 2 g of [bis(tri-tert-butylphosphine)palladium(0)], 37.1 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 73 g of I-65. (yield 70%, quality [M+] = 540)

[0678] Synthesis of I-66

[0679] After 40 g of I-65, 33.6 g of 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride, 31 g of K2CO3, 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 3 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, then treated with MgSO4 (anhydrous) and filtered. The filtered solution was recrystallized to obtain 51 g of I-66. (yield 85%, quality [M+] = 814)

[0680] Synthesis of I-67

[0681] After 40 g of I-66, 12.5 g of (2-hydroxy-9,9-dimethyl-9H-fluorene-3-yl)boric acid, 20.4 g of K2CO3, 0.5 g of [bis(tri-tert-butylphosphine)palladium(0)], 600 mL of tetrahydrofuran, and 300 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 26 g of I-67. (Yield 73%, mass [M+] = 723)

[0682]

[0683] Synthesis of I-68

[0684] After 20 g of I-67, 18.4 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.5 g of I-68. (Yield 37%, mass [M+] = 731)

[0685] Synthesis of F-37

[0686] After 7 g of I-68, 2.5 g of bis(4-(tert-butyl)phenyl)amine, 0.05 g of [bis(tri-tert-butylphosphine)palladium(0)], 2 g of sodium tert-butoxide, and 100 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 6.8 g of F-37. (Yield 73%, mass [M+] = 976)

[0687] Preparation Example of Compound 38 (F-38)

[0688]

[0689] Synthesis of I-69

[0690] After 30 g of 1-(3-bromo-5-chlorophenyl)adamantane, 45.5 g of 7,7,10,10-tetramethyl-N-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-7,8,9,10-tetrahydronaphtho[2,3-b]benzofuran-3-amine, 0.9 g of [bis(tri-tert-butylphosphine)palladium(0)], 17.7 g of sodium tert-butoxide, and 600 mL of toluene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the reaction solution was separated, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 51 g of I-69. (Yield 75%, mass [M+] = 740)

[0691] Synthesis of I-70

[0692] After 25 g of I-69, 8.6 g of (3-hydroxy-9,9-dimethyl-9H-fluorene-2-yl)boric acid, 14 g of K2CO3, 0.05 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were placed in a container, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, all solvents were removed, and the reaction solution was separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 22 g of I-70. (yield 71%, quality [M+] = 913)

[0693] Synthesis of F-38

[0694] After 20 g of I-70, 14.6 g of boron triiodide, and 200 mL of dichlorobenzene were placed in a container under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, then treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and then recrystallized to obtain 7.3 g of F-38. (yield 36%, mass [M+] = 921)

[0695] Example 1

[0696] A thin coating having a thickness of The glass substrate of indium tin oxide (ITO) is put into the distilled water dissolved with cleaning agent therein, and carries out ultrasonic cleaning.In this case, the product manufactured by Fischer Co. is used as cleaning agent, and the distilled water filtered twice by the filter manufactured by Millipore Co. is used as distilled water.After ITO was washed for 30 minutes, distilled water was used to repeat ultrasonic cleaning for 10 minutes twice.After using distilled water washing to complete, ultrasonic cleaning is carried out by using isopropyl alcohol, acetone and methanol solvent, and products therefrom is dried and then transported to plasma washing machine.In addition, by using oxygen plasma, substrate was cleaned for 5 minutes, and then transported to vacuum deposition machine.

[0697] The following HI-A and HAT-CN were thermally vacuum deposited on the ITO transparent electrode prepared as described to a thickness of and Thus, a hole injection layer is formed. The following HT-A is vacuum deposited on the hole injection layer to a thickness of Thus, a hole transport layer is formed. The following HT-B is vacuum deposited on the hole transport layer to a thickness of Subsequently, 2 parts by weight of the compound F-1 according to the chemical formula 1 of the present application as a light-emitting dopant based on 100 parts by weight of the light-emitting layer and the following BH as a host were vacuum-deposited on the electron blocking layer to a thickness of Next, the following compound ET-A was vacuum deposited on the light-emitting layer as the first electron transport layer to a thickness of Then, the following ET-B and LiQ were vacuum deposited at a weight ratio of 1:1 to form a film with a thickness of LiQ is vacuum deposited on the second electron transport layer to a thickness of Aluminum and silver are deposited on the electron injection layer at a weight ratio of 10:1 to a thickness of Aluminum is deposited thereon to a thickness of Thus, a negative electrode is formed.

[0698] In the preceding steps, the deposition rate of the organic material is maintained at to The deposition rate of aluminum at the negative electrode was kept at and maintaining the vacuum level during deposition to Thus, an organic light-emitting device is manufactured.

[0699]

[0700] Examples 2 to 38

[0701] The organic light-emitting devices of Examples 2 to 38 were manufactured in the same manner as in Example 1, except that the compounds in Table 1 below were used instead of Compound F-1 in Example 1. The voltage, efficiency, and lifetime of the organic light-emitting devices manufactured in Examples 2 to 37 and Comparative Examples 1 to 3 were measured, and the results are shown in Table 1 below.

[0702]

[0703]

[0704] Comparative Examples 1 to 6

[0705] Organic light-emitting devices of Comparative Examples 1 to 6 were manufactured in the same manner as in Example 1, except that the compounds in the following Table 1 were used instead of Compound F-1 in Example 1.

[0706]

[0707] The voltage, efficiency, and lifetime of the organic light emitting devices manufactured in Examples 1 to 38 and Comparative Examples 1 to 6 were measured, and the results are shown in Table 1 below.

[0708] [Table 1]

[0709]

[0710]

[0711] According to Table 1 above, it can be determined that the voltage of the organic light-emitting devices of Comparative Examples 1 and 2 using Comparative Example compounds BD1 and BD2 (wherein one or more of Ar1 to Ar3 of Chemical Formula 1 of the present application is a heterocycle containing nitrogen (N) as a heteroelement) is significantly higher than that of Examples 1 to 38 of the present application.

[0712] It can be determined that when X in Chemical Formula 1 of the present application is NR, the organic light-emitting devices of Comparative Examples 3 and 6 using Comparative Example compounds BD3 and BD6 (which do not include a ring in which at least one substituted or unsubstituted aliphatic hydrocarbon ring is fused) have high voltage, low efficiency and degraded service life characteristics compared with Examples 1 to 38 of the present application.

[0713] It can be determined that the organic light-emitting device of Comparative Example 4 using Comparative Example Compound BD4 (wherein at least one of Ar1, Ar2 and Ar3 of Chemical Formula 1 of the present application does not contain a heterocycle; or a substituted or unsubstituted aliphatic hydrocarbon ring) has significantly degraded efficiency and device characteristics compared to Examples 1 to 38 of the present application.

[0714] It can be determined that the organic light-emitting device of Comparative Example 5 using Comparative Example Compound BD5 (wherein Y in Chemical Formula 1 of the present application is N and the core structure of Chemical Formula 1 of the present application is different) has significantly higher voltage and degraded efficiency and device characteristics compared with Examples 1 to 38 of the present application.

[0715] In summary, it can be confirmed that the organic light-emitting devices of Examples 1 to 38 using the compound of Chemical Formula 1 according to the present specification have significantly superior voltage, efficiency, and lifespan characteristics compared to the organic light-emitting devices of Comparative Examples 1 to 6.

[0716] <Description of Reference Numerals and Symbols>

[0717] 1: Base

[0718] 2: Positive electrode

[0719] 3: Hole injection layer

[0720] 4: Hole transport layer

[0721] 5: Electron blocking layer

[0722] 6: Luminous layer

[0723] 7: First electron transport layer

[0724] 8: Second electron transport layer

[0725] 9: Electron injection layer

[0726] 10: Negative electrode

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] in, In Chemical Formula 1, X is NR, O or S, Y is O or S, Ar1, Ar2 and Ar3 are the same as or different from each other and are each independently a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring, provided that at least one of Ar1, Ar2 and Ar3 comprises a heterocyclic ring; or a substituted or unsubstituted aliphatic hydrocarbon ring, and further, when X is NR, at least one of R, Ar1, Ar2 and Ar3 comprises a ring to which a substituted or unsubstituted aliphatic hydrocarbon ring is fused, When X is NR, at least one of Ar1 and Ar3 is optionally bonded to R to form a ring, and Ar2 and Ar3 are optionally bonded to each other to form a ring, and R is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

2. The compound according to claim 1, wherein Ar1, Ar2 and Ar3 are the same as or different from each other and are each independently a substituted or unsubstituted aromatic hydrocarbon ring; a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocyclic ring; a fused ring of a substituted or unsubstituted heterocyclic ring and an aromatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted heterocyclic ring, an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and at least one of Ar1, Ar2 and Ar3 is a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocyclic ring; a fused ring of a substituted or unsubstituted heterocyclic ring and an aromatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted heterocyclic ring, an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.

3. The compound according to claim 1, wherein Ar1, Ar2 and Ar3 are the same as or different from each other and are each independently a substituted or unsubstituted aromatic hydrocarbon ring; a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocyclic ring containing O or S as a heteroelement; a fused ring of a substituted or unsubstituted heterocyclic ring containing O or S as a heteroelement and an aromatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted heterocyclic ring, an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and at least one of Ar1, Ar2 and Ar3 is a fused ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; a substituted or unsubstituted heterocyclic ring containing O or S as a heteroelement; a fused ring of a substituted or unsubstituted heterocyclic ring containing O or S as a heteroelement and an aromatic hydrocarbon ring; or a substituted or unsubstituted fused ring of a heterocyclic ring, an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.

4. The compound according to claim 1, wherein Ar1, Ar2 and Ar3 are the same as or different from each other and are each independently substituted or unsubstituted benzene, substituted or unsubstituted tetralin, substituted or unsubstituted fluorene, substituted or unsubstituted furan, substituted or unsubstituted benzofuran, substituted or unsubstituted dibenzofuran, substituted or unsubstituted tetrahydronaphthofuran, substituted or unsubstituted tetrahydrobenzonaphthofuran, substituted or unsubstituted thiophene, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzothiophene ... benzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted tetrahydronaphthofuran, substituted or unsubstituted tetrahydronaphthofuran, substituted or unsubstituted tetrahydronaphthofuran, substituted or unsubstituted benzofuran, substituted or unsubstituted tetrahydronaphthofuran, substituted or thiophene, or substituted or unsubstituted tetrahydrobenzonaphthothiophene, and at least one of Ar1, Ar2 and Ar3 is substituted or unsubstituted tetrahydronaphthalene, substituted or unsubstituted furan, substituted or unsubstituted benzofuran, substituted or unsubstituted dibenzofuran, substituted or unsubstituted tetrahydronaphthofuran, substituted or unsubstituted tetrahydrobenzonaphthofuran, substituted or unsubstituted thiophene, substituted or unsubstituted benzothiophene, or substituted or unsubstituted dibenzothiophene, substituted or unsubstituted tetrahydronaphthothiophene, or substituted or unsubstituted tetrahydrobenzonaphthothiophene.

5. The compound of claim 1, wherein at least one of Ar1, Ar2, and Ar3 comprises substituted or unsubstituted tetralin, or X is NR and R comprises substituted or unsubstituted tetralin.

6. The compound according to claim 1, wherein at least one of Ar1 and Ar2 is a substituted or unsubstituted tetralin, or X is NR and R is a substituted or unsubstituted tetralin, or at least one of Ar1 and Ar2 is a heterocyclic ring to which a substituted or unsubstituted tetralin is fused.

7. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 11 to 13: In Chemical Formulas 11 to 13, X and Y are the same as those defined in Chemical Formula 1, Z1 is CRxRy, O or S, and Ra to Rc, Rx, Ry, R and R' are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl; or are connected with adjacent groups to form a substituted or unsubstituted ring, a and c are each an integer from 0 to 4, b is an integer from 0 to 3, a' and c' are each an integer from 0 to 2, and b' is 0 or 1.

8. The compound according to claim 7, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 21 to 23: In Chemical Formulas 21 to 23, X, Y, Z1, Ra to Rc, a, b, c, a', b' and c' are the same as those described above, and Rd are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl; or are connected with adjacent groups to form a substituted or unsubstituted ring, and d is an integer from 0 to 4.

9. The compound according to claim 8, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 31 to 34: In Chemical Formulas 31 to 34, X, Y, Z1, Ra to Rd, a, b, c, d, a', b' and c' are the same as those described above, and Z2 and Z3 are the same as or different from each other and are each independently CRxRy, O or S, and the definitions of Rx and Ry are the same as those described above.

10. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 41 to 43: In Chemical Formulas 41 to 43, X and Y are the same as those defined in Chemical Formula 1, Z1 and Z2 are each independently CRxRy, O or S, and Ra to Rc, Rx, Ry, R, R', R" and R'" are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl; or are connected with adjacent groups to form a substituted or unsubstituted ring, a and c are each an integer from 0 to 4, and b is an integer from 0 to 3. 11 . The compound according to claim 10 , wherein R and R′ of Chemical Formula 43 are bonded to each other to form substituted or unsubstituted benzene, or substituted or unsubstituted tetralin.

12. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following compounds:

13. An organic light emitting device, comprising: Positive electrode; Negative electrode; and an organic material layer having one or more layers disposed between the positive electrode and the negative electrode, wherein one or more of the organic material layers comprises the compound according to any one of claims 1 to 12. 14 . The organic light emitting device according to claim 13 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer contains the compound.

15. The organic light emitting device according to claim 14, wherein the compound is included as a dopant.

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