Compound and organic light-emitting element comprising same

Abstract

The present specification provides a compound represented by Chemical Formula 1 in which at least one of three benzene rings directly or indirectly attached to boron is substituted with at least one of an aryl group, a silyl group, or a heterocyclic group, and at least one carbazolyl group, and an organic light-emitting device including the same.

Description

TECHNICAL FIELD

[0001] This application claims priority to and the benefit of Korean Patent Application Nos. 10-2023-0133061 and 10-2024-0061695, filed on October 6, 2023, and May 10, 2024, respectively, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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

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

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

[0005] TECHNICAL PROBLEM

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

[0007] TECHNICAL SOLUTION

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

[0009] [Chemical Formula 1]

[0010]

[0011] In Chemical Formula 1,

[0012] X is NR; or S,

[0013] Y is NR'; O; or S,

[0014] R and R' are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl; a substituted or unsubstituted silyl; or a substituted or unsubstituted aryl,

[0015] L1to L3and L11to L33are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0016] R1to R3and R11to R33are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0017] at least one of R1to R3is a substituted or unsubstituted carbazolyl group,

[0018] at least one of R11to R33is a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0019] n1, n2, m1, and m2are each an integer of 1 to 4,

[0020] n3and m3are each an integer of 1 to 3,

[0021] when n1to n3and m1to m3are each 2 or more, the substituents in the parentheses are each the same as or different from each other, and

[0022] n1+m1is 4 or less, n2+m2is 4 or less, and n3+m3is 3 or less.

[0023] Further, one exemplary embodiment of the present specification provides an organic light-emitting device including: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer comprise a compound represented by Chemical Formula 1.

[0024] Advantages

[0025] The compounds described in the present specification can be used as a material of an organic material layer of an organic light-emitting device. The compounds according to at least one exemplary embodiment of the present specification can improve efficiency, achieve a low driving voltage, and / or improve a lifespan characteristic in an organic light-emitting device. In particular, the compounds described in the present specification can be used as a material for light emission or hole blocking. BRIEF DESCRIPTION OF DRAWINGS

[0026] Figure 1 An example of an organic light-emitting device in which a substrate 1, a first electrode 2, a light-emitting layer 6, and a second electrode 9 are sequentially stacked is shown.

[0027] Figure 2An example of an organic light emitting device in which a substrate 1, a first electrode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a second electrode 9 are sequentially stacked is shown. DETAILED DESCRIPTION

[0028] Hereinafter, the present specification will be described in more detail.

[0029] In the present specification, when a part "comprises" a constituent element, unless specifically described otherwise, this does not mean excluding another constituent element, but means that another constituent element can also be included.

[0030] In the present specification, when a member is "provided on" another member, this includes not only a case where the member is in contact with the other member, but also a case where a further member is present between the two members.

[0031] In the present specification, or a dotted line means a position bonded to a chemical formula or a compound.

[0032] In the present specification, N% deuterium-substituted means that N% of hydrogens available in the corresponding structure are replaced with deuterium. For example, dibenzofuran 25% deuterium-substituted means that two of eight hydrogens of dibenzofuran are replaced with deuterium.

[0033] In the present specification, the degree of deuteration can be determined by a publicly known method such as nuclear magnetic resonance spectroscopy (1H NMR) or GC / MS.

[0034] Examples of substituents in the present specification will be described below, but are not limited thereto.

[0035] The term "substituted" means that a hydrogen atom of a compound bonded to a carbon atom is changed to another substituent, and the position of substitution is not limited as long as the position is a position where a hydrogen atom is replaced (i.e., a position where a substituent can be replaced), and when two or more are substituted, the two or more substituents can be the same as or different from each other.

[0036] 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 silyl group; an alkyl group; a cycloalkyl group; an arylalkyl group; an aryl group; and a heterocyclic group, substituted with two or more substituents of the exemplified substituents connected to each other, or not having a substituent.

[0037] 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; silyl; alkyl; aryl; and heterocyclic group, substituted with two or more substituents from among the exemplified substituents being connected, or not having a substituent.

[0038] Examples of substituents will be described below, however, the substituents are not limited thereto.

[0039] In the present specification, examples of a halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0040] In the present specification, a silyl group can be represented by the chemical formula -SiY a Y b Y c , and Y a , Y b , and Y c may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of a silyl group include trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyl dimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like, but are not limited thereto.

[0041] In the present specification, an alkyl group can be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 60. According to one 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 still another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of an alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, and the like, but are not limited thereto.

[0042] In the present specification, the above description of an alkyl group can be applied to an arylalkyl group, except that the arylalkyl group is substituted with an aryl group.

[0043] The substituents described in the present specification, including alkyl groups and other alkyl moieties, include both linear and branched forms.

[0044] In the present specification, a cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specific examples thereof can include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.

[0045] In the present specification, an aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms. According to one exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group can be an aryl group composed of a single ring or a polycyclic aryl group (an aryl group of a double ring or more). The aryl group composed of a single ring can also be represented by a monocyclic aryl group, and can mean a phenyl group; or a group in which two or more phenyl groups are linked. Examples of the aryl group composed of a single ring include a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like, but are not limited thereto. The polycyclic aryl group can mean a group in which two or more monocyclic rings (for example, a naphthyl group and a phenanthryl group) are fused. Examples of the polycyclic aryl group include a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a pyrenyl group, a fluorenyl group, a triphenylenyl group, and the like, but are not limited thereto.

[0046] In the present specification, a fluorenyl group can be substituted, and two substituents can be bonded to each other to form a spiro ring structure. In this case, the spiro ring structure can be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

[0047] When the fluorenyl group is substituted, the substituent can be a spirofluorenyl group such as and a substituted fluorenyl group such as a (9,9-dimethylfluorenyl) group, and a (9,9-diphenylfluorenyl) group. However, the fluorenyl group is not limited thereto.

[0048] In the present specification, a heterocyclic group is a cyclic group including 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 one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of the heterocyclic group include a pyridyl group, a pyrrolyl group, a pyrimidinyl group, a quinolyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a benzonaphthothiophenyl group, an indolocarbazolyl group, a triazinyl group, and the like, but are not limited thereto.

[0049] In the present specification, the above description of heteroaryl group can be applied to heterocyclyl group, except that heteroaryl group is aromatic.

[0050] In the present specification, the description of aryl group can be applied to arylene group, except that arylene group is divalent.

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

[0052] In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups, "ring" means a hydrocarbon ring; or a heterocyclic ring.

[0053] In the present specification, the term "ring fused with N rings" means a ring fused with N monocyclic rings, wherein the monocyclic ring can be a pentagonal ring or a hexagonal ring, and N is an integer of 1 or more. Examples of the ring fused with N rings include naphthalene, indole, indolizine, benzothiazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, imidazopyridine, phenoxazine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto. In the present specification, the term "ring fused with N rings" means a ring fused with N monocyclic rings, wherein the monocyclic ring can be a pentagonal ring or a hexagonal ring, and N is an integer of 1 or more. Examples of the ring fused with N rings include naphthalene, indole, indolizine, benzothiazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, imidazopyridine, phenoxazine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.

[0054] The hydrocarbon ring can be an aromatic ring, an aliphatic ring, or a fused ring of an aromatic ring and an aliphatic ring, and can be selected from examples of cycloalkyl or aryl.

[0055] In the present specification, bonding with adjacent groups to form a ring means bonding with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocyclic ring; a substituted or unsubstituted aromatic heterocyclic ring; or a fused ring thereof. The hydrocarbon ring means a ring composed of only carbon atoms and hydrogen atoms. The heterocyclic ring means a ring including one or more selected from elements such as N, O, P, S, Si, and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring, and the aromatic heterocyclic ring can be a monocyclic ring or a polycyclic ring.

[0056] In the present specification, the aliphatic hydrocarbon ring means a ring composed of only carbon atoms and hydrogen atoms as a non-aromatic ring. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, but are not limited thereto.

[0057] In the present specification, the aromatic hydrocarbon ring means an aromatic ring composed of only carbon atoms and hydrogen atoms. Examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, , fluoranthene, triphenylene, phenalene, pyrene, naphthacene, ​, pentacene, fluorene, indene, acenaphthene, benzofluorene, spirofluorene, etc., but are not limited thereto. In the present specification, the aromatic hydrocarbon ring may be interpreted as having the same meaning as the aryl group.

[0058] In this specification, an aliphatic heterocycle means an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include ethylene oxide, tetrahydrofuran, 1,4-dihydrofuran, Examples include, but are not limited to, oxane, pyrrolidine, piperidine, morpholine, oxepane, azacyclooctane, thiocane, and the like.

[0059] In the present specification, an aromatic heterocycle means an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, Azoles, isocyanates Azoles, thiazoles, isothiazoles, triazoles, diazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, Azine, thiazine, di Indole, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, diazine, triazaindene, indole, indolizine, benzothiazole, benzo azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phen Oxazine, indole and carbazole, indenocarbazole, etc., but are not limited thereto.

[0060] 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.

[0061] Chemical Formula 1 of the present invention is characterized in that at least one of the benzene rings included in the core structure is substituted with a carbazolyl group, and at least one of the other benzene rings may be substituted with a silyl group, an aryl group, or a heterocyclic group, thereby stabilizing the unstable structure and increasing the hole characteristics, and when the compound represented by Chemical Formula 1 is applied to an organic light-emitting device, an organic light-emitting device having high efficiency, low voltage, and / or long service life characteristics may be obtained.

[0062] Hereinafter, Chemical Formula 1 will be described in detail.

[0063] [Chemical Formula 1]

[0064]

[0065] In Chemical Formula 1,

[0066] X is NR; or S,

[0067] Y is NR'; O; or S,

[0068] R and R' are the same or different from each other, and each independently, hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted aryl group,

[0069] L1to L3and L11to L33are the same or different from each other, and each independently, a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0070] R1to R3and R11to R33are the same or different from each other, and each independently, hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0071] at least one of R1to R3is a substituted or unsubstituted carbazolyl group,

[0072] at least one of R11to R33is a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0073] n1, n2, m1, and m2are each an integer of 1 to 4,

[0074] n3and m3are each an integer of 1 to 3,

[0075] when n1to n3and m1to m3are each 2 or more, the substituents in the parentheses are each the same or different from each other, and

[0076] n1+m1is 4 or less, n2+m2is 4 or less, and n3+m3is 3 or less.

[0077] In one exemplary embodiment of the present specification, X is NR, and Y is NR'.

[0078] In one exemplary embodiment of the present specification, X is NR, and Y is O.

[0079] In one exemplary embodiment of the present specification, X is NR, and Y is S.

[0080] In one exemplary embodiment of the present specification, X is S, and Y is NR'.

[0081] In one exemplary embodiment of the present specification, X is S, and Y is O.

[0082] In an exemplary embodiment of the present specification, X is S, and Y is S.

[0083] In an exemplary embodiment of the present specification, R and R' are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms; a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0084] In an exemplary embodiment of the present specification, R and R' are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms; a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0085] In an exemplary embodiment of the present specification, R and R' are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0086] In an exemplary embodiment of the present specification, R and R' are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; or a substituted or unsubstituted naphthyl group.

[0087] In an exemplary embodiment of the present specification, R and R' are the same as or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0088] In an exemplary embodiment of the present specification, R and R' are the same as or different from each other, and each is independently hydrogen; deuterium; an unsubstituted or deuterium-substituted alkyl group having 1 to 10 carbon atoms; or an unsubstituted or deuterium-substituted aryl group having 6 to 12 carbon atoms.

[0089] In an exemplary embodiment of the present specification, R and R' are the same as or different from each other, and each is independently hydrogen; deuterium; an unsubstituted or deuterium-substituted butyl group; an unsubstituted or deuterium-substituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0090] In an exemplary embodiment of the present specification, R and R' are the same as or different from each other, and are each independently hydrogen; deuterium; or an unsubstituted or deuterium-substituted phenyl group.

[0091] In an exemplary embodiment of the present specification, R and R' are the same as or different from each other, and are each independently hydrogen; deuterium; or a phenyl group.

[0092] In an exemplary embodiment of the present specification, R and R' are the same as or different from each other, and are each independently hydrogen; or a phenyl group.

[0093] In an exemplary embodiment of the present specification, R and R' are the same as or different from each other, and are each independently a phenyl group; or a phenyl group substituted with deuterium.

[0094] In an exemplary embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and are each independently a direct bond; an arylene group; or a divalent heterocyclic group.

[0095] In an exemplary embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

[0096] In an exemplary embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms.

[0097] In an exemplary embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms containing one or more of N, O, S, and Si as a heteroatom.

[0098] In an exemplary embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms containing one or more of N, O, and S as a heteroatom.

[0099] In an exemplary embodiment of the present specification, L1to L3and L11to L33are the same as or different from each other, and 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 bivalent dibenzofuranyl group; a substituted or unsubstituted bivalent dibenzothiophenyl group; or a substituted or unsubstituted bivalent carbazolyl group.

[0100] In an exemplary embodiment of the present specification, L1to L3and L11to L33are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted bivalent dibenzofuranyl group; or a substituted or unsubstituted bivalent carbazolyl group.

[0101] In an exemplary embodiment of the present specification, L1to L3and L11to L33are the same as or different from each other, and each independently a direct bond; an arylene group having 6 to 20 carbon atoms which is unsubstituted or deuterium-substituted; or a bivalent heterocyclic group having 2 to 20 carbon atoms which is unsubstituted or deuterium-substituted.

[0102] In an exemplary embodiment of the present specification, L1to L3and L11to L33are the same as or different from each other, and each independently a direct bond; an arylene group having 6 to 20 carbon atoms which is unsubstituted or deuterium-substituted; or a bivalent heterocyclic group having 2 to 20 carbon atoms which comprises one or more of N, O, and S as a heteroatom and which is unsubstituted or deuterium-substituted.

[0103] In an exemplary embodiment of the present specification, L1to L3and L11to L33are the same as or different from each other, and each independently a direct bond; a phenylene group which is unsubstituted or deuterium-substituted; a biphenylene group which is unsubstituted or deuterium-substituted; a naphthylene group which is unsubstituted or deuterium-substituted; a bivalent dibenzofuranyl group which is unsubstituted or deuterium-substituted; a bivalent dibenzothiophenyl group which is unsubstituted or deuterium-substituted; or a bivalent carbazolyl group which is unsubstituted or deuterium-substituted.

[0104] In an exemplary embodiment of the present specification, L1to L3and L11to L33are the same as or different from each other, and each independently a direct bond; a phenylene group which is unsubstituted or deuterium-substituted; a bivalent dibenzofuranyl group which is unsubstituted or deuterium-substituted; or a bivalent carbazolyl group which is unsubstituted or deuterium-substituted.

[0105] In an exemplary embodiment of the present specification, L1to L3and L11to L33are the same as or different from each other, and each independently a direct bond; a phenylene group; a bivalent dibenzofuranyl group; or a bivalent carbazolyl group.

[0106] In an exemplary embodiment of the present specification, L1to L3are the same as or different from each other, and each is independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted bivalent dibenzofuranyl group; a substituted or unsubstituted bivalent dibenzothiophenyl group; or a substituted or unsubstituted bivalent carbazolyl group.

[0107] In an exemplary embodiment of the present specification, L1to L3are the same as or different from each other, and each is independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted bivalent carbazolyl group.

[0108] In an exemplary embodiment of the present specification, L1to L3are the same as or different from each other, and each is independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted bivalent dibenzofuranyl group; a substituted or unsubstituted bivalent dibenzothiophenyl group; or a substituted or unsubstituted bivalent carbazolyl group.

[0109] In an exemplary embodiment of the present specification, L1to L3are the same as or different from each other, and each is independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted bivalent carbazolyl group.

[0110] In an exemplary embodiment of the present specification, L1to L3are the same as or different from each other, and each is independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted bivalent dibenzofuranyl group; a substituted or unsubstituted bivalent dibenzothiophenyl group; or a substituted or unsubstituted bivalent carbazolyl group.

[0111] In an exemplary embodiment of the present specification, L1to L3are the same as or different from each other, and each is independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted bivalent carbazolyl group.

[0112] In an exemplary embodiment of the present specification, L11to L33are the same as or different from each other, and each is independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted bivalent carbazolyl group.

[0113] In an exemplary embodiment of the present specification, L11to L33are the same as or different from each other, and each is independently a direct bond; or a substituted or unsubstituted phenylene group.

[0114] In an exemplary embodiment of the present specification, L11to L33are the same as or different from each other, and each is independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted bivalent carbazolyl group.

[0115] In an exemplary embodiment of the present specification, L11to L33are the same as or different from each other, and each is independently a direct bond; or a substituted or unsubstituted phenylene group.

[0116] In an exemplary embodiment of the present specification, L11to L33are the same as or different from each other, and each is independently a direct bond; phenylene; or bivalent carbazolyl.

[0117] In an exemplary embodiment of the present specification, L11to L33are the same as or different from each other, and each is independently a direct bond; or phenylene.

[0118] In an exemplary embodiment of the present specification, R1to R3and R11to R33are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, at least one of R1to R3is a substituted or unsubstituted carbazolyl group, and at least one of R11to R33is a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0119] In an exemplary embodiment of the present specification, R1to R3and R11to R33are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl silyl group having 6 to 20 carbon atoms; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, at least one of R1to R3is a substituted or unsubstituted carbazolyl group, and at least one of R11to R33is a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl silyl group having 6 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0120] In an exemplary embodiment of the present specification, R1to R3and R11to R33are the same as or different from each other, and each is independently hydrogen; deuterium; alkylsilyl having 1 to 20 carbon atoms which is unsubstituted or substituted with deuterium; arylsilyl having 6 to 20 carbon atoms which is unsubstituted or substituted with deuterium; alkyl having 1 to 20 carbon atoms which is unsubstituted or substituted with deuterium; cycloalkyl having 3 to 20 carbon atoms which is unsubstituted or substituted with deuterium; aryl having 6 to 20 carbon atoms which is unsubstituted or substituted with deuterium; or heterocyclic group having 2 to 30 carbon atoms which is unsubstituted or substituted with deuterium, at least one of R1to R3is unsubstituted or deuterium-substituted carbazolyl group, and at least one of R11to R33is alkylsilyl having 1 to 20 carbon atoms which is unsubstituted or substituted with deuterium; arylsilyl having 6 to 20 carbon atoms which is unsubstituted or substituted with deuterium; aryl having 6 to 20 carbon atoms which is unsubstituted or substituted with deuterium; or heterocyclic group having 2 to 30 carbon atoms which is unsubstituted or substituted with deuterium.

[0121] In an exemplary embodiment of the present specification, R1to R3and R11to R33are the same as or different from each other, and each is independently hydrogen; deuterium; alkylsilyl having 1 to 20 carbon atoms; arylsilyl having 6 to 20 carbon atoms; alkyl having 1 to 20 carbon atoms; cycloalkyl having 3 to 20 carbon atoms; aryl having 6 to 20 carbon atoms; or heterocyclic group having 2 to 30 carbon atoms, at least one of R1to R3is carbazolyl group, and at least one of R11to R33is alkylsilyl having 1 to 20 carbon atoms; arylsilyl having 6 to 20 carbon atoms; aryl having 6 to 20 carbon atoms; or heterocyclic group having 2 to 30 carbon atoms.

[0122] In an exemplary embodiment of the present specification, at least one of R1to R3is substituted or unsubstituted carbazolyl group, and the others are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0123] In an exemplary embodiment of the present specification, at least two of R1to R3are substituted or unsubstituted carbazolyl group, and the others are hydrogen; or deuterium.

[0124] In an exemplary embodiment of the present specification, one or two of R1to R3is substituted or unsubstituted carbazolyl group.

[0125] In an exemplary embodiment of the present specification, all of R1to R3are substituted or unsubstituted carbazolyl group.

[0126] In an exemplary embodiment of the specification, at least one of R1to R3is unsubstituted or deuterium-substituted carbazolyl, and the rest are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0127] In an exemplary embodiment of the specification, at least two of R1to R3are unsubstituted or deuterium-substituted carbazolyl, and the rest are hydrogen; or deuterium.

[0128] In an exemplary embodiment of the specification, all of R1to R3are unsubstituted or deuterium-substituted carbazolyl.

[0129] In an exemplary embodiment of the specification, at least one of R1to R3is carbazolyl, and the rest are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0130] In an exemplary embodiment of the specification, at least two of R1to R3are carbazolyl, and the rest are hydrogen; or deuterium.

[0131] In an exemplary embodiment of the specification, at least one of R11to R33is a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and the rest are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0132] In an exemplary embodiment of the specification, at least one of R11to R33is a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms; a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, and the rest are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0133] In an exemplary embodiment of the specification, at least one of R11to R33is a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms; a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, and the rest are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0134] In an exemplary embodiment of the present specification, at least one of R11to R33is a substituted or unsubstituted triphenylsilyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted heterocyclic group including one or more of N and O as a heteroatom and having four or more condensed rings, and the others are the same as or different from each other, and each independently hydrogen; or deuterium.

[0135] In an exemplary embodiment of the present specification, at least one of R11to R33is a substituted or unsubstituted triphenylsilyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted heterocyclic group including one or more of N and O as a heteroatom and having four to seven condensed rings, and the others are the same as or different from each other, and each independently hydrogen; or deuterium.

[0136] In an exemplary embodiment of the present specification, at least one of R11to R33is a substituted or unsubstituted triphenylsilyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted heterocyclic group including one or more of N and O as a heteroatom and having five or seven condensed rings, and the others are the same as or different from each other, and each independently hydrogen; or deuterium.

[0137] In an exemplary embodiment of the present specification, at least one of R11to R33is an unsubstituted or deuterium-substituted silyl group; an unsubstituted or deuterium-substituted aryl group; or an unsubstituted or deuterium-substituted heterocyclic group, and the others are the same as or different from each other, and each independently hydrogen; or deuterium.

[0138] In an exemplary embodiment of the present specification, at least one of R11to R33is an unsubstituted or deuterium-substituted alkylsilyl group having 1 to 20 carbon atoms; an unsubstituted or deuterium-substituted arylsilyl group having 6 to 20 carbon atoms; an unsubstituted or deuterium-substituted aryl group having 6 to 20 carbon atoms; or an unsubstituted or deuterium-substituted heterocyclic group having 2 to 30 carbon atoms, and the others are the same as or different from each other, and each independently hydrogen; or deuterium.

[0139] In one exemplary embodiment of the present specification, at least one of R11to R33is an alkylsilyl group having 1 to 20 carbon atoms which is unsubstituted or substituted with deuterium; an arylsilyl group having 6 to 20 carbon atoms which is unsubstituted or substituted with deuterium; an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with deuterium; or a heterocyclic group having 2 to 30 carbon atoms which includes one or more of N, O, and S as a heteroatom and is unsubstituted or substituted with deuterium, and the rest are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0140] In one exemplary embodiment of the present specification, at least one of R11to R33is a triphenylsilyl group which is substituted with deuterium or unsubstituted; a phenyl group which is substituted with deuterium or unsubstituted; a biphenyl group which is substituted with deuterium or unsubstituted; a terphenyl group which is substituted with deuterium or unsubstituted; a naphthyl group which is substituted with deuterium or unsubstituted; a phenanthryl group which is substituted with deuterium or unsubstituted; a carbazolyl group which is substituted with deuterium or unsubstituted; a benzofuranyl group which is substituted with deuterium or unsubstituted; a dibenzofuranyl group which is substituted with deuterium or unsubstituted; a benzothiophenyl group which is substituted with deuterium or unsubstituted; a dibenzothiophenyl group which is substituted with deuterium or unsubstituted; or a heterocyclic group which includes one or more of N and O as a heteroatom, has four or more condensed rings, and is substituted with deuterium or unsubstituted, and the rest are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0141] In one exemplary embodiment of the present specification, at least one of R11to R33is a triphenylsilyl group which is unsubstituted or substituted with deuterium; a phenyl group which is unsubstituted or substituted with deuterium; a biphenyl group which is unsubstituted or substituted with deuterium; a naphthyl group which is unsubstituted or substituted with deuterium; a carbazolyl group which is unsubstituted or substituted with deuterium; a dibenzofuranyl group which is unsubstituted or substituted with deuterium; a dibenzothiophenyl group which is unsubstituted or substituted with deuterium; or a heterocyclic group which includes one or more of N and O as a heteroatom, has four to seven condensed rings, and is unsubstituted or substituted with deuterium, and the rest are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0142] In one exemplary embodiment of the present specification, at least one of R11to R33is a triphenylsilyl group which is unsubstituted or substituted with deuterium; a phenyl group which is unsubstituted or substituted with deuterium; a carbazolyl group which is unsubstituted or substituted with deuterium; a dibenzofuranyl group which is unsubstituted or substituted with deuterium; a dibenzothiophenyl group which is unsubstituted or substituted with deuterium; or a heterocyclic group which includes one or more of N and O as a heteroatom, has five or seven condensed rings, and is unsubstituted or substituted with deuterium, and the rest are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0143] In one illustrative embodiment of the present specification, at least one of R11to R33is an alkylsilyl group having 1 to 20 carbon atoms; an arylsilyl group having 6 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms including one or more of N, O, and S as a heteroatom, and the rest are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0144] In one illustrative embodiment of the present specification, at least one of R11to R33is an alkylsilyl group having 1 to 20 carbon atoms; an arylsilyl group having 6 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms including one or more of N, O, and S as a heteroatom, and the rest are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0145] In one illustrative embodiment of the present specification, at least one of R11to R33is a triphenylsilyl group; a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a phenanthryl group; a carbazolyl group; a benzofuranyl group; a dibenzofuranyl group; a benzothiophenyl group; a dibenzothiophenyl group; or a heterocyclic group including one or more of N and O as a heteroatom and having four or more condensed rings, and the rest are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0146] In one illustrative embodiment of the present specification, at least one of R11to R33is a triphenylsilyl group; a phenyl group; a biphenyl group; a naphthyl group; a carbazolyl group; a dibenzofuranyl group; a dibenzothiophenyl group; or a heterocyclic group including one or more of N and O as a heteroatom and having four to seven condensed rings, and the rest are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0147] In one illustrative embodiment of the present specification, at least one of R11to R33is a triphenylsilyl group; a phenyl group; a carbazolyl group; a dibenzofuranyl group; a dibenzothiophenyl group; or a heterocyclic group including one or more of N and O as a heteroatom and having five or seven condensed rings, and the rest are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0148] In one illustrative embodiment of the present specification, at least two of R11to R33are a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0149] In one illustrative embodiment of the present specification, at least two of R11to R33are a substituted or unsubstituted triphenylsilyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted heterocyclic group including one or more of N and O as a heteroatom and having five or seven condensed rings, and the rest are the same as or different from each other, and each independently hydrogen; or deuterium.

[0150] In one illustrative embodiment of the present specification, at least two of R11to R33are an unsubstituted or deuterium-substituted triphenylsilyl group; an unsubstituted or deuterium-substituted phenyl group; an unsubstituted or deuterium-substituted carbazolyl group; an unsubstituted or deuterium-substituted dibenzofuranyl group; an unsubstituted or deuterium-substituted dibenzothiophenyl group; or a heterocyclic group including one or more of N and O as a heteroatom, having five or seven condensed rings, and being unsubstituted or deuterium-substituted, and the rest are the same as or different from each other, and each independently hydrogen; or deuterium.

[0151] In one illustrative embodiment of the present specification, at least two of R11to R33are a triphenylsilyl group; a phenyl group; a carbazolyl group; a dibenzofuranyl group; a dibenzothiophenyl group; or a heterocyclic group including one or more of N and O as a heteroatom and having five or seven condensed rings, and the rest are the same as or different from each other, and each independently hydrogen; or deuterium.

[0152] In one illustrative embodiment of the present specification, at least one of R11to R33is a group represented by the following structural formula; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0153]

[0154] In the structural formula, P1to P3are a substituted or unsubstituted aryl group, and means a position bonded to L11to L33.

[0155] In one illustrative embodiment of the present specification, P1to P3are a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0156] In one illustrative embodiment of the present specification, P1to P3are a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0157] In one illustrative embodiment of the present specification, P1to P3are a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0158] In an exemplary embodiment of the specification, P1 to P3 are a substituted or unsubstituted phenyl group.

[0159] In an exemplary embodiment of the specification, P1 to P3 are an unsubstituted or deuterium-substituted phenyl group.

[0160] In an exemplary embodiment of the specification, P1 to P3 are a phenyl group.

[0161] In an exemplary embodiment of the specification, n1 is an integer of 1 to 4.

[0162] In an exemplary embodiment of the specification, n1 is an integer of 1 to 3.

[0163] In an exemplary embodiment of the specification, n1 is 3.

[0164] In an exemplary embodiment of the specification, n1 is 2.

[0165] In an exemplary embodiment of the specification, n1 is 1.

[0166] In an exemplary embodiment of the specification, n2 is an integer of 1 to 4.

[0167] In an exemplary embodiment of the specification, n2 is an integer of 1 to 3.

[0168] In an exemplary embodiment of the specification, n2 is 3.

[0169] In an exemplary embodiment of the specification, n2 is 2.

[0170] In an exemplary embodiment of the specification, n2 is 1.

[0171] In an exemplary embodiment of the specification, n3 is an integer of 1 to 3.

[0172] In an exemplary embodiment of the specification, n3 is an integer of 1 to 2.

[0173] In an exemplary embodiment of the specification, n3 is 2.

[0174] In an exemplary embodiment of the specification, n3 is 1.

[0175] In an exemplary embodiment of the specification, m1 is an integer of 1 to 4.

[0176] In an exemplary embodiment of the specification, m1 is an integer of 1 to 3.

[0177] In an exemplary embodiment of the present specification, m1 is 3.

[0178] In an exemplary embodiment of the present specification, m1 is 2.

[0179] In an exemplary embodiment of the present specification, m1 is 1.

[0180] In an exemplary embodiment of the present specification, m2 is an integer of 1 to 4.

[0181] In an exemplary embodiment of the present specification, m2 is an integer of 1 to 3.

[0182] In an exemplary embodiment of the present specification, m2 is 3.

[0183] In an exemplary embodiment of the present specification, m2 is 2.

[0184] In an exemplary embodiment of the present specification, m2 is 1.

[0185] In an exemplary embodiment of the present specification, m3 is an integer of 1 to 3.

[0186] In an exemplary embodiment of the present specification, m3 is an integer of 1 to 2.

[0187] In an exemplary embodiment of the present specification, m3 is 2.

[0188] In an exemplary embodiment of the present specification, m3 is 1.

[0189] In an exemplary embodiment of the present specification, n1+m1 is 2 or more and 4 or less.

[0190] In an exemplary embodiment of the present specification, n1+m1 is 3 or more and 4 or less.

[0191] In an exemplary embodiment of the present specification, n1+m1 is 4.

[0192] In an exemplary embodiment of the present specification, n1+m1 is 3.

[0193] In an exemplary embodiment of the present specification, n1+m1 is 2.

[0194] In an exemplary embodiment of the present specification, n2+m2 is 2 or more and 4 or less.

[0195] In an exemplary embodiment of the present specification, n2+m2 is 3 or more and 4 or less.

[0196] In one exemplary embodiment of the present specification, n2+m2 is 4.

[0197] In one exemplary embodiment of the present specification, n2+m2 is 3.

[0198] In one exemplary embodiment of the present specification, n2+m2 is 2.

[0199] In one exemplary embodiment of the present specification, n3+m3 is 2 or 3.

[0200] In one exemplary embodiment of the present specification, n3+m3 is 3.

[0201] In one exemplary embodiment of the present specification, n3+m3 is 2.

[0202] In one exemplary embodiment of the present specification, m1, n2, and n3 are 1.

[0203] In one exemplary embodiment of the present specification, n1, m2, and n3 are 1.

[0204] In one exemplary embodiment of the present specification, n1, n2, and m3 are 1.

[0205] In one exemplary embodiment of the present specification, n1, m2, and m3 are 1.

[0206] In one exemplary embodiment of the present specification, m1, n2, and m3 are 1.

[0207] In one exemplary embodiment of the present specification, m1, m2, and n3 are 1.

[0208] In one exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulae 1-1 to 1-6.

[0209] [Chemical Formula 1-1]

[0210]

[0211] [Chemical Formula 1-2]

[0212]

[0213] [Chemical Formula 1-3]

[0214]

[0215] [Chemical Formula 1-4]

[0216]

[0217] [Chemical Formula 1-5]

[0218]

[0219] [Chemical Formula 1-6]

[0220]

[0221] In Chemical Formulae 1-1 to 1-6,

[0222] X, Y, R11 to R33, L1 to L3, L11 to L33, and n1 to n3 are defined identically to those in Chemical Formula 1,

[0223] G1 to G3 are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0224] g1 to g3 are each an integer of 1 to 8, and when g1 to g3 are each 2 or more, G1 to G3 are each the same as or different from each other.

[0225] In one exemplary embodiment of the present specification, G1 to G3 are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0226] In one exemplary embodiment of the present specification, G1 to G3 are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0227] In an example embodiment of the specification, G1to G3are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted benzofuranyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted benzothienyl group; or a substituted or unsubstituted dibenzothienyl group.

[0228] In an example embodiment of the specification, G1to G3are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a nitrile group; an alkylsilyl group having 1 to 20 carbon atoms which is unsubstituted or substituted with deuterium; an arylsilyl group having 6 to 20 carbon atoms which is unsubstituted or substituted with deuterium; an alkyl group having 1 to 20 carbon atoms which is unsubstituted or substituted with deuterium; a cycloalkyl group having 3 to 20 carbon atoms which is unsubstituted or substituted with deuterium; an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with deuterium; or a heterocyclic group having 2 to 20 carbon atoms which is unsubstituted or substituted with deuterium.

[0229] In an example embodiment of the specification, G1to G3are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted benzofuranyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group.

[0230] In an example embodiment of the specification, G1to G3are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted benzofuranyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group.

[0231] In an example embodiment of the specification, G1to G3are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted benzofuranyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group.

[0232] In an example embodiment of the specification, G1to G3are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted benzofuranyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group.

[0233] In an example embodiment of the specification, G1to G3are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted benzofuranyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group.

[0234] In an example embodiment of the specification, g1to g3are 1.

[0235] In an example embodiment of the specification, g1to g3are 2.

[0236] In one exemplary embodiment of the present specification, g1 to g3 are 3.

[0237] In one exemplary embodiment of the present specification, g1 to g3 are 4.

[0238] In one exemplary embodiment of the present specification, g1 to g3 are 5.

[0239] In one exemplary embodiment of the present specification, g1 to g3 are 6.

[0240] In one exemplary embodiment of the present specification, g1 to g3 are 7.

[0241] In one exemplary embodiment of the present specification, g1 to g3 are 8.

[0242] In one exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulae 1-A-1 to 1-A-3.

[0243] [Chemical Formula 1-A-1]

[0244]

[0245] [Chemical Formula 1-A-2]

[0246]

[0247] [Chemical Formula 1-A-3]

[0248]

[0249] In Chemical Formulae 1-A-1 to 1-A-3,

[0250] X, Y, R11 to R33, L1 to L3, and L11 to L13 are the same as defined in Chemical Formula 1, and G1 to G3 and g1 to g3 are the same as defined in Chemical Formulae 1-1 to 1-6.

[0251] In one exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulae 1-B-1 to 1-B-3.

[0252] [Chemical Formula 1-B-1]

[0253]

[0254] [Chemical Formula 1-B-2]

[0255]

[0256] [Chemical Formula 1-B-3]

[0257]

[0258] In Chemical Formula 1-B-1 to Chemical Formula 1-B-3,

[0259] Definitions of X, Y, R11 to R33, L1 to L3, and L11 to L13 are the same as those in Chemical Formula 1, and definitions of G1 to G3 and g1 to g3 are the same as those in Chemical Formula 1-1 to Chemical Formula 1-6.

[0260] In an exemplary embodiment of the present specification, 20% or more of the compound represented by Chemical Formula 1 is substituted with deuterium. In another exemplary embodiment, 30% or more of the compound represented by Chemical Formula 1 is substituted with deuterium. In yet another exemplary embodiment, 40% or more of the compound represented by Chemical Formula 1 is substituted with deuterium. In yet another exemplary embodiment, 50% or more of the compound represented by Chemical Formula 1 is substituted with deuterium. In yet another exemplary embodiment, 60% or more of the compound represented by Chemical Formula 1 is substituted with deuterium. In another exemplary embodiment, 70% or more of the compound represented by Chemical Formula 1 is substituted with deuterium. In another exemplary embodiment, 80% or more of the compound represented by Chemical Formula 1 is substituted with deuterium. In yet another exemplary embodiment, 90% or more of the compound represented by Chemical Formula 1 is substituted with deuterium. In yet another exemplary embodiment, 100% of the compound represented by Chemical Formula 1 is substituted with deuterium.

[0261] In one exemplary embodiment of the present specification, the compound represented by Chemical Formula 1 contains 40% to 60% deuterium. In another exemplary embodiment, the compound represented by Chemical Formula 1 contains 40% to 80% deuterium. In yet another exemplary embodiment, the compound represented by Chemical Formula 1 contains 60% to 80% deuterium. In yet another exemplary embodiment, the compound represented by Chemical Formula 1 contains 80% to 100% deuterium.

[0262] In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following compounds.

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371] In the present specification, D＝x1～x2 means that the structure in parentheses contains x1 to x2 deuteriums, and the value thereof is an integer. For example, D＝1～41 means that it contains 1 to 41 deuteriums. As one example, the structure contains 1 to 50 deuteriums.

[0372]

[0373] The compound represented by Chemical Formula 1 according to one exemplary embodiment of the present specification can be synthesized by a synthetic method known in the art using starting materials, intermediates, etc. known in the art, substituents can be bonded by a method known in the art, and the type, position, or number of substituents can be changed according to a technique known in the art.

[0374] In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents to the core structure of the compound represented by Chemical Formula 1. Furthermore, in the present specification, the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure having the above structure.

[0375] Furthermore, the present specification provides an organic light emitting device including the above-described compound.

[0376] In the present specification, when one member is "on" another member, this includes not only a case in which one member is in contact with another member, but also a case in which a further member is present between the two members.

[0377] In the present specification, when one part "includes" one constituent element, unless specifically described otherwise, this does not mean excluding another constituent element, but means that another constituent element can also be included.

[0378] The organic light emitting device according to the present specification is an organic light emitting device including: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain the above-described compound represented by Chemical Formula 1.

[0379] The organic light emitting device of the present specification can be manufactured using typical manufacturing methods and materials of an organic light emitting device, except that the organic material layer is formed using the compound of Chemical Formula 1 described above.

[0380] The organic material layer of the organic light emitting device of the present specification can also have a single layer structure, but can have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present application can have a multi-layer structure including one or more layers of 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 as the organic material layer. However, the structure of the organic light emitting device of the present specification is not limited thereto, and can be a single layer structure. Furthermore, when the organic light emitting device is manufactured using the compound, the organic light emitting device can be manufactured to include a smaller number of layers not only by a vacuum deposition method, but also by a method such as a solvent method (for example, spin coating, dip coating, doctor blade coating, screen printing, inkjet printing, or thermal transfer method), but the method is not limited thereto.

[0381] In one exemplary embodiment of the present specification, the organic material layer including the compound of Chemical Formula 1 can have a thickness of to or to , preferably a thickness of to .

[0382] In another exemplary embodiment, the organic material layer can include other organic compounds, metals, or metal compounds in addition to the compound represented by Chemical Formula 1.

[0383] In one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer can include the compound represented by Chemical Formula 1.

[0384] In one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer can include the compound represented by Chemical Formula 1 as a host.

[0385] In one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer can include the compound represented by Chemical Formula 1 as an n-type host, specifically as an n-type phosphorescent host.

[0386] In one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Chemical Formula 1 as a first host and can further include an additional second host.

[0387] In one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes the compound represented by Chemical Formula 1 as an n-type first host and can further include a p-type second host, specifically, the first host is an n-type phosphorescent host, and the second host can be a p-type phosphorescent host.

[0388] In the present specification, an n-type can be defined as a material that can steal an electron from a base material (a material of an organic layer) and has a property capable of providing an electron to a lowest unoccupied molecular orbital (LUMO) energy level of the base.

[0389] In contrast, in the present specification, a p-type can be defined as a material that, when a layer is composed of only a p-type material, receives an electron at a highest occupied molecular orbital (HOMO) energy level of a material located in an adjacent cathode direction to generate a hole in the material in the adjacent cathode direction, and the closer the HOMO energy level of the material located in the cathode direction to the LUMO of the p-type material, the easier it is to steal an electron from the HOMO of the adjacent layer and generate a hole in the HOMO of the adjacent layer.

[0390] When any base is doped with a p-type material, a p-type can be defined as a material that receives an electron from a HOMO of a base material and generates as many holes as the electron in the HOMO of the base, and the closer the LUMO of the p-type material to the HOMO of the base, the easier it is to steal an electron and generate a hole in the base.

[0391] In one exemplary embodiment of the present specification, the p-type material can be any compound well known in the art, and can have a structure including, for example, an N-containing monocyclic ring, dibenzofuran, and / or carbazole.

[0392] In one exemplary embodiment of the present specification, the light-emitting layer can include a first host and a second host in a weight ratio of 2:8 to 8:2, specifically, a weight ratio of 4:6 to 6:4, and the first host can include a compound represented by Chemical Formula 1.

[0393] In one exemplary embodiment of the present specification, the light-emitting layer includes a first host and a second host in a weight ratio of 1:1, and the first host can include a compound of Chemical Formula 1.

[0394] In one exemplary embodiment of the present specification, the second host can be a carbazole-based compound.

[0395] In one exemplary embodiment of the present specification, the second host can be a biscarbazole-based compound.

[0396] In one exemplary embodiment of the present specification, the second host can be an aryl-substituted biscarbazole-based compound.

[0397] In one exemplary embodiment of the present specification, the second host can be a compound represented by Chemical Formula EB-1 described below.

[0398] In one exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer contains the compound represented by Chemical Formula 1 as a host, and can further contain a dopant.

[0399] In one exemplary embodiment of the present specification, the light-emitting layer contains the compound represented by Chemical Formula 1 as a first host, and can further contain a second host and a dopant.

[0400] In one exemplary embodiment of the present specification, the dopant is a phosphorescent dopant.

[0401] In one exemplary embodiment of the present specification, the dopant can be contained in an amount of 1 to 20 parts by weight with respect to 100 parts by weight of the host.

[0402] In one exemplary embodiment of the present specification, the light-emitting layer contains a dopant, and the dopant can include a phosphorescent dopant.

[0403] In one exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, the light-emitting layer contains a host and a dopant, the host includes the compound, and the dopant can include a phosphorescent dopant.

[0404] In one exemplary embodiment of the present specification, the light-emitting layer can be a layer emitting blue light.

[0405] In one exemplary embodiment of the present specification, the light-emitting layer can contain the host and the dopant in a weight ratio of 99:1 to 1:99. Specifically, the light-emitting layer can contain the host and the dopant in a weight ratio of 99:1 to 50:50, more specifically, in a weight ratio of 99:1 to 86:14.

[0406] When the light-emitting layer emits red light, as a light-emitting dopant, 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) can be used; or a fluorescent material such as tris(8-hydroxyquinoline)aluminum (Alq3) can be used, but the light-emitting dopant is not limited thereto. When the light-emitting layer emits green light, as a light-emitting dopant, a phosphorescent material such as face tris(2-phenylpyridine)iridium (Ir(ppy)3) can be used; or a fluorescent material such as tris(8-hydroxyquinoline)aluminum (Alq3) can be used, but the light-emitting dopant is not limited thereto. When the light-emitting layer emits blue light, as a light-emitting dopant, a platinum complex compound; 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, but the light-emitting dopant is not limited thereto.

[0407] In an exemplary embodiment of the present specification, the dopant may be a metal complex compound.

[0408] In an exemplary embodiment of the present specification, the dopant may be a platinum complex compound.

[0409] In an exemplary embodiment of the present specification, the dopant may be an iridium complex compound.

[0410] In an exemplary embodiment of the present specification, the dopant may be an iridium-based compound.

[0411] In an exemplary embodiment of the present specification, the dopant compound may be selected from the following structural formulas, but is not limited thereto.

[0412]

[0413]

[0414]

[0415]

[0416] In an exemplary embodiment of the present specification, the organic material layer may include a hole blocking layer.

[0417] In an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer may include a compound represented by Chemical Formula 1.

[0418] In one exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer can include the n-type compound represented by Chemical Formula 1.

[0419] In one exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, the hole blocking layer can include the n-type compound represented by Chemical Formula 1, and the n-type compound represented by Chemical Formula 1 can be the same or different compound from the n-type host included in the light emitting layer.

[0420] In one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer and a hole blocking layer, and the light emitting layer and the hole blocking layer can include the compound represented by Chemical Formula 1.

[0421] In one exemplary embodiment of the present specification, the organic material layer can further include one or more layers selected from a hole injecting layer, a hole transporting layer, a hole injecting and transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, an electron injecting layer, and an electron injecting and transporting layer.

[0422] In one exemplary embodiment of the present specification, the organic light emitting device can include a first electrode, a second electrode disposed to face the first electrode, a light emitting layer disposed between the first electrode and the second electrode, and an organic material layer having two or more layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode.

[0423] In one exemplary embodiment of the present specification, as the organic material layer having two or more layers, two or more thereof can be selected from a hole injecting layer, a hole transporting layer, a hole injecting and transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, an electron injecting and transporting layer, a hole blocking layer, and an electron blocking layer.

[0424] In one exemplary embodiment of the present specification, a hole transporting layer having two or more layers is included between the light emitting layer and the first electrode. The hole transporting layer having two or more layers can include materials that are the same as or different from each other.

[0425] In one exemplary embodiment of the present specification, the first electrode is a positive electrode or a negative electrode.

[0426] In one exemplary embodiment of the present specification, the second electrode is a negative electrode or a positive electrode.

[0427] In one exemplary embodiment of the present specification, the organic light emitting device can 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.

[0428] In one exemplary embodiment of the present specification, the organic light emitting device can be an inverted organic light emitting device in which a cathode, an organic material layer having one or more layers, and an anode are sequentially stacked on a substrate.

[0429] The organic light emitting device can have a stacked structure described below, for example, but the stacked structure is not limited thereto.

[0430] (1) First electrode / Hole transport layer / Light emitting layer / Second electrode

[0431] (2) First electrode / Hole injection layer / Hole transport layer / Light emitting layer / Second electrode

[0432] (3) First electrode / Hole injection layer / Hole buffer layer / Hole transport layer / Light emitting layer / Second electrode

[0433] (4) First electrode / Hole transport layer / Light emitting layer / Electron transport layer / Second electrode

[0434] (5) First electrode / Hole transport layer / Light emitting layer / Electron transport layer / Electron injection layer / Second electrode

[0435] (6) First electrode / Hole injection layer / Hole transport layer / Light emitting layer / Electron transport layer / Second electrode

[0436] (7) First electrode / Hole injection layer / Hole transport layer / Light emitting layer / Electron transport layer / Electron injection layer / Second electrode

[0437] (8) First electrode / Hole injection layer / Hole buffer layer / Hole transport layer / Light emitting layer / Electron transport layer / Second electrode

[0438] (9) First electrode / Hole injection layer / Hole buffer layer / Hole transport layer / Light emitting layer / Electron transport layer / Electron injection layer / Second electrode

[0439] (10) First electrode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Second electrode

[0440] (11) First electrode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Second electrode

[0441] (12) First electrode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Second electrode

[0442] (13) First electrode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Second electrode

[0443] (14) First electrode / Hole transport layer / Light emitting layer / Hole blocking layer / Electron transport layer / Second electrode

[0444] (15) first electrode / hole transporting layer / light emitting layer / hole blocking layer / electron transporting layer / electron injection layer / second electrode

[0445] (16) first electrode / hole injection layer / hole transporting layer / light emitting layer / hole blocking layer / electron transporting layer / second electrode

[0446] (17) first electrode / hole injection layer / hole transporting layer / light emitting layer / hole blocking layer / electron transporting layer / electron injection layer / second electrode

[0447] (18) first electrode / hole injection layer / hole transporting layer / electron blocking layer / light emitting layer / hole blocking layer / electron transporting and injection layer / second electrode

[0448] The organic light emitting device of the present specification can have Figure 1 to the structure shown in FIG. 3, but is not limited thereto.

[0449] Figure 1 An example of an organic light emitting device in which a substrate 1, a first electrode 2, a light emitting layer 6, and a second electrode 9 are sequentially stacked is shown. In the above structure, the compound can be contained in the light emitting layer 6.

[0450] Figure 2 An example of an organic light emitting device in which a substrate 1, a first electrode 2, a hole injection layer 3, a hole transporting layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron injection and transporting layer 8, and a second electrode 9 are sequentially stacked is shown. In the above structure, the compound can be contained in the light emitting layer 6 or the hole blocking layer 7.

[0451] In one exemplary embodiment of the present specification, the electron injection and transporting layer and the light emitting layer can be disposed adjacent to each other. For example, the electron injection and transporting layer and the light emitting layer can be disposed in physical contact with each other.

[0452] In one exemplary embodiment of the present specification, the hole blocking layer and the electron injection and transporting layer can be disposed adjacent to each other. For example, the hole blocking layer and the electron injection and transporting layer can be in physical contact with each other.

[0453] In one exemplary embodiment of the present specification, the hole blocking layer and the light emitting layer can be disposed adjacent to each other. For example, the hole blocking layer and the light emitting layer can be disposed in physical contact with each other.

[0454] The organic light emitting device of the present specification can be manufactured by materials and methods known in the art, except that one or more layers of the organic material layer contain the compound, i.e., the compound represented by Chemical Formula 1.

[0455] When the organic light emitting device includes a plurality of organic material layers, the organic material layers can be formed of the same material or different materials.

[0456] For example, the organic light emitting device according to the present specification can be manufactured by depositing a metal or a metal oxide having conductivity, or an alloy thereof on a substrate to form a first 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, an electron blocking layer, a light emitting layer, a hole blocking layer, and an electron injection and transport layer on the first electrode, and then depositing a material that can be used as a second 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 second electrode material, an organic material layer, and a first electrode material on a substrate.

[0457] As a positive electrode material, a material having a high work function is generally preferred to facilitate hole injection into the organic material layer. Examples thereof include a metal such as vanadium, chromium, copper, zinc, and gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO:Al or SnO2:Sb; a conductive polymer such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and the like, but are not limited thereto.

[0458] As a negative electrode material, a material having a low work function is generally preferred to facilitate electron injection into the organic material layer. Examples thereof include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; a multi-layered structure material such as LiF / Al or LiO2 / Al; and the like, but are not limited thereto.

[0459] The light emitting layer can include a host material and a dopant material. When the organic light emitting device according to one exemplary embodiment of the present specification includes another light emitting layer in addition to the light emitting layer including Chemical Formula 1, examples of the host material include a fused aromatic ring derivative, a heterocycle-containing compound, etc. Specific examples of the fused aromatic ring derivative include an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, etc., and specific examples of the heterocycle-containing compound include a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, etc., but examples are not limited thereto.

[0460] The hole injection layer is a layer that receives holes from the electrode. The hole injection material is preferably a material having a capability of transporting holes and having an effect of receiving holes from the positive electrode and having an excellent hole injection effect to the light emitting layer or light emitting material. In addition, the hole injection material is preferably a material excellent in a capability of preventing excitons generated by the light emitting layer from moving to the electron injection layer or electron injection material. In addition, the hole injection material is preferably a material excellent in a capability of forming a thin film. In addition, 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 the hole injection material include: metalloporphyrin, oligothiophene, and arylamine-based organic materials; hexacyno hexaazatriphenylene-based organic materials; quinacridone-based organic materials; phthaloperinone-based organic materials; conductive polymers based on polythiophene such as anthraquinone and polyaniline; and the like, but are not limited thereto.

[0461] In one exemplary embodiment of the present specification, the hole injection layer can include a compound represented by Chemical Formula HI-1, but is not limited thereto.

[0462] [Chemical Formula HI-1]

[0463]

[0464] In Chemical Formula HI-1,

[0465] R315 to R317 are the same as or different from each other, and each is independently selected from any one of hydrogen; deuterium; a substituted or unsubstituted alkyl; a substituted or unsubstituted aryl; a substituted or unsubstituted heteroaryl; and a combination thereof, or are bonded to an adjacent group to form a substituted or unsubstituted ring,

[0466] 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

[0467] 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.

[0468] In one exemplary embodiment of the present specification, R317 is selected from any one of a substituted or unsubstituted aryl; a substituted or unsubstituted heteroaryl; and a combination thereof.

[0469] In one exemplary embodiment of the present specification, R317 is selected from any one of a carbazolyl group; a phenyl group; a biphenyl group; a triphenylene group; and a combination thereof.

[0470] ​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 aryl group, or bond with an adjacent group to form an alkyl-substituted aromatic hydrocarbon ring.

[0471] 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 phenyl group or a biphenyl group, or bonded with an adjacent group to form an indene substituted with a methyl group.

[0472] In an exemplary embodiment of the present specification, Chemical Formula HI-1 may be represented by any one of the following compounds.

[0473]

[0474] In an exemplary embodiment of the present specification, the hole injection layer may include a compound represented by the following Chemical Formula HI-2, but is not limited thereto.

[0475] [Chemical formula HI-2]

[0476]

[0477] In the chemical formula HI-2,

[0478] R401 to R403 are the same as or different from each other and are each independently a halogen group, and

[0479] r401 to r403 are 4.

[0480] In an exemplary embodiment of the present specification, R401 to R403 are F.

[0481] In an exemplary embodiment of the present specification, Chemical Formula HI-2 may be represented by the following compounds.

[0482]

[0483] In an exemplary embodiment of the present specification, the hole injection layer may include a compound represented by Chemical Formula HI-1 and a compound represented by Chemical Formula HI-2.

[0484] In an exemplary embodiment of the present specification, the hole injection layer may include the compound represented by Chemical Formula HI-1 and the compound represented by Chemical Formula HI-2 at a weight ratio of 1:99 to 99:1, specifically, at a weight ratio of 5:95 to 95:5.

[0485] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is preferably a material having a high hole mobility that can receive holes from the positive electrode or the hole injection layer and transport the holes to the light emitting layer. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers having both conjugated and non-conjugated portions, etc., but are not limited thereto.

[0486] In one exemplary embodiment of the present specification, the hole transport layer can include a compound represented by Chemical Formula HI-1, but is not limited thereto.

[0487] In one exemplary embodiment of the present specification, the hole injection and transport layer is a layer that transports holes to the light emitting layer. The materials exemplified for the hole transport layer and the hole injection layer can be used, but the materials are not limited thereto.

[0488] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transport material is preferably a material having a high electron mobility that can well receive electrons from the negative electrode and transport the electrons to the light emitting layer. Specific examples thereof include an Al complex of 8-hydroxyquinoline; a complex including Alq3; an organic radical compound; a hydroxyflavone-metal complex; etc., but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in the art. In particular, a suitable cathode material is a typical material having a low work function, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum layer or a silver layer.

[0489] The electron injection layer is a layer that receives electrons from the electrode. The electron injection material is preferably excellent in the ability to transport electrons, and has an effect of receiving electrons from the negative electrode and an excellent electron injection effect on the light emitting layer or the light emitting material. In addition, the electron injection material is preferably a material that prevents excitons generated from the light emitting layer from moving to the hole injection layer and is excellent in the ability to form a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenylquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, tetracarboxylic acid, fluorenylmethane, anthrone, etc., and derivatives thereof; a metal complex compound; a nitrogen-containing 5-membered ring derivative; etc., but are not limited thereto.

[0490] Examples of the metal complex compound include lithium 8-hydroxyquinolate, zinc bis(8-hydroxyquinolate), copper bis(8-hydroxyquinolate), manganese bis(8-hydroxyquinolate), aluminum tris(8-hydroxyquinolate), aluminum tris(2-methyl-8-hydroxyquinolate), gallium tris(8-hydroxyquinolate), beryllium bis(10-hydroxybenzo[h]quinolate), zinc bis(10-hydroxybenzo[h]quinolate), chlorogallium bis(2-methyl-8-quinolate), gallium bis(2-methyl-8-quinolate)(o-cresol), aluminum bis(2-methyl-8-quinolate)(1-naphthol), gallium bis(2-methyl-8-quinolate)(2-naphthol), and the like, but are not limited thereto.

[0491] In one exemplary embodiment of the present specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. The materials exemplified for the electron transport layer and the electron injection layer can be used, but the materials are not limited thereto.

[0492] In one exemplary embodiment of the present specification, the electron injection and transport layer can include a compound represented by Chemical Formula ET-1, but is not limited thereto.

[0493] [Chemical Formula ET-1]

[0494]

[0495] In Chemical Formula ET-1,

[0496] at least one of Z11 to Z13 is N, and the rest are CH,

[0497] at least one of Z21 to Z23 is N, and the rest are CH,

[0498] L601 and L602 are the same as or different from each other, and each is independently a direct bond; a substituted or unsubstituted arylene; or a substituted or unsubstituted heteroarylene, and

[0499] Ar601 to Ar604 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl; or a substituted or unsubstituted heteroaryl.

[0500] In one exemplary embodiment of the present specification, Z11 to Z13 are all N.

[0501] In one exemplary embodiment of the present specification, Z21 to Z23 are all N.

[0502] In an exemplary embodiment of the present specification, L601and L602are the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic arylene having 6 to 20 carbon atoms. In an exemplary embodiment of the present specification, L601and L602are the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic arylene having 6 to 12 carbon atoms.

[0503] In an exemplary embodiment of the present specification, L601and L602are a substituted or unsubstituted phenylene.

[0504] In an exemplary embodiment of the present specification, L601and L602are a substituted or unsubstituted phenylene.

[0505] In an exemplary embodiment of the present specification, Ar601to Ar604are the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 20 carbon atoms.

[0506] In an exemplary embodiment of the present specification, Ar601to Ar604are the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 12 carbon atoms.

[0507] In an exemplary embodiment of the present specification, Ar601to Ar604are a substituted or unsubstituted phenyl.

[0508] In an exemplary embodiment of the present specification, Ar601to Ar604are a substituted or unsubstituted phenyl.

[0509] In an exemplary embodiment of the present specification, Chemical Formula ET-1 can be represented by the following compounds.

[0510]

[0511] In an exemplary embodiment of the present specification, the electron injection and transport layer can further include a metal complex compound. The metal complex compound is as described above.

[0512] The electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer into the hole injection layer. As a material having a high triplet energy, any known material can be used without limitation, and the materials exemplified in the description of the hole injection layer can be used, but the material is not limited thereto. The electron blocking layer can be formed between the light-emitting layer and the hole transport layer, between the light-emitting layer and the hole injection layer, or between the light-emitting layer and the layer that simultaneously injects and transports holes.

[0513] In one exemplary embodiment of the present specification, the electron-blocking layer can include a compound represented by Chemical Formula EB-1, but is not limited thereto.

[0514] [Chemical Formula EB-1]

[0515]

[0516] In Chemical Formula EB-1,

[0517] T1 to T14 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0518] L14 is a direct bond; or a substituted or unsubstituted arylene group, and

[0519] t13 is an integer of 1 to 3, and when t13 is 2 or more, two or more t13 are the same as or different from each other.

[0520] In one exemplary embodiment of the present specification, T1 to T14 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0521] In one exemplary embodiment of the present specification, T1 to T14 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0522] In one exemplary embodiment of the present specification, T1 to T14 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted triphenylsilyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0523] In one exemplary embodiment of the present specification, T1 to T14 are the same as or different from each other, and each is independently hydrogen; deuterium; a triphenylsilyl group; a phenyl group; or a biphenyl group.

[0524] In one exemplary embodiment of the present specification, T1 to T13 are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0525] In one exemplary embodiment of the present specification, T14 is an arylsilyl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0526] In one exemplary embodiment of the present specification, T14 is triphenylsilyl; phenyl; biphenyl; or naphthyl.

[0527] In one exemplary embodiment of the present specification, T14 is triphenylsilyl; or phenyl.

[0528] In one exemplary embodiment of the present specification, L14 is a direct bond; or substituted or unsubstituted arylene having 6 to 20 carbon atoms.

[0529] In one exemplary embodiment of the present specification, L14 is a direct bond; or substituted or unsubstituted arylene having 6 to 12 carbon atoms.

[0530] In one exemplary embodiment of the present specification, L14 is a direct bond; or substituted or unsubstituted phenylene; or substituted or unsubstituted naphthylene.

[0531] In one exemplary embodiment of the present specification, L14 is a direct bond; or phenylene.

[0532] In one exemplary embodiment of the present specification, Chemical Formula EB-1 can be represented by the following compound.

[0533]

[0534] A hole blocking layer can be provided between the electron transport layer and the light-emitting layer, and the hole blocking layer is a layer that blocks holes from reaching the cathode, and can be formed under the same conditions as the electron injection layer, for example.

[0535] In one exemplary embodiment of the present specification, the hole blocking layer can include a compound represented by Chemical Formula HB-1 or a compound represented by Chemical Formula 1, but is not limited thereto.

[0536] [Chemical Formula HB-1]

[0537]

[0538] In Chemical Formula HB-1,

[0539] Ar101, Ar102, and Ar103 are the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted silyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0540] In one exemplary embodiment of the present specification, Ar101, Ar102, and Ar103 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0541] In one exemplary embodiment of the present specification, Ar101, Ar102, and Ar103 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0542] In one exemplary embodiment of the present specification, Ar101, Ar102, and Ar103 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted triphenylsilyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted carbazolyl group.

[0543] In one exemplary embodiment of the present specification, Ar101, Ar102, and Ar103 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted triphenylsilyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted carbazolyl group.

[0544] In one exemplary embodiment of the present specification, Chemical Formula HB-1 can be represented by the following compound.

[0545]

[0546] When the organic light emitting device according to one exemplary embodiment of the present specification includes another hole blocking layer in addition to the hole blocking layer including the compound represented by Chemical Formula HB-1 or the compound represented by Chemical Formula 1, specifically, a compound selected from the group consisting of a benzimidazole derivative, a benzotriazole derivative, a phenanthroline derivative, an aluminum complex, and the like is used, but the compound is not limited thereto.

[0547] The organic light emitting device according to the present specification can be a top emission type, a bottom emission type, or a dual emission type, depending on the materials used.

[0548] The organic light emitting device according to the present specification can be included in various electronic devices and used. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, and the like, and is not limited thereto.

[0549] Inventive Embodiments

[0550] ​Hereinafter, the present specification will be described in detail with reference to embodiments, comparative examples, and the like for specifically describing the present specification. However, the embodiments and comparative examples according to the present specification can be modified in various forms, and should not be interpreted as limiting the scope of the present specification to the embodiments and comparative examples described below. The embodiments and comparative examples of the present specification are provided to more completely explain the present specification to those having ordinary skill in the art.

[0551] <Preparation Example>

[0552] Preparation Example of Compound 1 (F-1)

[0553]

[0554] Synthesis of I-1

[0555] After putting 40 g of 1,3-dibromo-5-chlorobenzene, 49.5 g of 3-(9H-carbazol-9-yl)-N-phenyl aniline, 0.75 g of [bis(tri-tert-butylphosphine)palladium(0)], 28.4 g of sodium tert-butoxide, and 800 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, then treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 58 g of I-1. (Yield 75%, mass [M+] = 524)

[0556] Synthesis of I-2

[0557] After putting 25 g of I-1, 7.0 g of (2-(phenylamino)phenyl)boronic acid, 13.2 g of K2CO3, 0.24 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, then 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 18 g of I-2. (Yield 62%, mass [M+] = 613)

[0558] Synthesis of I-3

[0559] After putting 15 g of I-2, 20 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 8.2 g of I-3. (Yield 54%, mass [M+] = 621)

[0560] Synthesis of F-1

[0561] After putting 8 g of I-3, 4.9 g of (3-(triphenylsilyl)phenyl)boronic acid, 3.6 g of K2CO3, 0.07 g of [bis(tri-tert-butylphosphine)palladium(0)], 160 mL of tetrahydrofuran, and 80 mL of water in a flask, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, all solvents were removed, and then 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 7.2 g of F-1.(Yield 61%, mass [M+] = 921)

[0562] Preparation Example of Compound 2 (F-2)

[0563]

[0564] Synthesis of I-4

[0565] After putting 40 g of 1,3-dibromo-5-chlorobenzene, 24.7 g of 9H-carbazole, 0.75 g of [bis(tri-tert-butylphosphine)palladium(0)], 28.4 g of sodium tert-butoxide, and 800 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 38 g of I-4.(Yield 72%, mass [M+] = 357)

[0566] Synthesis of I-5

[0567] After putting 25 g of I-4, 11.9 g of diphenylamine, 0.35 g of [bis(tri-tert-butylphosphine)palladium(0)], 16.9 g of sodium tert-butoxide, and 800 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 22 g of I-5.(Yield 71%, mass [M+] = 445)

[0568] Synthesis of I-6

[0569] After placing 20 g of I-5, 21.2 g of (2-(phenylamino)-5- (triphenylsilyl)phenyl)boronic acid, 12.4 g of K2CO3, 0.23 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-6. (Yield 61%, mass [M+] = 837)

[0570] Synthesis of F-2

[0571] After placing 14 g of I-6, 11.2 g of boron triiodide, and 280 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.6 g of F-2. (Yield 47%, mass [M+] = 845)

[0572] Preparation Example of Compound 3 (F-3)

[0573]

[0574] Synthesis of I-7

[0575] After placing 40 g of 1,3-dibromobenzene, 34.5 g of 4-chloro-N- phenylaniline, 0.86 g of [bis(triphenylphosphine)palladium(0)], 32.6 g of sodium tert-butoxide, and 800 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 43 g of I-7. (Yield 71%, mass [M+] = 359)

[0576] Synthesis of I-8

[0577] After placing 20 g of I-7, 21.1 g of (5-(9H-carbazol-9-yl)-2- hydroxyphenyl)boronic acid, 19.3 g of K2CO3, 0.35 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-8. (Yield 69%, mass [M+] = 538)

[0578] Synthesis of I-9

[0579] After placing 15 g of I-8, 18.6 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.7 g of I-9. (Yield 44%, mass [M+] = 546)

[0580] Synthesis of F-3

[0581] After placing 6 g of I-9, 3.4 g of (3-(triphenylsilyl)phenyl)boronic acid, 3.1 g of K2CO3, 0.06 g of [bis(triphenylphosphine)palladium(0)], 120 mL of tetrahydrofuran, and 60 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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 6 g of F-3. (Yield 64%, mass [M+] = 846)

[0582] Preparation Example of Compound 4 (F-4)

[0583]

[0584] Synthesis of I-10

[0585] After placing 15 g of I-5, 15.9 g of (4-hydroxy-3'-(triphenylsilyl)-[1,1'-biphenyl]-3-yl)boronic acid, 9.3 g of K2CO3, 0.17 g of [bis(tri-tert-butylphosphine)palladium(0)], 300 mL of tetrahydrofuran, and 150 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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 19 g of I-10. (Yield 67%, mass [M+] = 838)

[0586] Synthesis of F-4

[0587] After placing 15 g of I-10, 11.9 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.1 g of F-4. (Yield 40%, mass [M+] = 846)

[0588] Preparation Example of Compound 5 (F-5)

[0589]

[0590] Synthesis of I-11

[0591] After placing 40 g of 1,3-dibromobenzene, 69.6 g of 2'-(9H-carbazol-9-yl)-N-phenyl-[1,1'-biphenyl]-3-amine, 0.87 g of [bis(tri-tert-butylphosphine)palladium(0)], 32.6 g of sodium tert-butoxide, and 800 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 66 g of I-11. (Yield 69%, mass [M+] = 566)

[0592] Synthesis of I-12

[0593] After placing 20 g of I-11, 17.3 g of (4-mercapto-3'-(triphenylsilyl)-[1,1'-biphenyl]-3-yl)boronic acid, 9.8 g of K2CO3, 0.18 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-12. (Yield 76%, mass [M+] = 930)

[0594] Synthesis of F-5

[0595] After placing 15 g of I-11, 10.7 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 5.6 g of F-5. (Yield 37%, mass [M+] = 938)

[0596] Preparation Example of Compound 6 (F-6)

[0597]

[0598] Synthesis of I-13

[0599] After placing 30 g of I-4, 9.3 g of phenyl mercaptan, 0.43 g of [bis(tri-tert-butylphosphine)palladium(0)], 16.2 g of sodium tert-butoxide, and 800 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 24 g of I-13. (Yield 74%, mass [M+] = 387)

[0600] Synthesis of I-14

[0601] After placing 20 g of I-13, 28.4 g of (3-(phenylamino)-3'-(triphenylsilyl)-[1,1'-biphenyl]-4-yl)boronic acid, 14.3 g of K2CO3, 0.26 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-14. (Yield 63%, mass [M+] = 854)

[0602] Synthesis of F-6

[0603] After placing 15 g of I-14, 11.7 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 5.8 g of F-6. (Yield 38%, mass [M+] = 862)

[0604] Preparation Example of Compound 7 (F-7)

[0605]

[0606] Synthesis of I-15

[0607] After placing 30 g of 1,3-dibromo-5-chlorobenzene, 40.9 g of 3-(triphenylsilyl)benzenethiol, 0.57 g of [bis(tri-tert-butylphosphine)palladium(0)], 21.3 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 43 g of I-15. (Yield 69%, mass [M+] = 559)

[0608] Synthesis of I-16

[0609] After placing 20 g of I-15, 10.3 g of (2-(9H-carbazol-9-yl)phenyl)boronic acid, 9.9 g of K2CO3, 0.18 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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 17 g of I-16. (Yield 66%, mass [M+] = 721)

[0610] Synthesis of I-17

[0611] After placing 15 g of I-16, 2.9 g of (2-hydroxyphenyl)boronic acid, 5.8 g of K2CO3, 0.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 300 mL of tetrahydrofuran, and 150 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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 12 g of I-17. (Yield 74%, mass [M+] = 779)

[0612] Synthesis of F-7

[0613] After placing 12 g of I-17, 12.8 g of boron triiodide, and 240 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.2 g of F-7. (Yield 41%, mass [M+] = 787)

[0614] Preparation Example of Compound 8 (F-8)

[0615]

[0616] Synthesis of I-18

[0617] After placing 30 g of 1,3-dibromo-5-chlorobenzene, 49.3 g of 3'-(triphenylsilyl)-[1,1'-biphenyl]-3-thiol, 0.57 g of [bis(triphenylphosphine)palladium(0)], 21.3 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 46 g of I-18. (Yield 65%, mass [M+] = 635)

[0618] Synthesis of I-19

[0619] After placing 25 g of I-18, 6.6 g of 9H-carbazole, 0.2 g of [bis(triphenylphosphine)palladium(0)], 9.5 g of sodium tert-butoxide, and 500 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 21 g of I-19. (Yield 74%, mass [M+] = 721)

[0620] Synthesis of I-20

[0621] After placing 20 g of I-19, 8 g of (2-mercaptophenyl)boronic acid, 7.7 g of K2CO3, 0.15 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, then 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 16 g of I-20. (Yield 73%, mass [M+] = 795)

[0622] Synthesis of F-8

[0623] After placing 15 g of I-20, 12.6 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.4 g of F-8. (Yield 42%, mass [M+] = 803)

[0624] Preparation Example of Compound 9 (F-9)

[0625]

[0626] Synthesis of I-21

[0627] After placing 30 g of 3-bromo-5-chloro-1,1'-biphenyl, 37.5 g of 3-(9H-carbazol-9-yl)-N-phenyl aniline, 0.57 g of [bis(tri-tert-butylphosphine)palladium(0)], 21.6 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the reaction solution was separated, then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 45 g of I-21. (Yield 77%, mass [M+] = 522)

[0628] Synthesis of I-22

[0629] After placing 20 g of I-21, 8.2 g of (2-(phenylamino)phenyl)boronic acid, 10.7 g of K2CO3, 0.20 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, all solvents were removed, then 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 17 g of I-22. (Yield 68%, mass [M+] = 655)

[0630] Synthesis of F-9

[0631] After placing 15 g of I-22, 15.3 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.3 g of F-9. (Yield 42%, mass [M+] = 663)

[0632] Preparation Example of Compound 10 (F-10)

[0633]

[0634] Synthesis of I-23

[0635] After placing 20 g of I-21, 5.3 g of (2-hydroxyphenyl)boronic acid, 10.7 g of K2CO3, 0.20 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, all solvents were removed, and then 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 18 g of I-23. (Yield 81%, mass [M+] = 580)

[0636] Synthesis of F-10

[0637] After placing 15 g of I-23, 17.3 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.1 g of F-10. (Yield 40%, mass [M+] = 588)

[0638] Preparation Example of Compound 11 (F-11)

[0639]

[0640] Synthesis of I-24

[0641] After placing 30 g of 5-chloro-[1,1'-biphenyl]-3-thiol, 44 g of 9-(4-bromophenyl)-9H-carbazole, 0.7 g of [bis(tri-tert-butylphosphine)palladium(0)], 26.2 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 44 g of I-24. (Yield 70%, mass [M+] = 463)

[0642] Synthesis of I-25

[0643] After placing 20 g of I-24, 9.2 g of (2-(phenylamino)phenyl)boronic acid, 12 g of K2CO3, 0.22 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, all solvents were removed, and then 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 18 g of I-25. (Yield 70%, mass [M+] = 596)

[0644] Synthesis of F-11

[0645] After placing 15 g of I-25, 17 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.2 g of F-11. (Yield 40%, mass [M+] = 604)

[0646] Preparation Example of Compound 12 (F-12)

[0647]

[0648] Synthesis of I-26

[0649] After placing 30 g of 5-chloro-[1,1'-biphenyl]-3-thiol, 44 g of 9-(3-bromophenyl)-9H-carbazole, 0.7 g of [bis(tri-tert-butylphosphine)palladium(0)], 26.2 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 43 g of I-26. (Yield 68%, mass [M+] = 463)

[0650] Synthesis of I-27

[0651] After placing 20 g of I-26, 6.7 g of (2-mercapto phenyl)boronic acid, 12 g of K2CO3, 0.22 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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 16 g of I-27. (Yield 69%, mass [M+] = 537)

[0652] Synthesis of F-12

[0653] After placing 15 g of I-26, 18.6 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.2 g of F-12. (Yield 41%, mass [M+] = 545)

[0654] Preparation Example of Compound 13 (F-13)

[0655]

[0656] Synthesis of I-28

[0657] After placing 30 g of 5-chloro-[1,1'-biphenyl]-3-thiol, 44 g of 9-(4-bromophenyl)-9H-carbazole, 0.7 g of [bis(tri-tert-butylphosphine)palladium(0)], 26.2 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 45 g of I-28. (Yield 72%, mass [M+] = 463)

[0658] Synthesis of I-29

[0659] After placing 20 g of I-28, 9.3 g of (4-hydroxy-[l,l'-biphenyl]-3-yl)boronic acid, 12 g of K2CO3, 0.22 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, all solvents were removed, and then 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 16 g of I-29. (Yield 62%, mass [M+] = 597)

[0660] Synthesis of F-13

[0661] After placing 15 g of I-29, 16.7 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.4 g of F-13. (Yield 42%, mass [M+] = 605)

[0662] Preparation Example of Compound 14 (F-14)

[0663]

[0664] Synthesis of I-30

[0665] After placing 30 g of 9-(3-bromo-5-chlorophenyl)-9H-carbazole, 20.6 g of N-phenyl-[l,l'-biphenyl]-3-amine, 0.43 g of [bis(tri-tert-butylphosphine)palladium(0)], 16.2 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 34 g of I-30. (Yield 78%, mass [M+] = 522)

[0666] Synthesis of I-31

[0667] After putting 20 g of I-30, 8.2 g of (2-(phenylamino)phenyl)boronic acid, 11 g of K2CO3, 0.2 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water into a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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 17 g of I-31. (Yield 68%, mass [M+] = 655)

[0668] Synthesis of F-14

[0669] After putting 15 g of I-31, 15.3 g of boron triiodide, and 300 mL of dichlorobenzene into a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.1 g of F-14. (Yield 40%, mass [M+] = 663)

[0670] Preparation Example of Compound 15 (F-15)

[0671]

[0672] Synthesis of I-32

[0673] After putting 20 g of I-30, 5.3 g of (2-hydroxyphenyl)boronic acid, 11 g of K2CO3, 0.2 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water into a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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 16 g of I-32. (Yield 72%, mass [M+] = 580)

[0674] Synthesis of F-15

[0675] After putting 15 g of I-32, 17.3 g of boron triiodide, and 300 mL of dichlorobenzene into a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.5 g of F-15. (Yield 43%, mass [M+] = 588)

[0676] Preparation Example of Compound 16 (F-16)

[0677]

[0678] Synthesis of I-33

[0679] After putting 30 g of 1-bromo-3-chlorobenzene, 38.5 g of N-phenyl-[1,1'-biphenyl]-3- amine, 0.8 g of [bis(tri-tert-butylphosphine)palladium(0)], 30.1 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 43 g of I-33. (Yield 77%, mass [M+] = 357)

[0680] Synthesis of I-34

[0681] After putting 20 g of I-33, 21.3 g of (4-(9H-carbazol-9-yl)-2-(phenylamino)phenyl)boronic acid, 15.5 g of K2CO3, 0.3 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, then 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 27 g of I-34. (Yield 73%, mass [M+] = 655)

[0682] Synthesis of F-16

[0683] After putting 15 g of I-34, 15.3 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.4 g of F-16. (Yield 42%, mass [M+] = 663)

[0684] Preparation Example of Compound 17 (F-17)

[0685]

[0686] Synthesis of I-35

[0687] After placing 20 g of I-33, 17 g of (5-(9H-carbazol-9-yl)-2- hydroxyphenyl)boronic acid, 15.5 g of K2CO3, 0.29 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-35. (Yield 71%, mass [M+] = 580)

[0688] Synthesis of F-17

[0689] After placing 15 g of I-35, 17.3 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.2 g of F-17. (Yield 41%, mass [M+] = 588)

[0690] Preparation Example of Compound 18 (F-18)

[0691]

[0692] Synthesis of I-36

[0693] After placing 20 g of I-33, 18 g of (4-(9H-carbazol-9-yl)-2-mercapto- phenyl)boronic acid, 15.5 g of K2CO3, 0.29 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-36. (Yield 69%, mass [M+] = 596)

[0694] Synthesis of F-18

[0695] After placing 15 g of I-36, 16.8 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.4 g of F-18. (Yield 41%, mass [M+] = 604)

[0696] Preparation Example of Compound 19 (F-19)

[0697]

[0698] Synthesis of I-37

[0699] After putting 20 g of 9-(3-bromo-5-chlorophenyl)-9H-carbazole, 9.5 g of diphenylamine, 0.29 g of [bis(tri-tert-butylphosphine)palladium(0)], 10.8 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 20 g of I-37. (Yield 80%, mass [M+] = 446)

[0700] Synthesis of I-38

[0701] After putting 20 g of I-37, 17 g of (4-(dibenzo[b,d]furan-1-yl)-2-(phenylamino)phenyl)boronic acid, 12.4 g of K2CO3, 0.23 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, then 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-38. (Yield 72%, mass [M+] = 745)

[0702] Synthesis of F-19

[0703] After putting 15 g of I-38, 13.4 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.3 g of F-19. (Yield 42%, mass [M+] = 753)

[0704] Preparation Example of Compound 20 (F-20)

[0705]

[0706] Synthesis of I-39

[0707] After placing 20 g of I-37, 17.8 g of (4-(dibenzo[b,d]thiophen-l-yl)-2- (phenylamino)phenyl)boronic acid, 12.4 g of K2CO3, 0.23 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-39. (Yield 76%, mass [M+] = 761)

[0708] Synthesis of F-20

[0709] After placing 15 g of I-39, 13.2 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.6 g of F-20. (Yield 44%, mass [M+] = 769)

[0710] Preparation Example of Compound 21 (F-21)

[0711]

[0712] Synthesis of I-40

[0713] After placing 40 g of 1,3-dibromo-5-chlorobenzene, 49.5 g of 3-(9H-carbazol-9-yl)-N- phenylaniline, 0.75 g of [bis(triphenylphosphine)palladium(0)], 28.4 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 56 g of I-40. (Yield 72%, mass [M+] = 525)

[0714] Synthesis of I-41

[0715] After placing 30 g of I-40, 12.2 g of dibenzo[b,d]furan-1-yl boronic acid, 15.8 g of K2CO3, 0.3 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-41. (Yield 74%, mass [M+] = 612)

[0716] Synthesis of I-42

[0717] After placing 25 g of I-41, 5.6 g of (2-hydroxyphenyl)boronic acid, 11.3 g of K2CO3, 0.2 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-42. (Yield 77%, mass [M+] = 670)

[0718] Synthesis of F-21

[0719] After placing 15 g of I-42, 14.9 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.5 g of F-21. (Yield 43%, mass [M+] = 678)

[0720] Preparation Example of Compound 22 (F-22)

[0721]

[0722] Synthesis of I-43

[0723] After placing 40 g of 1,3-dibromo-5-chlorobenzene, 49.5 g of 4-(9H-carbazol-9-yl)-N- phenylaniline, 0.75 g of [bis(triphenylphosphine)palladium(0)], 28.4 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 55 g of I-43. (Yield 71%, mass [M+] = 525)

[0724] Synthesis of I-44

[0725] After placing 30 g of I-43, 12.2 g of dibenzo[b,d]furan-4-yl boronic acid, 15.8 g of K2CO3, 0.3 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, then 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-44. (Yield 80%, mass [M+] = 612)

[0726] Synthesis of I-45

[0727] After placing 25 g of I-44, 6.3 g of (2-mercaptophenyl)boronic acid, 11.3 g of K2CO3, 0.2 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, then 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-45. (Yield 79%, mass [M+] = 686)

[0728] Synthesis of F-22

[0729] After placing 15 g of I-45, 14.6 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.2 g of F-22. (Yield 41%, mass [M+] = 694)

[0730] Preparation Example of Compound 23 (F-23)

[0731]

[0732] Synthesis of I-46

[0733] After placing 40 g of 1-bromo-3-chlorobenzene, 85.8 g of 2'-(9H-carbazol-9-yl)-N- phenyl-[1,1'-biphenyl]-4-amine, 1.06 g of [bis(triphenylphosphine)palladium(0)], 40.2 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 58 g of I-46. (Yield 53%, mass [M+] = 522)

[0734] Synthesis of I-47

[0735] After placing 30 g of I-46, 17.5 g of (4-(dibenzo[b,d]furan-1-yl)-2-hydroxyphenyl)boronic acid, 15.9 g of K2CO3, 0.3 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, then 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-47. (Yield 75%, mass [M+] = 746)

[0736] Synthesis of F-23

[0737] After placing 15 g of I-47, 13.4 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, then treated with MgSO4(anhydrous) and filtered. The filtered solution was removed and recrystallized to obtain 6.0 g of F-23. (Yield 40%, mass [M+] = 754)

[0738] Preparation Example of Compound 24 (F-24)

[0739]

[0740] Synthesis of I-48

[0741] After placing 40 g of 1,3-dibromo-5-chlorobenzene, 40.7 g of 3-(9H-carbazol-9-yl)benzenethiol, 0.75 g of [bis(triphenylphosphine)palladium(0)], 28.4 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 49 g of I-48. (Yield 71%, mass [M+] = 466)

[0742] Synthesis of I-49

[0743] After placing 30 g of I-48, 13.7 g of dibenzo[b,d]furan-1-ylboronic acid, 17.8 g of K2CO3, 0.33 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, then 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 27 g of I-49. (Yield 76%, mass [M+] = 553)

[0744] Synthesis of I-50

[0745] After placing 25 g of I-49, 6.3 g of (2-hydroxyphenyl)boronic acid, 12.5 g of K2CO3, 0.2 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, then 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-50. (Yield 76%, mass [M+] = 611)

[0746] Synthesis of F-24

[0747] After placing 15 g of I-50, 16.4 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.6 g of F-24. (Yield 43%, mass [M+] = 619)

[0748] Preparation Example of Compound 25 (F-25)

[0749]

[0750] Synthesis of I-51

[0751] After placing 25 g of I-49, 9.7 g of (2-(phenylamino)phenyl)boronic acid, 12.5 g of K2CO3, 0.2 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, all solvents were removed, and then 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-51. (Yield 74%, mass [M+] = 686)

[0752] Synthesis of F-25

[0753] After placing 15 g of I-51, 14.6 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.5 g of F-25. (Yield 43%, mass [M+] = 694)

[0754] Preparation Example of Compound 26 (F-26)

[0755]

[0756] Synthesis of I-52

[0757] After placing 40 g of 9-(3-bromo-5-chlorophenyl)-9H-carbazole, 30.9 g of 3-(9H-carbazol-9-yl)-N-phenylaniline, 0.58 g of [bis(tri-tert-butylphosphine)palladium(0)], 21.6 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 48 g of I-52. (Yield 70%, mass [M+] = 611)

[0758] Synthesis of I-53

[0759] After placing 30 g of I-52, 10.5 g of (2-(phenylamino)phenyl)boronic acid, 13.6 g of K2CO3, 0.33 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-53. (Yield 77%, mass [M+] = 744)

[0760] Synthesis of F-26

[0761] After placing 15 g of I-53, 13.4 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, followed by treatment with MgSO4(anhydrous) and filtration. The filtered solution was then recrystallized to obtain 6.6 g of F-26. (Yield 44%, mass [M+] = 752)

[0762] Preparation Example of Compound 27 (F-27)

[0763]

[0764] Synthesis of I-54

[0765] After placing 40 g of 9-(3-bromo-5-chlorophenyl)-9H-carbazole, 19 g of diphenylamine, 0.6 g of [bis(triphenylphosphine)palladium(0)], 21.6 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, followed by treatment with MgSO4(anhydrous) and filtration. The filtered solution was recrystallized to obtain 37 g of I-54. (Yield 74%, mass [M+] = 446)

[0766] Synthesis of I-55

[0767] After placing 30 g of I-54, 25.5 g of (4-(9H-carbazol-9-yl)-2-(phenylamino)phenyl)boronic acid, 18.6 g of K2CO3, 0.33 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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 35 g of I-55. (Yield 70%, mass [M+] = 744)

[0768] Synthesis of F-27

[0769] After placing 15 g of I-55, 13.4 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.2 g of F-27. (Yield 41%, mass [M+] = 752)

[0770] Preparation Example of Compound 28 (F-28)

[0771]

[0772] Synthesis of I-56

[0773] After placing 40 g of 1-bromo-3-chlorobenzene, 70 g of 3-(9H-carbazol-9-yl)-N- phenyl aniline, 1.1 g of [bis(triphenylphosphine)palladium(0)], 50.2 g of sodium tert- butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 66 g of I-56. (Yield 71%, mass [M+] = 446)

[0774] Synthesis of I-57

[0775] After placing 30 g of I-56, 25.5 g of (5-(9H-carbazol-9-yl)-2-(phenylamino)phenyl)boronic acid, 18.6 g of K2CO3, 0.33 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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 36 g of I-57. (Yield 72%, mass [M+] = 744)

[0776] Synthesis of F-28

[0777] After placing 15 g of I-57, 13.4 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.7 g of F-28. (Yield 43%, mass [M+] = 752)

[0778] Preparation Example of Compound 29 (F-29)

[0779]

[0780] Synthesis of I-58

[0781] After placing 40 g of 9-(3-bromo-5-chlorophenyl)-9H-carbazole, 37.5 g of 3-(9H-carbazol-9-yl)-N-phenylaniline, 0.6 g of [bis(triphenylphosphine)palladium(0)], 22 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 49 g of I-58. (Yield 72%, mass [M+] = 611)

[0782] Synthesis of I-59

[0783] After putting 30 g of I-58, 6.8 g of (2-hydroxyphenyl)boronic acid, 13.6 g of K2CO3, 0.25 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water into a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-59. (Yield 76%, mass [M+] = 669)

[0784] Synthesis of F-29

[0785] After putting 15 g of I-59, 15 g of boron triiodide, and 300 mL of dichlorobenzene into a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.6 g of F-29. (Yield 43%, mass [M+] = 677)

[0786] Preparation Example of Compound 30 (F-30)

[0787]

[0788] Synthesis of I-60

[0789] After putting 40 g of 9-(3-bromo-5-chlorophenyl)-9H-carbazole, 19 g of diphenylamine, 0.6 g of [bis(tri-tert-butylphosphine)palladium(0)], 22 g of sodium tert-butoxide, and 600 mL of toluene into a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 38 g of I-60. (Yield 76%, mass [M+] = 446)

[0790] Synthesis of I-61

[0791] After putting 30 g of I-60, 21.5 g of (4-(9H-carbazol-9-yl)-2-mercaptophenyl)boronic acid, 18.6 g of K2CO3, 0.35 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-61. (Yield 72%, mass [M+] = 685)

[0792] Synthesis of F-30

[0793] After putting 15 g of I-61, 15 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.8 g of F-30. (Yield 45%, mass [M+] = 693)

[0794] Preparation Example of Compound 31 (F-31)

[0795]

[0796] Synthesis of I-62

[0797] After putting 40 g of 1-bromo-3-chlorobenzene, 57.5 g of 3-(9H-carbazol-9-yl)benzenethiol, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 40 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 58 g of I-62. (Yield 72%, mass [M+] = 387)

[0798] Synthesis of I-63

[0799] After putting 30 g of I-62, 24.8 g of (5-(9H-carbazol-9-yl)-2-mercaptophenyl)boronic acid, 21.5 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water into a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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 34 g of I-63. (Yield 70%, mass [M+] = 626)

[0800] Synthesis of F-31

[0801] After putting 15 g of I-63, 16 g of boron triiodide, and 300 mL of dichlorobenzene into a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.5 g of F-31. (Yield 43%, mass [M+] = 634)

[0802] Preparation Example of Compound 32 (F-32)

[0803]

[0804] Synthesis of I-64

[0805] After putting 40 g of 1,3-dibromo-5-chlorobenzene, 49.5 g of 3-(9H-carbazol-9-yl)-N-phenyl aniline, 0.8 g of [bis(tri-tert-butylphosphine)palladium(0)], 28 g of sodium tert-butoxide, and 600 mL of toluene into a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 57 g of I-64. (Yield 72%, mass [M+] = 534)

[0806] Synthesis of I-65

[0807] After placing 30 g of I-64, 17 g of 2-triphenyldibenzofuran boronic acid, 15.6 g of K2CO3, 0.3 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-65. (Yield 71%, mass [M+] = 702)

[0808] Synthesis of I-66

[0809] After placing 25 g of I-65, 7.6 g of (2-(phenylamino)phenyl)boronic acid, 9.9 g of K2CO3, 0.2 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-66. (Yield 74%, mass [M+] = 835)

[0810] Synthesis of F-32

[0811] After placing 15 g of I-66, 12 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.6 g of F-32. (Yield 44%, mass [M+] = 843)

[0812] Preparation Example of Compound 33 (F-33)

[0813]

[0814] Synthesis of I-67

[0815] After placing 30 g of I-64, 17 g of 1-triphenyldibenzofuran boronic acid, 15.6 g of K2CO3, 0.3 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-67. (Yield 73%, mass [M+] = 702)

[0816] Synthesis of I-68

[0817] After placing 25 g of I-67, 4.92 g of (2-(phenylamino)phenyl)boronic acid, 9.9 g of K2CO3, 0.2 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-68. (Yield 78%, mass [M+] = 760)

[0818] Synthesis of F-33

[0819] After placing 15 g of I-68, 13.2 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.7 g of F-33. (Yield 44%, mass [M+] = 768)

[0820] Preparation Example of Compound 34 (F-34)

[0821]

[0822] Synthesis of I-69

[0823] After putting 25 g of I-60, 21.2 g of (2-hydroxy-5-(indolo[3,2,1-jk]carbazol-2-yl)phenyl)boronic acid, 15.5 g of K2CO3, 0.3 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-69. (Yield 62%, mass [M+] = 743)

[0824] Synthesis of F-34

[0825] After putting 15 g of I-69, 13.5 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.1 g of F-34. (Yield 40%, mass [M+] = 751)

[0826] Preparation Example of Compound 35 (F-35)

[0827]

[0828] Synthesis of I-70

[0829] After putting 30 g of 9-(3-bromo-5-chlorophenyl)-9H-3,9'-bicarbazole, 37.2 g of 3-(9H-carbazol-9-yl)-N-phenylaniline, 0.6 g of [bis(tri-tert-butylphosphine)palladium(0)], 22 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 58 g of I-70. (Yield 67%, mass [M+] = 776)

[0830] Synthesis of I-71

[0831] After placing 30 g of I-70, 5.3 g of (2-hydroxyphenyl)boronic acid, 10.7 g of K2CO3, 0.2 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-71. (Yield 68%, mass [M+] = 834)

[0832] Synthesis of F-35

[0833] After placing 30 g of I-70, 5.3 g of (2-hydroxyphenyl)boronic acid, 10.7 g of K2CO3, 0.2 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-71. (Yield 68%, mass [M+] = 834)

[0834] Preparation Example of Compound 36 (F-36)

[0835]

[0836] Synthesis of I-72

[0837] After placing 30 g of I-70, 5.3 g of (2-hydroxyphenyl)boronic acid, 10.7 g of K2CO3, 0.2 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated and stirred under reflux for 8 hours. After terminating the reaction, all solvents were removed, and then 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-71. (Yield 68%, mass [M+] = 834)

[0838] Synthesis of I-73

[0839] After placing 30 g of I-72, 9.4 g of (2-((phenyl-d5)amino)phenyl-3,4,5,6-d4)boronic acid, 11.7 g of K2CO3, 0.2 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, all solvents were removed, and then 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-73. (Yield 64%, mass [M+] = 847)

[0840] Synthesis of F-36

[0841] After placing 15 g of I-73, 12 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.1 g of F-36. (Yield 40%, mass [M+] = 855)

[0842] Preparation Example of Compound 37 (F-37)

[0843]

[0844] Synthesis of I-74

[0845] After placing 30 g of (3'-bromo-5'-chloro-[1,1'-biphenyl]-3-yl-2,2',4,5,6,6'-d6)tris(phenyl-d5) silane, 9.8 g of N-(phenyl-2,3,4,5-d4)benzene-d5-amine, 0.3 g of [bis(tri-tert-butylphosphine)palladium(0)], 10.5 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 27 g of I-74. (Yield 76%, mass [M+] = 645)

[0846] Synthesis of I-75

[0847] After placing 25 g of I-74, 15.2 g of (3'-(9H-carbazol-9-yl-d8)-4-hydroxy- [1,1'-biphenyl]-3-yl-2',4',5,6-d4)boronic acid, 11 g of K2CO3, 0.2 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated under reflux and stirred for 8 hours. After the reaction was terminated, all the solvent was removed, and then 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-75. (yield 65%, mass [M+] = 956)

[0848] Synthesis of F-37

[0849] After placing 15 g of I-75, 10.5 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After the reaction was terminated, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.6 g of F-37. (yield 44%, mass [M+] = 964)

[0850] Preparation Example of Compound 38 (F-38)

[0851]

[0852] Synthesis of I-76

[0853] After placing 30 g of 3-bromo-5-chloro-1,1'-biphenyl-2,2',3',4',5',6,6'-d7, 31.3 g of 2-(9H-carbazol-9-yl-d8)benzene-3,4,5-d3-thiol, 0.6 g of [bis(tri-tert-butylphosphine)palladium(0)], 21 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After the reaction was terminated, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 33 g of I-76. (yield 63%, mass [M+] = 481)

[0854] Synthesis of I-77

[0855] After placing 25 g of I-76, 11.6 g of ((2-((phenyl-d5)amino)phenyl-3,4,5,6-d4)boronic acid, 14.4 g of K2CO3, 0.3 g of [bis(triphenylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water in a flask, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, all solvents were removed, and then 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-77. (Yield 71%, mass [M+] = 623)

[0856] Synthesis of F-38

[0857] After placing 15 g of I-77, 16 g of boron triiodide, and 300 mL of dichlorobenzene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the solution was separated by adding the resulting product to water, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was then recrystallized to obtain 6.6 g of F-38. (Yield 43%, mass [M+] = 631)

[0858] Preparation Example of Compound 39 (F-39)

[0859]

[0860] Synthesis of I-78

[0861] After placing 30 g of 9-(3-bromo-5-chlorophenyl-2,6-d2)-9H-carbazole-1,2,3,4,5,6,7,8-d8, 44.1 g of N-(phenyl-d5)-2'-(tris(phenyl-d5)silyl)-[1,1'-biphenyl]-2,3',4',5,5',6,6'-d7-3-amine, 0.5 g of [bis(triphenylphosphine)palladium(0)], 16 g of sodium tert-butoxide, and 600 mL of toluene in a flask under a nitrogen atmosphere, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the reaction solution was separated, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was recrystallized to obtain 45 g of I-78. (Yield 67%, mass [M+] = 818)

[0862] Synthesis of I-79

[0863] After 25 g of I-78, 4.3 g of (2-hydroxyphenyl-3,4,5,6-d4)boric acid, 8.5 g of K2CO3, 0.2 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were placed in a flask, the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, all solvents were removed, and the reaction solution was then separated by dissolving the resulting product in toluene, followed by treatment with MgSO4 (anhydrous) and filtration. The filtered solution was recrystallized to obtain 19 g of I-79. (Yield 71%, mass [M+] = 880)

[0864] Synthesis of F-39

[0865] 15 g of I-79, 11.4 g of boron triiodide, and 300 mL of dichlorobenzene were placed in a flask under a nitrogen atmosphere, and the resulting mixture was heated under reflux and stirred for 8 hours. After terminating the reaction, the resulting product was added to water, the solution was separated, then treated with MgSO (anhydrous) and filtered. The filtered solution was removed and recrystallized to obtain 6.1 g of F-39. (Yield 40%, mass [M+] = 888)

[0866] <Examples and Comparative Examples>

[0867] Example 1

[0868] A thin coating with a thickness of The glass substrate of tin oxide (ITO) is put into the distilled water that is wherein dissolved with detergent and carries out ultrasonic cleaning.In this case, use the product manufactured by Fischer Co. as detergent, and use the distilled water that utilizes the filter manufactured by Millipore Co. to filter twice as distilled water.After ITO was washed 30 minutes, by using distilled water to repeat twice ultrasonic cleaning 10 minutes.After using distilled water washing to complete, by using isopropyl alcohol, acetone and methanol solvent to carry out ultrasonic cleaning, and products therefrom is dried, then is transported to plasma washing machine.In addition, by using oxygen plasma, substrate is cleaned 5 minutes, then is transported to vacuum deposition machine.

[0869] On the transparent ITO electrode as the positive electrode thus prepared, the following compound HT1 and the following compound HI1 were thermally vacuum deposited at a ratio (molar ratio) of 95:5 to form a transparent ITO electrode having a A thickness of 1000 nm was formed to form a hole injection layer. A compound represented by the following chemical formula HT1 was vacuum deposited on the hole injection layer. Thereby forming a hole transport layer. Subsequently, compound BH (p-type) is vacuum deposited on the hole transport layer to have thickness of 100 A, thereby forming an electron blocking layer. Subsequently, on the electron blocking layer, a compound represented by the following Chemical Formula BH (p-type) and Compound 1 (n-type) synthesized in Preparation Example 1, which are mixed at a weight ratio of 86:14, were vacuum-deposited as a host for a light-emitting layer, and a compound represented by the following Chemical Formula BD was vacuum-deposited as a dopant for the light-emitting layer, thereby forming the light-emitting layer. On the light-emitting layer, Compound 1 (n-type) synthesized in Preparation Example 1 was vacuum-deposited to a thickness of 100 A, and then aluminum was vacuum-deposited to a thickness of 200 A, thereby forming a cathode. thickness of 100 A, thereby forming an electron blocking layer. Subsequently, on the electron blocking layer, a compound represented by the following Chemical Formula BH (p-type) and Compound 1 (n-type) synthesized in Preparation Example 1, which are mixed at a weight ratio of 86:14, were vacuum-deposited as a host for a light-emitting layer, and a compound represented by the following Chemical Formula BD was vacuum-deposited as a dopant for the light-emitting layer, thereby forming the light-emitting layer. On the light-emitting layer, Compound 1 (n-type) synthesized in Preparation Example 1 was vacuum-deposited to a thickness of 100 A, and then aluminum was vacuum-deposited to a thickness of 200 A, thereby forming a cathode. thickness of 100 A, thereby forming an electron blocking layer. Subsequently, on the electron blocking layer, a compound represented by the following Chemical Formula BH (p-type) and Compound 1 (n-type) synthesized in Preparation Example 1, which are mixed at a weight ratio of 86:14, were vacuum-deposited as a host for a light-emitting layer, and a compound represented by the following Chemical Formula BD was vacuum-deposited as a dopant for the light-emitting layer, thereby forming the light-emitting layer. On the light-emitting layer, Compound 1 (n-type) synthesized in Preparation Example 1 was vacuum-deposited to a thickness of 100 A, and then aluminum was vacuum-deposited to a thickness of 200 A, thereby forming a cathode. thickness of 100 A, thereby forming an electron blocking layer. Subsequently, on the electron blocking layer, a compound represented by the following Chemical Formula BH (p-type) and Compound 1 (n-type) synthesized in Preparation Example 1, which are mixed at a weight ratio of 86:14, were vacuum-deposited as a host for a light-emitting layer, and a compound represented by the following Chemical Formula BD was vacuum-deposited as a dopant for the light-emitting layer, thereby forming the light-emitting layer. On the light-emitting layer, Compound 1 (n-type) synthesized in Preparation Example 1 was vacuum-deposited to a thickness of 100 A, and then aluminum was vacuum-deposited to a thickness of 200 A, thereby forming a cathode. thickness of 100 A, thereby forming an electron blocking layer. Subsequently, on the electron blocking layer, a compound represented by the following Chemical Formula BH (p-type) and Compound 1 (n-type) synthesized in Preparation Example 1, which are mixed at a weight ratio of 86:14, were vacuum-deposited as a host for a light-emitting layer, and a compound represented by the following Chemical Formula BD was vacuum-deposited as a dopant for the light-emitting layer, thereby forming the light-emitting layer. On the light-emitting layer, Compound 1 (n-type) synthesized in Preparation Example 1 was vacuum-deposited to a thickness of 100 A, and then aluminum was vacuum-deposited to a thickness of 200 A, thereby forming a cathode.

[0870]

[0871] In the foregoing steps, the deposition rate of the organic material was maintained at to The deposition rate of lithium fluoride and aluminum of the cathode was maintained at and respectively, and the degree of vacuum during deposition was maintained at 2 x 10 -7 to 5 x 10 -6 torr, thereby manufacturing an organic light-emitting device.

[0872] Examples 2 to 39

[0873] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the following

[0874] compounds described in Table 1 were used instead of Compound 1 as the host for the light-emitting layer in Example 1.

[0875]

[0876]

[0877] Comparative Examples 1 to 6

[0878] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the following

[0879] compounds described in Table 1 were used instead of Compound 1 as the host for the light-emitting layer in Example 1.

[0880]

[0881] When a current was applied to the organic light emitting devices manufactured in Examples 1 to 39 and Comparative Examples 1 to 6, the voltage, efficiency, and lifespan (based on 1600 nits) of each of the organic light emitting devices were measured, and the results thereof are shown in Table 1 below. The lifespan T90 means the time taken for the luminance to decrease to 90% of the initial luminance (1600 nits).

[0882] [Table 1]

[0883]

[0884]

[0885]

[0886] In the case of the compounds BH1 to BH5 used in the organic light emitting devices of Comparative Examples 1 to 5, any one of the benzene rings of the core structure connected to boron has a substituted structure, but since the benzene ring becomes unstable due to the electron-withdrawing property of boron, the lifespan reduction property increases. As can be determined from Table 1 above, as the lifespan reduction property increases, the voltage increases and the efficiency decreases.

[0887] Further, in the case of the organic light emitting device of Comparative Example 6 using the compound BH6 in which any one of the benzene rings of the core structure connected to boron is not substituted, it can be determined that the compound is structurally unstable, and thus exhibits the shortest lifespan property.

[0888] However, in the case of the compound of Chemical Formula 1 according to the present application, at least one of the benzene rings of the core structure directly or indirectly connected to boron can be substituted with a carbazole group, and at least one of the other rings is substituted with an aryl group, a silyl group, or a heterocyclic group to stabilize the unstable structure and serve to increase the hole property, thereby enhancing the lifespan increase property. That is, the structural stability of the compound achieves a reduced voltage and increased efficiency at a high current.

[0889] [Explanation of Reference Numbers and Symbols]

[0890] 1: Substrate

[0891] 2: First Electrode

[0892] 3: Hole Injection Layer

[0893] 4: Hole Transport Layer

[0894] 5: Electron Blocking Layer

[0895] 6: Emission Layer

[0896] 7: Hole Blocking Layer

[0897] 8: Electron Injection and Transport Layer

[0898] 9: second electrode

Claims

1. A compound represented by the following Chemical Formula 1: [Chemical Formula 1] ###0001### in Chemical Formula 1, X is NR; or S, Y is NR'; O; or S, R and R' are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted aryl group, L1 to L3 and L11 to L33 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group, R1 to R3 and R11 to R33 are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, at least one of R1 to R3 is a substituted or unsubstituted carbazolyl group, at least one of R11 to R33 is a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, n1, n2, m1 and m2 are each an integer of 1 to 4, n3 and m3 are each an integer of 1 to 3, when n1 to n3 and m1 to m3 are each 2 or more, the substituents in the parentheses are each the same as or different from each other, and n1 + m1 is 4 or less, n2 + m2 is 4 or less, and n3 + m3 is 3 or less.

2. The compound according to claim 1, wherein L1 to L3 and L11 to L33 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms containing one or more of N, O and S as a heteroatom. wherein 3. The compound according to claim 1, wherein L1 to L3 are the same as or different from each other, and each independently a direct bond; an unsubstituted or deuterium-substituted phenylene group; an unsubstituted or deuterium-substituted divalent dibenzofuranyl group; an unsubstituted or deuterium-substituted divalent dibenzothiophenyl group; or an unsubstituted or deuterium-substituted divalent carbazolyl group.

4. The compound according to claim 1, wherein L11 to L33 are the same as or different from each other, and each independently a direct bond; an unsubstituted or deuterium-substituted phenylene group; or an unsubstituted or deuterium-substituted divalent carbazolyl group. ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ ​ 5. The compound of claim 1, wherein R1 to R3 and R11 to R33 are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms; a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, at least one of R1 to R3 is a substituted or unsubstituted carbazolyl group, and at least one of R11 to R33 is a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms; a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

6. The compound of claim 1, wherein at least one of R11 to R33 is an unsubstituted or deuterium-substituted triphenylsilyl group; an unsubstituted or deuterium-substituted phenyl group; an unsubstituted or deuterium-substituted biphenyl group; an unsubstituted or deuterium-substituted naphthyl group; an unsubstituted or deuterium-substituted carbazolyl group; an unsubstituted or deuterium-substituted dibenzofuranyl group; an unsubstituted or deuterium-substituted dibenzothiophenyl group; or a heterocyclic group comprising one or more of N and O as a heteroatom, having four to seven condensed rings, and being unsubstituted or deuterium-substituted, and the rest are the same as or different from each other, and each is independently hydrogen; or deuterium.

7. The compound of claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulae 1-1 to 1-6: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] In Chemical Formulae 1-1 to 1-6, the definitions of X, Y, R11 to R33, L1 to L3, L11 to L33, and n1 to n3 are the same as in Chemical Formula 1, G1 to G3 are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and g1 to g3 are each an integer of 1 to 8, and when g1 to g3 are each 2 or more, G1 to G3 are each the same as or different from each other.

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

9. An organic light emitting device comprising: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprises a compound according to any one of claims 1 to 8.

10. The organic light emitting device of claim 9, wherein the organic material layers comprise one or more of an electron injection layer, an electron transport layer, an electron injection and transport layer, and a hole blocking layer, and one or more of the electron injection layer, the electron transport layer, the electron injection and transport layer, and the hole blocking layer comprises the compound.

11. The organic light emitting device of claim 9, wherein the organic material layers comprise an emissive layer, and the emissive layer comprises the compound.

12. The organic light emitting device of claim 9, wherein the organic material layers comprise an emissive layer, and the emissive layer comprises the compound as an n-type host and further comprises a p-type host.

13. The organic light emitting device of claim 9, wherein the organic material layers comprise a hole blocking layer, and the hole blocking layer comprises the compound.

14. The organic light emitting device of claim 9, wherein the organic material layers comprise an emissive layer and a hole blocking layer, and the emissive layer and the hole blocking layer comprise the compound.

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