Compound and organic light-emitting element comprising same

Abstract

The present specification provides a compound and an organic light-emitting element comprising same, the compound being represented by chemical formula 1, in which one or more of three benzene rings directly or indirectly linked to boron are substituted with at least one carbazole group and at least one of an aryl group, a silyl group, or a heterocyclic group.

Description

Compound and organic light-emitting device containing the same

[0001] This application claims the benefit of Korean Patent Application No. 10-2023-0133061, filed with the Korean Intellectual Property Office on October 6, 2023, and Korean Patent Application No. 10-2024-0061695, filed with the Korean Intellectual Property Office on May 10, 2024, 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.

[0003] In general, organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light emitting devices that utilize the organic light emitting phenomenon typically have a structure that includes an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and can be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and when these excitons fall back to the ground state, light is emitted.

[0004] There is a continuing need for the development of new materials for organic light-emitting devices such as the above.

[0005] The present specification provides a compound and an organic light-emitting device comprising the same.

[0006] One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[0007] [Chemical Formula 1]

[0008]

[0009] In the above chemical formula 1,

[0010] X is NR; or S,

[0011] Y is NR'; O; or S,

[0012] R and R' are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted aryl group,

[0013] L1 to L3 and L11 to L33 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0014] R1 to R3 and R11 to R33 are the same or different and are 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,

[0015] At least one of R1 to R3 is a substituted or unsubstituted carbazole group,

[0016] 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,

[0017] n1, n2, m1 and m2 are integers from 1 to 4, respectively,

[0018] n3 and m3 are integers from 1 to 3, respectively,

[0019] When the above n1 to n3 and m1 to m3 are each 2 or more, the substituents in the parentheses are each the same or different,

[0020] n1+m1 is less than or equal to 4, n2+m2 is less than or equal to 4, and n3+m3 is less than or equal to 3.

[0021] In addition, one embodiment of the present specification provides an organic light-emitting device including a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by the chemical formula 1.

[0022] The compounds described herein can be used as materials for organic layers of organic light-emitting devices. The compounds according to at least one embodiment of the present disclosure can enhance efficiency, lower operating voltage, and / or improve lifespan characteristics in organic light-emitting devices. In particular, the compounds described herein can be used as light-emitting or hole-blocking materials.

[0023] Figure 1 illustrates 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 laminated.

[0024] Figure 2 illustrates an 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 laminated.

[0025] The following describes this specification in more detail.

[0026] In this specification, when a part is said to "include" a certain component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

[0027] In this specification, when it is said that a member is located “on” another member, this includes not only cases where the member is in contact with the other member, but also cases where another member exists between the two members.

[0028] In this specification, " " or dotted lines indicate positions where the chemical formula or compound is bonded.

[0029] In this specification, N% substitution with deuterium means that N% of the available hydrogens in the structure are replaced with deuterium. For example, if dibenzofuran is 25% substituted with deuterium, it means that two of the eight hydrogens in dibenzofuran are replaced with deuterium.

[0030] In this specification, the degree of deuteration can be confirmed by a known method such as nuclear magnetic resonance spectroscopy (1H NMR) or GC / MS.

[0031] Examples of substituents in this specification are described below, but are not limited thereto.

[0032] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where the hydrogen atom is replaced, i.e., a position where the substituent can be replaced, and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0033] The term "substituted or unsubstituted" in this specification means substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; silyl group; alkyl group; cycloalkyl group; arylalkyl group; aryl group; and heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

[0034] The term "substituted or unsubstituted" in this specification means substituted with one or more substituents selected from the group consisting of deuterium; silyl group; alkyl group; aryl group; and heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

[0035] Examples of the above substituents are described below, but are not limited thereto.

[0036] In this specification, examples of halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0037] In this specification, the silyl group is -SiY a Y b Y c It can be represented by the chemical formula of Y a , Y b and Y c Each may be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0038] In the present specification, the alkyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an n-pentyl group, a hexyl group, an n-hexyl group, a heptyl group, an n-heptyl group, an octyl group, an n-octyl group, etc.

[0039] In this specification, the description of the alkyl group described above may be applied to the arylalkyl group, except that the arylalkyl group is substituted with an aryl group.

[0040] The substituents comprising alkyl groups and other alkyl moieties described herein include both straight-chain and branched forms.

[0041] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. In one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples thereof include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0042] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group or a polycyclic aryl group (an aryl group having two or more rings). The monocyclic aryl group may also be expressed as a monocyclic aryl group, and may refer to a phenyl group; or a group in which two or more phenyl groups are connected. The monocyclic aryl group may include, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaternaryl group, and the like. The polycyclic aryl group may refer to a group in which two or more monocyclic rings are condensed, such as a naphthyl group, a phenanthrenyl group, and the like. The above polycyclic aryl group may include, but is not limited to, a naphthyl group, anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, etc.

[0043] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. In this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

[0044] When the above fluorenyl group is substituted, , , Spirofluorenyl group of etc. (9,9-dimethylfluorenyl group), and It can be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group), but is not limited thereto.

[0045] In the present specification, a heterocyclic group is a ring group containing at least one of N, O, P, S, Si, and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. 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, but are not limited to, a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, a triazinyl group, and the like.

[0046] In this specification, the description of the heterocyclic group described above may be applied, except that the heteroaryl group is aromatic.

[0047] In this specification, the description of the aryl group may be applied except that the arylene group is divalent.

[0048] In this specification, the description of the above heterocyclic group may be applied to the divalent heterocyclic group except that the divalent heterocyclic group is divalent.

[0049] In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, “ring” means a hydrocarbon ring; or a heterocycle.

[0050] In this specification, "N-ring fused ring" means a ring fused with N monocyclic rings, wherein the monocyclic rings may be pentagonal rings or hexagonal rings, and N is an integer greater than or equal to 1. Examples of N-ring fused rings include, but are not limited to, diazanaphthalene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, imidazopyridine, phenoxazine, indolocarbazole, and indenocarbazole.

[0051] The hydrocarbon ring may be an aromatic, aliphatic or aromatic-aliphatic condensed ring, and may be selected from examples of the cycloalkyl group or aryl group.

[0052] In the present specification, forming a ring by bonding with adjacent groups means forming a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a condensed ring thereof by bonding with adjacent groups. The hydrocarbon ring means a ring composed only of carbon and hydrogen atoms. The heterocycle means a ring containing one or more elements selected from N, O, P, S, Si, and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocycle, and the aromatic heterocycle may be monocyclic or polycyclic.

[0053] In this specification, an aliphatic hydrocarbon ring means a non-aromatic ring composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.

[0054] In this specification, an aromatic hydrocarbon ring means an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include, but are not limited to, benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, and spirofluorene. In this specification, an aromatic hydrocarbon ring can be interpreted to have the same meaning as an aryl group.

[0055] In the present specification, an aliphatic heterocycle means an aliphatic ring containing at least one heteroatom. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocane, and thiocane.

[0056] In this specification, an aromatic heterocycle means an aromatic ring containing at least one heteroatom. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, diazanaphthalene, dryazaindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, Examples include, but are not limited to, imidazopyridine, phenoxazine, indolocarbazole, and indenocarbazole.

[0057] Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention may be modified in various ways, and the scope of the present invention is not limited to the embodiments described below.

[0058] The 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 carbazole group, and at least one of the remaining benzene rings is substituted with a silyl group, an aryl group, or a heterocyclic group, thereby stabilizing an unstable structure and adding hole characteristics. When the compound represented by the chemical formula 1 is applied to an organic light-emitting device, an organic light-emitting device having high efficiency, low voltage, and / or long life characteristics can be obtained.

[0059] Hereinafter, chemical formula 1 is described in detail.

[0060] [Chemical Formula 1]

[0061]

[0062] In the above chemical formula 1,

[0063] X is NR; or S,

[0064] Y is NR'; O; or S,

[0065] R and R' are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; or a substituted or unsubstituted aryl group,

[0066] L1 to L3 and L11 to L33 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0067] R1 to R3 and R11 to R33 are the same or different and are 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,

[0068] At least one of R1 to R3 is a substituted or unsubstituted carbazole group,

[0069] 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,

[0070] n1, n2, m1 and m2 are integers from 1 to 4, respectively,

[0071] n3 and m3 are integers from 1 to 3, respectively,

[0072] When the above n1 to n3 and m1 to m3 are each 2 or more, the substituents in the parentheses are each the same or different,

[0073] n1+m1 is less than or equal to 4, n2+m2 is less than or equal to 4, and n3+m3 is less than or equal to 3.

[0074] In one embodiment of the present specification, X is NR and Y is NR'.

[0075] In one embodiment of the present specification, X is NR and Y is O.

[0076] In one embodiment of the present specification, X is NR and Y is S.

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

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

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

[0080] In one embodiment of the present specification, R and R' are the same as or different from each other, and each independently represents 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.

[0081] In one embodiment of the present specification, R and R' are the same as or different from each other, and each independently represents 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.

[0082] In one embodiment of the present specification, R and R' are the same as or different from each other, and each independently represents 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.

[0083] In one embodiment of the present specification, R and R' are the same as or different from each other, and each independently represents 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.

[0084] In one embodiment of the present specification, R and R' are the same as or different from each other, and each independently represents hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

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

[0086] In one embodiment of the present specification, R and R' are the same as or different from each other, and each independently represents hydrogen; deuterium; a butyl group substituted or unsubstituted with deuterium; a phenyl group substituted or unsubstituted with deuterium; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

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

[0088] In one embodiment of the present specification, R and R' are the same as or different from each other, and each independently represents hydrogen; deuterium; or a phenyl group.

[0089] In one embodiment of the present specification, R and R' are the same as or different from each other, and each independently represents hydrogen; or a phenyl group.

[0090] In one embodiment of the present specification, R and R' are the same as or different from each other, and each independently represents a phenyl group; or a phenyl group substituted with deuterium.

[0091] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and each independently represents a direct bond; an arylene group; or a divalent heterocyclic group.

[0092] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and each independently represents 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.

[0093] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and each independently represents 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.

[0094] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and each independently represents 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 at least one of N, O, S, and Si as a heteroatom.

[0095] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and each independently represents 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 at least one of N, O, and S as a heteroatom.

[0096] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthalene group; a substituted or unsubstituted divalent dibenzofuran group; a substituted or unsubstituted divalent dibenzothiophene group; or a substituted or unsubstituted divalent carbazole group.

[0097] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted divalent dibenzofuran group; or a substituted or unsubstituted divalent carbazole group.

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

[0099] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and each independently represents a direct bond; an arylene group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; or a divalent heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium, containing at least one of N, O, and S as a heteroatom.

[0100] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and each independently represents a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylene group substituted or unsubstituted with deuterium; a naphthalene group substituted or unsubstituted with deuterium; a divalent dibenzofuran group substituted or unsubstituted with deuterium; a divalent dibenzothiophene group substituted or unsubstituted with deuterium; or a divalent carbazole group substituted or unsubstituted with deuterium.

[0101] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and each independently represents a direct bond; a phenylene group substituted or unsubstituted with deuterium; a divalent dibenzofuran group substituted or unsubstituted with deuterium; or a divalent carbazole group substituted or unsubstituted with deuterium.

[0102] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same as or different from each other, and each independently represents a direct bond; a phenylene group; a divalent dibenzofuran group; or a divalent carbazole group.

[0103] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted divalent dibenzofuran group; a substituted or unsubstituted divalent dibenzothiophene group; or a substituted or unsubstituted divalent carbazole group.

[0104] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted divalent carbazole group.

[0105] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; a phenylene group substituted or unsubstituted with deuterium; a divalent dibenzofuran group substituted or unsubstituted with deuterium; a divalent dibenzothiophene group substituted or unsubstituted with deuterium; or a divalent carbazole group substituted or unsubstituted with deuterium.

[0106] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a direct bond; a phenylene group substituted or unsubstituted with deuterium; or a divalent carbazole group substituted or unsubstituted with deuterium.

[0107] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; a phenylene group; a divalent dibenzofuran group; a divalent dibenzothiophene group; or a divalent carbazole group.

[0108] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a direct bond; a phenylene group; or a divalent carbazole group.

[0109] In one embodiment of the present specification, L11 to L33 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted divalent carbazole group.

[0110] In one embodiment of the present specification, L11 to L33 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted phenylene group.

[0111] In one embodiment of the present specification, L11 to L33 are the same as or different from each other, and each independently represents a direct bond; a phenylene group substituted or unsubstituted with deuterium; or a divalent carbazole group substituted or unsubstituted with deuterium.

[0112] In one embodiment of the present specification, L11 to L33 are the same as or different from each other, and each independently represents a direct bond; or a phenylene group substituted or unsubstituted with deuterium.

[0113] In one embodiment of the present specification, L11 to L33 are the same as or different from each other, and each independently represents a direct bond; a phenylene group; or a divalent carbazole group.

[0114] In one embodiment of the present specification, L11 to L33 are the same as or different from each other, and are each independently a direct bond; or a phenylene group.

[0115] In one embodiment of the present specification, R1 to R3 and R11 to R33 are the same as or different from each other, and each independently represent 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, and at least one of R1 to R3 is a substituted or unsubstituted carbazole group, and at least one of R11 to R33 is 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.

[0116] In one embodiment of the present specification, 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 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, and at least one of R1 to R3 is a substituted or unsubstituted carbazole 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.

[0117] In one embodiment of the present specification, R1 to R3 and R11 to R33 are the same as or different from each other, and each independently hydrogen; deuterium; an alkylsilyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; an arylsilyl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 20 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; or a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium, and at least one of R1 to R3 is a carbazole group substituted or unsubstituted with deuterium, and at least one of R11 to R33 is an alkylsilyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; An arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted with deuterium; an aryl group having 6 to 20 carbon atoms, substituted or unsubstituted with deuterium; or a heterocyclic group having 2 to 30 carbon atoms, substituted or unsubstituted with deuterium.

[0118] In one embodiment of the present specification, R1 to R3 and R11 to R33 are the same as or different from each other, and each independently hydrogen; deuterium; an alkylsilyl group having 1 to 20 carbon atoms; an arylsilyl group having 6 to 20 carbon atoms; an alkyl group having 1 to 20 carbon atoms; a cycloalkyl group having 3 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms, and at least one of R1 to R3 is a carbazole group, and at least one of R11 to R33 is 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.

[0119] In one embodiment of the present specification, at least one of R1 to R3 is a substituted or unsubstituted carbazole group, and the others are the same or different from each other and are each independently hydrogen or deuterium.

[0120] In one embodiment of the present specification, at least two of R1 to R3 are substituted or unsubstituted carbazole groups, and the remainder are hydrogen or deuterium.

[0121] In one embodiment of the present specification, one or both of R1 to R3 are substituted or unsubstituted carbazole groups.

[0122] In one embodiment of the present specification, R1 to R3 are all substituted or unsubstituted carbazole groups.

[0123] In one embodiment of the present specification, at least one of R1 to R3 is a carbazole group substituted or unsubstituted with deuterium, and the others are the same as or different from each other and are each independently hydrogen or deuterium.

[0124] In one embodiment of the present specification, at least two of R1 to R3 are carbazole groups substituted or unsubstituted with deuterium, and the remainder are hydrogen; or deuterium.

[0125] In one embodiment of the present specification, R1 to R3 are all carbazole groups substituted or unsubstituted with deuterium.

[0126] In one embodiment of the present specification, at least one of R1 to R3 is a carbazole group, and the others are the same or different from each other and are each independently hydrogen or deuterium.

[0127] In one embodiment of the present specification, at least two of R1 to R3 are carbazole groups, and the remainder are hydrogen; or deuterium.

[0128] In one embodiment of the present specification, 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, and the others are the same as or different from each other and are each independently hydrogen; or deuterium.

[0129] In one embodiment of the present specification, 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, and the rest are the same as or different from each other and are each independently hydrogen; or deuterium.

[0130] In one embodiment of the present specification, 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 containing at least one of N, O, and S as a heteroatom, and the rest are the same as or different from each other, and are each independently hydrogen; or deuterium.

[0131] In one embodiment of the present specification, at least one of R11 to R33 is 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 phenanthrenyl group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted benzofuran group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted benzothiophene group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted heterocyclic group containing at least one of N and O as a heteroatom and having four or more rings condensed therewith, and the rest are the same or different from each other, and are each independently hydrogen; or deuterium.

[0132] In one embodiment of the present specification, at least one of R11 to R33 is 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 carbazole group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted heterocyclic group containing at least one of N and O as a heteroatom and having 4 to 7 rings fused together, and the rest are the same as or different from each other, and are each independently hydrogen; or deuterium.

[0133] In one embodiment of the present specification, at least one of R11 to R33 is a substituted or unsubstituted triphenylsilyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted heterocyclic group containing at least one of N and O as a heteroatom and having a condensed 5-ring or 7-ring, and the rest are the same as or different from each other and are each independently hydrogen; or deuterium.

[0134] In one embodiment of the present specification, at least one of R11 to R33 is a silyl group substituted or unsubstituted with deuterium; an aryl group substituted or unsubstituted with deuterium; or a heterocyclic group substituted or unsubstituted with deuterium, and the others are the same as or different from each other and are each independently hydrogen; or deuterium.

[0135] In one embodiment of the present specification, at least one of R11 to R33 is an alkylsilyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; an arylsilyl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; or a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium, and the rest are the same as or different from each other and are each independently hydrogen; or deuterium.

[0136] In one embodiment of the present specification, at least one of R11 to R33 is an alkylsilyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; an arylsilyl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; or a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium, containing at least one of N, O, and S as a heteroatom, and the rest are the same as or different from each other, and are each independently hydrogen; or deuterium.

[0137] In one embodiment of the present specification, at least one of R11 to R33 is a triphenylsilyl group substituted or unsubstituted with deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrenyl group substituted or unsubstituted with deuterium; a carbazole group substituted or unsubstituted with deuterium; a benzofuran group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a benzothiophene group substituted or unsubstituted with deuterium; a dibenzothiophene group substituted or unsubstituted with deuterium; or a heterocyclic group containing at least one of N and O as a heteroatom, having four or more rings condensed therewith, and substituted or unsubstituted with deuterium, and the rest are the same or different, and are each independently hydrogen; or deuterium.

[0138] In one embodiment of the present specification, at least one of R11 to R33 is a triphenylsilyl group substituted or unsubstituted with deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a carbazole group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a dibenzothiophene group substituted or unsubstituted with deuterium; or a heterocyclic group containing at least one of N and O as a heteroatom, wherein 4 to 7 rings are condensed, and which is substituted or unsubstituted with deuterium, and the rest are the same as or different from each other, and are each independently hydrogen; or deuterium.

[0139] In one embodiment of the present specification, at least one of R11 to R33 is a triphenylsilyl group substituted or unsubstituted with deuterium; a phenyl group substituted or unsubstituted with deuterium; a carbazole group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a dibenzothiophene group substituted or unsubstituted with deuterium; or a heterocyclic group including at least one of N and O as a heteroatom, a condensed 5-ring or 7-ring, and substituted or unsubstituted with deuterium, and the rest are the same as or different from each other, and are each independently hydrogen; or deuterium.

[0140] In one embodiment of the present specification, at least one of R11 to R33 is 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, and the others are the same as or different from each other and are each independently hydrogen; or deuterium.

[0141] In one embodiment of the present specification, at least one of R11 to R33 is 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 containing at least one of N, O, and S as a heteroatom, and the rest are the same as or different from each other and are each independently hydrogen; or deuterium.

[0142] In one embodiment of the present specification, at least one of R11 to R33 is a triphenylsilyl group; a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a phenanthrenyl group; a carbazole group; a benzofuran group; a dibenzofuran group; a benzothiophene group; a dibenzothiophene group; or a heterocyclic group containing at least one of N and O as heteroatoms and having four or more rings fused together, and the rest are the same or different from each other and are each independently hydrogen; or deuterium.

[0143] In one embodiment of the present specification, at least one of R11 to R33 is a triphenylsilyl group; a phenyl group; a biphenyl group; a naphthyl group; a carbazole group; a dibenzofuran group; a dibenzothiophene group; or a heterocyclic group having 4 to 7 rings fused together and containing at least one of N and O as heteroatoms, and the rest are the same or different and are each independently hydrogen; or deuterium.

[0144] In one embodiment of the present specification, at least one of R11 to R33 is a triphenylsilyl group; a phenyl group; a carbazole group; a dibenzofuran group; a dibenzothiophene group; or a heterocyclic group containing at least one of N and O as heteroatoms and having a condensed 5-ring or 7-ring, and the rest are the same or different from each other and are each independently hydrogen; or deuterium.

[0145] In one embodiment of the present specification, at least two of R11 to R33 are a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0146] In one embodiment of the present specification, at least two of R11 to R33 are a substituted or unsubstituted triphenylsilyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted heterocyclic group containing at least one of N and O as a heteroatom and having a condensed 5-ring or 7-ring, and the rest are the same as or different from each other and are each independently hydrogen; or deuterium.

[0147] In one embodiment of the present specification, at least two of R11 to R33 are a triphenylsilyl group substituted or unsubstituted with deuterium; a phenyl group substituted or unsubstituted with deuterium; a carbazole group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a dibenzothiophene group substituted or unsubstituted with deuterium; or a heterocyclic group including at least one of N and O as a heteroatom, a condensed 5-ring or 7-ring, and substituted or unsubstituted with deuterium, and the rest are the same as or different from each other, and are each independently hydrogen; or deuterium.

[0148] In one embodiment of the present specification, at least two of R11 to R33 are a triphenylsilyl group; a phenyl group; a carbazole group; a dibenzofuran group; a dibenzothiophene group; or a heterocyclic group including at least one of N and O as heteroatoms and a condensed 5-ring or 7-ring group, and the rest are the same or different and are each independently hydrogen; or deuterium.

[0149] In one embodiment of the present specification, at least one of R11 to R33 is a group represented by the following structural formula; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0150]

[0151] In the above structural formula, P1 to P3 are substituted or unsubstituted aryl groups, refers to the position where it is bonded to L11 to L33.

[0152] In one embodiment of the present specification, P1 to P3 are substituted or unsubstituted aryl groups having 6 to 60 carbon atoms.

[0153] In one embodiment of the present specification, P1 to P3 are substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0154] In one embodiment of the present specification, P1 to P3 are substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.

[0155] In one embodiment of the present specification, P1 to P3 are substituted or unsubstituted phenyl groups.

[0156] In one embodiment of the present specification, P1 to P3 are phenyl groups substituted or unsubstituted with deuterium.

[0157] In one embodiment of the present specification, P1 to P3 are phenyl groups.

[0158] In one embodiment of the present specification, n1 is an integer from 1 to 4.

[0159] In one embodiment of the present specification, n1 is an integer from 1 to 3.

[0160] In one embodiment of the present specification, n1 is 3.

[0161] In one embodiment of the present specification, n1 is 2.

[0162] In one embodiment of the present specification, n1 is 1.

[0163] In one embodiment of the present specification, n2 is an integer from 1 to 4.

[0164] In one embodiment of the present specification, n2 is an integer from 1 to 3.

[0165] In one embodiment of the present specification, n2 is 3.

[0166] In one embodiment of the present specification, n2 is 2.

[0167] In one embodiment of the present specification, n2 is 1.

[0168] In one embodiment of the present specification, n3 is an integer from 1 to 3.

[0169] In one embodiment of the present specification, n3 is an integer from 1 to 2.

[0170] In one embodiment of the present specification, n3 is 2.

[0171] In one embodiment of the present specification, n3 is 1.

[0172] In one embodiment of the present specification, m1 is an integer from 1 to 4.

[0173] In one embodiment of the present specification, m1 is an integer from 1 to 3.

[0174] In one embodiment of the present specification, m1 is 3.

[0175] In one embodiment of the present specification, m1 is 2.

[0176] In one embodiment of the present specification, m1 is 1.

[0177] In one embodiment of the present specification, m2 is an integer from 1 to 4.

[0178] In one embodiment of the present specification, m2 is an integer from 1 to 3.

[0179] In one embodiment of the present specification, m2 is 3.

[0180] In one embodiment of the present specification, m2 is 2.

[0181] In one embodiment of the present specification, m2 is 1.

[0182] In one embodiment of the present specification, m3 is an integer from 1 to 3.

[0183] In one embodiment of the present specification, m3 is an integer from 1 to 2.

[0184] In one embodiment of the present specification, m3 is 2.

[0185] In one embodiment of the present specification, m3 is 1.

[0186] In one embodiment of the present specification, n1+m1 is 2 or more and 4 or less.

[0187] In one embodiment of the present specification, n1+m1 is 3 or more and 4 or less.

[0188] In one embodiment of the present specification, n1+m1 is 4.

[0189] In one embodiment of the present specification, n1+m1 is 3.

[0190] In one embodiment of the present specification, n1+m1 is 2.

[0191] In one embodiment of the present specification, n2+m2 is 2 or more and 4 or less.

[0192] In one embodiment of the present specification, n2+m2 is 3 or more and 4 or less.

[0193] In one embodiment of the present specification, n2+m2 is 4.

[0194] In one embodiment of the present specification, n2+m2 is 3.

[0195] In one embodiment of the present specification, n2+m2 is 2.

[0196] In one embodiment of the present specification, n3+m3 is 2 or 3.

[0197] In one embodiment of the present specification, n3+m3 is 3.

[0198] In one embodiment of the present specification, n3+m3 is 2.

[0199] In one embodiment of the present specification, m1, n2 and n3 are 1.

[0200] In one embodiment of the present specification, n1, m2 and n3 are 1.

[0201] In one embodiment of the present specification, n1, n2 and m3 are 1.

[0202] In one embodiment of the present specification, n1, m2 and m3 are 1.

[0203] In one embodiment of the present specification, m1, n2 and m3 are 1.

[0204] In one embodiment of the present specification, m1, m2 and n3 are 1.

[0205] In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-6.

[0206] [Chemical Formula 1-1]

[0207]

[0208] [Chemical Formula 1-2]

[0209]

[0210] [Chemical Formula 1-3]

[0211]

[0212] [Chemical Formula 1-4]

[0213]

[0214] [Chemical Formula 1-5]

[0215]

[0216] [Chemical Formula 1-6]

[0217]

[0218] In the above chemical formulas 1-1 to 1-6,

[0219] The definitions of X, Y, R11 to R33, L1 to L3, L11 to L33 and n1 to n3 are the same as those in the chemical formula 1 above,

[0220] G1 to G3 are the same or different and are 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,

[0221] g1 to g3 are each integers from 1 to 8, and when g1 to g3 are each 2 or greater, G1 to G3 are each equal to or different from each other.

[0222] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each 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.

[0223] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each 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.

[0224] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each 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 carbazole group; a substituted or unsubstituted benzofuran group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted benzothiophene group; or a substituted or unsubstituted dibenzothiophene group.

[0225] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; an alkylsilyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; an arylsilyl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 20 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; or a heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0226] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen; deuterium; a butyl group substituted or unsubstituted with deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a carbazole group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; or a dibenzothiophene group substituted or unsubstituted with deuterium.

[0227] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen; deuterium; a butyl group; a phenyl group; a biphenyl group; a naphthyl group; a carbazole group; a dibenzofuran group; or a dibenzothiophene group.

[0228] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0229] In one embodiment of the present specification, G1 to G3 are hydrogen.

[0230] In one embodiment of the present specification, G1 to G3 are deuterium.

[0231] In one embodiment of the present specification, g1 to g3 are 1.

[0232] In one embodiment of the present specification, g1 to g3 are 2.

[0233] In one embodiment of the present specification, g1 to g3 are 3.

[0234] In one embodiment of the present specification, g1 to g3 are 4.

[0235] In one embodiment of the present specification, g1 to g3 are 5.

[0236] In one embodiment of the present specification, g1 to g3 are 6.

[0237] In one embodiment of the present specification, g1 to g3 are 7.

[0238] In one embodiment of the present specification, g1 to g3 are 8.

[0239] In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-A-1 to 1-A-3.

[0240] [Chemical Formula 1-A-1]

[0241]

[0242] [Chemical Formula 1-A-2]

[0243]

[0244] [Chemical Formula 1-A-3]

[0245]

[0246] In the above chemical formulas 1-A-1 to 1-A-3,

[0247] The definitions of X, Y, R11 to R33, L1 to L3 and L11 to L13 are the same as those in the chemical formula 1 above, and the definitions of G1 to G3 and g1 to g3 are the same as those in the chemical formulas 1-1 to 1-6 above.

[0248] In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-B-1 to 1-B-3.

[0249] [Chemical Formula 1-B-1]

[0250]

[0251] [Chemical Formula 1-B-2]

[0252]

[0253] [Chemical Formula 1-B-3]

[0254]

[0255] In the above chemical formulas 1-B-1 to 1-B-3,

[0256] The definitions of X, Y, R11 to R33, L1 to L3 and L11 to L13 are the same as those in the chemical formula 1 above, and the definitions of G1 to G3 and g1 to g3 are the same as those in the chemical formulas 1-1 to 1-6 above.

[0257] In one embodiment of the present specification, the compound represented by the chemical formula 1 is substituted by 20% or more with deuterium. In another embodiment, the compound represented by the chemical formula 1 is substituted by 30% or more with deuterium. In another embodiment, the compound represented by the chemical formula 1 is substituted by 40% or more with deuterium. In another embodiment, the compound represented by the chemical formula 1 is substituted by 50% or more with deuterium. In another embodiment, the compound represented by the chemical formula 1 is substituted by 60% or more with deuterium. In another embodiment, the compound represented by the chemical formula 1 is substituted by 70% or more with deuterium. In another embodiment, the compound represented by the chemical formula 1 is substituted by 80% or more with deuterium. In another embodiment, the compound represented by the chemical formula 1 is substituted by 90% or more with deuterium. In another embodiment, the compound represented by the above chemical formula 1 is 100% substituted with deuterium.

[0258] In one embodiment of the present specification, the compound represented by the chemical formula 1 contains 40% to 60% of deuterium. In another embodiment, the compound represented by the chemical formula 1 contains 40% to 80% of deuterium. In another embodiment, the compound represented by the chemical formula 1 contains 60% to 80% of deuterium. In another embodiment, the compound represented by the chemical formula 1 contains 80% to 100% of deuterium.

[0259] In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following compounds.

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[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] In this specification, [ ] D=x1~x2 means that the structure within the parentheses contains x1 to x2 deuterium atoms, and the value is an integer. For example, [ ] D=1~41 means that it contains 1 to 41 deuterium atoms. As an example, the structure below contains 1 to 50 deuterium atoms.

[0369]

[0370] The compound represented by chemical formula 1 according to one embodiment of the present specification can be synthesized by a synthetic method known in the art using starting materials, intermediate materials, etc. known in the art, and the substituents can be bonded by a method known in the art, and the type, position, or number of the substituents can be changed according to a technique known in the art.

[0371] In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above chemical formula 1. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can also be controlled by introducing various substituents into the core structure of the above structure.

[0372] In addition, the present specification provides an organic light-emitting device comprising the compound described above.

[0373] When it is said in this specification that a member is located "on" another member, this includes not only cases where the member is in contact with the other member, but also cases where another member exists between the two members.

[0374] When a part in this specification is said to "include" a certain component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

[0375] An organic light-emitting device according to the present specification is an organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by the above-described chemical formula 1.

[0376] The organic light-emitting device of the present specification can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that an organic layer is formed using the compound of the above-described chemical formula 1.

[0377] The organic layer of the organic light-emitting device of the present specification may be formed as a single layer structure, but may be formed as a multilayer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a multilayer structure including at least one layer 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 layer. However, the structure of the organic light-emitting device of the present specification is not limited thereto and may be a single layer structure. In addition, the compound may be manufactured in a smaller number of layers by a method such as a solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method, as well as a vacuum deposition method when manufacturing the organic light-emitting device, but is not limited thereto.

[0378] In one embodiment of the present specification, the thickness of the organic layer including the compound of the chemical formula 1 may be 5 Å to 2000 Å, or 5 Å to 500 Å, and preferably 10 Å to 400 Å.

[0379] In another embodiment, the organic layer may further include another organic compound, metal, or metal compound in addition to the compound represented by the chemical formula 1.

[0380] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include a compound represented by the chemical formula 1.

[0381] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include a compound represented by the chemical formula 1 as a host.

[0382] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include a compound represented by the chemical formula 1 as an n-type host, and specifically, may include an n-type phosphorescent host.

[0383] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the chemical formula 1 as a first host, and may further include an additional second host.

[0384] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the chemical formula 1 as a first n-type host, and may further include a second p-type host. Specifically, the first host may be an n-type phosphorescent host, and the second host may be a p-type phosphorescent host.

[0385] In this specification, n-type can be defined as a material that can take electrons from a matrix material (material of the organic layer) and has the property of donating electrons to the LUMO (lowest unoccupied molecular orbital) energy level of the matrix.

[0386] Conversely, in this specification, p-type can be defined as a material that, when forming a single layer with only p-type materials, receives electrons at the HOMO (highest occupied molecular orbital) energy level of a material located in the adjacent cathode direction and creates holes in the material located in the adjacent cathode direction, and the closer the HOMO level of the material located in the cathode direction is to the LUMO of the p-type material, the easier it is to steal electrons from the HOMO of the adjacent layer and create holes in the HOMO of the adjacent layer.

[0387] When a p-type material is doped into an arbitrary matrix, it can be defined as a material that receives electrons from the HOMO of the matrix material and creates holes in the HOMO of the matrix, and the closer the LUMO of the p-type material is to the HOMO of the matrix, the easier it is to steal electrons and create holes in the matrix.

[0388] In one embodiment of the present specification, the p-type material may be a compound generally known in the art, and may have a structure including, for example, an N-containing monocyclic ring; dibenzofuran; and / or carbazole.

[0389] In one embodiment of the present specification, the light-emitting layer may include the first host and the second host in a weight ratio of 2:8 to 8:2, specifically, in a weight ratio of 4:6 to 6:4, and the first host may include a compound represented by the chemical formula 1.

[0390] In one embodiment of the present specification, the light-emitting layer includes the first host and the second host in a weight ratio of 1:1, and the first host may include the compound of the chemical formula 1.

[0391] In one embodiment of the present specification, the second host may be a carbazole compound.

[0392] In one embodiment of the present specification, the second host may be a biscarbazole compound.

[0393] In one embodiment of the present specification, the second host may be a biscarbazole-based compound substituted with an aryl group.

[0394] In one embodiment of the present specification, the second host may be a compound represented by the chemical formula EB-1 described below.

[0395] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the chemical formula 1 as a host, and may further include a dopant.

[0396] In one embodiment of the present specification, the light-emitting layer includes a compound represented by the chemical formula 1 as a first host, and may further include a second host and a dopant.

[0397] In one embodiment of the present specification, the dopant is a phosphorescent dopant.

[0398] In one embodiment of the present specification, the dopant may be included in an amount of 1 to 20 parts by weight based on 100 parts by weight of the host.

[0399] In one embodiment of the present specification, the light-emitting layer includes a dopant, and the dopant may include a phosphorescent dopant.

[0400] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host and a dopant, the host includes the compound, and the dopant may include the phosphorescent dopant.

[0401] In one embodiment of the present specification, the light-emitting layer may be a blue light-emitting layer.

[0402] In one embodiment of the present specification, the light-emitting layer may include the host and the dopant in a weight ratio of 99:1 to 1:99. Specifically, it may include the host and the dopant in a weight ratio of 99:1 to 50:50, and more specifically, it may include the host and the dopant in a weight ratio of 99:1 to 86:14.

[0403] When the above-mentioned light-emitting layer emits red light, a phosphorescent material such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the light-emitting dopant, but is not limited thereto. When the light-emitting layer emits green light, a phosphorescent material such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium), or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the light-emitting dopant, but is not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as a platinum complex compound or (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distriarylene (DSA), PFO polymer, or PPV polymer can be used as a light-emitting dopant, but is not limited thereto.

[0404] In one embodiment of the present specification, the dopant may be a metal complex compound.

[0405] In one embodiment of the present specification, the dopant may be a platinum complex compound.

[0406] In one embodiment of the present specification, the dopant may be an iridium complex compound.

[0407] In one embodiment of the present specification, the dopant may be an iridium-based compound.

[0408] In one embodiment of the present specification, the dopant compound may be selected from the following structural formulas, but is not limited thereto.

[0409]

[0410]

[0411]

[0412]

[0413] In one embodiment of the present specification, the organic layer may include a hole blocking layer.

[0414] In one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer may include a compound represented by the chemical formula 1.

[0415] In one embodiment of the present specification, the organic layer may include a hole blocking layer, and the hole blocking layer may include an n-type compound represented by the chemical formula 1.

[0416] In one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer may include an n-type compound represented by the chemical formula 1, and the n-type compound represented by the chemical formula 1 may be a compound that is the same as or different from the n-type host included in the light-emitting layer.

[0417] In one embodiment of the present specification, the organic layer includes a light-emitting layer and a hole-blocking layer, and the light-emitting layer and the hole-blocking layer may include a compound represented by the chemical formula 1.

[0418] In one embodiment of the present specification, the organic layer may further include at least one layer of a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.

[0419] In one embodiment of the present specification, the organic light-emitting element may include a first electrode; a second electrode provided opposite the first electrode; a light-emitting layer provided between the first electrode and the second electrode; and two or more organic layers provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0420] In one embodiment of the present specification, the two or more organic layers may be selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0421] In one embodiment of the present specification, two or more hole transport layers are included between the light-emitting layer and the first electrode. The two or more hole transport layers may include the same or different materials.

[0422] In one embodiment of the present specification, the first electrode is an anode or a cathode.

[0423] In one embodiment of the present specification, the second electrode is a cathode or an anode.

[0424] In one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially laminated on a substrate.

[0425] In one embodiment of the present specification, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic layers, and an anode are sequentially laminated on a substrate.

[0426] The above organic light-emitting device may have a laminated structure, for example, as follows, but is not limited thereto.

[0427] (1) First electrode / hole transport layer / light-emitting layer / second electrode

[0428] (2) First electrode / hole injection layer / hole transport layer / light-emitting layer / second electrode

[0429] (3) First electrode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / second electrode

[0430] (4) First electrode / hole transport layer / light-emitting layer / electron transport layer / second electrode

[0431] (5) First electrode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / second electrode

[0432] (6) First electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / second electrode

[0433] (7) First electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / second electrode

[0434] (8) First electrode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / second electrode

[0435] (9) First electrode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / second electrode

[0436] (10) First electrode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / second electrode

[0437] (11) First electrode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / second electrode

[0438] (12) First electrode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / second electrode

[0439] (13) First electrode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / second electrode

[0440] (14) First electrode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / second electrode

[0441] (15) First electrode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / second electrode

[0442] (16) First electrode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / second electrode

[0443] (17) First electrode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / second electrode

[0444] (18) First electrode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport and injection layer / second electrode

[0445] The structure of the organic light-emitting device of this specification may have a structure as shown in FIGS. 1 to 3, but is not limited thereto.

[0446] Figure 1 illustrates 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 laminated. In such a structure, the compound may be included in the light-emitting layer (6).

[0447] Figure 2 illustrates an 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 laminated. In such a structure, the compound may be included in the light-emitting layer (6) or the hole blocking layer (7).

[0448] In one embodiment of the present specification, the electron injection and transport layer and the light-emitting layer may be provided adjacently. For example, the electron injection and transport layer and the light-emitting layer may be provided in physical contact.

[0449] In one embodiment of the present specification, the hole blocking layer and the electron injection and transport layer may be provided adjacently. For example, the hole blocking layer and the electron injection and transport layer may be provided in physical contact.

[0450] In one embodiment of the present specification, the hole blocking layer and the light emitting layer may be provided adjacently. For example, the hole blocking layer and the light emitting layer may be provided in physical contact.

[0451] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that at least one of the organic layers includes the compound, i.e., the compound represented by the chemical formula 1.

[0452] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0453] For example, the organic light-emitting device according to the present specification can be manufactured by forming a first electrode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, forming an organic 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 thereon, and then depositing a material that can be used as a second electrode thereon. In addition to this method, the organic light-emitting device can also be manufactured by sequentially depositing a second electrode material, an organic layer, and a first electrode material on a substrate.

[0454] As the anode material, a material having a high work function is generally preferred so that hole injection into the organic layer can be facilitated. Examples thereof include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0455] The cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Examples thereof include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0456] The above-described light-emitting layer may include a host material and a dopant material. When the organic light-emitting device according to one embodiment of the present specification includes an additional light-emitting layer other than the light-emitting layer including the chemical formula 1, the host material may be a condensed aromatic ring derivative or a heterocycle-containing compound. Specifically, the condensed aromatic ring derivative may include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocycle-containing compounds may include, but are not limited to, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like.

[0457] The above-mentioned hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injection material has the ability to transport holes, thereby having a hole receiving effect from the anode and an excellent hole injection effect into the light-emitting layer or light-emitting material. In addition, it is preferable that the material has an excellent ability to prevent the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material. In addition, it is preferable that the material has an excellent thin film forming ability. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrins, oligothiophenes, and arylamine-based organic materials; hexanitrilehexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; and polythiophene-based conductive polymers such as anthraquinone and polyaniline.

[0458] In one embodiment of the present specification, the hole injection layer may include a compound represented by the following chemical formula HI-1, but is not limited thereto.

[0459] [Chemical formula HI-1]

[0460]

[0461] In the above chemical formula HI-1,

[0462] R315 to R317 are the same or different, and each independently represent one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0463] r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 are the same as or different from each other,

[0464] r316 is an integer from 1 to 5, and when r316 is 2 or more, two or more R316 are the same as or different from each other.

[0465] In one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof.

[0466] In one embodiment of the present specification, R317 is any one selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; a triphenylene group; and combinations thereof.

[0467] In one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, or are combined with an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0468] In one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a phenyl group or a biphenyl group, or combine with an adjacent group to form an indene substituted with a methyl group.

[0469] In one embodiment of the present specification, the chemical formula HI-1 may be represented by any one of the following compounds.

[0470]

[0471] In one 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.

[0472] [Chemical formula HI-2]

[0473]

[0474] In the above chemical formula HI-2,

[0475] R401 to R403 are the same as or mentioned above, and each independently represents a halogen group,

[0476] r401 to r403 are 4.

[0477] In one embodiment of the present specification, R401 to R403 are F.

[0478] In one embodiment of the present specification, the chemical formula HI-2 may be represented by the following compound.

[0479]

[0480] In one embodiment of the present specification, the hole injection layer may include a compound represented by the chemical formula HI-1 and a compound represented by the chemical formula HI-2.

[0481] In one embodiment of the present specification, the hole injection layer may include a compound represented by the chemical formula HI-1 and a compound represented by the chemical formula HI-2 in a weight ratio of 1:99 to 99:1, and specifically, may include a compound represented by the chemical formula HI-2 in a weight ratio of 5:95 to 95:5.

[0482] The above-mentioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is preferably a material with high hole mobility that can receive holes from the anode or the hole injection layer and transport them to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0483] In one embodiment of the present specification, the hole transport layer may include a compound represented by the chemical formula HI-1, but is not limited thereto.

[0484] In one 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 in the hole transport layer and hole injection layer may be used, but are not limited thereto.

[0485] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is preferable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material, as used in the prior art. In particular, suitable cathode materials are conventional materials having a low work function and followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case followed by an aluminum layer or a silver layer.

[0486] The electron injection layer is a layer that receives electrons from the electrode. The electron injection material preferably has excellent electron transport ability, an electron receiving effect from the cathode, and an excellent electron injection effect for the light-emitting layer or light-emitting material. In addition, a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and has excellent thin film forming ability is preferred. Specific examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0487] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, Examples include, but are not limited to, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc.

[0488] In one 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 in the electron transport layer and electron injection layer may be used, but are not limited thereto.

[0489] In one embodiment of the present specification, the electron injection and transport layer may include, but is not limited to, a compound represented by the following chemical formula ET-1.

[0490] [Chemical formula ET-1]

[0491]

[0492] In the above chemical formula ET-1,

[0493] At least one of Z11 to Z13 is N, and the rest are CH,

[0494] At least one of Z21 to Z23 is N, and the rest are CH,

[0495] L601 and L602 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0496] Ar601 to Ar604 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0497] In one embodiment of the present specification, all of Z11 to Z13 are N.

[0498] In one embodiment of the present specification, all of Z21 to Z23 are N.

[0499] In one embodiment of the present specification, L601 and L602 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms. In one embodiment of the present specification, L601 and L602 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 12 carbon atoms.

[0500] In one embodiment of the present specification, L601 and L602 are substituted or unsubstituted phenylene groups.

[0501] In one embodiment of the present specification, L601 and L602 are phenylene groups.

[0502] In one embodiment of the present specification, Ar601 to Ar604 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0503] In one embodiment of the present specification, Ar601 to Ar604 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 12 carbon atoms.

[0504] In one embodiment of the present specification, Ar601 to Ar604 are substituted or unsubstituted phenyl groups.

[0505] In one embodiment of the present specification, Ar601 to Ar604 are phenyl groups.

[0506] In one embodiment of the present specification, the chemical formula ET-1 may be represented by the following compound.

[0507]

[0508] In one embodiment of the present specification, the electron injection and transport layer may further include a metal complex compound. The metal complex compound is as described above.

[0509] 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 and entering the hole injection layer. Any material known as a material with high triplet energy can be used without limitation, and the materials exemplified in the description of the hole injection layer can be used, but are 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 a layer that simultaneously injects and transports holes.

[0510] In one embodiment of the present specification, the electron blocking layer may include, but is not limited to, a compound represented by the following chemical formula EB-1.

[0511] [Chemical formula EB-1]

[0512]

[0513] In the above chemical formula EB-1,

[0514] T1 to T14 are the same or different and are each independently hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0515] L14 is a direct bond; or a substituted or unsubstituted arylene group,

[0516] t13 is an integer from 1 to 3, and when t13 is 2 or more, t13 of 2 or more are equal to or different from each other.

[0517] In one embodiment of the present specification, T1 to T14 are the same as or different from each other, and each independently represents 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.

[0518] In one embodiment of the present specification, T1 to T14 are the same as or different from each other, and each independently represents 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.

[0519] In one embodiment of the present specification, T1 to T14 are the same as or different from each other, and are each 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.

[0520] In one embodiment of the present specification, T1 to T14 are the same as or different from each other, and are each independently hydrogen; deuterium; a triphenylsilyl group; a phenyl group; or a biphenyl group.

[0521] In one embodiment of the present specification, T1 to T13 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0522] In one 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.

[0523] In one embodiment of the present specification, T14 is a triphenylsilyl group; a phenyl group; a biphenyl group; or a naphthyl group.

[0524] In one embodiment of the present specification, T14 is a triphenylsilyl group; or a phenyl group.

[0525] In one embodiment of the present specification, L14 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0526] In one embodiment of the present specification, L14 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0527] In one embodiment of the present specification, L14 is a direct bond; or a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0528] In one embodiment of the present specification, L14 is a direct bond; or a phenylene group.

[0529] In one embodiment of the present specification, the chemical formula EB-1 may be represented by the following compound.

[0530]

[0531] A hole blocking layer may be provided between the electron transport layer and the light emitting layer. The hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer.

[0532] In one embodiment of the present specification, the hole blocking layer may include a compound represented by the following chemical formula HB-1 or a compound represented by the above chemical formula 1, but is not limited thereto.

[0533] [Chemical formula HB-1]

[0534]

[0535] In the above chemical formula HB-1,

[0536] Ar101, Ar102 and Ar103 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0537] In one embodiment of the present specification, Ar101, Ar102 and Ar103 are the same as or different from each other, and each independently represents 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.

[0538] In one embodiment of the present specification, Ar101, Ar102 and Ar103 are the same as or different from each other, and each independently represents 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.

[0539] In one embodiment of the present specification, Ar101, Ar102 and Ar103 are the same as or different from each other, and are each 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 carbazole group.

[0540] In one embodiment of the present specification, Ar101, Ar102 and Ar103 are the same as or different from each other, and are each independently hydrogen; deuterium; a triphenylsilyl group; or a carbazole group.

[0541] In one embodiment of the present specification, the chemical formula HB-1 may be represented by the following compound.

[0542]

[0543] In the case where the organic light-emitting device according to one embodiment of the present specification includes an additional hole-blocking layer other than the hole-blocking layer including the compound represented by the chemical formula HB-1 or the compound represented by the chemical formula 1, specifically, the hole-blocking layer includes, but is not limited to, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, an aluminum complex, etc.

[0544] The organic light-emitting device according to the present specification may be a front-emitting, back-emitting or double-sided emitting device depending on the material used.

[0545] The organic light-emitting device according to the present specification can be incorporated into and used in various electronic devices. For example, the electronic devices may be, but are not limited to, display panels, touch panels, solar modules, lighting devices, etc.

[0546]

[0547] Hereinafter, the present specification will be described in detail with examples and comparative examples. However, the examples and comparative examples according to the present specification may be modified in various different forms, and the scope of the present specification is not construed as being limited to the examples and comparative examples described below. The examples and comparative examples of the present specification are provided to more fully explain the present specification to those with average knowledge in the art.

[0548]

[0549] <Manufacturing Example>

[0550] Preparation example of compound 1 (F-1)

[0551]

[0552] Synthesis of I-1

[0553] Under a nitrogen atmosphere, 40 g of 1,3-dibromo-5-chlorobenzene, 49.5 g of 3-(9H-carbazol-9-yl)-N-phenylaniline, 0.75 g of [bis(tri-tert-butylphosphine)palladium(0)], 28.4 g of sodium-tert-butoxide, and 800 mL of toluene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 58 g. (Yield 75%, Mass [M+] = 524)

[0554]

[0555] Synthesis of I-2

[0556] I-1 25g, (2-(phenylamino)phenyl)boronic acid 7.0g, K2CO3 13.2g, [bis(tri-tert-butylphosphine)palladium(0)] 0.24g, tetrahydrofuran 500mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 18g. (Yield 62%, Mass [M+] = 613)

[0557]

[0558] Synthesis of I-3

[0559] Under a nitrogen atmosphere, 15 g of I-2, 20 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 8.2 g. (Yield 54%, Mass [M+] = 621)

[0560]

[0561] Synthesis of F-1

[0562] I-3 8g, (3-(triphenylsilyl)phenyl)boronic acid 4.9g, K2CO3 3.6g, [bis(tri-tert-butylphosphine)palladium(0)] 0.07g, tetrahydrofuran 160mL, and water 80mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 7.2g. (Yield 61%, Mass [M+]=921)

[0563]

[0564] Preparation example of compound 2 (F-2)

[0565]

[0566] Synthesis of I-4

[0567] Under a nitrogen atmosphere, 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 38 g. (Yield 72%, Mass [M+] = 357)

[0568]

[0569] Synthesis of I-5

[0570] Under a nitrogen atmosphere, 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 22 g. (Yield 71%, Mass [M+] = 445)

[0571]

[0572] Synthesis of I-6

[0573] I-5 20g, (2-(phenylamino)-5-(triphenylsilyl)phenyl)boronic acid 21.2g, K2CO3 12.4g, [bis(tri-tert-butylphosphine)palladium(0)] 0.23g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 23g. (Yield 61%, Mass [M+]=837)

[0574]

[0575] F-2 synthesis

[0576] Under a nitrogen atmosphere, 14 g of I-6, 11.2 g of boron triiodide, and 280 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.6 g. (Yield 47%, Mass [M+] = 845)

[0577]

[0578] Preparation example of compound 3 (F-3)

[0579]

[0580] Synthesis of I-7

[0581] Under a nitrogen atmosphere, 40 g of 1,3-dibromobenzene, 34.5 g of 4-chloro-N-phenylaniline, 0.86 g of [bis(tri-tert-butylphosphine)palladium(0)], 32.6 g of sodium-tert-butoxide, and 800 mL of toluene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 43 g. (Yield 71%, Mass [M+] = 359)

[0582]

[0583] Synthesis of I-8

[0584] I-7 20g, (5-(9H-carbazol-9-yl)-2-hydroxyphenyl)boronic acid 21.1g, K2CO3 19.3g, [bis(tri-tert-butylphosphine)palladium(0)] 0.35g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 26g. (Yield 69%, Mass [M+] = 538)

[0585]

[0586] Synthesis of I-9

[0587] Under a nitrogen atmosphere, 15 g of I-8, 18.6 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.7 g. (Yield 44%, Mass [M+] = 546)

[0588]

[0589] F-3 synthesis

[0590] I-9 6g, (3-(triphenylsilyl)phenyl)boronic acid 3.4g, K2CO3 3.1g, [bis(tri-tert-butylphosphine)palladium(0)] 0.06g, tetrahydrofuran 120mL, and water 60mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 6g. (Yield 64%, Mass [M+] = 846)

[0591]

[0592] Preparation example of compound 4 (F-4)

[0593]

[0594] Synthesis of I-10

[0595] I-5 15g, (4-hydroxy-3'-(triphenylsilyl)-[1,1'-biphenyl]-3-yl)boronic acid 15.9g, K2CO3 9.3g, [bis(tri-tert-butylphosphine)palladium(0)] 0.17g, tetrahydrofuran 300mL, and water 150mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 19g. (Yield 67%, Mass [M+]=838)

[0596]

[0597] F-4 composite

[0598] Under a nitrogen atmosphere, 15 g of I-10, 11.9 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.1 g. (Yield 40%, Mass [M+] = 846)

[0599]

[0600] Preparation example of compound 5 (F-5)

[0601]

[0602] Synthesis of I-11

[0603] Under a nitrogen atmosphere, 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 66 g. (Yield 69%, Mass [M+] = 566)

[0604]

[0605] Synthesis of I-12

[0606] 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all the solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 25 g. (Yield 76%, Mass [M+] = 930)

[0607]

[0608] F-5 composite

[0609] Under a nitrogen atmosphere, 15 g of I-11, 10.7 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 5.6 g. (Yield 37%, Mass [M+] = 938)

[0610]

[0611] Preparation example of compound 6 (F-6)

[0612]

[0613] Synthesis of I-13

[0614] Under a nitrogen atmosphere, 30 g of I-4, 9.3 g of benzenethiol, 0.43 g of [bis(tri-tert-butylphosphine)palladium(0)], 16.2 g of sodium-tert-butoxide, and 800 mL of toluene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 24 g. (Yield 74%, Mass [M+] = 387)

[0615]

[0616] Synthesis of I-14

[0617] I-13 20g, ((3-(phenylamino)-3'-(triphenylsilyl)-[1,1'-biphenyl]-4-yl)boronic acid 28.4g, K2CO3 14.3g, [bis(tri-tert-butylphosphine)palladium(0)] 0.26g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 28g. (Yield 63%, Mass [M+]=854)

[0618]

[0619] F-6 composite

[0620] Under a nitrogen atmosphere, 15 g of I-14, 11.7 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 5.8 g. (Yield 38%, Mass [M+] = 862)

[0621]

[0622] Preparation example of compound 7 (F-7)

[0623]

[0624] Synthesis of I-15

[0625] Under a nitrogen atmosphere, 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 43 g. (Yield 69%, Mass [M+] = 559)

[0626]

[0627] Synthesis of I-16

[0628] 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all the solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 17 g. (Yield 66%, Mass [M+] = 721)

[0629]

[0630] Synthesis of I-17

[0631] I-16 15g, (2-hydroxyphenyl)boronic acid 2.9g, K2CO3 5.8g, [bis(tri-tert-butylphosphine)palladium(0)] 0.1g, tetrahydrofuran 300mL, and water 150mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 12g. (Yield 74%, Mass [M+] = 779)

[0632]

[0633] F-7 composite

[0634] Under a nitrogen atmosphere, 12 g of I-17, 12.8 g of boron triiodide, and 240 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.2 g. (Yield 41%, Mass [M+] = 787)

[0635]

[0636] Preparation example of compound 8 (F-8)

[0637]

[0638] Synthesis of I-18

[0639] Under a nitrogen atmosphere, 30 g of 1,3-dibromo-5-chlorobenzene, 49.3 g of 3'-(triphenylsilyl)-[1,1'-biphenyl]-3-thiol, 0.57 g of [bis(tri-tert-butylphosphine)palladium(0)], 21.3 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 46 g. (Yield 65%, Mass [M+] = 635)

[0640]

[0641] Synthesis of I-19

[0642] Under a nitrogen atmosphere, 25 g of I-18, 6.6 g of 9H-carbazole, 0.2 g of [bis(tri-tert-butylphosphine)palladium(0)], 9.5 g of sodium-tert-butoxide, and 500 mL of toluene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 21 g. (Yield 74%, Mass [M+] = 721)

[0643]

[0644] Synthesis of I-20

[0645] 20g of I-19, 8g of (2-mercaptophenyl)boronic acid, 7.7g of K2CO3, 0.15g of [bis(tri-tert-butylphosphine)palladium(0)], 400mL of tetrahydrofuran, and 250mL of water were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 16g. (Yield 73%, Mass [M+]=795)

[0646]

[0647] F-8 composite

[0648] Under a nitrogen atmosphere, 15 g of I-20, 12.6 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.4 g. (Yield 42%, Mass [M+] = 803)

[0649]

[0650] Preparation example of compound 9 (F-9)

[0651]

[0652] Synthesis of I-21

[0653] Under a nitrogen atmosphere, 30 g of 3-bromo-5-chloro-1,1'-biphenyl, 37.5 g of 3-(9H-carbazol-9-yl)-N-phenylaniline, 0.57 g of [bis(tri-tert-butylphosphine)palladium(0)], 21.6 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 45 g. (Yield 77%, Mass [M+] = 522)

[0654]

[0655] Synthesis of I-22

[0656] 20g of I-21, 8.2g of (2-(phenylamino)phenyl)boronic acid, 10.7g of K2CO3, 0.20g of [bis(tri-tert-butylphosphine)palladium(0)], 400mL of tetrahydrofuran, and 250mL of water were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 17g. (Yield 68%, Mass [M+] = 655)

[0657]

[0658] F-9 composite

[0659] Under a nitrogen atmosphere, 15 g of I-22, 15.3 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.3 g. (Yield 42%, Mass [M+] = 663)

[0660]

[0661] Preparation example of compound 10 (F-10)

[0662]

[0663] Synthesis of I-23

[0664] 20g of I-21, 5.3g of (2-hydroxyphenyl)boronic acid, 10.7g of K2CO3, 0.20g of [bis(tri-tert-butylphosphine)palladium(0)], 400mL of tetrahydrofuran, and 250mL of water were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 18g. (Yield 81%, Mass [M+] = 580)

[0665]

[0666] F-10 synthesis

[0667] Under a nitrogen atmosphere, 15 g of I-23, 17.3 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.1 g. (Yield 40%, Mass [M+] = 588)

[0668]

[0669] Preparation example of compound 11 (F-11)

[0670]

[0671] Synthesis of I-24

[0672] Under a nitrogen atmosphere, 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 44 g. (Yield 70%, Mass [M+] = 463)

[0673]

[0674] Synthesis of I-25

[0675] 20g of I-24, 9.2g of (2-(phenylamino)phenyl)boronic acid, 12g of K2CO3, 0.22g of [bis(tri-tert-butylphosphine)palladium(0)], 400mL of tetrahydrofuran, and 250mL of water were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 18g. (Yield 70%, Mass [M+]=596)

[0676]

[0677] F-11 composite

[0678] Under a nitrogen atmosphere, 15 g of I-25, 17 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.2 g. (Yield 40%, Mass [M+] = 604)

[0679]

[0680] Preparation example of compound 12 (F-12)

[0681]

[0682] Synthesis of I-26

[0683] Under a nitrogen atmosphere, 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 43 g. (Yield 68%, Mass [M+] = 463)

[0684]

[0685] Synthesis of I-27

[0686] 20g of I-26, 6.7g of (2-mercaptophenyl)boronic acid, 12g of K2CO3, 0.22g of [bis(tri-tert-butylphosphine)palladium(0)], 400mL of tetrahydrofuran, and 250mL of water were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 16g. (Yield 69%, Mass [M+]=537)

[0687]

[0688] F-12 composite

[0689] Under a nitrogen atmosphere, 15 g of I-26, 18.6 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.2 g. (Yield 41%, Mass [M+] = 545)

[0690]

[0691] Preparation example of compound 13 (F-13)

[0692]

[0693] Synthesis of I-28

[0694] Under a nitrogen atmosphere, 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 45 g. (Yield 72%, Mass [M+] = 463)

[0695]

[0696] Composite of I-29

[0697] 20g of I-28, 9.3g of (4-hydroxy-[1,1'-biphenyl]-3-yl)boronic acid, 12g of K2CO3, 0.22g of [bis(tri-tert-butylphosphine)palladium(0)], 400mL of tetrahydrofuran, and 250mL of water were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 16g. (Yield 62%, Mass [M+]=597)

[0698]

[0699] F-13 composite

[0700] Under a nitrogen atmosphere, 15 g of I-29, 16.7 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.4 g. (Yield 42%, Mass [M+] = 605)

[0701]

[0702] Preparation example of compound 14 (F-14)

[0703]

[0704] Synthesis of I-30

[0705] Under a nitrogen atmosphere, 30 g of 9-(3-bromo-5-chlorophenyl)-9H-carbazole, 20.6 g of N-phenyl-[1,1'-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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 34 g. (Yield 78%, Mass [M+] = 522)

[0706]

[0707] Synthesis of I-31

[0708] 20g of I-30, 8.2g of (2-(phenylamino)phenyl)boronic acid, 11g of K2CO3, 0.2g of [bis(tri-tert-butylphosphine)palladium(0)], 400mL of tetrahydrofuran, and 250mL of water were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 17g. (Yield 68%, Mass [M+]=655)

[0709]

[0710] F-14 composite

[0711] Under a nitrogen atmosphere, 15 g of I-31, 15.3 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.1 g. (Yield 40%, Mass [M+] = 663)

[0712]

[0713] Preparation example of compound 15 (F-15)

[0714]

[0715] Synthesis of I-32

[0716] 20g of I-30, 5.3g of (2-hydroxyphenyl)boronic acid, 11g of K2CO3, 0.2g of [bis(tri-tert-butylphosphine)palladium(0)], 400mL of tetrahydrofuran, and 250mL of water were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 16g. (Yield 72%, Mass [M+]=580)

[0717]

[0718] F-15 composite

[0719] Under a nitrogen atmosphere, 15 g of I-32, 17.3 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.5 g. (Yield 43%, Mass [M+] = 588)

[0720]

[0721] Preparation example of compound 16 (F-16)

[0722]

[0723] Synthesis of I-33

[0724] Under a nitrogen atmosphere, 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 43 g. (Yield 77%, Mass [M+] = 357)

[0725]

[0726] Synthesis of I-34

[0727] 20g of I-33, 21.3g of (4-(9H-carbazol-9-yl)-2-(phenylamino)phenyl)boronic acid, 15.5g of K2CO3, 0.3g of [bis(tri-tert-butylphosphine)palladium(0)], 400mL of tetrahydrofuran, and 250mL of water were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all of the solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 27g. (Yield 73%, Mass [M+]=655)

[0728]

[0729] F-16 composite

[0730] Under a nitrogen atmosphere, 15 g of I-34, 15.3 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.4 g. (Yield 42%, Mass [M+] = 663)

[0731]

[0732] Preparation example of compound 17 (F-17)

[0733]

[0734] Synthesis of I-35

[0735] 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(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all of the solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 23 g. (Yield 71%, Mass [M+] = 580)

[0736]

[0737] F-17 composite

[0738] Under a nitrogen atmosphere, 15 g of I-35, 17.3 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.2 g. (Yield 41%, Mass [M+] = 588)

[0739]

[0740] Preparation example of compound 18 (F-18)

[0741]

[0742] Synthesis of I-36

[0743] 20 g of I-33, 18 g of (4-(9H-carbazol-9-yl)-2-mercaptophenyl)boronic acid, 15.5 g of K2CO3, 0.29 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all of the solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 23 g. (Yield 69%, Mass [M+] = 596)

[0744]

[0745] F-18 composite

[0746] Under a nitrogen atmosphere, 15 g of I-36, 16.8 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.4 g. (Yield 41%, Mass [M+] = 604)

[0747]

[0748] Preparation example of compound 19 (F-19)

[0749]

[0750] Synthesis of I-37

[0751] Under a nitrogen atmosphere, 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 20 g. (Yield 80%, Mass [M+] = 446)

[0752]

[0753] Synthesis of I-38

[0754] 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all of the solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 24 g. (Yield 72%, Mass [M+]=745)

[0755]

[0756] F-19 composite

[0757] Under a nitrogen atmosphere, 15 g of I-38, 13.4 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.3 g. (Yield 42%, Mass [M+] = 753)

[0758]

[0759] Preparation example of compound 20 (F-20)

[0760]

[0761] Synthesis of I-39

[0762] I-37 20g, (4-(dibenzo[b,d]thiophen-1-yl)-2-(phenylamino)phenyl)boronic acid 17.8g, K2CO3 12.4g, [bis(tri-tert-butylphosphine)palladium(0)] 0.23g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 26g. (Yield 76%, Mass [M+]=761)

[0763]

[0764] F-20 composite

[0765] Under a nitrogen atmosphere, 15 g of I-39, 13.2 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.6 g. (Yield 44%, Mass [M+] = 769)

[0766]

[0767] Preparation example of compound 21 (F-21)

[0768]

[0769] I-40 Synthesis

[0770] Under a nitrogen atmosphere, 40 g of 1,3-dibromo-5-chlorobenzene, 49.5 g of 3-(9H-carbazol-9-yl)-N-phenylaniline, 0.75 g of [bis(tri-tert-butylphosphine)palladium(0)], 28.4 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 56 g. (Yield 72%, Mass [M+] = 525)

[0771]

[0772] Synthesis of I-41

[0773] I-40 30g, dibenzo[b,d]furan-1-ylboronic acid 12.2g, K2CO3 15.8g, [bis(tri-tert-butylphosphine)palladium(0)] 0.3g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 26g. (Yield 74%, Mass [M+]=612)

[0774]

[0775] Synthesis of I-42

[0776] 25g of I-41, 5.6g of (2-hydroxyphenyl)boronic acid, 11.3g of K2CO3, 0.2g of [bis(tri-tert-butylphosphine)palladium(0)], 400mL of tetrahydrofuran, and 250mL of water were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 21g. (Yield 77%, Mass [M+]=670)

[0777]

[0778] F-21 composite

[0779] Under a nitrogen atmosphere, 15 g of I-42, 14.9 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.5 g. (Yield 43%, Mass [M+] = 678)

[0780]

[0781] Preparation example of compound 22 (F-22)

[0782]

[0783] Synthesis of I-43

[0784] Under a nitrogen atmosphere, 40 g of 1,3-dibromo-5-chlorobenzene, 49.5 g of 4-(9H-carbazol-9-yl)-N-phenylaniline, 0.75 g of [bis(tri-tert-butylphosphine)palladium(0)], 28.4 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 55 g. (Yield 71%, Mass [M+] = 525)

[0785]

[0786] Synthesis of I-44

[0787] I-43 30g, dibenzo[b,d]furan-4-ylboronic acid 12.2g, K2CO3 15.8g, [bis(tri-tert-butylphosphine)palladium(0)] 0.3g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 28g. (Yield 80%, Mass [M+]=612)

[0788]

[0789] Composite of I-45

[0790] 25g of I-44, 6.3g of (2-mercaptophenyl)boronic acid, 11.3g of K2CO3, 0.2g of [bis(tri-tert-butylphosphine)palladium(0)], 400mL of tetrahydrofuran, and 250mL of water were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 22g. (Yield 79%, Mass [M+]=686)

[0791]

[0792] F-22 composite

[0793] Under a nitrogen atmosphere, 15 g of I-45, 14.6 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.2 g. (Yield 41%, Mass [M+] = 694)

[0794]

[0795] Preparation example of compound 23 (F-23)

[0796]

[0797] Synthesis of I-46

[0798] Under a nitrogen atmosphere, 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(tri-tert-butylphosphine)palladium(0)], 40.2 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 58 g. (Yield 53%, Mass [M+] = 522)

[0799]

[0800] Synthesis of I-47

[0801] I-46 30g, (4-(dibenzo[b,d]furan-1-yl)-2-hydroxyphenyl)boronic acid 17.5g, K2CO3 15.9g, [bis(tri-tert-butylphosphine)palladium(0)] 0.3g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 33g. (Yield 75%, Mass [M+]=746)

[0802]

[0803] F-23 composite

[0804] Under a nitrogen atmosphere, 15 g of I-47, 13.4 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.0 g. (Yield 40%, Mass [M+] = 754)

[0805]

[0806] Preparation example of compound 24 (F-24)

[0807]

[0808] Synthesis of I-48

[0809] Under a nitrogen atmosphere, 40 g of 1,3-dibromo-5-chlorobenzene, 40.7 g of 3-(9H-carbazol-9-yl)benzenethiol, 0.75 g of [bis(tri-tert-butylphosphine)palladium(0)], 28.4 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 49 g. (Yield 71%, Mass [M+] = 466)

[0810]

[0811] Composite of I-49

[0812] I-48 30g, dibenzo[b,d]furan-1-ylboronic acid 13.7g, K2CO3 17.8g, [bis(tri-tert-butylphosphine)palladium(0)] 0.33g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 27g. (Yield 76%, Mass [M+]=553)

[0813]

[0814] Synthesis of I-50

[0815] 25g of I-49, 6.3g of (2-hydroxyphenyl)boronic acid, 12.5g of K2CO3, 0.2g of [bis(tri-tert-butylphosphine)palladium(0)], 400mL of tetrahydrofuran, and 250mL of water were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 21g. (Yield 76%, Mass [M+]=611)

[0816]

[0817] F-24 composite

[0818] Under a nitrogen atmosphere, 15 g of I-50, 16.4 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.6 g. (Yield 43%, Mass [M+] = 619)

[0819]

[0820] Preparation example of compound 25 (F-25)

[0821]

[0822] Synthesis of I-51

[0823] 25g of I-49, 9.7g of (2-(phenylamino)phenyl)boronic acid, 12.5g of K2CO3, 0.2g of [bis(tri-tert-butylphosphine)palladium(0)], 400mL of tetrahydrofuran, and 250mL of water were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all of the solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 23g. (Yield 74%, Mass [M+]=686)

[0824]

[0825] F-25 composite

[0826] Under a nitrogen atmosphere, 15 g of I-51, 14.6 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.5 g. (Yield 43%, Mass [M+] = 694)

[0827]

[0828] Preparation example of compound 26 (F-26)

[0829]

[0830] Synthesis of I-52

[0831] Under a nitrogen atmosphere, 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 48 g. (Yield 70%, Mass [M+] = 611)

[0832]

[0833] Synthesis of I-53

[0834] I-52 30g, (2-(phenylamino)phenyl)boronic acid 10.5g, K2CO3 13.6g, [bis(tri-tert-butylphosphine)palladium(0)] 0.33g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 28g. (Yield 77%, Mass [M+] = 744)

[0835]

[0836] F-26 composite

[0837] Under a nitrogen atmosphere, 15 g of I-53, 13.4 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.6 g. (Yield 44%, Mass [M+] = 752)

[0838]

[0839] Preparation example of compound 27 (F-27)

[0840]

[0841] Synthesis of I-54

[0842] Under a nitrogen atmosphere, 40 g of 9-(3-bromo-5-chlorophenyl)-9H-carbazole, 19 g of diphenylamine, 0.6 g of [bis(tri-tert-butylphosphine)palladium(0)], 21.6 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 37 g. (Yield 74%, Mass [M+] = 446)

[0843]

[0844] Composite of I-55

[0845] I-54 30g, (4-(9H-carbazol-9-yl)-2-(phenylamino)phenyl)boronic acid 25.5g, K2CO3 18.6g, [bis(tri-tert-butylphosphine)palladium(0)] 0.33g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 35g. (Yield 70%, Mass [M+]=744)

[0846]

[0847] F-27 composite

[0848] Under a nitrogen atmosphere, 15 g of I-55, 13.4 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.2 g. (Yield 41%, Mass [M+] = 752)

[0849]

[0850] Preparation example of compound 28 (F-28)

[0851]

[0852] Synthesis of I-56

[0853] Under a nitrogen atmosphere, 40 g of 1-bromo-3-chlorobenzene, 70 g of 3-(9H-carbazol-9-yl)-N-phenylaniline, 1.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 50.2 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 66 g. (Yield 71%, Mass [M+] = 446)

[0854]

[0855] Synthesis of I-57

[0856] I-56 30g, (5-(9H-carbazol-9-yl)-2-(phenylamino)phenyl)boronic acid 25.5g, K2CO3 18.6g, [bis(tri-tert-butylphosphine)palladium(0)] 0.33g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 36g. (Yield 72%, Mass [M+]=744)

[0857]

[0858] F-28 composite

[0859] Under a nitrogen atmosphere, 15 g of I-57, 13.4 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.7 g. (Yield 43%, Mass [M+] = 752)

[0860]

[0861] Preparation example of compound 29 (F-29)

[0862]

[0863] Synthesis of I-58

[0864] Under a nitrogen atmosphere, 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(tri-tert-butylphosphine)palladium(0)], 22 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 49 g. (Yield 72%, Mass [M+]=611)

[0865]

[0866] Composite of I-59

[0867] I-58 30g, (2-hydroxyphenyl)boronic acid 6.8g, K2CO3 13.6g, [bis(tri-tert-butylphosphine)palladium(0)] 0.25g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 25g. (Yield 76%, Mass [M+] = 669)

[0868]

[0869] F-29 composite

[0870] Under a nitrogen atmosphere, 15 g of I-59, 15 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.6 g. (Yield 43%, Mass [M+] = 677)

[0871]

[0872] Preparation example of compound 30 (F-30)

[0873]

[0874] I-60 composite

[0875] Under a nitrogen atmosphere, 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 38 g. (Yield 76%, Mass [M+] = 446)

[0876]

[0877] Synthesis of I-61

[0878] 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all the solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 33 g. (Yield 72%, Mass [M+] = 685)

[0879]

[0880] F-30 composite

[0881] Under a nitrogen atmosphere, 15 g of I-61, 15 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.8 g. (Yield 45%, Mass [M+] = 693)

[0882]

[0883] Preparation example of compound 31 (F-31)

[0884]

[0885] Synthesis of I-62

[0886] Under a nitrogen atmosphere, 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 58 g. (Yield 72%, Mass [M+] = 387)

[0887]

[0888] Synthesis of I-63

[0889] I-62 30g, (5-(9H-carbazol-9-yl)-2-mercaptophenyl)boronic acid 24.8g, K2CO3 21.5g, [bis(tri-tert-butylphosphine)palladium(0)] 0.4g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 34g. (Yield 70%, Mass [M+] = 626)

[0890]

[0891] F-31 composite

[0892] Under a nitrogen atmosphere, 15 g of I-63, 16 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solution was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.5 g. (Yield 43%, Mass [M+] = 634)

[0893]

[0894] Preparation example of compound 32 (F-32)

[0895]

[0896] Synthesis of I-64

[0897] Under a nitrogen atmosphere, 40 g of 1,3-dibromo-5-chlorobenzene, 49.5 g of 3-(9H-carbazol-9-yl)-N-phenylaniline, 0.8 g of [bis(tri-tert-butylphosphine)palladium(0)], 28 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 57 g. (Yield 72%, Mass [M+] = 534)

[0898]

[0899] Composite of I-65

[0900] I-64 30g, 2-tribenzodibenzofuran boronic acid 17g, K2CO3 15.6g, [bis(tri-tert-butylphosphine)palladium(0)] 0.3g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 28g. (Yield 71%, Mass [M+] = 702)

[0901]

[0902] Synthesis of I-66

[0903] 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all of the solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 22 g. (Yield 74%, Mass [M+] = 835)

[0904]

[0905] F-32 composite

[0906] Under a nitrogen atmosphere, 15 g of I-66, 12 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.6 g. (Yield 44%, Mass [M+] = 843)

[0907]

[0908] Preparation example of compound 33 (F-33)

[0909]

[0910] Synthesis of I-67

[0911] I-64 30g, 1-tribenzodibenzofuran boronic acid 17g, K2CO3 15.6g, [bis(tri-tert-butylphosphine)palladium(0)] 0.3g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 29g. (Yield 73%, Mass [M+] = 702)

[0912]

[0913] Composite of I-68

[0914] I-67 25g, (2-(phenylamino)phenyl)boronic acid 4.92g, K2CO3 9.9g, [bis(tri-tert-butylphosphine)palladium(0)] 0.2g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 21g. (Yield 78%, Mass [M+]=760)

[0915]

[0916] F-33 ​​composite

[0917] Under a nitrogen atmosphere, 15 g of I-68, 13.2 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.7 g. (Yield 44%, Mass [M+] = 768)

[0918]

[0919] Preparation example of compound 34 (F-34)

[0920]

[0921] Composite of I-69

[0922] I-60 25g, (2-hydroxy-5-(indolo[3,2,1-jk]carbazol-2-yl)phenyl)boronic acid 21.2g, K2CO3 15.5g, [bis(tri-tert-butylphosphine)palladium(0)] 0.3g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 26g. (Yield 62%, Mass [M+]=743)

[0923]

[0924] F-34 composite

[0925] Under a nitrogen atmosphere, 15 g of I-69, 13.5 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.1 g. (Yield 40%, Mass [M+] = 751)

[0926]

[0927] Preparation example of compound 35 (F-35)

[0928]

[0929] I-70 composite

[0930] Under a nitrogen atmosphere, 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 58 g. (Yield 67%, Mass [M+]=776)

[0931]

[0932] Synthesis of I-71

[0933] I-70 30g, (2-hydroxyphenyl)boronic acid 5.3g, K2CO3 10.7g, [bis(tri-tert-butylphosphine)palladium(0)] 0.2g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 22g. (Yield 68%, Mass [M+] = 834)

[0934]

[0935] F-35 composite

[0936] Under a nitrogen atmosphere, 15 g of I-71, 12 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6 g. (Yield 40%, Mass [M+] = 842)

[0937]

[0938] Preparation example of compound 36 (F-36)

[0939]

[0940] Synthesis of I-72

[0941] Under a nitrogen atmosphere, 30 g of 3-bromo-5-chloro-1,1':3',1''-terphenyl-2,2',2'',3'',4',4'',5',5'',6,6',6''-d11, 36.4 g of 2'-(9H-carbazol-9-yl-d8)-N-(phenyl-d5)-[1,1'-biphenyl]-2,3,3',4',5',6,6'-d7-4-amine, 0.43 g of [bis(tri-tert-butylphosphine)palladium(0)], 16.3 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated to reflux, and stirred for 8 hours. After completion of the reaction, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 43 g (yield 72%, Mass [M+]=705).

[0942]

[0943] Synthesis of I-73

[0944] I-72 30g, (2-((phenyl-d5)amino)phenyl-3,4,5,6-d4)boronic acid 9.4g, K2CO3 11.7g, [bis(tri-tert-butylphosphine)palladium(0)] 0.2g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 23g. (Yield 64%, Mass [M+]=847)

[0945]

[0946] F-36 composite

[0947] Under a nitrogen atmosphere, 15 g of I-73, 12 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.1 g. (Yield 40%, Mass [M+] = 855)

[0948]

[0949] Preparation example of compound 37 (F-37)

[0950]

[0951] Composite of I-74

[0952] Under a nitrogen atmosphere, 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 27 g. (Yield 76%, Mass [M+]=645)

[0953]

[0954] Composite of I-75

[0955] 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, all of the solvent was removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 24 g. (Yield 65%, Mass [M+] = 956)

[0956]

[0957] F-37 composite

[0958] Under a nitrogen atmosphere, 15 g of I-75, 10.5 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.6 g. (Yield 44%, Mass [M+] = 964)

[0959]

[0960] Preparation example of compound 38 (F-38)

[0961]

[0962] Synthesis of I-76

[0963] Under a nitrogen atmosphere, 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 were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 33 g. (Yield 63%, Mass [M+] = 481)

[0964]

[0965] Synthesis of I-77

[0966] I-76 25g, ((2-((phenyl-d5)amino)phenyl-3,4,5,6-d4)boronic acid 11.6g, K2CO3 14.4g, [bis(tri-tert-butylphosphine)palladium(0)] 0.3g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4(anhydrous), and filtered. The filtered solution was recrystallized to obtain 23g. (Yield 71%, Mass [M+]=623)

[0967]

[0968] F-38 composite

[0969] Under a nitrogen atmosphere, 15 g of I-77, 16 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.6 g. (Yield 43%, Mass [M+] = 631)

[0970]

[0971] Preparation example of compound 39 (F-39)

[0972]

[0973] Synthesis of I-78

[0974] Under a nitrogen atmosphere, 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(tri-tert-butylphosphine)palladium(0)], 16 g of sodium-tert-butoxide, and 600 mL of toluene were added, heated to reflux, and stirred for 8 hours. After completion of the reaction, the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 45 g. (Yield 67%, Mass [M+]=818)

[0975]

[0976] Synthesis of I-79

[0977] I-78 25g, (2-hydroxyphenyl-3,4,5,6-d4)boronic acid 4.3g, K2CO3 8.5g, [bis(tri-tert-butylphosphine)palladium(0)] 0.2g, tetrahydrofuran 400mL, and water 250mL were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, dissolved in toluene, and the reaction solution was separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to obtain 19g. (Yield 71%, Mass [M+] = 880)

[0978]

[0979] F-39 composite

[0980] Under a nitrogen atmosphere, 15 g of I-79, 11.4 g of boron triiodide, and 300 mL of dichlorobenzene were added, heated to reflux, and stirred for 8 hours. After the reaction was completed, the product was poured into water, separated, treated with MgSO4 (anhydrous), and filtered. The filtered solution was removed and recrystallized to obtain 6.1 g. (Yield 40%, Mass [M+] = 888)

[0981]

[0982] <Examples and Comparative Examples>

[0983] Example 1

[0984] A glass substrate coated with an 800Å thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent was a Fischer Co. product, and the distilled water was secondarily filtered through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

[0985] On the ITO transparent electrode prepared in this way, a hole injection layer was formed by thermal vacuum depositing a compound of the following compound HT1 and the following compound HI1 at a ratio of 95:5 (molar ratio) to a thickness of 100 Å. On the hole injection layer, a hole transport layer was formed by vacuum depositing a compound represented by the following chemical formula HT1 (300 Å). Subsequently, an electron blocking layer was formed by vacuum depositing a compound of BH (p-type) at a film thickness of 50 Å on the hole transport layer. Subsequently, a compound in which the following chemical formula BH (p-type) and the compound 1 (n-type) synthesized in Preparation Example 1 were mixed in a 1:1 ratio as a host for the light emitting layer and a compound represented by the following chemical formula BD as a dopant for the light emitting layer were vacuum deposited at a weight ratio of 86:14 on the electron blocking layer to form a light emitting layer. A hole blocking layer was formed by vacuum-depositing the compound 1 (n-type) synthesized in Manufacturing Example 1 with a film thickness of 50 Å on the light-emitting layer. Subsequently, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 Å. Lithium fluoride (LiF) with a thickness of 10 Å and aluminum with a thickness of 800 Å were sequentially deposited on the electron injection and transport layer to form a cathode.

[0986]

[0987] In the above process, the deposition rate of organic materials was maintained at 0.4 to 0.7 Å / sec, lithium fluoride of the cathode was maintained at 0.3 Å / sec, and aluminum was maintained at 2 Å / sec, and the vacuum during deposition was 2ⅹ10 -7 ~ 5ⅹ10 -6 Torr was maintained, and an organic light-emitting device was fabricated.

[0988]

[0989] Examples 2 to 39

[0990] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound described in Table 1 below was used instead of Compound 1 as the host of the light-emitting layer in Example 1.

[0991]

[0992]

[0993] Comparative Examples 1 to 6

[0994] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound described in Table 1 below was used instead of Compound 1 as the host of the light-emitting layer in Example 1.

[0995]

[0996]

[0997] When current was applied to the organic light-emitting devices manufactured in Examples 1 to 39 and Comparative Examples 1 to 6, voltage, efficiency, and lifespan were measured (based on 1600 nit), and the results are shown in Table 1 below. Lifespan T90 refers to the time required for the luminance to decrease to 90% of the initial luminance (1600 nit).

[0998] Host compound voltage (V)@10mA / cm 2 Luminous efficacy (Cd / A) @10mA / cm 2Lifespan, T90(h)Example 1 Compound 1(F-1) 3.8423.3116Example 2 Compound 2(F-2) 3.8223.4117Example 3 Compound 3(F-3) 3.8323.2115Example 4 Compound 4(F-4) 3.8723.3118Example 5 Compound 5(F-5) 3.8423.5119Example 6 Compound 6(F-6) 3.8323.4118Example 7 Compound 7(F-7) 3.8223.3119Example 8 Compound 8(F-8) 3.8523.1118Example 9 Compound 9(F-9)3.7922.8122Example 10 Compound 10(F-10)3.7822.9122Example 11 Compound 11(F-11)3.7922.7123Example 12 Compound 12(F-12)3.7922.8121Example 13 Compound 13(F-13)3.7822.8124Example 14 Compound 14(F-14)3.8022.9122Example 15 Compound 15(F-15)3.7923.0124Example 16 Compound 16(F-16)3.7822.9123Example 17 Compound 17(F-17)3.7922.8124Example 18 Compound 18(F-18)3.8022.9124Example 19 Compound 19(F-19)3.8223.5127Example 20 Compound 20(F-20)3.8424.2126Example 21 Compound 21(F-21)3.8424.1128Example 22 Compound 22(F-22)3.8323.7127Example 23 Compound 23(F-23)3.8223.7129Example 24 Compound 24(F-24)3.8423.8128Example 25 Compound 25(F-25)3.8424.2129Example 26 Compound 26(F-26)3.7923.9128Example 27 Compound 27(F-27)3.8023.8129Example 28 Compound 28(F-28)3.7923.9128Example 29 Compound 29(F-29)3.7923.9128Example 30 Compound 30(F-30)3.8024.1129Example 31 Compound 31(F-31)3.7823.8128Example 32 Compound 32(F-32)3.8223.9127Example 33 Compound 33(F-33)3.8124.0129Example 34 Compound 34(F-34)3.8123.9125Example 35 Compound 35(F-35)3.8223.9126 Example 36 Compound 36 (F-36) 3.7 922.9166 Example 37 Compound 37 (F-37) 3.8 3 23.4 159 Example 38 Compound 38 (F-38) 3.8 0 23.3 162 Example 39 Compound 39 (F-39) 3.8 2 23.5 165 Comparative Example 1 BH 1 4.3 2 17.192 Comparative Example 2 BH 2 4.3 1 17.591 Comparative Example 3 BH 3 4.3 1 17.485 Comparative Example 4 BH 4 4.3 3 17.489 Comparative Example 5 BH 5 4.3 7 18.288 Comparative Example 6 BH 6 4.3 2 17.782.

[0999]

[1000] In the case of compounds BH1 to BH5 used in the organic light-emitting devices of Comparative Examples 1 to 5, one of the benzene rings connected to the boron of the core structure has a substituted structure, and as the benzene ring becomes unstable due to the electron-withdrawing property of boron, the lifespan reduction characteristic increases. As the lifespan reduction characteristic increases, it can be confirmed through Table 1 that the voltage increases and the efficiency decreases.

[1001] In addition, it can be confirmed that the organic light-emitting device of Comparative Example 6, which uses the compound BH6 in which none of the benzene rings connected to the boron of the core structure is substituted, exhibits the lowest lifespan characteristics because the compound is structurally unstable.

[1002] However, in the case of the compound according to the chemical formula 1 of the present invention, at least one of the benzene rings directly or indirectly connected to the boron of the core structure is substituted with a carbazole group, and at least one of the remaining rings is substituted with an aryl group, a silyl group, or a heterocyclic group, thereby stabilizing the unstable structure and playing a role in adding hole characteristics, thereby increasing the lifespan characteristic. That is, due to the structural stability of the compound, the voltage decreases and the efficiency increases at high currents.

[1003]

[1004] [Explanation of symbols]

[1005] 1: Substrate

[1006] 2: First electrode

[1007] 3: Hole injection layer

[1008] 4: Hole transport layer

[1009] 5: Electron blocking layer

[1010] 6: Emissive layer

[1011] 7: Hole blocking layer

[1012] 8: Electron injection and transport layer

[1013] 9: Second electrode

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X is NR; or S, Y is NR'; O; or S, R and R' are the same or different and each independently represent 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 or different from each other, and each independently represents 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 or different and are 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 carbazole 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 integers from 1 to 4, respectively, n3 and m3 are integers from 1 to 3, respectively, When the above n1 to n3 and m1 to m3 are each 2 or more, the substituents in the parentheses are each the same or different, n1+m1 is less than or equal to 4, n2+m2 is less than or equal to 4, and n3+m3 is less than or equal to 3.

2. In claim 1, A compound wherein the above L1 to L3 and L11 to L33 are the same or different from each other, and each independently represents 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 at least one of N, O, and S as a heteroatom.

3. In claim 1, A compound wherein L1 to L3 are the same as or different from each other, and each independently represents a direct bond; a phenylene group substituted or unsubstituted with deuterium; a divalent dibenzofuran group substituted or unsubstituted with deuterium; a divalent dibenzothiophene group substituted or unsubstituted with deuterium; or a divalent carbazole group substituted or unsubstituted with deuterium.

4. In claim 1, A compound wherein the above L11 to L33 are the same as or different from each other, and each independently represents a direct bond; a phenylene group substituted or unsubstituted with deuterium; or a divalent carbazole group substituted or unsubstituted with deuterium.

5. In claim 1, wherein R1 to R3 and R11 to R33 are the same as or different from each other, and each independently represent 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, and at least one of R1 to R3 is a substituted or unsubstituted carbazole 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 compound which is a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

6. In claim 1, A compound wherein at least one of R11 to R33 is a triphenylsilyl group substituted or unsubstituted with deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a carbazole group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a dibenzothiophene group substituted or unsubstituted with deuterium; or a heterocyclic group comprising at least one of N and O as a heteroatom, wherein 4 to 7 rings are condensed, and wherein the remaining atoms are the same or different and are each independently hydrogen; or deuterium.

7. In claim 1, The above chemical formula 1 is a compound represented by any one of the following chemical formulas 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 the above chemical formulas 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 those in the chemical formula 1 above, G1 to G3 are the same or different and are 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, g1 to g3 are each integers from 1 to 8, and when g1 to g3 are each 2 or greater, G1 to G3 are each equal to or different from each other.

8. In claim 1, The above chemical formula 1 is a compound represented by any one of the following compounds: .

9. An organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 8.

10. In claim 9, An organic light-emitting device wherein the organic layer comprises at least one of an electron injection layer, an electron transport layer, an electron injection and transport layer, and a hole blocking layer, and wherein at least one of the electron injection layer, the electron transport layer, the electron injection and transport layer, and the hole blocking layer comprises the compound.

11. In claim 9, An organic light-emitting device wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

12. In claim 9, An organic light-emitting device wherein the organic layer includes a light-emitting layer, the light-emitting layer includes the compound as an n-type host, and further includes a p-type host.

13. In claim 9, An organic light-emitting device wherein the organic layer includes a hole-blocking layer, and the hole-blocking layer includes the compound.

14. In claim 9, An organic light-emitting device wherein the organic layer includes a light-emitting layer and a hole-blocking layer, and the light-emitting layer and the hole-blocking layer include the compound.

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