Compound and organic light-emitting device containing the same

Abstract

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

Description

[Technical Field]

[0001] This application claims the benefit of the filing dates 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 including the same. [Background technology]

[0003] Generally, organic light-emitting devices (OLEDs) use organic materials to convert electrical energy into light energy. Organic light-emitting devices typically have a structure including an anode, a cathode, and an organic material layer between them. To enhance the efficiency and stability of the OLEDs, the organic material layer often has a multilayer structure composed of different materials, such as a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in such an OLED, holes are injected from the anode and electrons are injected from the cathode into the organic material layer. The injected holes and electrons combine to form excitons, which then emit light when they return to their ground state.

[0004] There is a continuing need to develop new materials for such organic light-emitting devices. Summary of the Invention [Problem to be solved by the invention]

[0005] The present specification provides a compound and an organic light-emitting device including the same. [Means for solving the problem]

[0006] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1: [Chemical formula 1] [ka] 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 and each independently represent 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 each independently represent 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 each an integer of 1 to 4, n3 and m3 are each an integer of 1 to 3, When n1 to n3 and m1 to m3 are each 2 or more, the substituents in the parentheses are the same or different from each other, n1+m1 is 4 or less, n2+m2 is 4 or less, and n3+m3 is 3 or less.

[0007] Furthermore, one embodiment of the present specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. [Effects of the Invention]

[0008] The compounds described herein can be used as materials for the organic layer of an organic light-emitting device. The compounds according to at least one embodiment of the present invention can improve the efficiency, reduce the driving voltage, and / or improve the lifespan characteristics of the organic light-emitting device. In particular, the compounds described herein can be used as light-emitting or hole-blocking materials. [Brief explanation of the drawings]

[0009] [Figure 1] 1 shows 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 laminated in this order. [Figure 2] This shows 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, an emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a second electrode 9 are sequentially stacked. DETAILED DESCRIPTION OF THE INVENTION

[0010] The present specification will be explained in more detail below.

[0011] In this specification, when a part is said to "comprise" a certain component, this does not mean that it excludes other components, but that it may further include other components, unless otherwise specified.

[0012] In this specification, when a member is said to be located "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member is present between the two members.

[0013] In this specification, " [ka] " or dotted line denotes a point of attachment to a chemical formula or compound.

[0014] As used herein, "N% deuterium substitution" means that N% of the available hydrogen atoms in the structure are substituted with deuterium atoms. For example, "25% deuterium substitution" in dibenzofuran means that two of the eight hydrogen atoms in dibenzofuran are substituted with deuterium atoms.

[0015] In this specification, the degree of deuteration can be confirmed by known methods such as nuclear magnetic resonance spectroscopy ( 1 H NMR) and GC / MS.

[0016] In this specification, examples of the substituents are described below, but are not limited to these.

[0017] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different.

[0018] As used herein, the term "substituted or unsubstituted" means that the group is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a silyl group, an alkyl group, a cycloalkyl group, an arylalkyl group, an aryl group, and a heterocyclic group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or has no substituents.

[0019] As used herein, the term "substituted or unsubstituted" means that the group is substituted with one or more substituents selected from the group consisting of deuterium; a silyl group; an alkyl group; an aryl group; and a heterocyclic group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked together, or has no substituents at all.

[0020] Examples of the substituents are described below, but are not limited to these.

[0021] As used herein, examples of halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0022] As used herein, a silyl group is —SiY a Y b Y c and the Y a , Y b , and Y c may each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are 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.

[0023] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms 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, and an n-octyl group.

[0024] In this specification, the same explanation as for the alkyl group as described above may be applied to the arylalkyl group, except that the arylalkyl group is substituted with an aryl group.

[0025] The alkyl groups and other alkyl moiety-containing substituents described herein include either straight-chain or branched-chain alkyl groups.

[0026] In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples of the cycloalkyl group 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.

[0027] In this 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 another 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 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 linked. Examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and a quaterphenyl group. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and a triphenylenyl group.

[0028] In this specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure, in which case the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

[0029] When the fluorenyl group is substituted, [ka] , [ka] , [ka] Spirofluorenyl groups such as [ka] (9,9-dimethylfluorenyl group), and [ka] The fluorenyl group may be a substituted fluorenyl group such as, but not limited to, a 9,9-diphenylfluorenyl group.

[0030] In this specification, a heterocyclic group is a cyclic group containing one or more heteroatoms selected from N, O, P, S, Si, and Se, and although the number of carbon atoms is not particularly limited, it is preferably 2 to 60. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. According to another embodiment, the number of carbon atoms in the heterocyclic group is 2 to 20. Examples of heterocyclic groups 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, and a triazinyl group.

[0031] In this specification, the heteroaryl group may be the same as the heterocyclic group described above, except that the heteroaryl group is aromatic.

[0032] In this specification, the same explanation as for the aryl group may be applied to the arylene group, except that the arylene group is divalent.

[0033] In this specification, the same explanation as for the heterocyclic group as above may be applied to the divalent heterocyclic group, except that it is divalent.

[0034] As used herein, the term "ring" refers to a substituted or unsubstituted ring formed by bonding adjacent groups to each other, and refers to a hydrocarbon ring or a hetero ring.

[0035] As used herein, the term "ring fused with N rings" refers to a ring fused with N monocyclic rings, where the monocyclic rings may be pentagonal or hexagonal, and N is an integer of 1 or greater. Examples of rings fused with N 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.

[0036] The hydrocarbon ring may be an aromatic, aliphatic, or fused aromatic and aliphatic ring, and may be selected from the exemplified cycloalkyl or aryl groups.

[0037] As used herein, "forming a ring by bonding with adjacent groups" means that adjacent groups bond with each other to form 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 fused ring thereof. The hydrocarbon ring refers to a ring consisting only of carbon and hydrogen atoms. The heterocycle refers to a ring containing one or more elements selected from N, O, P, S, Si, and Se. As used herein, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle may be monocyclic or polycyclic.

[0038] In this specification, the term "aliphatic hydrocarbon ring" refers to a non-aromatic ring consisting only of carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.

[0039] In this specification, the term "aromatic hydrocarbon ring" refers to an aromatic ring consisting of only 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, spirofluorene, etc. In this specification, the term "aromatic hydrocarbon ring" can be interpreted as meaning the same as an aryl group.

[0040] As used herein, the term "aliphatic heterocycle" refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocane, and thiocane.

[0041] In the present specification, the term "aromatic heterocycle" refers to an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include, but are not limited to, 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, triazaindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, and indenocarbazole.

[0042] Preferred embodiments of the present invention will be described in detail below. 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.

[0043] 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 properties. When the compound represented by Chemical Formula 1 is applied to an organic light emitting device, an organic light emitting device having high efficiency, low voltage, and / or long life properties can be obtained.

[0044] Chemical Formula 1 will be described in detail below. [Chemical formula 1] [ka] 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 and each independently represent 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 each independently represent 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 each an integer of 1 to 4, n3 and m3 are each an integer of 1 to 3, When n1 to n3 and m1 to m3 are each 2 or more, the substituents in the parentheses are the same or different from each other, n1+m1 is 4 or less, n2+m2 is 4 or less, and n3+m3 is 3 or less.

[0045] In one embodiment herein, X is NR and Y is NR'.

[0046] In one embodiment herein, X is NR and Y is O.

[0047] In one embodiment herein, X is NR and Y is S.

[0048] In one embodiment herein, X is S and Y is NR'.

[0049] In one embodiment herein, X is S and Y is O.

[0050] In one embodiment herein, X is S and Y is S.

[0051] In one embodiment of the present specification, R and R' are the same or different and each independently represent 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.

[0052] In one embodiment of the present specification, R and R' are the same or different and each independently represent 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.

[0053] In one embodiment of the present specification, R and R' are the same or different and each independently represent 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.

[0054] In one embodiment of the present specification, R and R' are the same or different and each independently represent 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.

[0055] In one embodiment of the present invention, R and R' are the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0056] In one embodiment of the present specification, R and R' are the same or different and each independently represent hydrogen; deuterium; an alkyl group having 1 to 10 carbon atoms and being unsubstituted or substituted with deuterium; or an aryl group having 6 to 12 carbon atoms and being unsubstituted or substituted with deuterium.

[0057] In one embodiment of the present specification, R and R' are the same or different and each independently represent 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.

[0058] In one embodiment of the present invention, R and R' are the same or different and each independently represent hydrogen; deuterium; or a phenyl group unsubstituted or substituted with deuterium.

[0059] In one embodiment of the present invention, R and R' are the same or different and each independently represent hydrogen; deuterium; or a phenyl group.

[0060] In one embodiment of the present invention, R and R' are the same or different and each independently represent a hydrogen atom or a phenyl group.

[0061] In one embodiment of the present specification, R and R' are the same or different and each independently represent a phenyl group; or a deuterium-substituted phenyl group.

[0062] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same or different and each independently represent a direct bond; an arylene group; or a divalent heterocyclic group.

[0063] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same or different and each independently represent 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.

[0064] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same or different and each independently represent 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.

[0065] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same or different and each independently represent 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 and containing one or more heteroatoms selected from N, O, S, and Si.

[0066] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same or different and each independently represent 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 and containing one or more heteroatoms selected from N, O, and S.

[0067] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same or different and each independently represent 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.

[0068] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same or different and each independently represent a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted divalent dibenzofuran group; or a substituted or unsubstituted divalent carbazole group.

[0069] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same or different and each independently represent a direct bond; an arylene group having 6 to 20 carbon atoms and substituted or unsubstituted with deuterium; or a divalent heterocyclic group having 2 to 20 carbon atoms and substituted or unsubstituted with deuterium.

[0070] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same or different and each independently represent a direct bond; an arylene group having 6 to 20 carbon atoms and substituted or unsubstituted with deuterium; or a divalent heterocyclic group having 2 to 20 carbon atoms and substituted or unsubstituted with deuterium, which contains one or more heteroatoms selected from N, O, and S.

[0071] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same or different and each independently represent a direct bond; a deuterium-substituted or unsubstituted phenylene group; a deuterium-substituted or unsubstituted biphenylene group; a deuterium-substituted or unsubstituted naphthalene group; a deuterium-substituted or unsubstituted divalent dibenzofuran group; a deuterium-substituted or unsubstituted divalent dibenzothiophene group; or a deuterium-substituted or unsubstituted divalent carbazole group.

[0072] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same or different and each independently represent a direct bond; a deuterium-substituted or unsubstituted phenylene group; a deuterium-substituted or unsubstituted divalent dibenzofuran group; or a deuterium-substituted or unsubstituted divalent carbazole group.

[0073] In one embodiment of the present specification, L1 to L3 and L11 to L33 are the same or different and each independently represent a direct bond; a phenylene group; a divalent dibenzofuran group; or a divalent carbazole group.

[0074] In one embodiment of the present specification, L1 to L3 are the same or different and each independently represent 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.

[0075] In one embodiment of the present specification, L1 to L3 are the same or different and each independently represent a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted divalent carbazole group.

[0076] In one embodiment of the present specification, L1 to L3 are the same or different and each independently represent a direct bond; a deuterium-substituted or unsubstituted phenylene group; a deuterium-substituted or unsubstituted divalent dibenzofuran group; a deuterium-substituted or unsubstituted divalent dibenzothiophene group; or a deuterium-substituted or unsubstituted divalent carbazole group.

[0077] In one embodiment of the present specification, L1 to L3 are the same or different and each independently represent a direct bond; a deuterium-substituted or unsubstituted phenylene group; or a deuterium-substituted or unsubstituted divalent carbazole group.

[0078] In one embodiment of the present specification, L1 to L3 are the same or different and each independently represent a direct bond; a phenylene group; a divalent dibenzofuran group; a divalent dibenzothiophene group; or a divalent carbazole group.

[0079] In one embodiment of the present specification, L1 to L3 are the same or different and each independently represent a direct bond; a phenylene group; or a divalent carbazole group.

[0080] In one embodiment of the present specification, L11 to L33 are the same or different and each independently represent a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted divalent carbazole group.

[0081] In one embodiment of the present specification, L11 to L33 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted phenylene group.

[0082] In one embodiment of the present specification, L11 to L33 are the same or different and each independently represent a direct bond; a phenylene group substituted or unsubstituted with deuterium; or a divalent carbazole group substituted or unsubstituted with deuterium.

[0083] In one embodiment of the present specification, L11 to L33 are the same or different and each independently represent a direct bond; or a phenylene group unsubstituted or substituted with deuterium.

[0084] In one embodiment of the present specification, L11 to L33 are the same or different and each independently represent a direct bond; a phenylene group; or a divalent carbazole group.

[0085] In one embodiment of the present specification, L11 to L33 are the same or different and each independently represent a direct bond or a phenylene group.

[0086] In one embodiment of the present specification, R1 to R3 and R11 to R33 are the same or different 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.

[0087] In one embodiment of the present specification, R1 to R3 and R11 to R33 are the same or different 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 substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0088] In one embodiment of the present specification, R1 to R3 and R11 to R33 are the same or different and each independently represent hydrogen; deuterium; a deuterium-substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms; a deuterium-substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; a deuterium-substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a deuterium-substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a deuterium-substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or deuterium. at least one of R1 to R3 is a deuterium-substituted or unsubstituted carbazole group; and at least one of R11 to R33 is a deuterium-substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms; a deuterium-substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; a deuterium-substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a deuterium-substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0089] In one embodiment of the present specification, R1 to R3 and R11 to R33 are the same or different and each independently represent 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.

[0090] In one embodiment of the present specification, at least one of R1 to R3 is a substituted or unsubstituted carbazole group, and the rest are the same or different and each independently hydrogen or deuterium.

[0091] 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.

[0092] In one embodiment of the present specification, one or two of R1 to R3 is a substituted or unsubstituted carbazole group.

[0093] In one embodiment of the present specification, R1 to R3 are all substituted or unsubstituted carbazole groups.

[0094] 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 rest are the same or different and each independently hydrogen or deuterium.

[0095] 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.

[0096] In one embodiment of the present specification, R1 to R3 are all carbazole groups which are unsubstituted or substituted with deuterium.

[0097] In one embodiment of the present specification, at least one of R1 to R3 is a carbazole group, and the rest are the same or different and each independently hydrogen or deuterium.

[0098] In one embodiment of the present specification, at least two of R1 to R3 are carbazole groups, and the rest are hydrogen or deuterium.

[0099] 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 rest are the same or different and each independently represent hydrogen or deuterium.

[0100] 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 or different and each independently represent hydrogen or deuterium.

[0101] 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 containing one or more heteroatoms selected from N, O, and S, and the remainders are the same or different and each independently represent hydrogen or deuterium.

[0102] 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 one or more N and O as heteroatoms and having four or more fused rings, and the remainders are the same or different and each independently represent hydrogen or deuterium.

[0103] 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 one or more N and O as heteroatoms and having 4 to 7 fused rings, and the remainders are the same or different and each independently represent hydrogen or deuterium.

[0104] 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 one or more N and O as heteroatoms and having 5 or 7 condensed rings, and the remainders are the same or different and each independently represent hydrogen or deuterium.

[0105] In one embodiment of the present specification, at least one of R11 to R33 is a deuterium-substituted or unsubstituted silyl group; a deuterium-substituted or unsubstituted aryl group; or a deuterium-substituted or unsubstituted heterocyclic group, and the rest are the same or different and each independently represent hydrogen or deuterium.

[0106] In one embodiment of the present specification, at least one of R11 to R33 is a deuterium-substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms; a deuterium-substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; a deuterium-substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a deuterium-substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, and the rest are the same or different and each independently represent hydrogen or deuterium.

[0107] In one embodiment of the present specification, at least one of R11 to R33 is a deuterium-substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms; a deuterium-substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; a deuterium-substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a deuterium-substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms and containing one or more heteroatoms selected from N, O, and S, and the remainders are the same or different and each independently represent hydrogen or deuterium.

[0108] In one embodiment of the present specification, at least one of R11 to R33 is a deuterium-substituted or unsubstituted triphenylsilyl group; a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; a deuterium-substituted or unsubstituted terphenyl group; a deuterium-substituted or unsubstituted naphthyl group; a deuterium-substituted or unsubstituted phenanthrenyl group; a deuterium-substituted or unsubstituted carbazole group; a deuterium-substituted or unsubstituted benzofuran group; a deuterium-substituted or unsubstituted dibenzofuran group; a deuterium-substituted or unsubstituted benzothiophene group; a deuterium-substituted or unsubstituted dibenzothiophene group; or a deuterium-substituted or unsubstituted heterocyclic group containing one or more N and O as heteroatoms and having four or more fused rings, and the remainders are the same or different and each independently represent hydrogen or deuterium.

[0109] In one embodiment of the present specification, at least one of R11 to R33 is a deuterium-substituted or unsubstituted triphenylsilyl group; a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; a deuterium-substituted or unsubstituted naphthyl group; a deuterium-substituted or unsubstituted carbazole group; a deuterium-substituted or unsubstituted dibenzofuran group; a deuterium-substituted or unsubstituted dibenzothiophene group; or a deuterium-substituted or unsubstituted heterocyclic group containing one or more N and O heteroatoms and having 4 to 7 fused rings, and the remainders are the same or different and each independently represent hydrogen or deuterium.

[0110] In one embodiment of the present specification, at least one of R11 to R33 is a deuterium-substituted or unsubstituted triphenylsilyl group; a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted carbazole group; a deuterium-substituted or unsubstituted dibenzofuran group; a deuterium-substituted or unsubstituted dibenzothiophene group; or a deuterium-substituted or unsubstituted heterocyclic group containing one or more N and O heteroatoms and having 5 or 7 fused rings, and the remainders are the same or different and each independently represent hydrogen or deuterium.

[0111] 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 rest are the same or different and each independently represent hydrogen or deuterium.

[0112] 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 containing one or more heteroatoms selected from N, O, and S, and the rest are the same or different and each independently represent hydrogen or deuterium.

[0113] 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; or a heterocyclic group containing one or more N and O as heteroatoms and having four or more condensed rings, and the remaining rings are the same or different and each independently represent hydrogen or deuterium.

[0114] 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 containing one or more N and O heteroatoms and having 4 to 7 condensed rings, and the remaining rings are the same or different and each independently represent hydrogen or deuterium.

[0115] 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 one or more N and O heteroatoms and having 5 or 7 condensed rings, and the remaining rings are the same or different and each independently represent hydrogen or deuterium.

[0116] 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.

[0117] 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 one or more N and O as heteroatoms and having 5 or 7 fused rings, and the remainders are the same or different and each independently represent hydrogen or deuterium.

[0118] In one embodiment of the present specification, at least two of R11 to R33 are a deuterium-substituted or unsubstituted triphenylsilyl group; a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted carbazole group; a deuterium-substituted or unsubstituted dibenzofuran group; a deuterium-substituted or unsubstituted dibenzothiophene group; or a deuterium-substituted or unsubstituted heterocyclic group containing one or more N and O heteroatoms and having 5 or 7 fused rings, and the remainders are the same or different and each independently represent hydrogen or deuterium.

[0119] 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 containing one or more N and O heteroatoms and having 5 or 7 condensed rings, and the remaining rings are the same or different and each independently represent hydrogen or deuterium.

[0120] 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. [ka] In the structural formula, P1 to P3 are substituted or unsubstituted aryl groups, [ka] means the position where L11 to L33 are bonded.

[0121] In one embodiment of the present specification, P1 to P3 are substituted or unsubstituted aryl groups having 6 to 60 carbon atoms.

[0122] In one embodiment of the present specification, P1 to P3 are substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0123] In one embodiment of the present specification, P1 to P3 are substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.

[0124] In one embodiment of the present specification, P1 to P3 are substituted or unsubstituted phenyl groups.

[0125] In one embodiment of the present specification, P1 to P3 are phenyl groups substituted or unsubstituted with deuterium.

[0126] In one embodiment of the present specification, P1 to P3 are phenyl groups.

[0127] In one embodiment of the present specification, n1 is an integer of 1 to 4.

[0128] In one embodiment of the present specification, n1 is an integer of 1 to 3.

[0129] In one embodiment herein, n1 is 3.

[0130] In one embodiment herein, n1 is 2.

[0131] In one embodiment herein, n1 is 1.

[0132] In one embodiment of the present specification, n2 is an integer of 1-4.

[0133] In one embodiment of the present specification, n2 is an integer of 1-3.

[0134] In one embodiment herein, n2 is 3.

[0135] In one embodiment herein, n2 is 2.

[0136] In one embodiment herein, n2 is 1.

[0137] In one embodiment of the present specification, n3 is an integer of 1 to 3.

[0138] In one embodiment of the present specification, n3 is an integer of 1-2.

[0139] In one embodiment herein, n3 is 2.

[0140] In one embodiment herein, n3 is 1.

[0141] In one embodiment of the present specification, m1 is an integer of 1-4.

[0142] In one embodiment of the present specification, m1 is an integer of 1-3.

[0143] In one embodiment herein, m1 is 3.

[0144] In one embodiment herein, m1 is 2.

[0145] In one embodiment herein, m1 is 1.

[0146] In one embodiment of the present specification, m2 is an integer of 1-4.

[0147] In one embodiment of the present specification, m2 is an integer of 1-3.

[0148] In one embodiment herein, m2 is 3.

[0149] In one embodiment herein, m2 is 2.

[0150] In one embodiment herein, m2 is 1.

[0151] In one embodiment of the present specification, m3 is an integer of 1 to 3.

[0152] In one embodiment of the present specification, m3 is an integer of 1-2.

[0153] In one embodiment herein, m3 is 2.

[0154] In one embodiment herein, m3 is 1.

[0155] In one embodiment of the present specification, n1+m1 is 2 or more and 4 or less.

[0156] In one embodiment of the present specification, n1+m1 is 3 or more and 4 or less.

[0157] In one embodiment herein, n1+m1 is 4.

[0158] In one embodiment herein, n1+m1 is 3.

[0159] In one embodiment herein, n1+m1 is 2.

[0160] In one embodiment of the present specification, n2+m2 is 2 or more and 4 or less.

[0161] In one embodiment of the present specification, n2+m2 is 3 or more and 4 or less.

[0162] In one embodiment herein, n2+m2 is 4.

[0163] In one embodiment herein, n2+m2 is 3.

[0164] In one embodiment herein, n2+m2 is 2.

[0165] In one embodiment herein, n3+m3 is 2 or 3.

[0166] In one embodiment herein, n3+m3 is 3.

[0167] In one embodiment herein, n3+m3 is 2.

[0168] In one embodiment herein, m1, n2, and n3 are 1.

[0169] In one embodiment herein, n1, m2, and n3 are 1.

[0170] In one embodiment herein, n1, n2, and m3 are 1.

[0171] In one embodiment herein, n1, m2, and m3 are 1.

[0172] In one embodiment herein, m1, n2, and m3 are 1.

[0173] In one embodiment herein, m1, m2, and n3 are 1.

[0174] 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. [Chemical formula 1-1] [ka] [Chemical formula 1-2] [ka] [Chemical formula 1-3] [ka] [Chemical formula 1-4] [ka] [Chemical formula 1-5] [ka] [Chemical formula 1-6] [ka] 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 Chemical Formula 1. G1 to G3 are the same or different and each independently represent 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 an integer of 1 to 8, and when g1 to g3 are each 2 or greater, G1 to G3 are the same or different from one another.

[0175] In one embodiment of the present specification, G1 to G3 are the same or different 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.

[0176] In one embodiment of the present specification, G1 to G3 are the same or different 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 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.

[0177] In one embodiment of the present specification, G1 to G3 are the same as or different from one another and each independently represent 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.

[0178] In one embodiment of the present specification, G1 to G3 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a nitrile group; a deuterium-substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms; a deuterium-substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; a deuterium-substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a deuterium-substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a deuterium-substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a deuterium-substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0179] In one embodiment of the present specification, G1 to G3 are the same as or different from one another and each independently represent hydrogen; deuterium; a deuterium-substituted or unsubstituted butyl group; a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; a deuterium-substituted or unsubstituted naphthyl group; a deuterium-substituted or unsubstituted carbazole group; a deuterium-substituted or unsubstituted dibenzofuran group; or a deuterium-substituted or unsubstituted dibenzothiophene group.

[0180] In one embodiment of the present specification, G1 to G3 are the same or different and each independently represent hydrogen, deuterium, a butyl group, a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group.

[0181] In one embodiment of the present specification, G1 to G3 are the same or different and each independently represent hydrogen or deuterium.

[0182] In one embodiment of the present specification, G1 to G3 are hydrogen.

[0183] In one embodiment of the present specification, G1 to G3 are deuterium.

[0184] In one embodiment of the present specification, g1 to g3 are 1.

[0185] In one embodiment of the present specification, g1 to g3 are 2.

[0186] In one embodiment of the present specification, g1 to g3 are 3.

[0187] In one embodiment of the present specification, g1 to g3 are 4.

[0188] In one embodiment of the present specification, g1 to g3 are 5.

[0189] In one embodiment of the present specification, g1 to g3 are 6.

[0190] In one embodiment of the present specification, g1 to g3 are 7.

[0191] In one embodiment of the present specification, g1 to g3 are 8.

[0192] In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulae 1-A-1 to 1-A-3. [Chemical formula 1-A-1] [ka] [Chemical formula 1-A-2] [ka] [Chemical formula 1-A-3] [ka] In the chemical formulas 1-A-1 to 1-A-3, The definitions of X, Y, R11 to R33, L1 to L3, and L11 to L33 are the same as those in the above-mentioned chemical formula 1, and the definitions of G1 to G3 and g1 to g3 are the same as those in the above-mentioned chemical formulas 1-1 to 1-6.

[0193] In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulae 1-B-1 to 1-B-3. [Chemical formula 1-B-1] [ka] [Chemical formula 1-B-2] [ka] [Chemical formula 1-B-3] [ka] In the chemical formulas 1-B-1 to 1-B-3, The definitions of X, Y, R11 to R33, L1 to L3, and L11 to L33 are the same as those in the above-mentioned chemical formula 1, and the definitions of G1 to G3 and g1 to g3 are the same as those in the above-mentioned chemical formulas 1-1 to 1-6.

[0194] In one embodiment of the present specification, the compound represented by Chemical Formula 1 is substituted by 20% or more deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted by 30% or more deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 is substituted by 40% or more deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 is substituted by 50% or more deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 is substituted by 60% or more deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 is substituted by 70% or more deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 is substituted by 80% or more deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 is substituted by 90% or more deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 is substituted by 100% deuterium.

[0195] In one embodiment of the present specification, the compound represented by Chemical Formula 1 contains 40% to 60% deuterium. In another embodiment, the compound represented by Chemical Formula 1 contains 40% to 80% deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 contains 60% to 80% deuterium. In yet another embodiment, the compound represented by Chemical Formula 1 contains 80% to 100% deuterium.

[0196] In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following compounds: [ka] [ka] [ka] [ka] [ka]

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

[0197] In this specification, [ ] D=x1~x2 means that the structure in the brackets 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 following structure contains 1 to 50 deuterium atoms. [ka]

[0198] The compound represented by Chemical Formula 1 according to one embodiment of the present specification can be synthesized by a synthesis method known in the art using starting materials, intermediates, etc. known in the art, and substituents can be attached by a method known in the art, and the type, position, or number of substituents can be changed by a technique known in the art.

[0199] The present invention provides a method for synthesizing compounds having various energy band gaps by introducing various substituents into the core structure of the compound represented by Chemical Formula 1. The present invention also provides a method for adjusting the HOMO and LUMO energy levels of the compound by introducing various substituents into the core structure of the above-described structure.

[0200] The present specification also provides an organic light-emitting device comprising the compound described above.

[0201] In this specification, when a member is said to be located "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member is present between the two members.

[0202] In this specification, when a part is said to "comprise" a certain component, this does not mean that it excludes other components, but that it may further include other components, unless otherwise specified.

[0203] The organic light-emitting device according to the present specification is an organic light-emitting device including a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Chemical Formula 1 described above.

[0204] The organic light emitting device of the present invention may be manufactured using a conventional method and material for manufacturing an organic light emitting device, except that the organic material layer is formed using the compound of Chemical Formula 1 described above.

[0205] The organic material layer of the organic light-emitting device of the present invention may have a single-layer structure or a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a multi-layer structure including one or more organic material layers selected from the group consisting 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. However, the structure of the organic light-emitting device of the present invention is not limited thereto and may also have a single-layer structure. Furthermore, during the fabrication of the organic light-emitting device, the compound may be formed into fewer layers by a solvent process, such as, but not limited to, a vacuum deposition method or a solvent process such as spin coating, dip coating, doctor blade, screen printing, inkjet printing, or thermal transfer.

[0206] In one embodiment of the present specification, the thickness of the organic layer containing the compound of Chemical Formula 1 may be 5 Å to 2000 Å, may be 5 Å to 500 Å, and preferably 10 Å to 400 Å.

[0207] In one embodiment, the organic layer may further contain, in addition to the compound represented by Chemical Formula 1, other organic compounds, metals, or metal compounds.

[0208] In one embodiment of the present specification, the organic layer may include a light-emitting layer, and the light-emitting layer may include a compound represented by Chemical Formula 1 above.

[0209] In one embodiment of the present specification, the organic layer may include a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1 as a host.

[0210] In one embodiment of the present specification, the organic material layer includes an emitting layer, and the emitting layer may include the compound represented by Chemical Formula 1 as an n-type host, specifically, as an n-type phosphorescent host.

[0211] In one embodiment of the present specification, the organic layer includes an emitting layer, and the emitting layer includes the compound represented by Chemical Formula 1 as a first host, and may further include an additional second host.

[0212] In one embodiment of the present specification, the organic material layer includes an emitting layer, which includes the compound represented by Chemical Formula 1 as an n-type first host and may further include a p-type second host. Specifically, the first host may be an n-type phosphorescent host, and the second host may be a p-type phosphorescent host.

[0213] In this specification, n-type can be defined as a material that can steal 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.

[0214] Conversely, in this specification, p-type can be defined as a material that, when a layer is composed solely of p-type material, receives electrons at the HOMO (highest occupied molecular orbital) energy level of an adjacent material located toward the cathode, thereby generating holes in the adjacent material toward the cathode. The closer the HOMO level of a material located toward the cathode is to the LUMO of the p-type material, the more likely it is that electrons will be removed from the HOMO of the adjacent layer, thereby generating holes in the HOMO of the adjacent layer.

[0215] When a p-type material is doped into a matrix, it can be defined as a material that accepts electrons into the HOMO of the matrix material, generating holes in the HOMO of the matrix accordingly. The closer the LUMO of the p-type material is to the HOMO of the matrix, the more likely it is to steal electrons and generate holes in the matrix.

[0216] In one embodiment of the present specification, the p-type material may be a compound generally known in the art, such as a structure containing an N-containing monocyclic ring; dibenzofuran; and / or carbazole.

[0217] In one embodiment of the present specification, the light-emitting layer may contain the first host and the second host in a weight ratio of 2:8 to 8:2, specifically 4:6 to 6:4, and the first host may include a compound represented by Chemical Formula 1.

[0218] 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 1:1, and the first host may include the compound of Chemical Formula 1.

[0219] In one embodiment of the present specification, the second host may be a carbazole-based compound.

[0220] In one embodiment of the present specification, the second host may be a biscarbazole-based compound.

[0221] In one embodiment of the present specification, the second host may be a biscarbazole compound substituted with an aryl group.

[0222] In one embodiment of the present specification, the second host may be a compound represented by the chemical formula EB-1 described below.

[0223] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1 as a host, and may further include a dopant.

[0224] In one embodiment of the present specification, the light-emitting layer contains the compound represented by Chemical Formula 1 as a first host, and may further contain a second host and a dopant.

[0225] In one embodiment of the present specification, the dopant is a phosphorescent dopant.

[0226] 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.

[0227] In one embodiment of the present specification, the light-emitting layer includes a dopant, and the dopant may include a phosphorescent dopant.

[0228] In one embodiment of the present specification, the organic layer may include an emitting layer, and the emitting layer may include a host and a dopant, the host may include the compound, and the dopant may include the phosphorescent dopant.

[0229] In one embodiment of the present specification, the light-emitting layer may be a blue light-emitting layer.

[0230] In one embodiment of the present specification, the light-emitting layer may contain the host and the dopant in a weight ratio of 99:1 to 1:99. Specifically, the weight ratio may be 99:1 to 50:50, more specifically, 99:1 to 86:14.

[0231] When the light-emitting layer emits red light, the light-emitting dopant may be, but is not limited to, a phosphorescent material such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), or PtOEP(octaethylporphyrin platinum), or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum). When the light-emitting layer emits green light, the light-emitting dopant may be, but is not limited to, a phosphorescent material such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium), or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum). When the light-emitting layer emits blue light, the light-emitting dopant may be, but is not limited to, a platinum complex compound, a phosphorescent substance such as (4,6-F2ppy)2Irpic, or a fluorescent substance such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), a PFO-based polymer, or a PPV-based polymer.

[0232] In one embodiment of the present specification, the dopant may be a metal complex compound.

[0233] In one embodiment of the present specification, the dopant may be a platinum complex compound.

[0234] In one embodiment of the present specification, the dopant may be an iridium complex compound.

[0235] In one embodiment of the present specification, the dopant may be an iridium-based compound.

[0236] In one embodiment of the present specification, the dopant compound may be selected from, but is not limited to, the following structural formulas: [ka] [ka] [ka] [ka]

[0237] In one embodiment of the present specification, the organic layer may include a hole-blocking layer.

[0238] In one embodiment of the present specification, the organic layer may include a hole-blocking layer, and the hole-blocking layer may include a compound represented by Chemical Formula 1 above.

[0239] 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 Chemical Formula 1 above.

[0240] 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 Chemical Formula 1, and the n-type compound represented by Chemical Formula 1 may be the same as or different from the n-type host included in the light-emitting layer.

[0241] 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 Chemical Formula 1 above.

[0242] In one embodiment of the present specification, the organic layer may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.

[0243] 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.

[0244] In one embodiment of the present specification, the two or more organic layers may be two or more selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, an 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.

[0245] In one embodiment of the present specification, two or more hole transport layers are included between the light emitting layer and the first electrode, and the two or more hole transport layers may contain the same or different materials.

[0246] In one embodiment of the present specification, the first electrode is an anode or a cathode.

[0247] In one embodiment of the present specification, the second electrode is a cathode or an anode.

[0248] In one embodiment of the present specification, the organic light-emitting device may be a normal type organic light-emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

[0249] 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 material layers, and an anode are sequentially stacked on a substrate.

[0250] The organic light emitting device may have, for example, the following laminated structure, but is not limited thereto. (1) First electrode / hole transport layer / light-emitting layer / second electrode (2) First electrode / hole injection layer / hole transport layer / light-emitting layer / second electrode (3) First electrode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / second electrode (4) First electrode / hole transport layer / light-emitting layer / electron transport layer / second electrode (5) First electrode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / second electrode (6) First electrode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / second electrode (7) First electrode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / second electrode (8) First electrode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / second electrode (9) First electrode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / second electrode (10) First electrode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / second electrode (11) First electrode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / second electrode (12) First electrode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / second electrode (13) First electrode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / second electrode (14) First electrode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / second electrode (15) First electrode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / second electrode (16) First electrode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / second electrode (17) First electrode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / second electrode (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

[0251] The structure of the organic light-emitting device of the present specification may have the structures shown in FIGS. 1 and 2, but is not limited thereto.

[0252] 1 shows an example of an organic light-emitting device in which a substrate 1, a first electrode 2, an emitting layer 6, and a second electrode 9 are sequentially stacked. In such a structure, the compound may be contained in the emitting layer 6.

[0253] 2 shows 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, an emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a second electrode 9 are sequentially stacked. In this structure, the compound may be contained in the emitting layer 6 or the hole blocking layer 7.

[0254] In one embodiment of the present specification, the electron injection and transport layer and the light-emitting layer may be provided adjacent to each other. For example, the electron injection and transport layer and the light-emitting layer may be provided in physical contact with each other.

[0255] In one embodiment of the present specification, the hole blocking layer and the electron injection and transport layer may be provided adjacent to each other. For example, the hole blocking layer and the electron injection and transport layer may be provided in physical contact with each other.

[0256] In one embodiment of the present specification, the hole-blocking layer and the light-emitting layer may be provided adjacent to each other. For example, the hole-blocking layer and the light-emitting layer may be provided in physical contact with each other.

[0257] The organic light-emitting device of the present specification may be manufactured using materials and methods well known in the art, except that at least one layer of the organic material layers contains the compound, i.e., the compound represented by Chemical Formula 1.

[0258] When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0259] For example, the organic light emitting device according to the present invention can be fabricated by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a first electrode, forming organic layers including a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, and an electron injection and transport layer thereon, and then depositing a material usable as a second electrode thereon.In addition to this method, the organic light emitting device can also be fabricated by sequentially depositing the second electrode material, the organic layer, and the first electrode material on a substrate.

[0260] The anode material is preferably a material with a high work function to facilitate hole injection into the organic layer. Examples of the anode material 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 SnO:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0261] The cathode material is preferably a material with a small work function to facilitate electron injection into the organic layer, including, but not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO / Al.

[0262] The light-emitting layer may include a host material and a dopant material. When the organic light-emitting device according to an embodiment of the present specification includes an additional light-emitting layer in addition to the light-emitting layer containing Chemical Formula 1, the host material may include a fused aromatic ring derivative or a heterocycle-containing compound. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and examples of the heterocycle-containing compound include, but are not limited to, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives.

[0263] The hole injection layer is a layer that receives holes from the electrode. The hole injection material preferably has the ability to transport holes, and thus has excellent hole-receiving properties from the anode and hole-injecting properties toward the light-emitting layer or light-emitting material. Furthermore, a material that is excellent in preventing excitons generated from the light-emitting layer from migrating to the electron injection layer or electron injection material is preferred. Furthermore, a material that is excellent in thin-film formation is preferred. Furthermore, the HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, and arylamine-based organic materials; hexanitrile hexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; and polythiophene-based conductive polymers such as anthraquinone and polyaniline.

[0264] In one embodiment of the present specification, the hole injection layer may include, but is not limited to, a compound represented by the following chemical formula HI-1: [Chemical formula HI-1] [ka] In the chemical formula HI-1, 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 are bonded to adjacent groups to form a substituted or unsubstituted ring; r315 is an integer of 1 to 5, and when r315 is 2 or more, the two or more R315's are the same or different from each other, r316 is an integer of 1 to 5, and when r316 is 2 or more, the two or more R316's are the same or different from each other.

[0265] 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.

[0266] 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.

[0267] In one embodiment of the present specification, R315 and R316 are the same or different and each independently represent a substituted or unsubstituted aryl group, or are bonded to adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0268] In one embodiment of the present specification, R315 and R316 are the same or different from each other, and each independently represent a phenyl group or a biphenyl group, or are bonded to adjacent groups to form indene substituted with a methyl group.

[0269] In one embodiment of the present specification, the chemical formula HI-1 may be represented by any one of the following compounds: [ka]

[0270] In one embodiment of the present specification, the hole injection layer may include, but is not limited to, a compound represented by the following chemical formula HI-2: [Chemical formula HI-2] [ka] In the chemical formula HI-2, R401 to R403 are the same or different and each independently represents a halogen group; r401~r403 are 4.

[0271] In one embodiment of the present specification, R401 to R403 are F.

[0272] In one embodiment of the present specification, the chemical formula HI-2 may be represented by the following compound: [ka]

[0273] In one embodiment of the present specification, the hole injection layer may contain the compound represented by the chemical formula HI-1 and the compound represented by the chemical formula HI-2.

[0274] In one embodiment of the present specification, the hole injection layer may contain the compound represented by the chemical formula HI-1 and the compound represented by the chemical formula HI-2 in a weight ratio of 1:99 to 99:1, specifically in a weight ratio of 5:95 to 95:5.

[0275] The hole transport layer receives holes from the hole injection layer and transports them to the light emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transport them to the light emitting layer, and is preferably a material with high hole mobility. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0276] In one embodiment of the present specification, the hole transport layer may include, but is not limited to, a compound represented by the chemical formula HI-1.

[0277] 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 for the hole transport layer and the hole injection layer may be used, but are not limited to these.

[0278] The electron transport layer receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material that can smoothly receive electrons injected from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is preferred. Specific examples include, but are not limited to, 8-hydroxyquinoline aluminum complexes; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer may be used with any desired cathode material, as used in the prior art. In particular, suitable cathode materials are conventional materials with low work functions followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0279] The electron injection layer is a layer that accepts electrons from the electrode. The electron injection material preferably has excellent electron transport ability, accepts electrons from the cathode, and injects electrons into the light-emitting layer or light-emitting material. Furthermore, a material that prevents excitons generated in the light-emitting layer from migrating to the hole injection layer and has excellent thin-film forming ability is preferred. Specific examples of the electron injection material include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0280] Examples of the metal complex compounds include, but are not limited to, 8-hydroxyquinolinatolithium, 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-cresolate)gallium, bis(2-methyl-8-quinolinato)(1-naphtholate)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtholate)gallium.

[0281] 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 for the electron transport layer and the electron injection layer may be used, but are not limited to these.

[0282] 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: [Chemical formula ET-1] [ka] In the formula ET-1, At least one of Z11 to Z13 is N, and the rest are CH; At least one of Z21 to Z23 is N and the rest are CH; L601 and L602 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; Ar601 to Ar604 are the same or different and each independently represent a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0283] In one embodiment of the present specification, Z11 to Z13 are all N.

[0284] In one embodiment of the present specification, Z21 to Z23 are all N.

[0285] In one embodiment of the present specification, L601 and L602 are the same or different and each independently represent 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 or different and each independently represent a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 12 carbon atoms.

[0286] In one embodiment of the present specification, L601 and L602 are each a substituted or unsubstituted phenylene group.

[0287] In one embodiment of the present specification, L601 and L602 are phenylene groups.

[0288] In one embodiment of the present specification, Ar601 to Ar604 are the same or different and each independently represent a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0289] In one embodiment of the present specification, Ar601 to Ar604 are the same or different and each independently represent a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 12 carbon atoms.

[0290] In one embodiment of the present specification, Ar601 to Ar604 are substituted or unsubstituted phenyl groups.

[0291] In one embodiment of the present specification, Ar601 to Ar604 are phenyl groups.

[0292] In one embodiment of the present specification, the chemical formula ET-1 may be represented by the following compound: [ka]

[0293] In one embodiment of the present specification, the electron injection and transport layer may further contain a metal complex compound. The metal complex compound is as described above.

[0294] The electron blocking layer prevents electrons injected from the electron injection layer from passing through the light emitting layer to the hole injection layer, thereby improving the lifetime and efficiency of the device. Any known material with high triplet energy may be used, including, but not limited to, the materials exemplified in the description of the hole injection layer. The electron blocking layer may 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.

[0295] 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: [Chemical formula EB-1] [ka] In the above chemical formula EB-1, T1 to T14 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; L14 is a direct bond; or a substituted or unsubstituted arylene group; t13 is an integer of 1 to 3, and when t13 is 2 or more, the two or more T13's are the same or different from each other.

[0296] In one embodiment of the present specification, T1 to T14 are the same or different and each independently represent 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.

[0297] In one embodiment of the present specification, T1 to T14 are the same or different and each independently represent 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.

[0298] In one embodiment of the present specification, T1 to T14 are the same or different and each independently represent 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.

[0299] In one embodiment of the present specification, T1 to T14 are the same or different and each independently represent hydrogen; deuterium; a triphenylsilyl group; a phenyl group; or a biphenyl group.

[0300] In one embodiment of the present specification, T1 to T13 are the same or different and each independently represent hydrogen or deuterium.

[0301] 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.

[0302] In one embodiment of the present specification, T14 is a triphenylsilyl group; a phenyl group; a biphenyl group; or a naphthyl group.

[0303] In one embodiment of the present specification, T14 is a triphenylsilyl group; or a phenyl group.

[0304] 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.

[0305] 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.

[0306] In one embodiment of the present specification, L14 is a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0307] In one embodiment of the present specification, L14 is a direct bond; or a phenylene group.

[0308] In one embodiment of the present specification, the chemical formula EB-1 may be represented by the following compound: [ka]

[0309] 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 may generally be formed under the same conditions as those for the electron injection layer.

[0310] In one embodiment of the present specification, the hole-blocking layer may include, but is not limited to, a compound represented by the following formula HB-1 or a compound represented by the above formula 1. [Chemical formula HB-1] [ka] In the formula HB-1, 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.

[0311] In one embodiment of the present specification, Ar101, Ar102, and Ar103 are the same or different and each independently represent 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.

[0312] In one embodiment of the present specification, Ar101, Ar102, and Ar103 are the same or different and each independently represent 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.

[0313] In one embodiment of the present specification, Ar101, Ar102, and Ar103 are the same as or different from each other and each independently represent 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.

[0314] In one embodiment of the present specification, Ar101, Ar102, and Ar103 are the same as or different from each other and each independently represent hydrogen; deuterium; a triphenylsilyl group; or a carbazole group.

[0315] In one embodiment of the present specification, the chemical formula HB-1 may be represented by the following compound: [ka]

[0316] When the organic light emitting device according to an embodiment of the present specification includes an additional hole blocking layer in addition to the hole blocking layer containing the compound represented by Chemical Formula HB-1 or the compound represented by Chemical Formula 1, specific examples of the additional hole blocking layer include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0317] The organic light emitting devices according to the present invention may be top-emitting, bottom-emitting, or dual-sided emitting, depending on the materials used.

[0318] The organic light emitting device according to the present disclosure may be included in various electronic devices, such as, but not limited to, a display panel, a touch panel, a solar module, and a lighting device. [Example]

[0319] Hereinafter, the present specification will be described in detail with reference to examples and comparative examples. However, the examples and comparative examples according to the present specification may be modified into various other forms, and the scope of the present specification should not be construed as being limited to the examples and comparative examples described below. The examples and comparative examples in the present specification are provided to more completely explain the present specification to those skilled in the art.

[0320] <Production example>

[0321] Preparation example of compound 1 (F-1) [ka]

[0322] Synthesis of I-1 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 58 g (yield 75%, Mass [M+] = 524).

[0323] Synthesis of I-2 25 g of I-1, 7.0 g of (2-(phenylamino)phenyl)boronic acid, 13.2 g of K2CO3, 0.24 g of [bis(tri-tert-butylphosphine)palladium(0)], 500 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 18 g (yield 62%, Mass [M+] = 613).

[0324] Synthesis of I-3 Under a nitrogen atmosphere, 15 g of I-2, 20 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 8.2 g (yield 54%, Mass [M+] = 621).

[0325] Synthesis of F-1 8 g of I-3, 4.9 g of (3-(triphenylsilyl)phenyl)boronic acid, 3.6 g of K2CO3, 0.07 g of [bis(tri-tert-butylphosphine)palladium(0)], 160 mL of tetrahydrofuran, and 80 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 7.2 g (yield 61%, Mass [M+] = 921).

[0326] Preparation example of compound 2 (F-2) [ka]

[0327] Synthesis of I-4 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 38 g (yield 72%, Mass [M+] = 357).

[0328] Synthesis of I-5 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 22 g (yield 71%, Mass [M+] = 445).

[0329] Synthesis of I-6 20 g of I-5, 21.2 g of (2-(phenylamino)-5-(triphenylsilyl)phenyl)boronic acid, 12.4 g of K2CO3, 0.23 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 23 g (yield 61%, Mass [M+] = 837).

[0330] Synthesis of F-2 Under a nitrogen atmosphere, 14 g of I-6, 11.2 g of boron triiodide, and 280 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.6 g (47% yield, Mass [M+] = 845).

[0331] Preparation example of compound 3 (F-3) [ka]

[0332] Synthesis of I-7 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 43 g (yield 71%, Mass [M+] = 359).

[0333] Synthesis of I-8 20 g of I-7, 21.1 g of (5-(9H-carbazol-9-yl)-2-hydroxyphenyl)boronic acid, 19.3 g of K2CO3, 0.35 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 26 g (yield 69%, Mass [M+] = 538).

[0334] Synthesis of I-9 Under a nitrogen atmosphere, 15 g of I-8, 18.6 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.7 g (44% yield, Mass [M+] = 546).

[0335] Synthesis of F-3 6 g of I-9, 3.4 g of (3-(triphenylsilyl)phenyl)boronic acid, 3.1 g of K2CO3, 0.06 g of [bis(tri-tert-butylphosphine)palladium(0)], 120 mL of tetrahydrofuran, and 60 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 6 g (yield 64%, Mass [M+] = 846).

[0336] Preparation of Compound 4 (F-4) [ka]

[0337] Synthesis of I-10 A mixture of 15 g of I-5, 15.9 g of (4-hydroxy-3'-(triphenylsilyl)-[1,1'-biphenyl]-3-yl)boronic acid, 9.3 g of K2CO3, 0.17 g of [bis(tri-tert-butylphosphine)palladium(0)], 300 mL of tetrahydrofuran, and 150 mL of water was heated to reflux and stirred for 8 hours. After the reaction was complete, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to give 19 g (yield 67%, Mass [M+] = 838).

[0338] Synthesis of F-4 Under a nitrogen atmosphere, 15 g of I-10, 11.9 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was complete, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.1 g (40% yield, Mass [M+] = 846).

[0339] Preparation of Compound 5 (F-5) [ka]

[0340] Synthesis of I-11 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 66 g (yield 69%, Mass [M+] = 566).

[0341] Synthesis of I-12 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 25 g (yield 76%, Mass [M+] = 930).

[0342] Synthesis of F-5 Under a nitrogen atmosphere, 15 g of I-12, 10.7 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 5.6 g (yield 37%, Mass [M+] = 938).

[0343] Preparation of Compound 6 (F-6) [ka]

[0344] Synthesis of I-13 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 24 g (yield 74%, Mass [M+] = 387).

[0345] Synthesis of I-14 A mixture of 20 g of I-13, 28.4 g of ((3-(phenylamino)-3'-(triphenylsilyl)-[1,1'-biphenyl]-4-yl)boronic acid, 14.3 g of K2CO3, 0.26 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water was heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, and the reaction mixture was dissolved in toluene and separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 28 g (yield 63%, Mass [M+] = 854).

[0346] Synthesis of F-6 Under a nitrogen atmosphere, 15 g of I-14, 11.7 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 5.8 g (yield 38%, Mass [M+] = 862).

[0347] Preparation of Compound 7 (F-7) [ka]

[0348] Synthesis of I-15 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 43 g (yield 69%, Mass [M+] = 559).

[0349] Synthesis of I-16 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to give 17 g (yield 66%, Mass [M+] = 721).

[0350] Synthesis of I-17 15 g of I-16, 2.9 g of (2-hydroxyphenyl)boronic acid, 5.8 g of K2CO3, 0.1 g of [bis(tri-tert-butylphosphine)palladium(0)], 300 mL of tetrahydrofuran, and 150 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 12 g (yield 74%, Mass [M+] = 779).

[0351] Synthesis of F-7 Under a nitrogen atmosphere, 12 g of I-17, 12.8 g of boron triiodide, and 240 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.2 g (41% yield, Mass [M+] = 787).

[0352] Preparation of Compound 8 (F-8) [ka]

[0353] Synthesis of I-18 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 46 g (yield 65%, Mass [M+] = 635).

[0354] Synthesis of I-19 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 21 g (yield 74%, Mass [M+] = 721).

[0355] Synthesis of I-20 20 g of I-19, 8 g of (2-mercaptophenyl)boronic acid, 7.7 g of K2CO3, 0.15 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 16 g (yield 73%, Mass [M+] = 795).

[0356] Synthesis of F-8 Under a nitrogen atmosphere, 15 g of I-20, 12.6 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was complete, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.4 g (42% yield, Mass [M+] = 803).

[0357] Preparation of Compound 9 (F-9) [ka]

[0358] Synthesis of I-21 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 45 g (yield 77%, Mass [M+] = 522).

[0359] Synthesis of I-22 20 g of I-21, 8.2 g of (2-(phenylamino)phenyl)boronic acid, 10.7 g of K2CO3, 0.20 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 17 g (yield 68%, Mass [M+] = 655).

[0360] Synthesis of F-9 Under a nitrogen atmosphere, 15 g of I-22, 15.3 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.3 g (42% yield, Mass [M+] = 663).

[0361] Preparation of Compound 10 (F-10) [ka]

[0362] Synthesis of I-23 20 g of I-21, 5.3 g of (2-hydroxyphenyl)boronic acid, 10.7 g of K2CO3, 0.20 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was complete, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to give 18 g (yield 81%, Mass [M+] = 580).

[0363] Synthesis of F-10 Under a nitrogen atmosphere, 15 g of I-23, 17.3 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.1 g (40% yield, Mass [M+] = 588).

[0364] Preparation of Compound 11 (F-11) [ka]

[0365] Synthesis of I-24 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 44 g (yield 70%, Mass [M+] = 463).

[0366] Synthesis of I-25 20 g of I-24, 9.2 g of (2-(phenylamino)phenyl)boronic acid, 12 g of K2CO3, 0.22 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 18 g (yield 70%, Mass [M+] = 596).

[0367] Synthesis of F-11 Under a nitrogen atmosphere, 15 g of I-25, 17 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.2 g (40% yield, Mass [M+] = 604).

[0368] Preparation of Compound 12 (F-12) [ka]

[0369] Synthesis of I-26 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 43 g (yield 68%, Mass [M+] = 463).

[0370] Synthesis of I-27 20 g of I-26, 6.7 g of (2-mercaptophenyl)boronic acid, 12 g of K2CO3, 0.22 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 16 g (yield 69%, Mass [M+] = 537).

[0371] Synthesis of F-12 Under a nitrogen atmosphere, 15 g of I-27, 18.6 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.2 g (41% yield, Mass [M+] = 545).

[0372] Preparation of Compound 13 (F-13) [ka]

[0373] Synthesis of I-28 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 45 g (yield 72%, Mass [M+] = 463).

[0374] Synthesis of I-29 20 g of I-28, 9.3 g of (4-hydroxy-[1,1'-biphenyl]-3-yl)boronic acid, 12 g of K2CO3, 0.22 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to give 16 g (yield 62%, Mass [M+] = 597).

[0375] Synthesis of F-13 Under a nitrogen atmosphere, 15 g of I-29, 16.7 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was complete, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.4 g (42% yield, Mass [M+] = 605).

[0376] Preparation of Compound 14 (F-14) [ka]

[0377] Synthesis of I-30 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 34 g (yield 78%, Mass [M+] = 522).

[0378] Synthesis of I-31 20 g of I-30, 8.2 g of (2-(phenylamino)phenyl)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 and heated to reflux and stirred for 8 hours. After the reaction was complete, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 17 g (yield 68%, Mass [M+] = 655).

[0379] F-14 synthesis Under a nitrogen atmosphere, 15 g of I-31, 15.3 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the mixture was recrystallized to obtain 6.1 g (40% yield, Mass [M+] = 663).

[0380] Preparation of Compound 15 (F-15) [ka]

[0381] Synthesis of I-32 20 g of I-30, 5.3 g of (2-hydroxyphenyl)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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 16 g (72% yield, Mass [M+] = 580).

[0382] F-15 synthesis Under a nitrogen atmosphere, 15 g of I-32, 17.3 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was complete, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.5 g (43% yield, Mass [M+] = 588).

[0383] Preparation of Compound 16 (F-16) [ka]

[0384] Synthesis of I-33 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 43 g (yield 77%, Mass [M+] = 357).

[0385] Synthesis of I-34 20 g of I-33, 21.3 g of (4-(9H-carbazol-9-yl)-2-(phenylamino)phenyl)boronic acid, 15.5 g of K2CO3, 0.3 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 27 g (yield 73%, Mass [M+] = 655).

[0386] F-16 synthesis Under a nitrogen atmosphere, 15 g of I-34, 15.3 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.4 g (42% yield, Mass [M+] = 663).

[0387] Preparation of Compound 17 (F-17) [ka]

[0388] Synthesis of I-35 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to give 23 g (yield 71%, Mass [M+] = 580).

[0389] F-17 synthesis Under a nitrogen atmosphere, 15 g of I-35, 17.3 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.2 g (41% yield, Mass [M+] = 588).

[0390] Preparation of Compound 18 (F-18) [ka]

[0391] Synthesis of I-36 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to give 23 g (yield 69%, Mass [M+] = 596).

[0392] F-18 synthesis Under a nitrogen atmosphere, 15 g of I-36, 16.8 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was complete, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.4 g (41% yield, Mass [M+] = 604).

[0393] Preparation of Compound 19 (F-19) [ka]

[0394] Synthesis of I-37 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 20 g (yield 80%, Mass [M+] = 446).

[0395] Synthesis of I-38 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, all the solvent was removed, and the reaction mixture was dissolved in toluene and separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 24 g (yield 72%, Mass [M+] = 745).

[0396] F-19 synthesis Under a nitrogen atmosphere, 15 g of I-38, 13.4 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was complete, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.3 g (42% yield, Mass [M+] = 753).

[0397] Preparation of Compound 20 (F-20) [ka]

[0398] Synthesis of I-39 20 g of I-37, 17.8 g of (4-(dibenzo[b,d]thiophen-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 and heated to reflux and stirred for 8 hours. After the reaction was completed, all the solvent was removed, and the reaction mixture was dissolved in toluene and separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 26 g (yield 76%, Mass [M+] = 761).

[0399] Synthesis of F-20 Under a nitrogen atmosphere, 15 g of I-39, 13.2 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was complete, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.6 g (44% yield, Mass [M+] = 769).

[0400] Preparation of Compound 21 (F-21) [ka]

[0401] Synthesis of I-40 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 56 g (yield 72%, Mass [M+] = 525).

[0402] Synthesis of I-41 30 g of I-40, 12.2 g of dibenzo[b,d]furan-1-ylboronic acid, 15.8 g of K2CO3, 0.3 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was complete, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 26 g (yield 74%, Mass [M+] = 612).

[0403] Synthesis of I-42 25 g of I-41, 5.6 g of (2-hydroxyphenyl)boronic acid, 11.3 g of K2CO3, 0.2 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 21 g (yield 77%, Mass [M+] = 670).

[0404] Synthesis of F-21 Under a nitrogen atmosphere, 15 g of I-42, 14.9 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.5 g (43% yield, Mass [M+] = 678).

[0405] Preparation of Compound 22 (F-22) [ka]

[0406] Synthesis of I-43 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 55 g (yield 71%, Mass [M+] = 525).

[0407] Synthesis of I-44 30 g of I-43, 12.2 g of dibenzo[b,d]furan-4-ylboronic acid, 15.8 g of K2CO3, 0.3 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 28 g (yield 80%, Mass [M+] = 612).

[0408] Synthesis of I-45 25 g of I-44, 6.3 g of (2-mercaptophenyl)boronic acid, 11.3 g of K2CO3, 0.2 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 22 g (yield 79%, Mass [M+] = 686).

[0409] F-22 synthesis Under a nitrogen atmosphere, 15 g of I-45, 14.6 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.2 g (41% yield, Mass [M+] = 694).

[0410] Preparation of Compound 23 (F-23) [ka]

[0411] Synthesis of I-46 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 58 g (yield 53%, Mass [M+] = 522).

[0412] Synthesis of I-47 30 g of I-46, 17.5 g of (4-(dibenzo[b,d]furan-1-yl)-2-hydroxyphenyl)boronic acid, 15.9 g of K2CO3, 0.3 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, all the solvent was removed, and the reaction mixture was dissolved in toluene and separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 33 g (yield 75%, Mass [M+] = 746).

[0413] Synthesis of F-23 Under a nitrogen atmosphere, 15 g of I-47, 13.4 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.0 g (40% yield, Mass [M+] = 754).

[0414] Preparation of Compound 24 (F-24) [ka]

[0415] Synthesis of I-48 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 49 g (yield 71%, Mass [M+] = 466).

[0416] Synthesis of I-49 30 g of I-48, 13.7 g of dibenzo[b,d]furan-1-ylboronic acid, 17.8 g of K2CO3, 0.33 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 27 g (yield 76%, Mass [M+] = 553).

[0417] Synthesis of I-50 25 g of I-49, 6.3 g of (2-hydroxyphenyl)boronic acid, 12.5 g of K2CO3, 0.2 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 21 g (yield 76%, Mass [M+] = 611).

[0418] F-24 synthesis Under a nitrogen atmosphere, 15 g of I-50, 16.4 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was complete, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.6 g (43% yield, Mass [M+] = 619).

[0419] Preparation of Compound 25 (F-25) [ka]

[0420] Synthesis of I-51 25 g of I-49, 9.7 g of (2-(phenylamino)phenyl)boronic acid, 12.5 g of K2CO3, 0.2 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 23 g (yield 74%, Mass [M+] = 686).

[0421] F-25 Synthesis Under a nitrogen atmosphere, 15 g of I-51, 14.6 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.5 g (43% yield, Mass [M+] = 694).

[0422] Preparation of Compound 26 (F-26) [ka]

[0423] Synthesis of I-52 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 48 g (yield 70%, Mass [M+] = 611).

[0424] Synthesis of I-53 30 g of I-52, 10.5 g of (2-(phenylamino)phenyl)boronic acid, 13.6 g of K2CO3, 0.33 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 28 g (yield 77%, Mass [M+] = 744).

[0425] F-26 Synthesis Under a nitrogen atmosphere, 15 g of I-53, 13.4 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.6 g (44% yield, Mass [M+] = 752).

[0426] Preparation of Compound 27 (F-27) [ka]

[0427] Synthesis of I-54 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 37 g (yield 74%, Mass [M+] = 446).

[0428] Synthesis of I-55 30 g of I-54, 25.5 g of (4-(9H-carbazol-9-yl)-2-(phenylamino)phenyl)boronic acid, 18.6 g of K2CO3, 0.33 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 35 g (yield 70%, Mass [M+] = 744).

[0429] F-27 Synthesis Under a nitrogen atmosphere, 15 g of I-55, 13.4 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.2 g (41% yield, Mass [M+] = 752).

[0430] Preparation of Compound 28 (F-28) [ka]

[0431] Synthesis of I-56 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 66 g (yield 71%, Mass [M+] = 446).

[0432] Synthesis of I-57 30 g of I-56, 25.5 g of (5-(9H-carbazol-9-yl)-2-(phenylamino)phenyl)boronic acid, 18.6 g of K2CO3, 0.33 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to give 36 g (yield 72%, Mass [M+] = 744).

[0433] F-28 synthesis Under a nitrogen atmosphere, 15 g of I-57, 13.4 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was complete, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.7 g (43% yield, Mass [M+] = 752).

[0434] Preparation of Compound 29 (F-29) [ka]

[0435] Synthesis of I-58 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 49 g (yield 72%, Mass [M+] = 611).

[0436] Synthesis of I-59 30 g of I-58, 6.8 g of (2-hydroxyphenyl)boronic acid, 13.6 g of K2CO3, 0.25 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 25 g (yield 76%, Mass [M+] = 669).

[0437] F-29 synthesis Under a nitrogen atmosphere, 15 g of I-59, 15 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.6 g (43% yield, Mass [M+] = 677).

[0438] Preparation of Compound 30 (F-30) [ka]

[0439] Synthesis of I-60 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 38 g (yield 76%, Mass [M+] = 446).

[0440] Synthesis of I-61 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to give 33 g (yield 72%, Mass [M+] = 685).

[0441] F-30 synthesis Under a nitrogen atmosphere, 15 g of I-61, 15 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.8 g (45% yield, Mass [M+] = 693).

[0442] Preparation of Compound 31 (F-31) [ka]

[0443] Synthesis of I-62 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 58 g (yield 72%, Mass [M+] = 387).

[0444] Synthesis of I-63 30 g of I-62, 24.8 g of (5-(9H-carbazol-9-yl)-2-mercaptophenyl)boronic acid, 1.5 g of K2CO3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to give 34 g (yield 70%, Mass [M+] = 626).

[0445] Synthesis of F-31 Under a nitrogen atmosphere, 15 g of I-63, 16 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.5 g (43% yield, Mass [M+] = 634).

[0446] Preparation of Compound 32 (F-32) [ka]

[0447] Synthesis of I-64 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 57 g (yield 72%, Mass [M+] = 534).

[0448] Synthesis of I-65 30 g of I-64, 17 g of 2-tribenzodibenzofuranboronic acid, 15.6 g of K2CO3, 0.3 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 28 g (yield 71%, Mass [M+] = 702).

[0449] Synthesis of I-66 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 22 g (yield 74%, Mass [M+] = 835).

[0450] F-32 Synthesis Under a nitrogen atmosphere, 15 g of I-66, 12 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.6 g (44% yield, Mass [M+] = 843).

[0451] Preparation of Compound 33 (F-33) [ka]

[0452] Synthesis of I-67 30 g of I-64, 17 g of 1-tribenzodibenzofuranboronic acid, 15.6 g of K2CO3, 0.3 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 29 g (yield 73%, Mass [M+] = 702).

[0453] Synthesis of I-68 25 g of I-67, 4.92 g of (2-hydroxyphenyl)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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 21 g (yield 78%, Mass [M+] = 760).

[0454] F-33 ​​Synthesis Under a nitrogen atmosphere, 15 g of I-68, 13.2 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.7 g (44% yield, Mass [M+] = 768).

[0455] Preparation of Compound 34 (F-34) [ka]

[0456] Synthesis of I-69 A mixture of 25 g of I-60, 21.2 g of (2-hydroxy-5-(indolo[3,2,1-jk]carbazol-2-yl)phenyl)boronic acid, 15.5 g of K2CO3, 0.3 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water was heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to give 26 g (yield 62%, Mass [M+] = 743).

[0457] F-34 Synthesis Under a nitrogen atmosphere, 15 g of I-69, 13.5 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.1 g (40% yield, Mass [M+] = 751).

[0458] Preparation of Compound 35 (F-35) [ka]

[0459] Synthesis of I-70 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 58 g (yield 67%, Mass [M+] = 776).

[0460] Synthesis of I-71 30 g of I-70, 5.3 g of (2-hydroxyphenyl)boronic acid, 10.7 g of K2CO3, 0.2 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 22 g (yield 68%, Mass [M+] = 834).

[0461] F-35 Synthesis Under a nitrogen atmosphere, 15 g of I-71, 12 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the mixture was recrystallized to obtain 6 g (40% yield, Mass [M+] = 842).

[0462] Preparation of Compound 36 (F-36) [ka]

[0463] Synthesis of I-72 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 and heated to reflux and stirred for 8 hours. After completion of the reaction, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to give 43 g (yield 72%, Mass [M+] = 705).

[0464] Synthesis of I-73 30 g of I-72, 9.4 g of (2-((phenyl-d5)amino)phenyl-3,4,5,6-d4)boronic acid, 11.7 g of K2CO3, 0.2 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to obtain 23 g (yield 64%, Mass [M+] = 847).

[0465] F-36 Synthesis Under a nitrogen atmosphere, 15 g of I-73, 12 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.1 g (40% yield, Mass [M+] = 855).

[0466] Preparation of Compound 37 (F-37) [ka]

[0467] Synthesis of I-74 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 and heated to reflux and stirred for 8 hours. After completion of the reaction, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 27 g (76% yield, Mass [M+] = 645).

[0468] Synthesis of I-75 A mixture of 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 was heated to reflux and stirred for 8 hours. After the reaction was complete, the solvent was removed, and the reaction mixture was dissolved in toluene. The mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to give 24 g (yield 65%, Mass [M+] = 956).

[0469] F-37 Synthesis Under a nitrogen atmosphere, 15 g of I-75, 10.5 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was complete, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.6 g (44% yield, Mass [M+] = 964).

[0470] Preparation of Compound 38 (F-38) [ka]

[0471] Synthesis of I-76 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 and heated to reflux and stirred for 8 hours. After the reaction was completed, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to obtain 33 g (yield 63%, Mass [M+] = 481).

[0472] Synthesis of I-77 A mixture of 25 g of I-76, 11.6 g of ((2-((phenyl-d5)amino)phenyl-3,4,5,6-d4)boronic acid, 14.4 g of K2CO3, 0.3 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water was heated to reflux and stirred for 8 hours. After the reaction was completed, the solvent was completely removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to give 23 g (yield 71%, Mass [M+] = 623).

[0473] F-38 Synthesis Under a nitrogen atmosphere, 15 g of I-77, 16 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.6 g (43% yield, Mass [M+] = 631).

[0474] Preparation of Compound 39 (F-39) [ka]

[0475] Synthesis of I-78 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 and heated to reflux and stirred for 8 hours. After completion of the reaction, the reaction mixture was separated, treated with anhydrous MgSO4, and filtered. The filtered solution was recrystallized to give 45 g (67% yield, Mass [M+] = 818).

[0476] Synthesis of I-79 25 g of I-78, 4.3 g of (2-hydroxyphenyl-3,4,5,6-d4)boronic acid, 8.5 g of K2CO3, 0.2 g of [bis(tri-tert-butylphosphine)palladium(0)], 400 mL of tetrahydrofuran, and 250 mL of water were added and heated to reflux and stirred for 8 hours. After the reaction was complete, the solvent was removed, and the reaction mixture was dissolved in toluene and separated. The mixture was treated with anhydrous MgSO4 and filtered. The filtered solution was recrystallized to give 19 g (71% yield, Mass [M+] = 880).

[0477] F-39 Synthesis Under a nitrogen atmosphere, 15 g of I-79, 11.4 g of boron triiodide, and 300 mL of dichlorobenzene were added and heated to reflux and stirred for 8 hours. After the reaction was completed, the mixture was poured into water, separated, treated with anhydrous MgSO4, and filtered. After removing the filtered solution, the product was recrystallized to obtain 6.1 g (40% yield, Mass [M+] = 888).

[0478] <Examples and Comparative Examples>

[0479] Example 1 A glass substrate coated with an 800Å-thick thin film of ITO (indium tin oxide) was placed in distilled water containing a detergent and ultrasonically cleaned. The detergent used was from Fischer Co., and the distilled water was filtered through a Millipore Co. filter. After cleaning the ITO for 30 minutes, it was ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning, the substrate was ultrasonically cleaned with a solvent consisting of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned using oxygen plasma for 5 minutes and then transferred to a vacuum deposition machine.

[0480] On the ITO transparent electrode (anode) thus prepared, a hole injection layer was formed by thermal vacuum deposition of the following compound HT1 and the following compound HI1 in a molar ratio of 95:5 to a thickness of 100 Å. A hole transport layer was formed on the hole injection layer by vacuum deposition of a compound represented by the following formula HT1 (300 Å). Next, an electron blocking layer was formed on the hole transport layer by vacuum deposition of a compound represented by BH (p-type) to a thickness of 50 Å. Next, an emitting layer was formed on the electron blocking layer by vacuum deposition of a 1:1 mixture of the following compound BH (p-type) and the compound 1 (n-type) synthesized in Preparation Example 1 as the emitting layer host and a compound represented by the following formula BD as the emitting layer dopant in a weight ratio of 86:14. A hole blocking layer was formed on the emitting layer by vacuum deposition of the compound 1 (n-type) synthesized in Preparation Example 1 as the emitting layer host. Next, a compound represented by the following formula ET1 and a compound represented by the following formula LiQ were vacuum-deposited on the hole-blocking layer in a 1:1 weight ratio to form an electron-injecting and transporting layer to a thickness of 300 Å. Lithium fluoride (LiF) and aluminum were sequentially deposited on the electron-injecting and transporting layer to a thickness of 10 Å and 800 Å, respectively, to form a cathode.

[0481] [ka]

[0482] During the above process, the deposition rate of the organic material was maintained at 0.4-0.7 Å / sec, the deposition rate of the cathode lithium fluoride was maintained at 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. The vacuum during deposition was 2×10 -7 ~5×10 -6 The organic light-emitting device was fabricated while maintaining a high pressure (torr).

[0483] Examples 2 to 39 An organic light-emitting device was fabricated in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of Compound 1 as the host of the light-emitting layer.

[0484] [ka] [ka]

[0485] Comparative Examples 1 to 6 An organic light-emitting device was fabricated in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of Compound 1 as the host of the light-emitting layer.

[0486] [ka]

[0487] The voltage, efficiency, and lifetime when a current was applied to the organic light-emitting devices fabricated in Examples 1 to 39 and Comparative Examples 1 to 6 were measured (based on 1600 nit), and the results are shown in Table 1. The lifetime T90 refers to the time it takes for the brightness to decrease to 90% from the initial brightness (1600 nit).

[0488] [Table 1] JPEG2026508422000191.jpg149137

[0489] 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 in the core structure is substituted, but the electron-withdrawing property of boron makes the benzene ring unstable, resulting in a significant reduction in lifetime. As can be seen from Table 1, the increased lifetime reduction results in an increase in voltage and a decrease in efficiency.

[0490] In addition, it can be seen that the organic light-emitting device of Comparative Example 6, which uses compound BH6 in which any one of the benzene rings connected to boron in the core structure is unsubstituted, exhibits the shortest lifespan characteristics due to the structural instability of the compound.

[0491] However, in the case of the compound of Formula 1 of the present application, at least one of the benzene rings directly or indirectly connected to boron in the core structure is substituted with a carbazole group, and at least one of the remaining rings is substituted with an aryl group, silyl group, or heterocyclic group, which stabilizes the unstable structure and adds hole characteristics, thereby increasing the lifetime. In other words, the structural stability of the compound reduces voltage at high currents and increases efficiency. [Explanation of symbols]

[0492] 1. Circuit board 2...1st electrode 3. Hole injection layer 4. Hole transport layer 5. Electron blocking layer 6. Emitting layer 7. Hole-blocking layer 8. Electron Injection and Transport Layer 9...Second electrode

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] 【Chemistry 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 and each independently represent 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 each independently represent 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 each an integer of 1 to 4; n3 and m3 are each an integer of 1 to 3, When n1 to n3 and m1 to m3 are each 2 or more, the substituents in the parentheses are the same or different from each other, n1+m1 is 4 or less, n2+m2 is 4 or less, and n3+m3 is 3 or less.

2. The compound according to claim 1, wherein L1 to L3 and L11 to L33 are the same or different and each independently represent 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 and containing one or more heteroatoms selected from N, O, and S.

3. The compound according to claim 1, wherein L1 to L3 are the same or different and each independently represent a direct bond; a deuterium-substituted or unsubstituted phenylene group; a deuterium-substituted or unsubstituted divalent dibenzofuran group; a deuterium-substituted or unsubstituted divalent dibenzothiophene group; or a deuterium-substituted or unsubstituted divalent carbazole group.

4. The compound according to claim 1, wherein L11 to L33 are the same or different and each independently represent a direct bond; a deuterium-substituted or unsubstituted phenylene group; or a deuterium-substituted or unsubstituted divalent carbazole group.

5. the R1 to R3 and R11 to R33 are the same or different 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 substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

6. the compound according to claim 1, wherein at least one of R11 to R33 is a deuterium-substituted or unsubstituted triphenylsilyl group; a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; a deuterium-substituted or unsubstituted naphthyl group; a deuterium-substituted or unsubstituted carbazole group; a deuterium-substituted or unsubstituted dibenzofuran group; a deuterium-substituted or unsubstituted dibenzothiophene group; or a deuterium-substituted or unsubstituted heterocyclic group containing one or more N and O heteroatoms and having 4 to 7 fused rings, and wherein the remaining rings are the same or different and each independently represent hydrogen or deuterium.

7. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-6: [Chemical formula 1-1] 【Chemistry 10】 [Chemical formula 1-2] 【Chemistry 11】 [Chemical formula 1-3] 【Chemistry 12】 [Chemical formula 1-4] 【Chemistry 13】 [Chemical formula 1-5] 【Chemistry 14】 [Chemical formula 1-6] 【Chemistry 15】 In the 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 Chemical Formula 1. G1 to G3 are the same or different and each independently represent 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 an integer of 1 to 8, and when g1 to g3 are each 2 or more, G1 to G3 are each the same or different.

8. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following compounds: 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 [Transformation 50] 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemistry 54】 【Transformation 55】 【Transformation 56】 【Chemistry 57】 【Transformation 58】 【Chemistry 59】 【Transformation 60】 【Chemistry 61】 【Transformation 62】 【Transformation 63】 【Chemistry 64】 【Transformation 65】 【Chemical Formula 66】 【Transformation 67】 【Transformation 68】 【Transformation 69】 【Transformation 70】 【Chemistry 71】 【Chemistry 72】 【Transformation 73】 【Chemistry 74】 【Chemistry 75】 【Transformation 76】 【Chemical 77】 【Transformation 78】 【Chemistry 79】 【Chemistry 80】 【Chemistry 81】 【Chemistry 82】 【Chemistry 83】 【Chemical 84】 【Chemical 85】 【Chemical 86】 【Transformation 87】 【Chemical 88】 【Chemistry 89】 【Chemistry 90】 【Chemistry 91】 【Chemistry 92】 【Chemistry 93】 【Chemical 94】 【Chemical 95】 【Chemistry 96】 【Chemistry 97】 【Chem.98】 【Chem.99】 【Chemistry 100】 【Chemistry 101】 【Chemical Engineering 102】 【Chemistry 103】 【Chemical 104】 【Chemistry 105】 【Chemistry 106】 【Chemistry 107】 【Chemistry 108】 【Chemistry 109】 【Chemical 110】 【Chemistry 111】 【Chemistry 112】 【Chemistry 113】 【Chemical 114】 【Chemical 115】 【Chemistry 116】 【Chemistry 117】 【Chemistry 118】 【Chemical 119】 【Chemical 120】 【Chemistry 121】 【Chemistry 122】 【Chemical 123】 【Chemistry 124】 【Chemistry 125】 【Chemistry 126】 【Chemistry 127】 【Chemistry 128】 【Chemistry 129】 。

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

10. 10. The organic light emitting device according to claim 9, wherein the organic material 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 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. The organic light-emitting element according to claim 9 , wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound.

12. The organic light-emitting device according to claim 9, wherein the organic material layer includes a light-emitting layer, the light-emitting layer including the compound as an n-type host and further including a p-type host.

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

14. The organic light emitting device according to claim 9 , wherein the organic material layer comprises an emitting layer and a hole blocking layer, and the emitting layer and the hole blocking layer comprise the compound.

Images