Compound and organic light-emitting device comprising same

Abstract

The present specification provides a compound represented by chemical formula 1, and an organic light-emitting device comprising same.

Description

Compound and organic light-emitting device containing the same

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

[0002] This application claims the benefit of Korean Patent Application No. 10-2023-0133371 filed with the Korean Intellectual Property Office on October 6, 2023, the entire contents of which are incorporated herein by reference.

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

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

[0005] [Prior Art Literature]

[0006] [Patent Document]

[0007] (Patent Document 1) Japanese Publication No. 2021-095342 A

[0008] The present specification provides a compound and an organic light-emitting device comprising the same.

[0009] One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] X is NR; O; or S,

[0014] At least one of R and R1 to R3 is a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and the others are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted cycloalkyl group,

[0015] L1 to L3 and L11 to L13 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0016] G1 to G3 are the same or different and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0017] n1 and n2 are integers from 1 to 4, respectively, and m1 and m2 are integers from 0 to 4, respectively.

[0018] n3 is an integer from 1 to 3, m3 is an integer from 0 to 3,

[0019]

[0020] g1 to g3 are integers from 0 to 8, respectively,

[0021] When the above n1 to n3, m1 to m3 and g1 to g3 are each 2 or more, the substituents in the parentheses are each the same or different,

[0022] n1+m1 is less than or equal to 4, n2+m2 is less than or equal to 4, n3+m3 is less than or equal to 3,

[0023] m1+m2+m3 are integers greater than or equal to 1.

[0024] In addition, one embodiment of the present specification provides an organic light-emitting device including an anode; a cathode; and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers includes a compound represented by the chemical formula 1.

[0025] The compounds described herein can be used as materials for an organic layer of an organic light-emitting device. The compounds according to at least one embodiment of the present disclosure can improve efficiency, lower operating voltage, and / or lifespan characteristics in an organic light-emitting device.

[0026] In particular, the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, luminescence, hole blocking, electron transport, or electron injection materials. In addition, compared to existing organic light-emitting devices, they have the effects of low operating voltage, high efficiency, and / or long life.

[0027] Figure 1 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a light-emitting layer (6), and a cathode (10) are sequentially stacked.

[0028] Figure 2 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light-emitting layer (6), a hole blocking layer (7), an electron transport layer (8), an electron injection layer (9), and a cathode (10) are sequentially laminated.

[0029] Figure 3 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light-emitting layer (6), a hole blocking layer (7), an electron transport and injection layer (11), and a cathode (10) are sequentially laminated.

[0030] The following describes this specification in more detail.

[0031] In this specification, when a part is said to "include" a certain component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

[0032] In this specification, when it is said that a member is located “on” another member, this includes not only cases where the member is in contact with the other member, but also cases where another member exists between the two members.

[0033] In this specification, N% substitution with deuterium means that N% of the available hydrogens in the structure are replaced with deuterium. For example, if dibenzofuran is 25% substituted with deuterium, it means that two of the eight hydrogens in dibenzofuran are replaced with deuterium.

[0034] In this specification, the degree of deuteration can be confirmed by a known method such as nuclear magnetic resonance spectroscopy (1H NMR) or GC / MS.

[0035] Examples of substituents in this specification are described below, but are not limited thereto.

[0036] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where the hydrogen atom is replaced, i.e., a position where the substituent can be replaced, and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0037] The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group (-CN); a nitro group; a hydroxyl group; an alkyl group; a cycloalkyl group; an alkoxy group; a phosphine oxide group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an arylsulfoxy group; an alkenyl group; a silyl group; a boron group; an amine group; an aryl group; or a heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are connected, or having no substituents. For example, "a substituent connected with two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent in which two phenyl groups are connected.

[0038] The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; nitro group; hydroxy group; amino group; silyl group; boron group; alkoxy group; aryloxy group; alkyl group; cycloalkyl group; aryl group; and heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

[0039] The term "substituted or unsubstituted" in this specification means substituted with one or more substituents selected from the group consisting of deuterium; alkyl groups; aryl groups; and heterocyclic groups, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

[0040] Examples of the above substituents are described below, but are not limited thereto.

[0041] In this specification, examples of halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0042] In this specification, the silyl group is -SiY aY b Y c It can be represented by the chemical formula of Y, a , Y b and Y c Each may be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0043] In this specification, the boron group is -BY d Y e It can be represented by the chemical formula of Y, d and Y e Each may be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group.

[0044] In the present specification, the alkyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an n-pentyl group, a hexyl group, an n-hexyl group, a heptyl group, an n-heptyl group, an octyl group, an n-octyl group, etc.

[0045] In this specification, the description of the alkyl group described above may be applied to the arylalkyl group, except that the arylalkyl group is substituted with an aryl group.

[0046] In the present specification, the alkoxy group may be linear, branched, or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but is not limited thereto.

[0047] Substituents comprising alkyl groups, alkoxy groups and other alkyl moieties described herein include both straight-chain and branched forms.

[0048] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 6. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, and styrenyl groups.

[0049] In the present specification, the alkynyl group is a substituent containing a triple bond between carbon atoms, may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkynyl group is 2 to 10.

[0050] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. In one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples thereof include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0051] In the present specification, the amine group is -NH2, and the amine group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The carbon number of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the carbon number of the amine group is 1 to 20. According to one embodiment, the carbon number of the amine group is 1 to 10. Specific examples of substituted amine groups include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a 9,9-dimethylfluorenylphenylamine group, a pyridylphenylamine group, a diphenylamine group, a phenylpyridylamine group, a naphthylamine group, a biphenylamine group, anthracenylamine group, a dibenzofuranylphenylamine group, a 9-methylanthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a diphenylamine group, and the like.

[0052] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group or a polycyclic aryl group (an aryl group having two or more rings). The monocyclic aryl group may also be expressed as a monocyclic aryl group, and may refer to a phenyl group; or a group in which two or more phenyl groups are connected. The monocyclic aryl group may include, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaternaryl group, and the like. The polycyclic aryl group may refer to a group in which two or more monocyclic rings are condensed, such as a naphthyl group, a phenanthrenyl group, and the like. The above polycyclic aryl group may include, but is not limited to, a naphthyl group, anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, etc.

[0053] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. In this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

[0054] When the above fluorenyl group is substituted, , , Spirofluorenyl group of etc. (9,9-dimethylfluorenyl group), and It can be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group), but is not limited thereto.

[0055] In this specification, the aryl group among the aryloxy groups may be applied to the description of the aryl group described above.

[0056] In this specification, the description regarding the alkyl group described above may be applied to the alkyl group among the alkylthioxy group and alkylsulfoxy group.

[0057] In this specification, the description regarding the aryl group described above can be applied to the aryl group among the arylthioxy group and arylsulfoxy group.

[0058] In the present specification, a heterocyclic group is a ring group containing at least one of N, O, P, S, Si, and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of the heterocyclic group include, but are not limited to, a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, a triazinyl group, and the like.

[0059] In this specification, the description of the heterocyclic group described above may be applied, except that the heteroaryl group is aromatic.

[0060] In this specification, the description of the aryl group may be applied except that the arylene group is divalent.

[0061] In this specification, the description of the above heterocyclic group may be applied to the divalent heterocyclic group except that the divalent heterocyclic group is divalent.

[0062] In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, “ring” means a hydrocarbon ring; or a heterocycle.

[0063] The above hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the above cycloalkyl group or aryl group.

[0064] In the present specification, forming a ring by bonding with adjacent groups means forming a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a condensed ring thereof by bonding with adjacent groups. The hydrocarbon ring means a ring composed only of carbon and hydrogen atoms. The heterocycle means a ring containing one or more elements selected from N, O, P, S, Si, and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocycle, and the aromatic heterocycle may be monocyclic or polycyclic.

[0065] In this specification, an aliphatic hydrocarbon ring means a non-aromatic ring composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.

[0066] In this specification, an aromatic hydrocarbon ring means an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include, but are not limited to, benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, and spirofluorene. In this specification, an aromatic hydrocarbon ring can be interpreted to have the same meaning as an aryl group.

[0067] In the present specification, an aliphatic heterocycle means an aliphatic ring containing at least one heteroatom. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocane, and thiocane.

[0068] In this specification, an aromatic heterocycle means an aromatic ring containing at least one heteroatom. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, diazanaphthalene, dryazaindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, Examples include, but are not limited to, imidazopyridine, phenoxazine, indolocarbazole, and indenocarbazole.

[0069] Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention may be modified in various ways, and the scope of the present invention is not limited to the embodiments described below.

[0070] The compound represented by the chemical formula 1 of the present invention is characterized in that a carbazole group is connected to a benzene ring included in a multi-resonance core structure containing boron, and a silyl group or aryl group is connected thereto. When the carbazole group and the silyl group or aryl group are connected to the core structure as described above, the bulkiness of the molecule itself is increased compared to a structure in which one carbazole group is substituted, thereby increasing the distance between molecules and preventing aggregation of molecules, thereby suppressing quenching caused by this, thereby having the effect of increasing the efficiency and lifespan of the organic light-emitting device.

[0071] Therefore, when the compound represented by the chemical formula 1 of the present invention is applied to an organic light-emitting device, an organic light-emitting device having high efficiency, low voltage, and / or long life characteristics can be obtained.

[0072] Hereinafter, chemical formula 1 is described in detail.

[0073] [Chemical Formula 1]

[0074]

[0075] In the above chemical formula 1,

[0076] X is NR; O; or S,

[0077] At least one of R and R1 to R3 is a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and the others are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted cycloalkyl group,

[0078] L1 to L3 and L11 to L13 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0079] G1 to G3 are the same or different and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0080] n1 and n2 are integers from 1 to 4, respectively, and m1 and m2 are integers from 0 to 4, respectively.

[0081] n3 is an integer from 1 to 3, m3 is an integer from 0 to 3,

[0082] g1 to g3 are integers from 0 to 8, respectively,

[0083] When the above n1 to n3, m1 to m3 and g1 to g3 are each 2 or more, the substituents in the parentheses are each the same or different,

[0084] n1+m1 is less than or equal to 4, n2+m2 is less than or equal to 4, n3+m3 is less than or equal to 3,

[0085] m1+m2+m3 are integers greater than or equal to 1.

[0086] In one embodiment of the present specification, X is NR; O; or S.

[0087] In one embodiment of the present specification, X is NR.

[0088] In one embodiment of the present specification, X is O.

[0089] In one embodiment of the present specification, X is S.

[0090] In one embodiment of the present specification, R is hydrogen; deuterium; a halogen group; a nitrile 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.

[0091] In one embodiment of the present specification, R is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0092] In one embodiment of the present specification, R is a substituted or unsubstituted aryl group.

[0093] In one embodiment of the present specification, R is a phenyl group or a biphenyl group.

[0094] In one embodiment of the present specification, at least one of R1 to R3 is a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and the others are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted cycloalkyl group.

[0095] In one embodiment of the present specification, at least one of R1 to R3 is a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms.

[0096] In one embodiment of the present specification, at least one of R1 to R3 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, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms.

[0097] In one embodiment of the present specification, at least one of R1 to R3 is a substituted or unsubstituted silyl group; 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, and the rest are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms.

[0098] In one embodiment of the present specification, at least one of R1 to R3 is a silyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; an aryl group unsubstituted or substituted with deuterium or an aryl group; or a heterocyclic group unsubstituted or substituted with deuterium or a heterocyclic group, and the others are the same as or different from each other and are each independently hydrogen; or deuterium.

[0099] In one embodiment of the present specification, at least one of R1 to R3 is a silyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 60 carbon atoms, or an aryl group having 6 to 60 carbon atoms; an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium or an aryl group having 6 to 60 carbon atoms; or a heterocyclic group having 2 to 60 carbon atoms substituted or unsubstituted with deuterium or a heterocyclic group having 2 to 60 carbon atoms, and the rest are the same as or different from each other and are each independently hydrogen; or deuterium.

[0100] In one embodiment of the present specification, at least one of R1 to R3 is a silyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium or a heterocyclic group having 2 to 30 carbon atoms, and the rest are the same as or different from each other and are each independently hydrogen; or deuterium.

[0101] In one embodiment of the present specification, at least one of R1 to R3 is a silyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; or a heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium or a heterocyclic group having 2 to 20 carbon atoms, and the rest are the same as or different from each other and are each independently hydrogen; or deuterium.

[0102] In one embodiment of the present specification, at least one of R1 to R3 is a silyl group substituted with a phenyl group; a phenyl group; a biphenyl group; a carbazole group; a dibenzofuran group; a dibenzothiophene group; or a heterocyclic group having 2 to 60 carbon atoms and containing at least one of N and O as a heteroatom, and the rest are the same or different and are each independently hydrogen; or deuterium.

[0103] In one embodiment of the present specification, at least one of R1 to R3 is a triphenylsilyl group; a phenyl group; a biphenyl group; a carbazole group; a dibenzofuran group; a benzofuranodibenzofuran group; or an indolocarbazole group, and the others are the same as or different from each other and are each independently hydrogen; or deuterium.

[0104] In one embodiment of the present specification, the benzofuranodibenzofuran group is a benzo[1,2-b:3,4-b']bisbenzofuran group.

[0105] In one embodiment of the present specification, the indolocarbazole group is indolo[3,2,1-jk]carbazole.

[0106] In one embodiment of the present specification, at least one of R1 to R3 is a group represented by the following structural formula, or a substituted or unsubstituted aryl group.

[0107]

[0108] In the above structural formula, P1 to P3 are substituted or unsubstituted aryl groups, refers to the position where it is bound to L1 to L3.

[0109] In one embodiment of the present specification, P1 to P3 are substituted or unsubstituted aryl groups having 6 to 60 carbon atoms.

[0110] In one embodiment of the present specification, P1 to P3 are substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0111] In one embodiment of the present specification, P1 to P3 are substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.

[0112] In one embodiment of the present specification, P1 to P3 are phenyl groups.

[0113] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group.

[0114] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.

[0115] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

[0116] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms.

[0117] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group.

[0118] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; or an arylene group having 6 to 60 carbon atoms.

[0119] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; or an arylene group having 6 to 30 carbon atoms.

[0120] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; or an arylene group having 6 to 20 carbon atoms.

[0121] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; or a phenylene group.

[0122] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group.

[0123] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.

[0124] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

[0125] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms.

[0126] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and each independently represent a direct bond; or a substituted or unsubstituted arylene group.

[0127] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and are each independently a direct bond; or an arylene group.

[0128] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and are each independently a direct bond; or an arylene group having 6 to 60 carbon atoms.

[0129] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and are each independently a direct bond; or an arylene group having 6 to 30 carbon atoms.

[0130] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and are each independently a direct bond; or an arylene group having 6 to 20 carbon atoms.

[0131] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and are each independently a direct bond; or a phenylene group.

[0132] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0133] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

[0134] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0135] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0136] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0137] In one embodiment of the present specification, G1 to G3 are hydrogen.

[0138] In one embodiment of the present specification, n1 and n2 are each integers from 1 to 4, and m1 and m2 are each integers from 0 to 4.

[0139] In one embodiment of the present specification, n3 is an integer from 1 to 3, and m3 is an integer from 0 to 3.

[0140] In one embodiment of the present specification, n1 is 1.

[0141] In one embodiment of the present specification, n2 is 1.

[0142] In one embodiment of the present specification, n3 is 1.

[0143] In one embodiment of the present specification, m1 is 0.

[0144] In one embodiment of the present specification, m1 is 1.

[0145] In one embodiment of the present specification, m2 is 0.

[0146] In one embodiment of the present specification, m2 is 1.

[0147] In one embodiment of the present specification, m3 is 0.

[0148] In one embodiment of the present specification, m3 is 1.

[0149] In one embodiment of the present specification, g1 to g3 are each integers from 0 to 8.

[0150] In one embodiment of the present specification, g1 to g3 are 0.

[0151] In one embodiment of the present specification, g1 to g3 are 8.

[0152] In one embodiment of the present specification, n1+m1 is 4 or less, n2+m2 is 4 or less, and n3+m3 is 3 or less.

[0153] In one embodiment of the present specification, m1+m2+m3 are integers greater than or equal to 1.

[0154] In one embodiment of the present specification, m1+m2+m3 is 1 to 3.

[0155] In one embodiment of the present specification, m1+m2+m3 is 1 or 2.

[0156] In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-A-1 to 1-A-3.

[0157] [Chemical Formula 1-A-1]

[0158]

[0159] [Chemical Formula 1-A-2]

[0160]

[0161] [Chemical Formula 1-A-3]

[0162]

[0163] In the above chemical formulas 1-A-1 to 1-A-3,

[0164] The definitions of X, R1 to R3, L1 to L3, L11 to L13, G1 to G3 and g1 to g3 are the same as those in the above chemical formula 1.

[0165] In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-B-1 to 1-B-3.

[0166] [Chemical Formula 1-B-1]

[0167]

[0168] [Chemical Formula 1-B-2]

[0169]

[0170] [Chemical Formula 1-B-3]

[0171]

[0172] In the above chemical formulas 1-B-1 to 1-B-3,

[0173] The definitions of X, R1 to R3, L1 to L3, L11 to L13, G1 to G3 and g1 to g3 are the same as those in the above chemical formula 1.

[0174] In one embodiment of the present specification, the compound of chemical formula 1 containing deuterium can be prepared by a known deuteration reaction. In one embodiment of the present specification, the compound represented by chemical formula 1 can be formed by using a deuterated compound as a precursor, or deuterium can be introduced into the compound through a hydrogen-deuterium exchange reaction in the presence of an acid catalyst using a deuterated solvent.

[0175] In one embodiment of the present specification, the compound represented by the chemical formula 1 is substituted by 20% or more with deuterium. In another embodiment, the compound represented by the chemical formula 1 is substituted by 30% or more with deuterium. In another embodiment, the compound represented by the chemical formula 1 is substituted by 40% or more with deuterium. In another embodiment, the compound represented by the chemical formula 1 is substituted by 50% or more with deuterium. In another embodiment, the compound represented by the chemical formula 1 is substituted by 60% or more with deuterium. In another embodiment, the compound represented by the chemical formula 1 is substituted by 70% or more with deuterium. In another embodiment, the compound represented by the chemical formula 1 is substituted by 80% or more with deuterium. In another embodiment, the compound represented by the chemical formula 1 is substituted by 90% or more with deuterium. In another embodiment, the compound represented by the above chemical formula 1 is 100% substituted with deuterium.

[0176] In one embodiment of the present specification, the compound represented by the chemical formula 1 contains 40% to 60% of deuterium. In another embodiment, the compound represented by the chemical formula 1 contains 40% to 80% of deuterium. In another embodiment, the compound represented by the chemical formula 1 contains 60% to 80% of deuterium. In another embodiment, the compound represented by the chemical formula 1 contains 80% to 100% of deuterium.

[0177] In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following compounds.

[0178]

[0179]

[0180] Above [ ] D=x1~x2 means that the structure within the parentheses contains x1 to x2 deuterium atoms, and the value is an integer. For example, [ ] D=1~41 means containing 1 to 41 deuterium atoms.

[0181] The compound represented by Chemical Formula 1 according to one embodiment of the present specification can have a core structure manufactured as shown in the following Reaction Scheme 1. The substituents can be bonded by a method known in the art, and the type, position, or number of the substituents can be changed according to a technique known in the art.

[0182] <Reaction Scheme 1>

[0183]

[0184]

[0185] In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above chemical formula 1. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can also be controlled by introducing various substituents into the core structure of the above structure.

[0186] In addition, the present specification provides an organic light-emitting device comprising the compound described above.

[0187] In one embodiment of the present invention, an organic light-emitting device is provided, comprising an anode; a cathode; and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers comprises a compound represented by the above-described chemical formula 1.

[0188] The organic material layer of the organic light-emitting device according to this specification may be formed as a single-layer structure, but may be formed as a multi-layer structure in which two or more organic material layers are laminated.

[0189] In one embodiment of the present specification, the organic layer may include at least one layer of a hole transport layer, a hole injection layer, an electron blocking layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer.

[0190] In one embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, electron transport layer, or electron injection and transport layer includes a compound represented by the chemical formula 1.

[0191] In one embodiment of the present specification, the organic layer includes an electron control layer, and the electron control layer includes a compound represented by the chemical formula 1.

[0192] In one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes a compound represented by the chemical formula 1.

[0193] In one embodiment of the present specification, the organic layer includes a hole blocking layer and a light emitting layer, and the hole blocking layer and the light emitting layer include a compound represented by the chemical formula 1. At this time, the compounds represented by the chemical formula 1 included in the light emitting layer and the hole blocking layer may be the same or different.

[0194] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include a compound represented by the chemical formula 1.

[0195] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include a compound represented by the chemical formula 1 as a host.

[0196] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include a compound represented by the chemical formula 1 as an n-type phosphorescent host of the light-emitting layer.

[0197] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the chemical formula 1 as a host, and may further include a host and a dopant.

[0198] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include two or more compounds represented by the chemical formula 1 as a host.

[0199] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the chemical formula 1 as a first host, and may further include an additional second host.

[0200] In one embodiment of the present specification, the first host is an n-type phosphorescent host, and the second host is a p-type phosphorescent host. At this time, the weight ratio of the first host and the second host may be 2:8 to 8:2, 4:6 to 6:4, or 5:5. The n-type may be a material that is generally known as a material that can steal electrons from a matrix material (material of the organic layer), but is not limited thereto. That is, the n-type may be defined as a material that has a characteristic of providing electrons to the LUMO (lowest unoccupied molecular orbital) energy level of the matrix. On the other hand, the p-type refers to a material that receives electrons from the HOMO (highest occupied molecular orbital) energy level of a material located in the adjacent cathode direction when forming a single layer using only p-type materials, thereby generating holes in the material located in the adjacent cathode direction, or, when a p-type material is doped into an arbitrary matrix, refers to a material that receives electrons from the HOMO of the matrix material and generates holes in the HOMO of the matrix to that extent. To this end, when forming a layer using only p-type materials, the closer the HOMO level of the material located in the cathode direction is to the LUMO of the p-type material, the easier it is to steal electrons from the HOMO of the adjacent layer and generate holes in the HOMO of the adjacent layer, and also, when a p-type material is doped into an arbitrary matrix, the closer the LUMO of the p-type material is to the HOMO of the matrix, the easier it is to steal electrons and generate holes in the matrix.

[0201] The above p-type host can be a compound generally known in the art, and can have a structure including, for example, an N-containing monocyclic ring; dibenzofuran; and / or carbazole.

[0202] In one embodiment of the present specification, the second host is a carbazole compound.

[0203] In one embodiment of the present specification, the second host is a biscarbazole compound.

[0204] In one embodiment of the present specification, the second host is a biscarbazole compound substituted with an aryl group.

[0205] In one embodiment of the present specification, the light-emitting layer includes a first host and a second host, and may further include a dopant, and the dopant may be a phosphorescent dopant. In one embodiment of the present specification, the light-emitting layer may be a blue light-emitting layer, a red light-emitting layer, or a green light-emitting layer.

[0206] In one embodiment of the present specification, the light-emitting layer may be a blue light-emitting layer.

[0207] In one embodiment of the present specification, the light-emitting layer may include a host and a dopant. Specifically, the dopant may be a fluorescent dopant or a phosphorescent dopant.

[0208] In one embodiment of the present specification, the dopant is included in an amount of 1 to 20 parts by weight based on 100 parts by weight of the host.

[0209] In one embodiment of the present specification, the light-emitting layer includes the host and the dopant in a weight ratio of 99:1 to 1:99. Specifically, the weight ratio is 99:1 to 50:50, 99:1 to 70:30, 99:1 to 80:20, 99:1 to 90:10, or 99:1 to 95:5.

[0210] In one embodiment of the present specification, the dopant may include an arylamine compound, a heterocyclic compound containing boron and nitrogen, a metal complex compound, a platinum complex compound, an iridium complex compound, or an iridium compound.

[0211] For example, when the light-emitting layer emits red light, a phosphorescent material such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the light-emitting dopant, but is not limited thereto. When the light-emitting layer emits green light, a phosphorescent material such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium), or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as the light-emitting dopant, but is not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as a platinum complex compound or (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distriarylene (DSA), PFO polymer, or PPV polymer can be used as a light-emitting dopant, but is not limited thereto.

[0212] In one embodiment of the present specification, the dopant is a metal complex compound.

[0213] In one embodiment of the present specification, the dopant is a platinum complex compound.

[0214] In one embodiment of the present specification, the dopant is an iridium complex compound.

[0215] In one embodiment of the present specification, the dopant is an iridium-based compound.

[0216] In one embodiment of the present specification, the dopant compound may be selected from the following structural formulas, but is not limited thereto.

[0217]

[0218]

[0219]

[0220]

[0221]

[0222] In one embodiment of the present specification, the organic layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes a compound represented by the chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by the chemical formula 1 may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.

[0223] In one embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, other materials except for the compound represented by the chemical formula 1 may be the same or different from each other.

[0224] When the organic layer containing the compound represented by the above chemical formula 1 is an electron transport layer, an electron injection layer, or an electron transport and injection layer, the electron transport layer, the electron injection layer, or the electron transport and injection layer may further contain an n-type dopant or an organometallic compound. The n-type dopant or organometallic compound may be one known in the art, and may be, for example, a metal or a metal complex.

[0225] For example, the n-type dopant or organometallic compound may be, but is not limited to, LiQ. The electron transport layer, electron injection layer, or electron transport and injection layer including the compound represented by the above chemical formula 1 may further include LiQ (Lithium Quinolate).

[0226] In one example, the compound represented by the above chemical formula 1 and the n-type dopant or organometallic compound may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4. In one example, the compound represented by the above chemical formula 1 and the n-type dopant or organometallic compound may be included in a weight ratio of 1:1.

[0227] In one embodiment of the present invention, the organic layer may further include another organic compound, metal, or metal compound in addition to the compound represented by the above-described chemical formula 1.

[0228] In one embodiment of the present specification, the organic layer may further include a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazolyl group, or a benzocarbazolyl group, in addition to the organic layer including the compound represented by the chemical formula 1.

[0229] In one embodiment of the present specification, the thickness of the organic layer including the compound of the chemical formula 1 may be 5 Å to 2000 Å, or 5 Å to 500 Å, and preferably 10 Å to 400 Å.

[0230] In one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0231] In one embodiment of the present specification, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0232] The above organic light-emitting device may have a laminated structure, for example, as follows, but is not limited thereto.

[0233] (1) Anode / hole transport layer / light emitting layer / cathode

[0234] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0235] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0236] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0237] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0238] (6) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0239] (7) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0240] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0241] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0242] (10) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

[0243] (11) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0244] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

[0245] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0246] (14)

[0247] Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0248] (15) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

[0249] (16) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0250] (17) Anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

[0251] (18) Anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0252] (19) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport and injection layer / cathode

[0253] The structure of the organic light-emitting device of this specification may have a structure as shown in FIGS. 1 to 3, but is not limited thereto.

[0254] Figure 1 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a light-emitting layer (6), and a cathode (10) are sequentially laminated. In such a structure, the compound may be included in the light-emitting layer (6).

[0255] Figure 2 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light-emitting layer (6), a hole blocking layer (7), an electron transport layer (8), an electron injection layer (9), and a cathode (10) are sequentially laminated. In this structure, the compound may be included in the hole injection layer (3), the hole transport layer (4), the electron blocking layer (5), the light-emitting layer (6), the hole blocking layer (7), the electron transport layer (8), or the electron injection layer (9).

[0256] Figure 3 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light-emitting layer (6), a hole blocking layer (7), an electron transport and injection layer (11), and a cathode (10) are sequentially laminated. In this structure, the compound may be included in the hole injection layer (3), the hole transport layer (4), the electron blocking layer (5), the light-emitting layer (6), the hole blocking layer (7), or the electron transport and injection layer (11).

[0257] In one embodiment of the present specification, the hole blocking layer and the light emitting layer may be provided adjacently. For example, the hole blocking layer and the light emitting layer may be provided in physical contact.

[0258] An organic light-emitting device according to the present specification can be manufactured using materials and manufacturing methods of conventional organic light-emitting devices, except that at least one of the organic layers includes a compound represented by the above chemical formula 1.

[0259] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0260] For example, the organic light-emitting device according to the present specification can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, forming an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, the organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0261] In addition, the compound of the above chemical formula 1 can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc.

[0262] In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing an organic layer, an anode material, and a cathode material on a substrate. However, the manufacturing method is not limited to this.

[0263] The anode is an electrode that injects holes, and as the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

[0264] The above cathode is an electrode that injects electrons, and the cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0265] The above-mentioned hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injection material has the ability to transport holes, thereby having a hole receiving effect from the anode and an excellent hole injection effect into the light-emitting layer or light-emitting material. In addition, a material having an excellent ability to prevent the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material is preferable. In addition, a material having an excellent thin-film forming ability is preferable. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, and arylamine series organic materials; hexanitrilehexaazatriphenylene series organic materials; quinacridone series organic materials; perylene series organic materials; There are conductive polymers of the polythiophene series, such as anthraquinone and polyaniline, but they are not limited thereto.

[0266] In one embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following chemical formula HI-1.

[0267] [Chemical formula HI-1]

[0268]

[0269] In the above chemical formula HI-1,

[0270] R315 to R317 are the same or different, and each independently represent one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0271] r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 are the same as or different from each other,

[0272] r316 is an integer from 1 to 5, and when r316 is 2 or more, two or more R316 are the same as or different from each other.

[0273] 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.

[0274] 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.

[0275] In one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, or are combined with an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0276] In one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a phenyl group or a biphenyl group, or combine with an adjacent group to form an indene substituted with a methyl group.

[0277] In one embodiment of the present specification, the chemical formula HI-1 is represented by any one of the following compounds.

[0278]

[0279]

[0280] In one embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following chemical formula HI-2.

[0281] [Chemical formula HI-2]

[0282]

[0283] In the above chemical formula HI-2,

[0284] R401 to R403 are the same as or mentioned above, and each independently represents a halogen group,

[0285] r401 to r403 are 4.

[0286] In one embodiment of the present specification, R401 to R403 are F.

[0287] In one embodiment of the present specification, the chemical formula HI-2 is represented by the following compound.

[0288]

[0289] In one embodiment of the present specification, the hole injection layer includes the chemical formulas HI-1 and HI-2.

[0290] In one embodiment of the present specification, the hole injection layer comprises the chemical formulas HI-1 and HI-2 in a weight ratio of 1:99 to 99:1.

[0291] The thickness of the hole injection layer may be 1 nm to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in that the hole injection characteristics can be prevented from being deteriorated, and if it is 150 nm or less, there is an advantage in that the driving voltage can be prevented from being increased to improve hole movement due to the hole injection layer being too thick.

[0292] In one embodiment of the present specification, the hole injection layer may include an arylamine compound including a carbazole group and a p-type dopant. In one example, the amine compound is represented as Het101-L101-N(Ar101)(Ar102), where Het101 is a substituted or unsubstituted carbazole group, L101 is a direct bond or a substituted or unsubstituted arylene group, and Ar101 and Ar102 are the same as or different from each other and may each independently be a substituted or unsubstituted aryl group. The amine compound and the p-type dopant may be included in an appropriate molar ratio, and in one example, the amine compound and the p-type dopant may be included in a molar ratio of 99.9:0.1 to 90:10.

[0293] The above-mentioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is preferably a material with high hole mobility that can receive holes from the anode or the hole injection layer and transport them to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0294] In one embodiment of the present specification, the hole transport layer may include an arylamine compound containing a carbazole group.

[0295] In one embodiment of the present specification, the hole transport layer includes, but is not limited to, a compound represented by the chemical formula HI-1.

[0296] The above hole injection and transport layer is a layer that transports holes to the light-emitting layer. The materials exemplified in the hole transport layer and hole injection layer may be used, but are not limited thereto.

[0297] An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.

[0298] An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may be formed using the above-described compound or a material known in the art.

[0299] The electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. Known materials can be used without limitation, and the materials exemplified in the description of the hole injection layer can be used, but are not limited thereto. The electron blocking layer can be formed between the light-emitting layer and the hole transport layer, between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.

[0300] In one embodiment of the present specification, the electron blocking layer includes, but is not limited to, a compound represented by the following chemical formula EB-1.

[0301] [Chemical formula EB-1]

[0302]

[0303] In the above chemical formula EB-1,

[0304] T1 to T14 are the same or different and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0305] t13 is an integer from 1 to 3, and when t13 is 2 or more, t13 of 2 or more are equal to or different from each other.

[0306] In one embodiment of the present specification, T1 to T14 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0307] In one embodiment of the present specification, T1 to T14 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0308] In one embodiment of the present specification, T1 to T14 are the same as or different from each other, and are each independently hydrogen; deuterium; a phenyl group; a biphenyl group; or a naphthyl group.

[0309] In one embodiment of the present specification, T1 to T13 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0310] In one embodiment of the present specification, T14 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0311] In one embodiment of the present specification, T14 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0312] In one embodiment of the present specification, T14 is a phenyl group; a biphenyl group; or a naphthyl group.

[0313] In one embodiment of the present specification, the chemical formula EB-1 may include, but is not limited to, the following compounds.

[0314]

[0315] In one embodiment of the present specification, the chemical formula EB-1 may be used as a second host material of the light-emitting layer.

[0316] The above-mentioned light-emitting layer can emit red, green, or blue light, and can be made of a phosphorescent material or a fluorescent material. The above-mentioned light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from a hole transport layer and an electron transport layer, respectively, and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole series compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; benzoxazole, benzthiazole, and benzimidazole series compounds; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0317] The above-described light-emitting layer may include a host material and a dopant material. When the organic light-emitting device according to one embodiment of the present specification includes an additional light-emitting layer other than the light-emitting layer including the chemical formula 1, the host material may be a condensed aromatic ring derivative or a heterocycle-containing compound. Specifically, the condensed aromatic ring derivative may include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocycle-containing compounds may include, but are not limited to, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like.

[0318] The above dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specifically, the present invention includes, but is not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. In addition, the metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.

[0319] The above hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. When the organic light-emitting device according to one embodiment of the present specification includes an additional hole blocking layer other than the hole blocking layer including the chemical formula 1, specifically, the hole blocking layer includes, but is not limited to, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, an aluminum complex, etc.

[0320] A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.

[0321] In one embodiment of the present specification, the hole blocking layer may include a compound including an N-containing heterocyclic group and a fluorene ring.

[0322] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is preferable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material, as used according to the prior art. In particular, suitable cathode materials are conventional materials having a low work function and followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case followed by an aluminum layer or a silver layer.

[0323] The thickness of the electron transport layer may be 1 nm to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in that the electron transport characteristics can be prevented from being deteriorated, and if the thickness of the electron transport layer is 50 nm or less, there is an advantage in that the driving voltage can be prevented from being increased to improve electron movement due to the electron transport layer being too thick.

[0324] In one embodiment of the present specification, the electron transport layer may include a compound including two N-containing heterocyclic groups, and may further include an n-type dopant or an organometallic compound. In one example, the n-type dopant or organometallic compound may be LiQ, and the compound including two N-containing heterocyclic groups and the n-type dopant (or organometallic compound) may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.

[0325] The electron injection layer is a layer that receives electrons from the electrode. It is preferable that the electron injecting material have excellent electron transport ability, an electron receiving effect from the second electrode, and an excellent electron injection effect for the light-emitting layer or light-emitting material. In addition, a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and has excellent thin film forming ability is preferable. Specifically, examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0326] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

[0327] In one embodiment of the present specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. The materials exemplified in the electron transport layer and electron injection layer may be used, but are not limited thereto.

[0328] In one embodiment of the present specification, the electron injection and transport layer includes, but is not limited to, a compound represented by the following chemical formula ET-1.

[0329] [Chemical formula ET-1]

[0330]

[0331] In the above chemical formula ET-1,

[0332] At least one of Z11 to Z13 is N, and the rest are CH,

[0333] At least one of Z21 to Z23 is N, and the rest are CH,

[0334] L601 and L602 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0335] Ar601 to Ar604 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0336] In one embodiment of the present specification, L601 and L602 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0337] In one embodiment of the present specification, L601 and L602 are phenylene groups.

[0338] In one embodiment of the present specification, Ar601 to Ar604 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0339] In one embodiment of the present specification, Ar601 to Ar604 are phenyl groups.

[0340] In one embodiment of the present specification, the chemical formula ET-1 is represented by the following compound.

[0341]

[0342] In one embodiment of the present specification, the electron injection and transport layer may further include a metal complex compound. The metal complex compound is as described above.

[0343] The organic light-emitting device according to the present invention may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

[0344] The organic light-emitting device according to the present specification can be incorporated into and used in various electronic devices. For example, the electronic devices may be, but are not limited to, display panels, touch panels, solar modules, lighting devices, etc.

[0345] Hereinafter, examples will be provided to specifically explain the present specification. However, the embodiments described herein may be modified in various ways, and the scope of the present application is not limited to the embodiments described below. The embodiments of the present application are provided to more fully explain the present specification to those of ordinary skill in the art.

[0346] < Manufacturing Example >

[0347] Preparation example of compound 1

[0348]

[0349] Synthesis of intermediate 1

[0350] Under a nitrogen atmosphere, 24 g of the starting materials 3-(triphenylsilyl)phenol, 20 g of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole, 17 g of potassium carbonate, and 500 mL of dimethylformamide (DMF) were added, heated at 160°C, and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, separated by adding water and ethyl acetate, treated with MgSO4 (anhydrous), and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 28 g of intermediate 1. (Yield 70%, Mass [M+]=663)

[0351]

[0352] Synthesis of intermediate 2

[0353] Under a nitrogen atmosphere, 28 g of intermediate 1, 7.0 g of 2-hydroxyphenylboronic acid, 27 g of potassium phosphate, 320 mL of dioxane, and 80 mL of water were added, and then 0.4 g of bis(tri-tert-butylphosphine)palladium(0) Pd(PtBu3)2 was added, heated at 120 ℃, and stirred for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, separated by adding water and toluene, treated with MgSO4(anhydrous), and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 23 g of intermediate 2. (Yield 76%, Mass [M+]=721)

[0354]

[0355] Synthesis of compound 1

[0356] In a flask containing 23 g of intermediate 2 dissolved in 300 mL of toluene (anhydrous) cooled to 0 ℃ under a nitrogen atmosphere, 47 mL of tert-butyllithium [1.7 M in hexane] was slowly added dropwise, and the mixture was stirred at 70 ℃ for 5 hours. When the lithium halogen exchange reaction was completed, the mixture was cooled to 0 ℃ again, 9.2 mL of boron tribromide was slowly added dropwise, and the temperature was raised to 70 ℃ and stirred for 10 hours. After the reaction was completed, the reaction solution was cooled to room temperature, separated by adding water and aq. NH4Cl, treated with MgSO4 (anhydrous), and filtered. The filtered solution was distilled off under reduced pressure and purified twice by recrystallization (toluene / hexane) to obtain 3.8 g of compound 1. (Yield 17%, Mass [M+]=694)

[0357]

[0358] Preparation example of compound 2

[0359]

[0360] Synthesis of intermediate 3

[0361] Intermediate 3 was prepared in the same manner as in Synthetic Example 1, except that 23 g of 3'-(triphenylsilyl)-[1,1'-biphenyl]-4-ol was used instead of the starting material 3-(triphenylsilyl)phenol, and 20 g of 9-(3',4'-dichloro-5'-fluoro-[1,1'-biphenyl]-2-yl)-9H-carbazole was used instead of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole, thereby obtaining 23 g of Intermediate 3. (Yield 57%, Mass [M+]=815)

[0362]

[0363] Synthesis of intermediate 4

[0364] Intermediate 4 (18 g) was obtained by preparing the same method as for intermediate 2 in Synthetic Example 1, except that 23 g of intermediate 3 was used instead of intermediate 1. (Yield 73%, Mass [M+]=873)

[0365]

[0366] Synthesis of compound 2

[0367] Compound 2 was obtained in 2.7 g by the same method as in Synthesis Example 1, except that 18 g of Intermediate 4 was used instead of Intermediate 2. (Yield 15%, Mass [M+]=846)

[0368]

[0369] Preparation example of compound 3

[0370]

[0371]

[0372] Synthesis of intermediate 5

[0373] Intermediate 5 was prepared in the same manner as in Synthetic Example 1, except that 26 g of 3'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-ol was used instead of the starting material 3-(triphenylsilyl)phenol, and 15 g of 1-bromo-3-chloro-5-fluorobenzene was used instead of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole, thereby obtaining 28 g of Intermediate 5. (Yield 74%, Mass [M+]=525)

[0374]

[0375] Synthesis of intermediate 6

[0376] Under a nitrogen atmosphere, 28 g of intermediate 5, 18 g of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 22 g of potassium carbonate, 400 mL of tetrahydrofuran, and 100 mL of water were added, and then 0.6 g of tetrakis(triphenylphosphine)palladium(0) Pd(PPh3)4 was added, heated at 80 ℃, and stirred for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, separated by adding water and toluene, treated with MgSO4(anhydrous), and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 22 g of intermediate 6. (Yield 69%, Mass [M+]=599)

[0377]

[0378] Synthesis of intermediate 7

[0379] Intermediate 7 (24 g) was obtained by preparing the same method as for intermediate 2 in Synthetic Example 1, except that 22 g of intermediate 6 was used instead of intermediate 1. (Yield 74%, Mass [M+]=656)

[0380]

[0381] Synthesis of compound 3

[0382] Under a nitrogen atmosphere, 17 g of boron triiodide was added to a flask containing 15 g of intermediate 7 dissolved in 500 mL of 1,2-dichlorobenzene (DCB), and the mixture was stirred at 120°C for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, separated by adding water and sodium thiosulfate solution, and then treated with MgSO4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 4.7 g of compound 3. (Yield 31%, Mass [M+]=664)

[0383]

[0384] Preparation example of compound 4

[0385]

[0386]

[0387] Synthesis of intermediate 8

[0388] Intermediate 8 was prepared in the same manner as in Synthetic Example 1, except that 9.9 g of phenol was used instead of the starting material 3-(triphenylsilyl)phenol, and 20 g of 1-bromo-3-chloro-5-fluorobenzene was used instead of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole, thereby obtaining 21 g of Intermediate 8. (Yield 78%, Mass [M+]=284)

[0389]

[0390] Synthesis of intermediate 9

[0391] Intermediate 8 (21 g) was used instead of Intermediate 5, and 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. However, the method for preparing Intermediate 6 in Synthetic Example 3 was the same as that for preparing Intermediate 6, except that 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-9H-carbazole (33 g) was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. 23 g of Intermediate 9 was obtained. (Yield 70%, Mass [M+]=446)

[0392]

[0393] Synthesis of intermediate 10

[0394] Under a nitrogen atmosphere, 23 g of intermediate 9, 16 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 15 g of potassium acetate, and 400 mL of dioxane were added, followed by the addition of 0.23 g of palladium acetate(∥) Pd(OAc)2 and 0.58 g of tricyclohexylphosphine PCy3, heating at 120 ℃, and stirring for 12 hours. After completion of the reaction, the reaction solution was cooled to room temperature, separated by adding water and toluene, and then treated with MgSO4(anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 20 g of intermediate 10. (Yield 72%, Mass [M+]=538)

[0395]

[0396] Synthesis of intermediate 11

[0397] Under a nitrogen atmosphere, 20 g of intermediate 10, 9.3 g of 2-bromo-5-chlorophenol, 24 g of potassium phosphate, 280 mL of tetrahydrofuran, and 70 mL of water were added, and then 0.19 g of bis(tri-tert-butylphosphine)palladium(0) Pd(PtBu3)2 was added, heated at 100 °C, and stirred for 6 hours. After completion of the reaction, the reaction solution was cooled to room temperature, separated by adding water and toluene, treated with MgSO4(anhydrous), and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 16 g of intermediate 11. (Yield 80%, Mass [M+]=539)

[0398]

[0399] Synthesis of intermediate 12

[0400] Intermediate 12 (8.2 g) was obtained by preparing the compound 3 in Synthetic Example 3 in the same manner as in Example 3, except that 16 g of intermediate 11 was used instead of intermediate 7. (Yield 51%, Mass [M+] = 546)

[0401]

[0402] Synthesis of compound 4

[0403] Under a nitrogen atmosphere, 4.0 g of intermediate 12, 2.1 g of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 4.7 g of potassium phosphate, 56 mL of dioxane, and 14 mL of water were added, and then 0.07 g of bis(tri-tert-butylphosphine)palladium(0) Pd(PtBu3)2 was added, heated at 130 ℃, and stirred for 14 hours. After completion of the reaction, the reaction solution was cooled to room temperature, separated by adding water and toluene, treated with MgSO4(anhydrous), and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 3.8 g of compound 4. (Yield 78%, Mass [M+]=664)

[0404]

[0405] Preparation example of compound 5

[0406]

[0407] Compound 5 was prepared in the same manner as in Synthetic Example 4, except that 2.8 g of 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-9H-carbazole was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, thereby obtaining 4.1 g of compound 5. (Yield 74%, Mass [M+]=753)

[0408]

[0409] Preparation example of compound 6

[0410]

[0411]

[0412] Synthesis of intermediate 13

[0413] Intermediate 13 was prepared in the same manner as in Synthetic Example 1, except that 20 g of 3-(9H-carbazol-9-yl)phenol was used instead of the starting material 3-(triphenylsilyl)phenol, and 15 g of 1-bromo-3-chloro-5-chlorobenzene was used instead of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole, thereby obtaining 25 g of Intermediate 13. (Yield 78%, Mass [M+]=449)

[0414]

[0415] Synthesis of intermediate 14

[0416] Intermediate 13 (25 g) was used instead of Intermediate 5, and 2-(dibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (20 g) was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. The method for preparing Intermediate 6 in Synthetic Example 3 was the same as that for preparing Intermediate 6, except that 23 g of Intermediate 14 was obtained. (Yield 77%, Mass [M+]=537)

[0417]

[0418] Synthesis of intermediate 15

[0419] Intermediate 15 (19 g) was obtained by preparing the same method as for intermediate 2 in Synthetic Example 1, except that 23 g of intermediate 14 was used instead of intermediate 1. (Yield 75%, Mass [M+]=594)

[0420]

[0421] Synthesis of compound 6

[0422] Compound 6 (4.2 g) was obtained by preparing the compound 3 in the same manner as in Synthetic Example 3, except that 10 g of intermediate 15 was used instead of intermediate 7. (Yield 41%, Mass [M+] = 602)

[0423]

[0424] Preparation example of compound 7

[0425]

[0426]

[0427] Synthesis of intermediate 16

[0428] Intermediate 16 (10 g) was obtained in the same manner as in the preparation of Intermediate 6 of Synthetic Example 3, except that 8.5 g of 2-(2-(dibenzo[b,d]furan-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. (Yield 76%, Mass [M+]=689)

[0429]

[0430] Synthesis of intermediate 17

[0431] Intermediate 17 was prepared in the same manner as in Synthetic Example 1, except that 10 g of Intermediate 16 was used instead of Intermediate 1, thereby obtaining 7.6 g of Intermediate 17. (Yield 70%, Mass [M+]=746)

[0432]

[0433] Synthesis of compound 7

[0434] Compound 7 was prepared in the same manner as in Synthetic Example 3 except that 7.6 g of intermediate 17 was used instead of intermediate 7, thereby obtaining 3.1 g of compound 7. (Yield 40%, Mass [M+]=754)

[0435]

[0436] Preparation example of compound 8

[0437]

[0438]

[0439] Synthesis of intermediate 18

[0440] Under a nitrogen atmosphere, 15 g of intermediate 8, 21 g of 9H-3,9'-bicarbazole, 34 g of potassium phosphate, and 500 mL of xylene were added, followed by the addition of 0.97 g of Tris(dibenzylideneacetone)dipalladium(0) Pd2(dba)3 and 1.2 g of Xantphos, heated at 160 ℃, and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, separated by adding water and toluene, treated with MgSO4(anhydrous), and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 24 g of intermediate 18. (Yield 85%, Mass [M+]=536)

[0441]

[0442] Synthesis of intermediate 19

[0443] Intermediate 19 (21 g) was obtained by preparing the same method as for intermediate 10 in Synthetic Example 4, except that 24 g of intermediate 18 was used instead of intermediate 9. (Yield 75%, Mass [M+]=627)

[0444]

[0445] Synthesis of intermediate 20

[0446] Intermediate 20 was prepared in the same manner as in Synthetic Example 4, except that 21 g of Intermediate 19 was used instead of Intermediate 10, thereby obtaining 16 g of Intermediate 20. (Yield 76%, Mass [M+]=628)

[0447]

[0448] Synthesis of intermediate 21

[0449] Intermediate 21 (7.1 g) was obtained by preparing the compound 3 in Synthetic Example 3 in the same manner as in Example 3, except that 16 g of intermediate 20 was used instead of intermediate 7. (Yield 44%, Mass [M+]=635)

[0450]

[0451] Synthesis of compound 8

[0452] Compound 8 was prepared in the same manner as in Synthetic Example 4, except that 3.5 g of intermediate 21 was used instead of intermediate 12, and 2.1 g of 2-(2-(dibenzo[b,d]furan-3-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. 3.5 g of compound 8 was obtained. (Yield 75%, Mass [M+]=843)

[0453]

[0454] Preparation example of compound 9

[0455]

[0456]

[0457] Synthesis of intermediate 22

[0458] Intermediate 22 (26 g) was obtained by preparing the same method as for intermediate 18 in Synthetic Example 8, except that 20 g of intermediate 13 was used instead of intermediate 8. (Yield 83%, Mass [M+]=701)

[0459]

[0460] Synthesis of intermediate 23

[0461] Intermediate 23 (22 g) was obtained in the same manner as in the preparation of Intermediate 2 in Synthesis Example 1, except that 26 g of Intermediate 22 was used instead of Intermediate 1. (Yield 78%, Mass [M+]=758)

[0462]

[0463] Synthesis of compound 9

[0464] Compound 9 was prepared in the same manner as in Synthetic Example 3 except that 10 g of intermediate 23 was used instead of intermediate 7, thereby obtaining 3.2 g of compound 9. (Yield 32%, Mass [M+]=766)

[0465]

[0466] Preparation example of compound 10

[0467]

[0468]

[0469] Synthesis of intermediate 24

[0470] Intermediate 24 (20 g) was obtained in the same manner as in the preparation of Intermediate 18 of Synthetic Example 8, except that 20 g of Intermediate 13 was used instead of Intermediate 8 and 9.0 g of carbazole was used instead of 9H-3,9'-bicarbazole. (Yield 84%, Mass [M+]=536)

[0471]

[0472] Synthesis of intermediate 25

[0473] Intermediate 25 (17 g) was obtained by preparing the same method as for intermediate 2 in Synthetic Example 1, except that 20 g of intermediate 24 was used instead of intermediate 1. (Yield 77%, Mass [M+]=593)

[0474]

[0475] Synthesis of compound 10

[0476] Compound 10 was prepared in the same manner as in Synthetic Example 3, except that 10 g of intermediate 25 was used instead of intermediate 7, to obtain 4.3 g of compound 10. (Yield 42%, Mass [M+]=601)

[0477]

[0478] Preparation example of compound 11

[0479]

[0480]

[0481] Synthesis of intermediate 26

[0482] Intermediate 13 (20 g) was used instead of Intermediate 5, and 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. However, the method for preparing Intermediate 6 in Synthetic Example 3 was the same as that for preparing Intermediate 6, except that 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-9H-carbazole was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. 21 g of Intermediate 26 was obtained. (Yield 77%, Mass [M+]=612)

[0483]

[0484] Synthesis of intermediate 27

[0485] Intermediate 27 (17 g) was obtained by preparing the same method as for intermediate 2 in Synthetic Example 1, except that 21 g of intermediate 26 was used instead of intermediate 1. (Yield 74%, Mass [M+]=669)

[0486]

[0487] Synthesis of compound 11

[0488] Compound 11 (3.8 g) was obtained by preparing the compound 3 in Synthetic Example 3, except that 10 g of intermediate 27 was used instead of intermediate 7. (Yield 38%, Mass [M+]=677)

[0489]

[0490] Preparation example of compound 12

[0491]

[0492]

[0493] Synthesis of intermediate 28

[0494] Intermediate 28 was prepared in the same manner as in Synthetic Example 1, except that 18 g of 2'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-3-ol was used instead of the starting material 3-(tetraphenylsilyl)phenol, and 10 g of 1-bromo-3-chloro-5-fluorobenzene was used instead of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole, thereby obtaining 19 g of Intermediate 28. (Yield 76%, Mass [M+]=525)

[0495]

[0496] Synthesis of intermediate 29

[0497] Intermediate 29 (16 g) was obtained in the same manner as in the preparation of Intermediate 6 of Synthetic Example 3, except that 19 g of Intermediate 28 was used instead of Intermediate 5, and 17 g of tribenzodifuran-dioxaboralane was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. (Yield 63%, Mass [M+]=703)

[0498]

[0499] Synthesis of intermediate 30

[0500] Intermediate 30 (12 g) was obtained by preparing it in the same manner as in the preparation of Intermediate 2 of Synthetic Example 1, except that 16 g of Intermediate 29 was used instead of Intermediate 1. (Yield 69%, Mass [M+]=760)

[0501]

[0502] Synthesis of compound 12

[0503] Compound 12 (3.1 g) was obtained by preparing the compound 3 in the same manner as in Synthetic Example 3, except that 8.0 g of intermediate 30 was used instead of intermediate 7. (Yield 38%, Mass [M+]=768)

[0504]

[0505] Preparation example of compound 13

[0506]

[0507]

[0508] Synthesis of intermediate 31

[0509] Intermediate 31 was prepared in the same manner as in Synthetic Example 1, except that 17 g of 2'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-ol was used instead of the starting material 3-(triphenylsilyl)phenol, and 10 g of 1-bromo-3-chloro-5-fluorobenzene was used instead of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole, thereby obtaining 28 g of Intermediate 31. (Yield 74%, Mass [M+]=525)

[0510]

[0511] Synthesis of intermediate 32

[0512] Intermediate 31 (28 g) was used instead of Intermediate 5, and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane (24 g) was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. However, the method for preparing Intermediate 6 in Synthetic Example 3 was the same as that for preparing Intermediate 6 in Synthetic Example 3, and 26 g of Intermediate 32 was obtained. (Yield 71%, Mass [M+]=689)

[0513]

[0514] Synthesis of intermediate 33

[0515] Intermediate 33 (20 g) was obtained by preparing the same method as for intermediate 2 in Synthetic Example 1, except that 26 g of intermediate 32 was used instead of intermediate 1. (Yield 71%, Mass [M+]=743)

[0516]

[0517] Synthesis of compound 13

[0518] Compound 13 (3.2 g) was obtained by preparing the compound 3 in the same manner as in Synthetic Example 3, except that 10 g of intermediate 33 was used instead of intermediate 7. (Yield 32%, Mass [M+]=751)

[0519]

[0520] Preparation example of compound 14

[0521]

[0522]

[0523] Synthesis of intermediate 34

[0524] Intermediate 34 (16 g) was obtained in the same manner as in the preparation of Intermediate 19 of Synthetic Example 8, except that 20 g of Intermediate 26 was used instead of Intermediate 18. (Yield 70%, Mass [M+]=703)

[0525]

[0526] Synthesis of intermediate 35

[0527] Intermediate 35 (12 g) was obtained by preparing it in the same manner as in Synthetic Example 4, except that 16 g of Intermediate 34 was used instead of Intermediate 10. (Yield 75%, Mass [M+]=704)

[0528]

[0529] Synthesis of intermediate 36

[0530] Intermediate 36 was prepared in the same manner as in Synthetic Example 3, except that 12 g of Intermediate 35 was used instead of Intermediate 7, thereby obtaining 4.8 g of Intermediate 36. (Yield 40%, Mass [M+]=712)

[0531]

[0532] Synthesis of compound 14

[0533] Compound 14 was prepared in the same manner as in Synthetic Example 4, except that 4.8 g of intermediate 36 was used instead of intermediate 12, and 2.6 g of 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)-9H-carbazole was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, to obtain 4.3 g of compound 14. (Yield 69%, Mass [M+]=918)

[0534]

[0535] Preparation example of compound 15

[0536]

[0537]

[0538] Synthesis of intermediate 37

[0539] Intermediate 37 was prepared in the same manner as in Synthetic Example 1, except that 10 g of 3'-(triphenylsilyl)-[1,1'-biphenyl]-3-ol was used instead of the starting material 3-(triphenylsilyl)phenol, and 14 g of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole was used instead of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole, thereby obtaining 16 g of Intermediate 37. (Yield 72%, Mass [M+]=739)

[0540]

[0541] Synthesis of intermediate 38

[0542] Intermediate 38 (12 g) was obtained by the same method as for preparing Intermediate 2 in Synthetic Example 1, except that 16 g of Intermediate 37 was used instead of Intermediate 1, and 5.5 g of 2-(phenylamino)phenyl)boronic acid was used instead of 2-hydroxyphenylboronic acid. (Yield 64%, Mass [M+]=872)

[0543]

[0544] Synthesis of compound 15

[0545] Compound 15 (2.3 g) was obtained by preparing the compound 1 in the same manner as in Synthetic Example 1, except that 12 g of intermediate 38 was used instead of intermediate 2. (Yield 20%, Mass [M+]=845)

[0546]

[0547] Preparation example of compound 16

[0548]

[0549]

[0550] Synthesis of intermediate 39

[0551] Intermediate 10 (15 g) was prepared in the same manner as in Synthesis Example 4, except that 7.5 g of 2-bromo-5-chlorobenzenethiol was used instead of 2-bromo-5-chlorophenol, thereby obtaining 10 g of Intermediate 39. (Yield 65%, Mass [M+]=555)

[0552]

[0553] Synthesis of intermediate 40

[0554] Intermediate 40 was prepared in the same manner as in Synthesis Example 3, except that 10 g of Intermediate 39 was used instead of Intermediate 7, thereby obtaining 3.5 g of Intermediate 40. (Yield 35%, Mass [M+]=562)

[0555]

[0556] Synthesis of compound 16

[0557] Compound 16 was prepared in the same manner as in Synthetic Example 4, except that 3.5 g of intermediate 40 was used instead of intermediate 12, and 1.9 g of 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, thereby obtaining 3.4 g of compound 16. (Yield 79%, Mass [M+]=694)

[0558]

[0559] Preparation example of compound 17

[0560]

[0561]

[0562] Synthesis of intermediate 41

[0563] The method for preparing intermediate 1 in Synthetic Example 1 was the same as that for preparing intermediate 1, except that 15 g of 2'-(tris(phenyl-d5)silyl)-[1,1'-biphenyl]-2,3',4,4',5,5',6,6'-d8-3-ol was used instead of the starting material 3-(triphenylsilyl)phenol, and 10 g of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 was used instead of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole, thereby obtaining 16 g of intermediate 41. (Yield 70%, Mass [M+]=770)

[0564]

[0565] Synthesis of intermediate 42

[0566] Intermediate 42 (13 g) was obtained by preparing it in the same manner as in the preparation of Intermediate 2 of Synthesis Example 1, except that 16 g of Intermediate 41 was used instead of Intermediate 1. (Yield 75%, Mass [M+]=832)

[0567]

[0568] Synthesis of compound 17

[0569] Compound 17 (2.2 g) was obtained by preparing the compound 1 in the same manner as in Synthetic Example 1, except that 13 g of intermediate 42 was used instead of intermediate 2. (Yield 18%, Mass [M+]=804)

[0570]

[0571] Preparation example of compound 18

[0572]

[0573]

[0574] Synthesis of intermediate 43

[0575] Intermediate 43 was prepared in the same manner as in Synthetic Example 1, except that 14 g of 4-(9H-carbazol-9-yl-d8)phen-2,3,5,6-d4-ol was used instead of the starting material 3-(triphenylsilyl)phenol, and 10 g of 1-bromo-3-chloro-5-fluorobenzene was used instead of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole, thereby obtaining 18 g of Intermediate 43. (Yield 82%, Mass [M+]=461)

[0576]

[0577] Synthesis of intermediate 44

[0578] Intermediate 44 (17 g) was obtained in the same manner as in Synthetic Example 8, except that 18 g of Intermediate 43 was used instead of Intermediate 8, and 8.2 g of 9H-carbazole-1,2,3,4,5,6,7,8-d8 was used instead of 9H-3,9'-bicarbazole. (Yield 78%, Mass [M+]=556)

[0579]

[0580] Synthesis of intermediate 45

[0581] Intermediate 45 (13 g) was obtained by preparing it in the same manner as in the preparation of Intermediate 2 of Synthesis Example 1, except that 18 g of Intermediate 44 was used instead of Intermediate 1. (Yield 69%, Mass [M+]=613)

[0582]

[0583] Synthesis of compound 18

[0584] Compound 18 (3.5 g) was obtained by preparing the compound 3 in Synthetic Example 3, except that 8.0 g of intermediate 45 was used instead of intermediate 7. (Yield 43%, Mass [M+]=620)

[0585]

[0586] Preparation example of compound 19

[0587]

[0588]

[0589] Synthesis of intermediate 46

[0590] Intermediate 46 (20 g) was obtained in the same manner as in the preparation of Intermediate 1 of Synthetic Example 1, except that 18 g of 2'-(9H-carbazol-9-yl-d8)-[1,1'-biphenyl]-2,3',4,4',5,5',6,6'-d8-3-ol was used instead of the starting material 3-(triphenylsilyl)phenol, and 10 g of 1-bromo-3-chloro-5-fluorobenzene was used instead of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole. (Yield 78%, Mass [M+]=540)

[0591]

[0592] Synthesis of intermediate 47

[0593] Intermediate 47 (20 g) was obtained in the same manner as in the preparation of Intermediate 6 of Synthetic Example 3, except that 20 g of Intermediate 46 was used instead of Intermediate 5, and 17 g of 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. (Yield 76%, Mass [M+]=715)

[0594]

[0595] Synthesis of intermediate 48

[0596] Intermediate 48 (16 g) was obtained by preparing it in the same manner as in the preparation of Intermediate 2 of Synthetic Example 1, except that 20 g of Intermediate 47 was used instead of Intermediate 1. (Yield 74%, Mass [M+]=777)

[0597]

[0598] Synthesis of compound 19

[0599] Compound 19 (3.6 g) was obtained by preparing the compound 3 in Synthetic Example 3 in the same manner as in Example 3, except that 8.0 g of intermediate 48 was used instead of intermediate 7. (Yield 45%, Mass [M+] = 784)

[0600]

[0601] Preparation example of compound 20

[0602]

[0603]

[0604] Synthesis of intermediate 49

[0605] Intermediate 49 (13 g) was obtained in the same manner as in the preparation of Intermediate 6 of Synthetic Example 3, except that 15 g of Intermediate 46 was used instead of Intermediate 5, and 10 g of 2-(dibenzo[b,d]furan-3-yl-d7)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. (Yield 74%, Mass [M+]=635)

[0606]

[0607] Synthesis of intermediate 50

[0608] Intermediate 50 (11 g) was obtained by preparing it in the same manner as in the preparation of Intermediate 2 of Synthetic Example 1, except that 13 g of Intermediate 49 was used instead of Intermediate 1. (Yield 78%, Mass [M+]=692)

[0609]

[0610] Synthesis of compound 20

[0611] Compound 20 was prepared in the same manner as in Synthetic Example 3, except that 11 g of intermediate 50 was used instead of intermediate 7, to obtain 4.4 g of compound 20. (Yield 40%, Mass [M+]=700)

[0612]

[0613] <Examples and Comparative Examples>

[0614] Example 1

[0615] A glass substrate coated with an 800Å thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent was a Fischer Co. product, and the distilled water was secondarily filtered through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

[0616] On the ITO transparent electrode prepared in this way, a hole injection layer was formed by thermal vacuum depositing a compound of the following compound HT1 and the following compound HI1 at a ratio of 95:5 (molar ratio) to a thickness of 100 Å. On the hole injection layer, a hole transport layer was formed by vacuum depositing a compound represented by the following chemical formula HT1 (300 Å). Subsequently, an electron blocking layer was formed by vacuum depositing a compound of BH (p-type) at a film thickness of 50 Å on the hole transport layer. Subsequently, a compound in which the following chemical formula BH (p-type) and the compound 1 (n-type) synthesized in Preparation Example 1 were mixed in a 1:1 ratio as a host for the light emitting layer and a compound represented by the following chemical formula BD as a dopant for the light emitting layer were vacuum deposited at a weight ratio of 86:14 on the electron blocking layer to form a light emitting layer. A hole blocking layer was formed by vacuum-depositing the compound 1 (n-type) synthesized in Manufacturing Example 1 with a film thickness of 50 Å on the light-emitting layer. Subsequently, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 Å. Lithium fluoride (LiF) with a thickness of 10 Å and aluminum with a thickness of 800 Å were sequentially deposited on the electron injection and transport layer to form a cathode.

[0617]

[0618]

[0619] In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride of the cathode was maintained at 0.3 Å / sec, and the aluminum was maintained at 2 Å / sec. The vacuum during deposition was maintained at 2ⅹ10-7 to 5ⅹ10-6 torr, thereby producing an organic light-emitting device.

[0620]

[0621] Examples 2 to 20

[0622] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound described in Table 1 below was used instead of Compound 1 as the host of the light-emitting layer in Example 1.

[0623]

[0624] Examples 21 and 22

[0625] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound described in Table 1 below was used instead of Compound 1 as the host of the light-emitting layer in Example 1, and Compound 10 was used instead of Compound 1 as the hole-blocking layer.

[0626]

[0627]

[0628] Comparative Examples 1 to 5

[0629] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound described in Table 1 below was used instead of Compound 1 as the host of the light-emitting layer in Example 1.

[0630]

[0631]

[0632] When current was applied to the organic light-emitting devices manufactured in Examples 1 to 20 and Comparative Examples 1 to 5, voltage, efficiency, and lifespan were measured (based on 1600 nit), and the results are shown in Table 1 below. Lifespan T90 refers to the time required for the luminance to decrease to 90% of the initial luminance (1600 nit).

[0633] Host compound voltage (V)@10mA / cm 2 Luminous efficacy (Cd / A) @10mA / cm 2Lifespan, T90(h) Example 1 Compound 1 3.90 2 2.3 1 1 4 Example 2 Compound 2 3.85 2 3.4 1 2 3 Example 3 Compound 3 3.87 2 3.0 1 1 9 Example 4 Compound 4 3.88 2 3.2 1 2 1 Example 5 Compound 5 3.81 2 2.5 1 2 5 Example 6 Compound 6 3.87 2 3.4 1 2 8 Example 7 Compound 7 3.87 2 2.7 1 2 6 Example 8 Compound 8 3.85 2 3.2 1 2 4 Example 9 Compound 93.85 23.4122 Example 10 Compound 103.812 3.8133 Example 11 Compound 113.83 24.0129 Example 12 Compound 123.87 22.5120 Example 13 Compound 133.812 2.1123 Example 14 Compound 143.812 4.4127 Example 15 Compound 153.90 23.0119 Example 16 Compound 163.87 22.7116 Example 17 Compound 173.83 23.4136 Example 18 Compound 18 3.8 1 2 4.7 1 4 9 Example 19 Compound 19 3.8 3 2 4.2 1 6 0 Example 20 Compound 20 3.8 5 2 3.8 1 5 5 5 Example 21 Compound 4 3.8 5 2 3.4 1 2 5 5 Example 22 Compound 15 3.8 7 2 3.2 1 2 2 Comparative Example 1 BH 14.2 2 1 5.5 8 4 Comparative Example 2 BH 2 4.1 0 2 0.2 1 0 2 Comparative Example 3 BH 3 4.1 4 1 8.7 9 3 Comparative Example 4 BH 4 4.1 8 1 7.7 9 9 Comparative Example 5 BH 5 4.4 7 1 1.2 3 2

[0634] Compound BH1 used in Comparative Example 1 had a carbazole group and a silyl group or an aryl group unsubstituted on the benzene ring included in the core structure, and therefore it was confirmed that the voltage, efficiency, and lifespan were significantly deteriorated compared to Examples 1 to 20.

[0635] Compound BH2 used in Comparative Example 2 is a compound in which only carbazole is substituted in the benzene ring included in the core structure, and can achieve high efficiency and long life, but it was confirmed that it has a high voltage compared to Examples 1 to 20.

[0636] Compound BH3 used in Comparative Example 3 was found to have significantly lower voltage, efficiency, and lifespan compared to Examples 1 to 20, as only the carbazole group was substituted on the benzene ring included in the core structure and the silyl group was substituted on the carbazole group.

[0637] Since the compounds BH4 and BH5 used in Comparative Examples 4 and 5 have different core structures, it was confirmed that the voltage, efficiency, and lifespan were significantly deteriorated compared to Examples 1 to 20.

[0638]

[0639] [Explanation of symbols]

[0640] 1: Substrate

[0641] 2: Anode

[0642] 3: Hole injection layer

[0643] 4: Hole transport layer

[0644] 5: Electron blocking layer

[0645] 6: Emissive layer

[0646] 7: Hole blocking layer

[0647] 8: Electron transport layer

[0648] 9: Electron injection layer

[0649] 10: Cathode

[0650] 11: Electron transport and injection layer

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X is NR; O; or S, At least one of R and R1 to R3 is a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and the others are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted cycloalkyl group, L1 to L3 and L11 to L13 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group, G1 to G3 are the same or different and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, n1 and n2 are integers from 1 to 4, respectively, and m1 and m2 are integers from 0 to 4, respectively. n3 is an integer from 1 to 3, m3 is an integer from 0 to 3, g1 to g3 are integers from 0 to 8, respectively, When the above n1 to n3, m1 to m3 and g1 to g3 are each 2 or more, the substituents in the parentheses are each the same or different, n1+m1 is less than or equal to 4, n2+m2 is less than or equal to 4, n3+m3 is less than or equal to 3, m1+m2+m3 are integers greater than or equal to 1.

2. In claim 1, A compound wherein the above L1 to L3 and L11 to L13 are the same or different from each other, and each independently represents a direct bond; an arylene group; or a divalent heterocyclic group.

3. In claim 1, A compound wherein at least one of the above R1 to R3 is a silyl group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; an aryl group substituted or unsubstituted with deuterium or an aryl group; or a heterocyclic group substituted or unsubstituted with deuterium or a heterocyclic group, and the others are the same as or different from each other and are each independently hydrogen; or deuterium.

4. In claim 1, A compound wherein the above m1+m2+m3 are 1 or 2.

5. In claim 1, The above chemical formula 1 is a compound represented by any one of the following chemical formulas 1-A-1 to 1-A-3: [Chemical Formula 1-A-1] [Chemical Formula 1-A-2] [Chemical Formula 1-A-3] In the above chemical formulas 1-A-1 to 1-A-3, The definitions of X, R1 to R3, L1 to L3, L11 to L13, G1 to G3 and g1 to g3 are the same as those in the above chemical formula 1.

6. In claim 1, The above chemical formula 1 is a compound represented by any one of the following chemical formulas 1-B-1 to 1-B-3: [Chemical Formula 1-B-1] [Chemical Formula 1-B-2] [Chemical Formula 1-B-3] In the above chemical formulas 1-B-1 to 1-B-3, The definitions of X, R1 to R3, L1 to L3, L11 to L13, G1 to G3 and g1 to g3 are the same as those in the above chemical formula 1.

7. In claim 1, At least one of the above R1 to R3 is a triphenylsilyl group; a phenyl group; a biphenyl group; a carbazole group; a dibenzofuran group; a dibenzothiophene group; a benzofuranodibenzofuran group; or an indolocarbazole group, and the others are the same or different and are each independently hydrogen; or deuterium, The above L1 to L3 and L11 to L13 are the same or different from each other, and each independently represents a direct bond; or a phenylene group, A compound wherein G1 to G3 are the same or different and are each independently hydrogen or deuterium.

8. In claim 1, The above chemical formula 1 is a compound represented by any one of the following compounds: [ ] D=x1~x2 means that the structure within the parentheses contains x1 to x2 deuterium atoms, and its value is an integer.

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

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

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

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

13. In claim 9, An organic light-emitting device wherein the organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, electron transport layer, or electron injection and transport layer comprises the compound.

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

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