Compounds and organic light-emitting devices containing them

Abstract

This specification provides a compound represented by chemical formula 1 and an organic light-emitting element containing the same.

Description

[Technical Field]

[0001] This specification relates to compounds and organic light-emitting devices containing the same.

[0002] This application claims the benefit as of the filing date of Korean Patent Application No. 10-2023-0133371, filed with the Korean Intellectual Property Office on October 6, 2023, and all its contents are incorporated herein by reference. [Background technology]

[0003] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices that utilize organic light emission typically have a structure that includes a positive electrode, a negative electrode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made up of different materials to enhance the efficiency and stability of the organic light-emitting device, and can consist 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 such an organic light-emitting device structure, when a voltage is applied between the two electrodes, holes are injected into the organic layer at the positive electrode and electrons are injected into the organic layer at the negative electrode. When the injected holes and electrons meet, an exciton is formed, and when this exciton falls back to the ground state, light is emitted.

[0004] The development of new materials for organic light-emitting devices, as described above, continues to be required. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] Japanese Patent Publication No. 2021-095342 [Overview of the project] [Problems that the invention aims to solve]

[0006] This specification provides compounds and organic light-emitting devices containing the same. [Means for solving the problem]

[0007] One embodiment of this specification provides a compound represented by the following chemical formula 1.

[0008] [Chemical formula 1] [ka]

[0009] In the aforementioned chemical formula 1, X is NR;O; or S, R and at least one of R1-R3 are substituted or unsubstituted silyl groups; substituted or unsubstituted aryl groups; or substituted or unsubstituted heterocyclic groups, and the remainder are identical or different from each other, independently of hydrogen; deuterium; halogen groups; nitrile groups; substituted or unsubstituted alkyl groups; or substituted or unsubstituted cycloalkyl groups. L1-L3 and L11-L13 are either identical or different from each other, and each is independently directly bonded; a substituted or unsubstituted allylene group; or a substituted or unsubstituted divalent heterocyclic group. G1 to G3 are either identical or different from each other, and each is independently a hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group. n1 and n2 are integers between 1 and 4, and m1 and m2 are integers between 0 and 4. n3 is an integer between 1 and 3, and m3 is an integer between 0 and 3. g1 to g3 are integers from 0 to 8, If n1-n3, m1-m3, and g1-g3 are each 2 or more, the substituents in parentheses are either identical or different from each other. n1+m1 is less than or equal to 4, n2+m2 is less than or equal to 4, and n3+m3 is less than or equal to 3. m1 + m2 + m3 are integers greater than or equal to 1.

[0010] In addition, one embodiment of the present specification provides an organic light-emitting device including an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers contain a compound represented by Chemical Formula 1.

Effects of the Invention

[0011] The compounds described in the present specification can be used as materials for the organic layers of organic light-emitting devices. The compounds according to at least one embodiment of the present specification can improve efficiency, lower driving voltage, and / or improve lifetime characteristics in organic light-emitting devices.

[0012] In particular, the compounds described in the present specification can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, light-emitting, hole blocking, electron transport, or electron injection materials. Further, compared with conventional organic light-emitting devices, there are effects of lower driving voltage, higher efficiency, and / or longer lifetime. <00故0087>

Brief Description of the Drawings

[0013] ]故 [Figure 1] It is a diagram showing 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. [Figure 2] It is a diagram showing 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. [Figure 3] It is a diagram showing 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 injection and transport layer 11, and a cathode 10 are sequentially laminated.

Modes for Carrying Out the Invention

[0014] Hereinafter, the present specification will be described in more detail.

[0015] In this specification, when a part is said to "include" a component, unless otherwise stated, it means that it may include other components rather than excluding them.

[0016] In this specification, the term "on top of" another member includes not only cases where one member is in contact with another member, but also cases where another member is located between the two members.

[0017] In this specification, "N% substituted with deuterium" means that N% of the available hydrogens in the structure are substituted with deuterium. For example, if dibenzofuran is 25% substituted with deuterium, it means that 2 of the 8 hydrogens in dibenzofuran are substituted with deuterium.

[0018] In this specification, the degree of deuteration can be confirmed by known methods such as nuclear magnetic resonance spectroscopy (1H NMR) and GC / MS.

[0019] Examples of substituents in this specification are given below, but are not limited to these.

[0020] The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The position of substitution is not limited to any position where a hydrogen atom can be substituted, i.e., any position where a substituent can be substituted. If two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0021] In this specification, the term “substituted or unsubstituted” means substituted with one or more substituents selected from the group consisting of deuterium; halogen groups; nitrile groups (-CN); nitro groups; hydroxyl groups; alkyl groups; cycloalkyl groups; alkoxy groups; phosphine oxide groups; aryloxy groups; alkylthiooxy groups; arylthiooxy groups; alkylsulfoxy groups; arylsulfoxy groups; alkenyl groups; silyl groups; boron groups; amine groups; aryl groups; or heterocyclic groups, or substituted with substituents in which two or more substituents from the exemplified substituents are linked, or having no substituents at all. For example, “substituents in which two or more substituents are linked” may be biphenyl groups. That is, a biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are linked.

[0022] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium; halogen groups; nitrile groups; nitro groups; hydroxyl groups; amino groups; silyl groups; boron groups; alkoxy groups; aryloxy groups; alkyl groups; cycloalkyl groups; aryl groups; and heterocyclic groups; substituted with substituents in which two or more of the above-described substituents are linked; or having no substituents at all.

[0023] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium; alkyl groups; aryl groups; and heterocyclic groups, or substituted with substituents in which two or more substituents from the exemplified substituents are linked together, or having no substituents at all.

[0024] Examples of the substituents mentioned above are described below, but are not limited to these.

[0025] In this specification, examples of halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0026] In this specification, a silyl group is -SiY Y b Y c and can be represented by the chemical formula, where the Y a , Y b and Y c may each independently be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc.

[0027] In this specification, a boron group is -BY d Y e and can be represented by the chemical formula, where the Y d and Y e may each independently be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the boron group include, but are not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, etc.

[0028] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to still another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include, but are not limited to, methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n-hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, etc.

[0029] In this specification, the above-described description of alkyl groups applies to arylalkyl groups, except that they are substituted with aryl groups.

[0030] In this specification, the alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferably 1 to 20. Specifically, examples include, but are not limited to, 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, and n-decyloxy.

[0031] The alkyl groups, alkoxy groups, and other alkyl group-containing substituted products described herein include all linear or branched chain forms.

[0032] In this 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. In one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. In another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. In yet another embodiment, the number of carbon atoms of 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 styrenel groups.

[0033] In this specification, the alkynyl group is a substituent containing a triple bond between carbon atoms, and may be linear or branched. The number of carbon atoms is not particularly limited, but is preferably 2 to 40. In one embodiment, the number of carbon atoms in the alkynyl group is 2 to 20. In another embodiment, the number of carbon atoms in the alkynyl group is 2 to 10.

[0034] In this 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 yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups.

[0035] In this specification, the amine group is -NH2, and the amine group may be substituted with the alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof as described above. The number of carbon atoms in the substituted amine group is not particularly limited, but is preferably 1 to 30. In one embodiment, the number of carbon atoms in the amine group is 1 to 20. In another embodiment, the number of carbon atoms in the amine group is 1 to 10. Specific examples of substituted amine groups include, but are not limited to, methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, diphenylamine group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, and diphenylamine group.

[0036] In this specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms. In one embodiment, the aryl group has 6 to 30 carbon atoms. In another embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group or a polycyclic aryl group (an aryl group with two or more rings). A monocyclic aryl group can also be expressed as a monocyclic aryl group and can mean a phenyl group; or a group in which two or more phenyl groups are linked. Examples of monocyclic aryl groups include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, etc. A polycyclic aryl group can mean a group in which two or more monocyclic rings are fused together, such as a naphthyl group or a phenantrenyl group. Examples of polycyclic aryl groups include, but are not limited to, a naphthyl group, anthracenyl group, phenantrenyl group, pyrenyl group, perilenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc.

[0037] In this specification, the fluorenyl group may be substituted, or 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.

[0038] When the fluorenyl group is substituted, [ka] , [ka] , [ka] Spirofluorenyl groups such as [ka] (9,9-dimethylfluorenyl group), and [ka] It can be a substituted fluorenyl group, such as (9,9-diphenylfluorenyl group). However, it is not limited to these.

[0039] In this specification, the aryl group in an aryloxy group can be described in the above-mentioned explanation for aryl groups.

[0040] In this specification, the alkyl groups in the alkylthiooxy group and alkylsulfoxy group can be referred to in the description of alkyl groups described above.

[0041] In this specification, the aryl group in the aryl thioxy group and the aryl sulfoxy group can be described in the above-mentioned description of the aryl group.

[0042] In this specification, a heterocyclic group is a ring group containing one or more heteroatoms from N, O, P, S, Si, and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms in the heterocyclized group is 2 to 20. Examples of heterocyclic groups include, but are not limited to, a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridadinyl 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.

[0043] In this specification, the description of heterocyclic groups described above can be applied to heteroaryl groups, except that they are aromatic.

[0044] In this specification, the description relating to the aryl group can be applied to the allylene group, except that it is divalent.

[0045] In this specification, the description relating to a divalent heterocyclic group can be applied to a divalent heterocyclic group, except that it is divalent.

[0046] In this specification, in substituted or unsubstituted rings formed by the bonding of adjacent groups to each other, “ring” means a hydrocarbon ring; or a heteroring.

[0047] The hydrocarbon ring may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic groups, and can be selected from the examples of cycloalkyl groups or aryl groups.

[0048] In this specification, the meaning of bonding with adjacent groups to form a ring means bonding with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a condensed ring thereof. The hydrocarbon ring means a ring consisting only of carbon and hydrogen atoms. The heterocycle means a ring containing one or more elements selected from elements such as N, O, P, S, Si, and Se. In this specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle may be monocyclic or polycyclic.

[0049] In this specification, an aliphatic hydrocarbon ring means a non-aromatic ring consisting 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.

[0050] In this specification, an aromatic hydrocarbon ring means an aromatic ring consisting only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include, but are not limited to, benzene, naphthalene, anthracene, phenanthrene, perylene, fluorantene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, and spirofluorene. In this specification, an aromatic hydrocarbon ring can be interpreted as having the same meaning as an aryl group.

[0051] In this specification, an aliphatic heterocycle means an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepan, azocaine, and thiocaine.

[0052] In this specification, an aromatic heterocycle means an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include, but are not limited to, pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, dithiazole, tetrazol, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine, phenantholidine, diazanaphthalene, triazyden, indole, indidine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, and indenocarbazole.

[0053] Preferred embodiments of the present invention will be described in detail below. However, embodiments of the present invention can be modified in various ways, and the scope of the present invention is not limited to the embodiments described below.

[0054] The compound represented by Chemical Formula 1 of the present invention is characterized in that a carbazole group is linked to a benzene ring contained in a boron-containing multi-resonance core structure, and a silyl group or aryl group is also linked to it. As described above, when a carbazole group and a silyl group or aryl group are linked to the core structure, the bulkiness of the molecule itself is increased compared to a structure in which only one carbazole group is substituted, the distance between molecules increases, and molecular aggregation is prevented, thereby suppressing quenching and increasing the efficiency and lifespan of the organic light-emitting element.

[0055] Therefore, when the compound represented by chemical formula 1 of the present invention is applied to an organic light-emitting element, an organic light-emitting element with high efficiency, low voltage, and / or long lifespan can be obtained.

[0056] The following provides a detailed explanation of chemical formula 1. [Chemical formula 1] [ka]

[0057] In the above chemical formula 1 X is NR;O; or S, R and at least one of R1-R3 are substituted or unsubstituted silyl groups; substituted or unsubstituted aryl groups; or substituted or unsubstituted heterocyclic groups, and the remainder are identical or different from each other, independently of hydrogen; deuterium; halogen groups; nitrile groups; substituted or unsubstituted alkyl groups; or substituted or unsubstituted cycloalkyl groups. L1-L3 and L11-L13 are either identical or different from each other, and each is independently directly bonded; a substituted or unsubstituted allylene group; or a substituted or unsubstituted divalent heterocyclic group. G1 to G3 are either identical or different from each other, and each is independently a hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group. n1 and n2 are integers between 1 and 4, and m1 and m2 are integers between 0 and 4. n3 is an integer between 1 and 3, and m3 is an integer between 0 and 3. g1 to g3 are integers from 0 to 8, If n1-n3, m1-m3, and g1-g3 are each 2 or more, the substituents in parentheses are either identical or different from each other. n1+m1 is less than or equal to 4, n2+m2 is less than or equal to 4, and n3+m3 is less than or equal to 3. m1 + m2 + m3 are integers greater than or equal to 1.

[0058] In one embodiment of this specification, X is NR;O; or S.

[0059] In one embodiment of this specification, X is NR.

[0060] In one embodiment of this specification, X is O.

[0061] In one embodiment of this specification, X is S.

[0062] In one embodiment of this specification, R is hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group.

[0063] In one embodiment of this specification, R is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0064] In one embodiment of this specification, R is a substituted or unsubstituted aryl group.

[0065] In one embodiment of this specification, R is a phenyl group or a biphenyl group.

[0066] In one embodiment of this 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 remainder are identical or different from each other and independently of each other, hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted alkyl group; or substituted or unsubstituted cycloalkyl group.

[0067] In one embodiment of this specification, at least one of R1 to R3 is a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heterocyclic group, and the remainder are identical or different from each other and independently of each other: hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted C1-C60 alkyl group; or substituted or unsubstituted C3-C60 cycloalkyl group.

[0068] In one embodiment of this specification, at least one of R1 to R3 is a substituted or unsubstituted silyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heterocyclic group, and the remainder are identical or different from each other and independently of each other: hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted C1 to C30 alkyl group; or substituted or unsubstituted C3 to C30 cycloalkyl group.

[0069] In one embodiment of this specification, at least one of R1 to R3 is a substituted or unsubstituted silyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heterocyclic group, and the remainder are identical or different from each other and independently of each other are hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted C1 to C20 alkyl group; or a substituted or unsubstituted C3 to C20 cycloalkyl group.

[0070] In one embodiment of this specification, at least one of 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 remainder are identical or different from each other, and each is independently hydrogen; or deuterium.

[0071] In one embodiment of this specification, at least one of R1 to R3 is a silyl group substituted or unsubstituted with deuterium, a C1-C60 alkyl group or a C6-C60 aryl group; a C6-C60 aryl group substituted or unsubstituted with deuterium or a C6-C60 aryl group; or a C2-C60 heterocyclic group substituted or unsubstituted with deuterium or a C2-C60 heterocyclic group, and the remainder are identical or different from each other, each independently of being hydrogen; or deuterium.

[0072] In one embodiment of this specification, at least one of R1 to R3 is a silyl group substituted or unsubstituted with deuterium, a C1-C30 alkyl group or a C6-C30 aryl group; a C6-C30 aryl group substituted or unsubstituted with deuterium or a C6-C30 aryl group; or a C2-C30 heterocyclic group substituted or unsubstituted with deuterium or a C2-C30 heterocyclic group, and the remainder are identical or different from each other, each independently being hydrogen; or deuterium.

[0073] In one embodiment of this specification, at least one of R1 to R3 is a silyl group substituted or unsubstituted with deuterium, a C1-C20 alkyl group or a C6-C20 aryl group; a C6-C20 aryl group substituted or unsubstituted with deuterium or a C6-C20 aryl group; or a C2-C20 heterocyclic group substituted or unsubstituted with deuterium or a C2-C20 heterocyclic group, and the remainder are identical or different from each other, each independently being hydrogen; or deuterium.

[0074] In one embodiment of this 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 containing one or more N and O as heteroatoms, and the remainder are identical or different from each other, and each is independently hydrogen; or deuterium.

[0075] In one embodiment of this 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 benzofuran dibenzofuran group; or an indolocarbazole group, and the remainder are identical or different from each other, and each is independently hydrogen; or deuterium.

[0076] In one embodiment of this specification, the benzofuranodibenzofuran group is a benzo[1,2-b:3,4-b']bisbenzofuran group.

[0077] In one embodiment of this specification, the indrocarbazole group is indro[3,2,1-jk]carbazole.

[0078] In one embodiment of this specification, at least one of R1 to R3 is a group represented by the following structural formula, or a substituted or unsubstituted aryl group.

[0079] [ka]

[0080] In the above structural formula, P1 to P3 are substituted or unsubstituted aryl groups. [ka] This indicates the position where it is joined to L1-L3.

[0081] In one embodiment of this specification, P1 to P3 are substituted or unsubstituted aryl groups having 6 to 60 carbon atoms.

[0082] In one embodiment of this specification, P1 to P3 are substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0083] In one embodiment of this specification, P1 to P3 are substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.

[0084] In one embodiment of this specification, P1 to P3 are phenyl groups.

[0085] In one embodiment of this specification, L1 to L3 are identical or different from each other and are independently directly bonded; substituted or unsubstituted allylene groups; or substituted or unsubstituted divalent heterocyclic groups.

[0086] In one embodiment of this specification, L1 to L3 are identical or different from each other and are independently directly bonded; substituted or unsubstituted C6-C60 allylene groups; or substituted or unsubstituted C2-C60 divalent heterocyclic groups.

[0087] In one embodiment of this specification, L1 to L3 are identical or different from each other and are independently directly bonded; substituted or unsubstituted C6-C30 allylene groups; or substituted or unsubstituted C2-C30 divalent heterocyclic groups.

[0088] In one embodiment of this specification, L1 to L3 are identical or different from each other and are independently directly bonded; substituted or unsubstituted C6-C20 allylene groups; or substituted or unsubstituted C2-C20 divalent heterocyclic groups.

[0089] In one embodiment of this specification, L1 to L3 are identical or different from each other, and each is independently directly bonded; or substituted or unsubstituted aliene groups.

[0090] In one embodiment of this specification, L1 to L3 are identical or different from each other, and are directly bonded to each other independently; or are allylene groups having 6 to 60 carbon atoms.

[0091] In one embodiment of this specification, L1 to L3 are identical or different from each other, and are directly bonded to each other independently; or are allylene groups having 6 to 30 carbon atoms.

[0092] In one embodiment of this specification, L1 to L3 are identical or different from each other, and are directly bonded to each other independently; or are allylene groups having 6 to 20 carbon atoms.

[0093] In one embodiment of this specification, L1 to L3 are identical or different from each other, independently, directly bonded; or phenylene groups.

[0094] In one embodiment of this specification, L11 to L13 are identical or different from each other and are independently directly bonded; substituted or unsubstituted allylene groups; or substituted or unsubstituted divalent heterocyclic groups.

[0095] In one embodiment of this specification, L11 to L13 are identical or different from each other and are independently directly bonded; substituted or unsubstituted C6-C60 allylene groups; or substituted or unsubstituted C2-C60 divalent heterocyclic groups.

[0096] In one embodiment of this specification, L11 to L13 are identical or different from each other and are independently directly bonded; substituted or unsubstituted C6-C30 allylene groups; or substituted or unsubstituted C2-C30 divalent heterocyclic groups.

[0097] In one embodiment of this specification, L11 to L13 are identical or different from each other and are independently directly bonded; substituted or unsubstituted C6-C20 allylene groups; or substituted or unsubstituted C2-C20 divalent heterocyclic groups.

[0098] In one embodiment of this specification, L11 to L13 are identical or different from each other, and independently, directly bonded; or substituted or unsubstituted aliene groups.

[0099] In one embodiment of this specification, L11 to L13 are identical or different from each other, independently, directly bonded; or are allylene groups.

[0100] In one embodiment of this specification, L11 to L13 are identical or different from each other, and each is directly bonded; or are aliene groups having 6 to 60 carbon atoms.

[0101] In one embodiment of this specification, L11 to L13 are identical or different from each other, and are directly bonded to each other independently; or are allylene groups having 6 to 30 carbon atoms.

[0102] In one embodiment of this specification, L11 to L13 are identical or different from each other, and are directly bonded to each other independently; or are allylene groups having 6 to 20 carbon atoms.

[0103] In one embodiment of this specification, L11 to L13 are identical or different from each other, independently, directly bonded; or are phenylene groups.

[0104] In one embodiment of this specification, G1 to G3 are identical or different from each other and are independently hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group.

[0105] In one embodiment of this specification, G1 to G3 are identical or different from each other and are independently hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted silyl group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C6-C60 aryl group; or substituted or unsubstituted C2-C60 heterocyclic group.

[0106] In one embodiment of this specification, G1 to G3 are identical or different from each other and are independently hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted silyl group; substituted or unsubstituted C1-C30 alkyl group; substituted or unsubstituted C3-C30 cycloalkyl group; substituted or unsubstituted C6-C30 aryl group; or substituted or unsubstituted C2-C30 heterocyclic group.

[0107] In one embodiment of this specification, G1 to G3 are identical or different from each other and are independently hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted silyl group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C3-C20 cycloalkyl group; substituted or unsubstituted C6-C20 aryl group; or substituted or unsubstituted C2-C20 heterocyclic group.

[0108] In one embodiment of this specification, G1 to G3 are identical or different from each other, and each is independently hydrogen; or deuterium.

[0109] In one embodiment of this specification, G1 to G3 are hydrogen.

[0110] In one embodiment of this specification, n1 and n2 are integers from 1 to 4, and m1 and m2 are integers from 0 to 4.

[0111] In one embodiment of this specification, n3 is an integer between 1 and 3, and m3 is an integer between 0 and 3.

[0112] In one embodiment of this specification, n1 is 1.

[0113] In one embodiment of this specification, n2 is 1.

[0114] In one embodiment of this specification, n3 is 1.

[0115] In one embodiment of this specification, m1 is 0.

[0116] In one embodiment of this specification, m1 is 1.

[0117] In one embodiment of this specification, m2 is 0.

[0118] In one embodiment of this specification, m2 is 1.

[0119] In one embodiment of this specification, m3 is 0.

[0120] In one embodiment of this specification, m3 is 1.

[0121] In one embodiment of this specification, g1 to g3 are integers from 0 to 8.

[0122] In one embodiment of this specification, g1 to g3 are 0.

[0123] In one embodiment of this specification, g1 to g3 are 8.

[0124] In one embodiment of this specification, n1+m1 is 4 or less, n2+m2 is 4 or less, and n3+m3 is 3 or less.

[0125] In one embodiment of this specification, m1 + m2 + m3 are integers greater than or equal to 1.

[0126] In one embodiment of this specification, m1+m2+m3 are 1 to 3.

[0127] In one embodiment of this specification, m1+m2+m3 is 1 or 2.

[0128] In one embodiment of this specification, the chemical formula 1 is represented by any of the following chemical formulas 1-A-1 to 1-A-3.

[0129] [Chemical formula 1-A-1] [ka] [Chemical formula 1-A-2] [ka] [Chemical formula 1-A-3] [ka]

[0130] In the above chemical formulas 1-A-1 to 1-A-3, The definitions of X, R1-R3, L1-L3, L11-L13, G1-G3, and g1-g3 are the same as those in Chemical Formula 1 above.

[0131] In one embodiment of this specification, the chemical formula 1 is represented by any of the following chemical formulas 1-B-1 to 1-B-3.

[0132] [Chemical formula 1-B-1] [ka] [Chemical formula 1-B-2] [ka] [Chemical formula 1-B-3] [ka]

[0133] In the above chemical formulas 1-B-1 to 1-B-3, The definitions of X, R1-R3, L1-L3, L11-L13, G1-G3, and g1-g3 are the same as those in Chemical Formula 1 above.

[0134] In one embodiment of this specification, a compound of chemical formula 1 containing deuterium can be produced by a known deuteration reaction. In one embodiment of this specification, the compound represented by chemical formula 1 can be formed using a deuterated compound as a precursor, or deuterium can be introduced into the compound via a hydrogen-deuterium exchange reaction under acid catalysis using a deuterated solvent.

[0135] In one embodiment of this specification, the compound represented by chemical formula 1 is substituted with deuterium by 20% or more. In another embodiment, the compound represented by chemical formula 1 is substituted with deuterium by 30% or more. In yet another embodiment, the compound represented by chemical formula 1 is substituted with deuterium by 40% or more. In yet another embodiment, the compound represented by chemical formula 1 is substituted with deuterium by 50% or more. In yet another embodiment, the compound represented by chemical formula 1 is substituted with deuterium by 60% or more. In yet another embodiment, the compound represented by chemical formula 1 is substituted with deuterium by 70% or more. In yet another embodiment, the compound represented by chemical formula 1 is substituted with deuterium by 80% or more. In yet another embodiment, the compound represented by chemical formula 1 is substituted with deuterium by 90% or more. In yet another embodiment, the compound represented by chemical formula 1 is substituted with deuterium by 100%.

[0136] In one embodiment of this specification, the compound represented by chemical formula 1 contains 40% to 60% deuterium. In another embodiment, the compound represented by chemical formula 1 contains 40% to 80% deuterium. In yet another embodiment, the compound represented by chemical formula 1 contains 60% to 80% deuterium. In yet another embodiment, the compound represented by chemical formula 1 contains 80% to 100% deuterium.

[0137] In one embodiment of this specification, the chemical formula 1 is represented by any of the following compounds. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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[0138] The above [ ] D=x1~x2 This means that the structure inside the parentheses contains x1 to x2 deuterium atoms, and its value is an integer. For example, [ ] D=1~41 This means that it contains 1 to 41 deuterium atoms.

[0139] A compound represented by chemical formula 1 according to one embodiment of this specification may have a core structure prepared as shown in reaction formula 1 below. Substituents can be attached by methods known in the art, and the type, position, or number of substituents may be modified by techniques known in the art.

[0140] <Reaction Equation 1> [ka]

[0141] This specification describes how compounds with various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by chemical formula 1. Furthermore, this specification describes how the HOMO and LUMO energy levels of the compound can also be adjusted by introducing various substituents into the core structure of the aforementioned structure.

[0142] Furthermore, this specification provides an organic light-emitting device containing the aforementioned compound.

[0143] In one embodiment of the present invention, an organic light-emitting element is provided, comprising an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers contain a compound represented by the chemical formula 1.

[0144] The organic layer of the organic light-emitting element according to this specification may have a single-layer structure, or it may have a multilayer structure in which two or more organic layers are stacked.

[0145] In one embodiment of this specification, the organic layer may include one or more layers selected from a hole transport layer, a hole injection layer, an electron barrier layer, a hole injection and transport layer, an emitting layer, an electron transport layer, an electron injection layer, a hole barrier layer, and an electron injection and transport layer.

[0146] In one embodiment of this specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, wherein the electron injection layer, electron transport layer, or electron injection and transport layer includes a compound represented by chemical formula 1.

[0147] In one embodiment of this specification, the organic layer includes an electronically regulated layer, and the electronically regulated layer includes a compound represented by the chemical formula 1.

[0148] In one embodiment of this specification, the organic layer includes a hole-blocking layer, and the hole-blocking layer includes a compound represented by the chemical formula 1.

[0149] In one embodiment of this specification, the organic layer includes a hole-blocking layer and a light-emitting layer, and the hole-blocking layer and the light-emitting layer contain a compound represented by chemical formula 1. In this case, the compounds represented by chemical formula 1 contained in the light-emitting layer and the hole-blocking layer may be the same or different.

[0150] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1.

[0151] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1 as a host.

[0152] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1 as an n-type phosphorescent host of the light-emitting layer.

[0153] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1 as a host, and may further include a host and a dopant.

[0154] 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 Chemical Formula 1 as hosts.

[0155] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1 as a first host, and may further include an additional second host.

[0156] In one embodiment of this specification, the first host is an n-type phosphorescent host, and the second host is a p-type phosphorescent host. In this case, the weight ratio of the first host to the second host may be 2:8 to 8:2, 4:6 to 6:4, or 5:5. The n-type host can be any material generally known to be able to steal electrons from the matrix material (organic layer material), and is not limited to this. In other words, the n-type host can be defined as a material having the property of being able to provide electrons to the LUMO (lowest unoccupied molecular orbital) energy level of the matrix. Conversely, the aforementioned p-type material is a material that, when a layer is composed solely of p-type materials, accepts electrons from the HOMO (highest occupied molecular orbital) energy level of an adjacent material located in the cathode direction, thereby generating holes in the adjacent material. Alternatively, when a p-type material is doped into an arbitrary matrix, it accepts electrons from the HOMO of the matrix material, thereby generating holes in the HOMO of the matrix. To achieve this, when a layer is formed solely of p-type materials, the closer the HOMO level of a material located in the cathode direction is to the LUMO of the p-type material, the more electrons it will take from the HOMO of the adjacent layer, thus generating holes in the adjacent layer. Similarly, 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 more electrons it will take, thus generating holes in the matrix.

[0157] The p-type host may be a compound commonly known in the art, and may, for example, have a structure containing a nitrogen-containing monocyclic ring; a dibenzofuran; and / or a carbazole.

[0158] In one embodiment of this specification, the second host is a carbazole compound.

[0159] In one embodiment of this specification, the second host is a biscarbazole compound.

[0160] In one embodiment of this specification, the second host is a biscarbazole compound substituted with an aryl group.

[0161] In one embodiment of this specification, the light-emitting layer comprises a first host and a second host, and may further comprise a dopant, the dopant of which may be a phosphorescent dopant. In one embodiment of this specification, the light-emitting layer may be a blue light-emitting layer, a red light-emitting layer, or a green light-emitting layer.

[0162] In one embodiment of this specification, the light-emitting layer may be a blue light-emitting layer.

[0163] In one embodiment of this specification, the light-emitting layer may include a host and a dopant. Specifically, the dopant may be a fluorescent dopant or a phosphorescent dopant.

[0164] In one embodiment of this specification, the dopant is present in an amount of 1 to 20 parts by weight per 100 parts by weight of the host.

[0165] In one embodiment of this specification, the light-emitting layer comprises a host and a dopant in a weight ratio of 99:1 to 1:99. Specifically, it comprises a weight ratio of 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.

[0166] In one embodiment of this specification, the dopant may include arylamine compounds, heterocyclic compounds containing boron and nitrogen, metal complex compounds, platinum complex compounds, iridium complex compounds, or iridium compounds.

[0167] For example, when the light-emitting layer emits red light, phosphorescent substances such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum), or fluorescent substances such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used as the light-emitting dopant, but are not limited to these. When the light-emitting layer emits green light, phosphorescent substances such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium) or fluorescent substances such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used as the light-emitting dopant, but are not limited to these. When the light-emitting layer emits blue light, phosphorescent materials such as platinum complex compounds and (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylmarylylene (DSA), PFO-based polymers, and PPV-based polymers can be used as light-emitting dopants, but are not limited to these.

[0168] In one embodiment of this specification, the dopant is a metal complex compound.

[0169] In one embodiment of this specification, the dopant is a platinum complex compound.

[0170] In one embodiment of this specification, the dopant is an iridium complex compound.

[0171] In one embodiment of this specification, the dopant is an iridium-based compound.

[0172] In one embodiment of this specification, the dopant compound can be selected from, but is not limited to, the following structural formulas.

[0173]

Chem.

Chem.

Chem.

Chem.

[0174] 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 contains the compound represented by Chemical Formula 1. Specifically, in one embodiment of the present specification, the compound represented by Chemical Formula 1 may be contained in one of the two or more electron transport layers, or may be contained in each of the two or more electron transport layers.

[0175] In one embodiment of the present specification, when the compound is contained in each of the two or more electron transport layers, the other materials excluding the compound represented by Chemical Formula 1 may be the same as or different from each other.

[0176] When the organic layer containing the compound represented by Chemical Formula 1 is an electron transport layer, an electron injection layer, or an electron injection and transport layer, the electron transport layer, the electron injection layer, or the electron injection and transport layer may further contain an n-type dopant or an organometallic compound. The n-type dopant or organometallic compound may be those known in the art, and for example, a metal or a metal complex can be used.

[0177] For example, the n-type dopant or organometallic compound may be LiQ, but is not limited thereto. The electron transport layer, the electron injection layer, or the electron injection and transport layer containing the compound represented by Chemical Formula 1 may further contain LiQ (Lithium Quinolate).

[0178] For example, the compound represented by chemical formula 1 and the n-type dopant or organometallic compound may be present in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4. For example, the compound represented by chemical formula 1 and the n-type dopant or organometallic compound may be present in a weight ratio of 1:1.

[0179] In one embodiment of the present invention, the organic layer may further contain other organic compounds, metals, or metal compounds in addition to the compound represented by the chemical formula 1 described above.

[0180] In one embodiment of this specification, the organic layer may further include, in addition to the organic layer containing the compound represented by chemical formula 1, a hole implantation layer or a hole transport layer containing a compound containing an arylamine group, a carbazolyl group, or a benzocarbazolyl group.

[0181] In one embodiment of this specification, the thickness of the organic layer containing the compound of chemical formula 1 may be 5 Å to 2000 Å, or 5 Å to 500 Å, preferably 10 Å to 400 Å.

[0182] In one embodiment of this specification, the organic light-emitting element may be an organic light-emitting element of the normal type, in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0183] In one embodiment of this specification, the organic light-emitting element may be an inverted type organic light-emitting element in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0184] The organic light-emitting element may have, for example, a stacked structure as shown below, but is not limited thereto.

[0185] (1) Anode / Hole transport layer / Emitting layer / Cathode (2) Anode / Hole injection layer / Hole transport layer / Emitting layer / Cathode (3) Anode / Hole injection layer / Hole buffer layer / Hole transport layer / Emission layer / Cathode (4) Anode / Hole transport layer / Emitting layer / Electron transport layer / Cathode (5) Anode / Hole transport layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode (6) Anode / Hole injection layer / Hole transport layer / Emitting layer / Electron transport layer / Cathode (7) Anode / Hole injection layer / Hole transport layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode (8) Anode / Hole injection layer / Hole buffer layer / Hole transport layer / Emitting layer / Electron transport layer / Cathode (9) Anode / Hole injection layer / Hole buffer layer / Hole transport layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode (10) Anode / Hole transport layer / Electron barrier layer / Emitting layer / Electron transport layer / Cathode (11) Anode / Hole transport layer / Electron barrier layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode (12) Anode / Hole injection layer / Hole transport layer / Electron barrier layer / Emitting layer / Electron transport layer / Cathode (13) Anode / Hole injection layer / Hole transport layer / Electron barrier layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode (14) Anode / Hole Injection Layer / Hole Transport Layer / Electron Barrier Layer / Emitting Layer / Hole Barrier Layer / Electron Transport Layer / Electron Injection Layer / Cathode (15) Anode / Hole transport layer / Emitting layer / Hole blocking layer / Electron transport layer / Cathode (16) Anode / Hole transport layer / Emitting layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode (17) Anode / Hole injection layer / Hole transport layer / Emitting layer / Hole blocking layer / Electron transport layer / Cathode (18) Anode / Hole injection layer / Hole transport layer / Emitting layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode (19) Anode / Hole injection layer / Hole transport layer / Electron barrier layer / Emitting layer / Hole barrier layer / Electron injection and transport layer / Cathode

[0186] The structure of the organic light-emitting element described herein may have, but is not limited to, the structures shown in Figures 1 to 3.

[0187] Figure 1 shows 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. In such a structure, the compound may be included in the light-emitting layer 6.

[0188] Figure 2 shows an example of an organic light-emitting element in which a substrate 1, anode 2, hole injection layer 3, hole transport layer 4, electron barrier layer 5, light-emitting layer 6, hole barrier layer 7, electron transport layer 8, electron injection layer 9, and cathode 10 are sequentially stacked. In such a structure, the compound may be included in the hole injection layer 3, hole transport layer 4, electron barrier layer 5, light-emitting layer 6, hole barrier layer 7, electron transport layer 8, or electron injection layer 9.

[0189] Figure 3 shows an example of an organic light-emitting element in which a substrate 1, anode 2, hole injection layer 3, hole transport layer 4, electron barrier layer 5, light-emitting layer 6, hole barrier layer 7, electron injection and transport layer 11, and cathode 10 are sequentially stacked. In such a structure, the compound may be included in the hole injection layer 3, hole transport layer 4, electron barrier layer 5, light-emitting layer 6, hole barrier layer 7, or electron injection and transport layer 11.

[0190] In one embodiment of this specification, the hole-blocking layer and the light-emitting layer may be provided adjacent to each other. For example, the hole-blocking layer and the light-emitting layer may be provided in physical contact.

[0191] The organic light-emitting element according to this specification may be manufactured using the materials and manufacturing methods of a normal organic light-emitting element, except that one or more layers of the organic material contain the compound represented by the chemical formula 1.

[0192] If the organic light-emitting element includes multiple organic layers, the organic layers may be formed from the same material or different materials.

[0193] For example, the organic light-emitting element according to this specification can be manufactured by depositing a metal or a conductive metal oxide or an alloy thereof onto a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode, then forming an organic layer on top of the anode that includes a hole injection layer, a hole transport layer, an emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer, and finally depositing a material that can be used as a cathode on top of that. In addition to this method, an organic light-emitting element can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto a substrate.

[0194] Furthermore, the compound of chemical formula 1 may be formed in the organic layer not only by vacuum deposition but also by solution coating during the manufacture of organic light-emitting devices. Here, solution coating means, but is not limited to, spin coating, dip coating, doctor blade, inkjet printing, screen printing, spray method, roll coating, etc.

[0195] Besides this method, organic light-emitting diodes can also be fabricated by sequentially depositing a cathode material, an organic layer, and an anode material onto a substrate. However, the manufacturing method is not limited to this.

[0196] The anode is an electrode that injects holes, and as the anode material, a material with a large work function is generally preferred so that holes are injected into the organic layer smoothly. Specific examples of anode materials that can be used in the present invention include, but are not limited to, metals or alloys thereof such as vanadium, chromium, copper, zinc, and gold; 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.

[0197] The cathode is an electrode into which electrons are injected, and the cathode material is preferably a material with a small work function so that electrons can be easily injected into the organic layer. Specific examples of cathode materials include, but are not limited to, metals or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; and multilayer materials such as LiF / Al or LiO2 / Al.

[0198] The hole injection layer is a layer that receives holes from the electrode. The hole injection material is preferably one that has the ability to transport holes and has an excellent hole injection effect on the anode and on the light-emitting layer or light-emitting material. It is also preferably a material that has an excellent ability to prevent excitons generated in the light-emitting layer from moving to the electron injection layer or electron injection material. Furthermore, it is preferably a material with excellent thin-film formation ability. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic materials; hexanitrile hexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; and polythiophene-based conductive polymers such as anthraquinone and polyaniline.

[0199] In one embodiment of this specification, the hole injection layer contains, but is not limited to, a compound represented by the following chemical formula HI-1.

[0200] [Chemical formula HI-1] [ka]

[0201] In the aforementioned chemical formula HI-1, R315~R317 are either identical or different from each other, and each is independently selected from the group consisting of hydrogen; deuterium; substituted or unsubstituted alkyl groups; substituted or unsubstituted aryl groups; substituted or unsubstituted heteroaryl groups; and combinations thereof, or bonded to adjacent groups to form substituted or unsubstituted rings. r315 is an integer from 1 to 5, and if r315 is 2 or greater, then 2 or more R315s are either the same or different from each other. r316 is an integer from 1 to 5, and if r316 is 2 or greater, then 2 or more R316s are either the same or different from each other.

[0202] In one embodiment of this specification, R317 is selected from the group consisting of substituted or unsubstituted aryl groups; substituted or unsubstituted heteroaryl groups; and combinations thereof.

[0203] In one embodiment of this specification, R317 is selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; a triphenylene group; and combinations thereof.

[0204] In one embodiment of this specification, R315 and R316 are identical or different from each other, and independently are substituted or unsubstituted aryl groups, or bonded to adjacent groups to form an alkyl-substituted aromatic hydrocarbon ring.

[0205] In one embodiment of this specification, R315 and R316 are identical or different from each other, and independently are phenyl or biphenyl groups, or bonded to adjacent groups to form methyl-substituted indene.

[0206] In one embodiment of this specification, the chemical formula HI-1 is represented by any of the following compounds.

[0207] [ka] [ka]

[0208] In one embodiment of this specification, the hole injection layer contains, but is not limited to, a compound represented by the following chemical formula HI-2.

[0209] [Chemical formula HI-2] [ka]

[0210] In the aforementioned chemical formula HI-2 R401 to R403 are halogen groups, which are either identical or different from each other, and each is independent of the others. r401~r403 is 4.

[0211] In one embodiment of this specification, R401 to R403 are F.

[0212] In one embodiment of this specification, the chemical formula HI-2 is represented by the following compound.

[0213] [ka]

[0214] In one embodiment of this specification, the hole injection layer comprises the chemical formulas HI-1 and HI-2.

[0215] In one embodiment of this specification, the hole injection layer contains the chemical formulas HI-1 and HI-2 in a weight ratio of 1:99 to 99:1.

[0216] The thickness of the hole injection layer may be between 1 nm and 150 nm. If the thickness of the hole injection layer is 1 nm or more, it has the advantage of preventing a decrease in hole injection characteristics, and if it is 150 nm or less, it has the advantage of preventing the drive voltage from increasing to improve hole movement due to the hole injection layer being too thick.

[0217] In one embodiment of this specification, the hole implantation layer may contain an arylamine compound containing a carbazole group and a p-type dopant. For example, the amine compound is represented as Het101-L101-N(Ar101)(Ar102), where Het101 is a substituted or unsubstituted carbazole group, L101 is a directly bonded or substituted or unsubstituted allylene group, and Ar101 and Ar102 may be identical or different from each other, and each may be independently a substituted or unsubstituted aryl group. The amine compound and the p-type dopant may be present in an appropriate molar ratio, for example, the amine compound and the p-type dopant may be present in a molar ratio of 99.9:0.1 to 90:10.

[0218] The 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 a material that can receive holes from the anode or hole injection layer and move them to the light-emitting layer, and a material with high mobility for holes is preferred. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which conjugated and unconjugated parts coexist.

[0219] In one embodiment of this specification, the hole transport layer may contain an arylamine compound containing a carbazole group.

[0220] In one embodiment of this specification, the hole transport layer contains, but is not limited to, the compound represented by the chemical formula HI-1.

[0221] The hole injection and transport layer is a layer that transports holes to the light-emitting layer. The materials exemplified in the hole transport layer and hole injection layer can be used, but are not limited thereto.

[0222] A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.

[0223] An electron-blocking layer may be provided between the hole transport layer and the light-emitting layer. The electron-blocking layer may be made of the aforementioned compound or a material known in the art.

[0224] The electron-blocking layer is a layer that prevents electrons injected from the electron injection layer from passing through the light-emitting layer into the hole injection layer, thereby improving the lifespan and efficiency of the device. Known materials can be used without limitation, and the materials exemplified in the description of the hole injection layer may be used, but are not limited thereto. The electron-blocking layer may be formed between the light-emitting layer and the hole transport layer, between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that performs both hole injection and hole transport simultaneously.

[0225] In one embodiment of this specification, the electron barrier layer comprises, but is not limited to, a compound represented by the following chemical formula EB-1.

[0226] [Chemical formula EB-1] [ka]

[0227] In the aforementioned chemical formula EB-1, T1 to T14 are either identical or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. t13 is an integer between 1 and 3, and if t13 is 2 or greater, then the values ​​of t13 that are 2 or greater are either the same or different from each other.

[0228] In one embodiment of this specification, T1 to T14 are identical or different from each other and are independently hydrogen; deuterium; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0229] In one embodiment of this specification, T1 to T14 are identical or different from each other and are independently hydrogen; deuterium; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0230] In one embodiment of this specification, T1 to T14 are identical or different from each other and are independently hydrogen; deuterium; a phenyl group; a biphenyl group; or a naphthyl group.

[0231] In one embodiment of this specification, T1 to T13 are identical or different from each other and are independently hydrogen; or deuterium.

[0232] In one embodiment of this specification, T14 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0233] In one embodiment of this specification, T14 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0234] In one embodiment of this specification, T14 is a phenyl group; a biphenyl group; or a naphthyl group.

[0235] In one embodiment of this specification, the chemical formula EB-1 may include, but is not limited to, the following compounds.

[0236] [ka]

[0237] In one embodiment of this specification, the chemical formula EB-1 may be used as a second host material for the light-emitting layer.

[0238] The light-emitting layer can emit red, green, or blue light and may be made of a phosphorescent or fluorescent material. The light-emitting material is a material that can emit light in the visible light region by transporting and bonding holes and electrons from a hole transport layer and an electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole compounds, dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzthiazole, and benzimidazole compounds; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc.

[0239] The light-emitting layer may include a host material and a dopant material. If an organic light-emitting device according to one embodiment of this specification includes an additional light-emitting layer other than the light-emitting layer containing chemical formula 1, the host material may be a condensed aromatic ring derivative or a heterocycle-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluorantene compounds, etc., and heterocycle-containing compounds include, but are not limited to, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc.

[0240] Examples of the dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluorantene compounds, and metal complexes. Specifically, aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and perifurantene, which have arylamine groups. Styrylamine compounds are compounds in which at least one aryl vinyl group is substituted onto a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamine groups are substituted or unsubstituted. Specifically, examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. Examples of metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0241] The hole-blocking layer is a layer that prevents holes from reaching the cathode and can generally be formed under the same conditions as the electron injection layer. If an organic light-emitting element according to one embodiment of this specification includes an additional hole-blocking layer other than the hole-blocking layer comprising chemical formula 1, it may include, but is not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0242] A hole-blocking layer may be provided between the electron transport layer and the light-emitting layer, and materials known in the art may be used.

[0243] In one embodiment of this specification, the hole-blocking layer may contain a compound comprising an N-containing heterocyclic group and a fluorene ring.

[0244] 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 preferably a material that can successfully inject electrons from the cathode and transfer them to the light-emitting layer, and which has high electron mobility. 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 ordinary materials with a low work function followed by an aluminum or silver layer. Specifically, these include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0245] The thickness of the electron transport layer may be between 1 nm and 50 nm. A thickness of 1 nm or more has the advantage of preventing a decrease in electron transport characteristics, while a thickness of 50 nm or less has the advantage of preventing the driving voltage from increasing to improve electron movement due to the electron transport layer being too thick.

[0246] In one embodiment of this specification, the electron transport layer may contain a compound comprising two N-containing heterocyclic groups, and may further contain an n-type dopant or an organometallic compound. For example, the n-type dopant or organometallic compound may be LiQ, and the compound comprising the two N-containing heterocyclic groups and the n-type dopant (or organometallic compound) may be present in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.

[0247] The electron injection layer is a layer that receives electrons from the electrode. The electron injection material is preferably one that has excellent electron transport capabilities and exhibits an excellent electron receiving effect from the second electrode and an excellent electron injection effect on the light-emitting layer or light-emitting material. Furthermore, a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and exhibits excellent thin-film formation capabilities is preferred. Specifically, examples include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0248] Examples of the aforementioned metal complex compounds include, but are not limited to, 8-hydroxyquinolinatotritium, 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-crezolat)gallium, bis(2-methyl-8-quinolinato)(1-naphthorato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphthorato)gallium.

[0249] In one embodiment of this specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. The materials exemplified can be used in the electron transport layer and the electron injection layer, but are not limited thereto.

[0250] In one embodiment of this specification, the electron injection and transport layer comprises, but is not limited to, a compound represented by the following chemical formula ET-1.

[0251] [Chemical formula ET-1] [ka]

[0252] In the aforementioned chemical formula ET-1, At least one of Z11-Z13 is N, and the rest are CH. At least one of Z21-Z23 is N, and the rest are CH. L601 and L602 are identical or different from each other, and independently of each other, they are directly bonded; substituted or unsubstituted allylene groups; or substituted or unsubstituted heteroalylene groups. Ar601 to Ar604 are identical or different from each other, and each is independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0253] In one embodiment of this specification, L601 and L602 are identical or different from each other, and are independently substituted or unsubstituted monocyclic or polycyclic allylene groups having 6 to 30 carbon atoms.

[0254] In one embodiment of this specification, L601 and L602 are phenylene groups.

[0255] In one embodiment of this specification, Ar601 to Ar604 are identical or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0256] In one embodiment of this specification, Ar601 to Ar604 are phenyl groups.

[0257] In one embodiment of this specification, the chemical formula ET-1 is represented by the following compound.

[0258] [ka]

[0259] In one embodiment of this specification, the electron injection and transport layers may further include a metal complex compound, as described above. The organic light-emitting element according to the present invention may be a front-emitting type, a rear-emitting type, or a double-sided emitting type, depending on the material used.

[0260] The organic light-emitting elements described herein may be used in various electronic devices. For example, such electronic devices may be, but are not limited to, display panels, touch panels, solar modules, lighting devices, and the like.

[0261] The following describes the Specification in detail with reference to examples. However, the examples relating to this Specification can be modified in various other forms, and the scope of this application shall not be construed as being limited to the examples described below. The examples of this application are provided to give a more complete explanation of this Specification to a person of average skill in the art. [Examples]

[0262] <Manufacturing example>

[0263] Example of compound 1 preparation [ka]

[0264] Synthesis of Intermediate 1 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, and the mixture was heated at 160°C and stirred for 5 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, water and ethyl acetate were added, and the mixture was separated. The mixture was then treated with MgSO4 (anhydrous) and filtered. The filtered solution was removed by distillation under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 28 g of intermediate 1. (Yield 70%, Mass[M+]=663)

[0265] Synthesis of Intermediate 2 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. Then, 0.4 g of bis(tri-tert-butylphosphine)palladium(0)Pd(PtBu3)2 was added, and the mixture was heated at 120°C and stirred for 8 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and after liquid-liquid extraction with water and toluene, it was treated with MgSO4 (anhydrous) and filtered. The filtered solution was removed by distillation under reduced pressure, and purified by recrystallization (toluene / hexane) to obtain 23 g of intermediate 2. (Yield 76%, Mass[M+]=721)

[0266] Synthesis of Compound 1 Under a nitrogen atmosphere, 23 g of intermediate 2, dissolved in 300 mL of toluene (anhydrous) cooled to 0°C, was added dropwise to a flask. 47 mL of t-butyllithium [t-Butyllithium, 1.7 M in hexane] was then slowly added dropwise, and the mixture was stirred at 70°C for 5 hours. Once the lithium halogen exchange reaction was complete, the mixture was cooled again to 0°C, and 9.2 mL of boron tribromide was slowly added dropwise. The temperature was then raised to 70°C and the mixture was stirred for 10 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, water and aq.NH4Cl were added, and the mixture was separated. The mixture was then treated with MgSO4 (anhydrous) and filtered. The filtered solution was removed by distillation under reduced pressure and purified twice by recrystallization (toluene / hexane) to obtain 3.8 g of compound 1. (Yield 17%, Mass[M+]=694)

[0267] Example of compound 2 preparation [ka]

[0268] Synthesis of Intermediate 3 The intermediate was prepared in the same manner as in Synthesis 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. 23 g of intermediate 3 was obtained. (Yield 57%, Mass[M+]=815)

[0269] Synthesis of Intermediate 4 Except for using 23g of intermediate 3 instead of intermediate 1, the preparation was carried out in the same manner as the preparation of intermediate 2 in Synthesis Example 1, yielding 18g of intermediate 4. (Yield 73%, Mass[M+]=873)

[0270] Synthesis of Compound 2 Compound 2 was prepared in the same manner as compound 1 in Synthesis Example 1, except that 18 g of intermediate 4 was used instead of intermediate 2, yielding 2.7 g of compound 2. (Yield 15%, Mass[M+]=846)

[0271] Example of compound 3 preparation [ka]

[0272] Synthesis of Intermediate 5 The intermediate was prepared in the same manner as in Synthesis Example 1, except that 26 g of 3'-(9H-carbazole-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. 28 g of intermediate 5 was obtained. (Yield 74%, Mass[M+]=525)

[0273] Synthesis of Intermediate 6 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. Then, 0.6 g of tetrakis(triphenylphosphine)palladium(0)Pd(PPh3)4 was added, and the mixture was heated at 80°C and stirred for 8 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and after liquid-liquid extraction with water and toluene, it was treated with MgSO4 (anhydrous) and filtered. The filtered solution was removed by distillation under reduced pressure, and purified by recrystallization (toluene / hexane) to obtain 22 g of intermediate 6. (Yield 69%, Mass[M+]=599)

[0274] Synthesis of Intermediate 7 Except for using 22g of intermediate 6 instead of intermediate 1, the preparation was carried out in the same manner as the preparation of intermediate 2 in Synthesis Example 1, yielding 24g of intermediate 7. (Yield 74%, Mass[M+]=656)

[0275] Synthesis of Compound 3 Under a nitrogen atmosphere, 15 g of intermediate 7, dissolved in 500 mL of 1,2-dichlorobenzene (DCB), was added to a flask containing 17 g of borontriiodide. The mixture was then stirred at 120°C for 5 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and after liquid-liquid extraction with water and sodium thiosulfate solution, it was treated with MgSO4 (anhydrous) and filtered. The filtered solution was removed by distillation under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 4.7 g of compound 3. (Yield 31%, Mass[M+]=664)

[0276] Example of compound 4 preparation [ka]

[0277] Synthesis of Intermediate 8 The intermediate was prepared in the same manner as in Synthesis 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. 21 g of intermediate 8 was obtained. (Yield 78%, Mass[M+]=284)

[0278] Synthesis of Intermediate 9 Intermediate 9 was prepared in the same manner as intermediate 6 in Synthesis Example 3, except that 21 g of intermediate 8 was used instead of intermediate 5, and 33 g of 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan. 23 g of intermediate 9 was obtained. (Yield 70%, Mass[M+]=446)

[0279] Synthesis of intermediate 10 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. Then, 0.23 g of palladium(II) acetate (Pd(OAc)2) and 30.58 g of tricyclohexylphosphine (PCy) were added, and the mixture was heated at 120°C and stirred for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and after liquid-liquid extraction with water and toluene, it was treated with MgSO4 (anhydrous) and filtered. The filtered solution was removed by distillation under reduced pressure, and purified by recrystallization (toluene / hexane) to obtain 20 g of intermediate 10. (Yield 72%, Mass[M+]=538)

[0280] Synthesis of intermediate 11 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. Then, 20.19 g of bis(tri-tert-butylphosphine)palladium(0)Pd(PtBu3) was added, and the mixture was heated at 100°C and stirred for 6 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and after liquid-liquid extraction with water and toluene, it was treated with MgSO4 (anhydrous) and filtered. The filtered solution was removed by distillation under reduced pressure, and purified by recrystallization (toluene / hexane) to obtain 16 g of intermediate 11. (Yield 80%, Mass[M+]=539)

[0281] Synthesis of intermediate 12 The compound was prepared in the same manner as in Synthesis Example 3, except that 16 g of intermediate 11 was used instead of intermediate 7, yielding 8.2 g of intermediate 12. (Yield 51%, Mass[M+]=546)

[0282] Synthesis of Compound 4 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. Then, 0.07 g of bis(tri-tert-butylphosphine)palladium(0)Pd(PtBu3)2 was added, and the mixture was heated at 130°C and stirred for 14 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and after liquid-liquid extraction with water and toluene, it was treated with MgSO4 (anhydrous) and filtered. The filtered solution was removed by distillation under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 3.8 g of compound 4. (Yield 78%, Mass[M+]=664)

[0283] Example of compound 5 preparation [ka]

[0284] Compound 5 was prepared in the same manner as Compound 4 in Synthesis Example 4, except that 2.8 g of 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan, yielding 4.1 g of Compound 5. (Yield 74%, Mass[M+]=753)

[0285] Example of compound 6 preparation [ka]

[0286] Synthesis of intermediate 13 The intermediate was prepared in the same manner as in Synthesis Example 1, except that 20 g of 3-(9H-carbazole-9-yl)phenol 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. 25 g of intermediate 13 was obtained. (Yield 78%, Mass[M+]=449)

[0287] Synthesis of intermediate 14 The intermediate was prepared in the same manner as the method for producing intermediate 6 in Synthesis Example 3, except that 25 g of intermediate 13 was used instead of intermediate 5, and 20 g of 2-(dibenzo[b,d]furan-4-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). 23 g of intermediate 14 was obtained. (Yield 77%, Mass[M+]=537)

[0288] Synthesis of intermediate 15 Except for using 23g of intermediate 14 instead of intermediate 1, the preparation was carried out in the same manner as the preparation of intermediate 2 in Synthesis Example 1, yielding 19g of intermediate 15. (Yield 75%, Mass[M+]=594)

[0289] Synthesis of Compound 6 Compound 6 was prepared in the same manner as compound 3 in Synthesis Example 3, except that 10 g of intermediate 15 was used instead of intermediate 7, yielding 4.2 g of compound 6. (Yield 41%, Mass[M+]=602)

[0290] Manufacturing example of compound 7 [ka]

[0291] Synthesis of intermediate 16 The intermediate was prepared in the same manner as intermediate 6 in Synthesis 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, yielding 10 g of intermediate 16. (Yield 76%, Mass[M+]=689)

[0292] Synthesis of intermediate 17 Except for using 10g of intermediate 16 instead of intermediate 1, the preparation was carried out in the same manner as the preparation method for intermediate 2 in Synthesis Example 1, yielding 7.6g of intermediate 17. (Yield 70%, Mass[M+]=746)

[0293] Synthesis of Compound 7 The compound was prepared in the same manner as compound 3 in Synthesis Example 3, except that 7.6 g of intermediate 17 was used instead of intermediate 7, yielding 3.1 g of compound 7. (Yield 40%, Mass[M+]=754)

[0294] Example of compound 8 preparation [ka]

[0295] Synthesis of intermediate 18 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. Then, 30.97 g of Tris(dibenzylideneacetone)dipalladium(0)Pd2(dba) and 1.2 g of xanthophos were added, and the mixture was heated at 160°C and stirred for 5 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and after liquid-liquid extraction with water and toluene, it was treated with MgSO4 (anhydrous) and filtered. The filtered solution was removed by distillation under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 24 g of intermediate 18. (Yield 85%, Mass[M+]=536)

[0296] Synthesis of intermediate 19 The intermediate 19 was prepared in the same manner as the preparation of intermediate 10 in Synthesis Example 4, except that 24 g of intermediate 18 was used instead of intermediate 9, yielding 21 g of intermediate 19. (Yield 75%, Mass[M+]=627)

[0297] Synthesis of intermediate 20 The intermediate 20 was prepared in the same manner as intermediate 11 in Synthesis Example 4, except that 21 g of intermediate 19 was used instead of intermediate 10, yielding 16 g of intermediate 20. (Yield 76%, Mass[M+]=628)

[0298] Synthesis of intermediate 21 The compound was prepared in the same manner as compound 3 in Synthesis Example 3, except that 16 g of intermediate 20 was used instead of intermediate 7, yielding 7.1 g of intermediate 21. (Yield 44%, Mass[M+]=635)

[0299] Synthesis of compound 8 Compound 8 was prepared in the same manner as compound 4 in Synthesis 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), yielding 3.5 g of compound 8. (Yield 75%, Mass[M+]=843)

[0300] Example of compound 9 preparation [ka]

[0301] Synthesis of intermediate 22 Except for using 20g of intermediate 13 instead of intermediate 8, the intermediate 22 was prepared in the same manner as the preparation example for intermediate 18 in synthesis example 8, yielding 26g of intermediate 22. (Yield 83%, Mass[M+]=701)

[0302] Synthesis of intermediate 23 Except for using 26g of intermediate 22 instead of intermediate 1, the preparation was carried out in the same manner as the preparation of intermediate 2 in Synthesis Example 1, yielding 22g of intermediate 23. (Yield 78%, Mass[M+]=758)

[0303] Synthesis of compound 9 Compound 9 was prepared in the same manner as compound 3 in Synthesis Example 3, except that 10 g of intermediate 23 was used instead of intermediate 7, yielding 3.2 g of compound 9. (Yield 32%, Mass[M+]=766)

[0304] Example of compound 10 preparation [ka]

[0305] Synthesis of intermediate 24 The intermediate 24 was prepared in the same manner as intermediate 18 in synthesis 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. 20 g of intermediate 24 was obtained. (Yield 84%, Mass[M+]=536)

[0306] Synthesis of intermediate 25 Except for using 20g of intermediate 24 instead of intermediate 1, the preparation was carried out in the same manner as the preparation of intermediate 2 in Synthesis Example 1, yielding 17g of intermediate 25. (Yield 77%, Mass[M+]=593)

[0307] Synthesis of compound 10 Compound 10 was prepared in the same manner as compound 3 in Synthesis Example 3, except that 10 g of intermediate 25 was used instead of intermediate 7, yielding 4.3 g of compound 10. (Yield 42%, Mass[M+]=601)

[0308] Production example of compound 11 [ka]

[0309] Synthesis of intermediate 26 The intermediate was prepared in the same manner as intermediate 6 in Synthesis Example 3, except that 20 g of intermediate 13 was used instead of intermediate 5, and 20 g of 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan, and 21 g of intermediate 26 was obtained. (Yield 77%, Mass[M+]=612)

[0310] Synthesis of intermediate 27 Except for using 21 g of intermediate 26 instead of intermediate 1, the preparation was carried out in the same manner as the preparation of intermediate 2 in Synthesis Example 1, yielding 17 g of intermediate 27. (Yield 74%, Mass[M+]=669)

[0311] Synthesis of compound 11 Compound 11 was prepared in the same manner as compound 3 in Synthesis Example 3, except that 10 g of intermediate 27 was used instead of intermediate 7, yielding 3.8 g of compound 11. (Yield 38%, Mass[M+]=677)

[0312] Example of compound 12 preparation [ka]

[0313] Synthesis of intermediate 28 The intermediate was prepared in the same manner as in Synthesis Example 1, except that 18 g of 2'-(9H-carbazole-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. 19 g of intermediate 28 was obtained. (Yield 76%, Mass[M+]=525)

[0314] Synthesis of intermediate 29 The intermediate was prepared in the same manner as intermediate 6 in Synthesis 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-dioxaborane, yielding 16 g of intermediate 29. (Yield 63%, Mass[M+]=703)

[0315] Synthesis of intermediate 30 The intermediate 30 was prepared in the same manner as in Synthesis Example 1, except that 16 g of intermediate 29 was used instead of intermediate 1, yielding 12 g of intermediate 30. (Yield 69%, Mass[M+]=760)

[0316] Synthesis of compound 12 Compound 12 was prepared in the same manner as compound 3 in Synthesis Example 3, except that 8.0 g of intermediate 30 was used instead of intermediate 7, yielding 3.1 g of compound 12. (Yield 38%, Mass[M+]=768)

[0317] Production example of compound 13 [ka]

[0318] Synthesis of intermediate 31 The intermediate was prepared in the same manner as in Synthesis Example 1, except that 17 g of 2'-(9H-carbazole-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. 28 g of intermediate 31 was obtained. (Yield 74%, Mass[M+]=525)

[0319] Synthesis of intermediate 32 The intermediate was prepared in the same manner as intermediate 6 in Synthesis Example 3, except that 28 g of intermediate 31 was used instead of intermediate 5, and 24 g of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoro[3,2,1-jk]carbazole was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan, and 26 g of intermediate 32 was obtained. (Yield 71%, Mass[M+]=689)

[0320] Synthesis of intermediate 33 The intermediate 33 was prepared in the same manner as the preparation method for intermediate 2 in Synthesis Example 1, except that 26 g of intermediate 32 was used instead of intermediate 1, yielding 20 g of intermediate 33. (Yield 71%, Mass[M+]=743)

[0321] Synthesis of compound 13 Compound 13 was prepared in the same manner as compound 3 in Synthesis Example 3, except that 10 g of intermediate 33 was used instead of intermediate 7, yielding 3.2 g of compound 13. (Yield 32%, Mass[M+]=751)

[0322] Preparation example of compound 14 [ka]

[0323] Synthesis of intermediate 34 The intermediate 34 was prepared in the same manner as intermediate 19 in Synthesis Example 8, except that 20 g of intermediate 26 was used instead of intermediate 18, yielding 16 g of intermediate 34. (Yield 70%, Mass[M+]=703)

[0324] Synthesis of intermediate 35 The intermediate 35 was prepared in the same manner as intermediate 11 in Synthesis Example 4, except that 16 g of intermediate 34 was used instead of intermediate 10, yielding 12 g of intermediate 35. (Yield 75%, Mass[M+]=704)

[0325] Synthesis of intermediate 36 The compound was prepared in the same manner as compound 3 in Synthesis Example 3, except that 12 g of intermediate 35 was used instead of intermediate 7, yielding 4.8 g of intermediate 36. (Yield 40%, Mass[M+]=712)

[0326] Synthesis of compound 14 Compound 14 was prepared in the same manner as compound 4 in Synthesis 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-dioxaborolan-2-yl)phenyl)-9H-carbazole was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole. 4.3 g of compound 14 was obtained. (Yield 69%, Mass[M+]=918)

[0327] Production example of compound 15 [ka]

[0328] Synthesis of intermediate 37 The intermediate was prepared in the same manner as in Synthesis 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. 16 g of intermediate 37 was obtained. (Yield 72%, Mass[M+]=739)

[0329] Synthesis of intermediate 38 The intermediate was prepared in the same manner as in Synthesis Example 1 for intermediate 2, 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, yielding 12 g of intermediate 38. (Yield 64%, Mass[M+]=872)

[0330] Synthesis of Compound 15 Compound 15 was prepared in the same manner as compound 1 in Synthesis Example 1, except that 12 g of intermediate 38 was used instead of intermediate 2, yielding 2.3 g of compound 15. (Yield 20%, Mass[M+]=845)

[0331] Production example of compound 16 [ka]

[0332] Synthesis of intermediate 39 Intermediate 10 was prepared in the same manner as intermediate 11 in Synthesis Example 4, except that 15 g of intermediate 10 was used, and 7.5 g of 2-bromo-5-chlorobenzenethiol was used instead of 2-bromo-5-chlorophenol. 10 g of intermediate 39 was obtained. (Yield 65%, Mass[M+]=555)

[0333] Synthesis of intermediate 40 The compound was prepared in the same manner as compound 3 in Synthesis Example 3, except that 10 g of intermediate 39 was used instead of intermediate 7, and 3.5 g of intermediate 40 was obtained. (Yield 35%, Mass[M+]=562)

[0334] Synthesis of compound 16 Compound 16 was prepared in the same manner as compound 4 in Synthesis 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. 3.4 g of compound 16 was obtained. (Yield 79%, Mass[M+]=694)

[0335] Manufacturing example of compound 17 [ka]

[0336] Synthesis of intermediate 41 The intermediate was prepared in the same manner as in Synthesis Example 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. 16 g of intermediate 41 was obtained. (Yield 70%, Mass[M+]=770)

[0337] Synthesis of intermediate 42 The intermediate 42 was prepared in the same manner as the preparation method for intermediate 2 in Synthesis Example 1, except that 16 g of intermediate 41 was used instead of intermediate 1, yielding 13 g of intermediate 42. (Yield 75%, Mass[M+]=832)

[0338] Synthesis of Compound 17 Compound 17 was prepared in the same manner as compound 1 in Synthesis Example 1, except that 13 g of intermediate 42 was used instead of intermediate 2, yielding 2.2 g of compound 17. (Yield 18%, Mass[M+]=804)

[0339] Preparation example of compound 18 [ka]

[0340] Synthesis of intermediate 43 The intermediate was prepared in the same manner as in Synthesis Example 1, except that 14 g of 4-(9H-carbazole-9-yl-d8)pen-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. 18 g of intermediate 43 was obtained. (Yield 82%, Mass[M+]=461)

[0341] Synthesis of intermediate 44 The intermediate was prepared in the same manner as intermediate 18 in Synthesis 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, yielding 17 g of intermediate 44. (Yield 78%, Mass[M+]=556)

[0342] Synthesis of intermediate 45 Except for using 18g of intermediate 44 instead of intermediate 1, the preparation was carried out in the same manner as the preparation of intermediate 2 in Synthesis Example 1, yielding 13g of intermediate 45. (Yield 69%, Mass[M+]=613)

[0343] Synthesis of compound 18 Compound 18 was prepared in the same manner as compound 3 in Synthesis Example 3, except that 8.0 g of intermediate 45 was used instead of intermediate 7, yielding 3.5 g of compound 18. (Yield 43%, Mass[M+]=620)

[0344] Production example of compound 19 [ka]

[0345] Synthesis of intermediate 46 The intermediate was prepared in the same manner as in Synthesis 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-carbazol. 20 g of intermediate 46 was obtained. (Yield 78%, Mass[M+]=540)

[0346] Synthesis of intermediate 47 The intermediate was prepared in the same manner as the preparation of intermediate 6 in Synthesis 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-dioxaborolan-2-yl)phenyl-3,4,5,6-d4)-9H-carbazole-1,2,3,4,5,5,6,7,8-d8 was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan. 20 g of intermediate 47 was obtained. (Yield 76%, Mass[M+]=715)

[0347] Synthesis of intermediate 48 The intermediate 48 was prepared in the same manner as the preparation method for intermediate 2 in Synthesis Example 1, except that 20 g of intermediate 47 was used instead of intermediate 1, yielding 16 g of intermediate 48. (Yield 74%, Mass[M+]=777)

[0348] Synthesis of compound 19 Compound 19 was prepared in the same manner as compound 3 in Synthesis Example 3, except that 8.0 g of intermediate 48 was used instead of intermediate 7, yielding 3.6 g of compound 19. (Yield 45%, Mass[M+]=784)

[0349] Example of compound 20 preparation [ka]

[0350] Synthesis of intermediate 49 The intermediate was prepared in the same manner as intermediate 6 in Synthesis 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. 13 g of intermediate 49 was obtained. (Yield 74%, Mass[M+]=635)

[0351] Synthesis of intermediate 50 The intermediate 50 was prepared in the same manner as in Synthesis Example 1, except that 13 g of intermediate 49 was used instead of intermediate 1, yielding 11 g of intermediate 50. (Yield 78%, Mass[M+]=692)

[0352] Synthesis of compound 20 Compound 20 was prepared in the same manner as compound 3 in Synthesis Example 3, except that 11 g of intermediate 50 was used instead of intermediate 7, yielding 4.4 g of compound 20. (Yield 40%, Mass[M+]=700)

[0353] <Examples and Comparative Examples>

[0354] Example 1 A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 800 Å was ultrasonically cleaned in distilled water with detergent dissolved in it. Fischer Co. products were used as the detergent, and distilled water that had been secondarily filtered using a Millipore Co. filter was used. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes each time. After the distilled water cleaning, ultrasonic cleaning was performed using isopropyl alcohol, acetone, and methanol solvents, followed by drying, and then transport to a plasma cleaning machine. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes before being transported to a vacuum deposition machine.

[0355] On the ITO transparent electrode, which served as the positive electrode, a hole injection layer was formed by vacuum deposition of the compounds HT1 and HI1 shown below in a molar ratio of 95:5 to a thickness of 100 Å. A hole transport layer was formed on the hole injection layer by vacuum deposition of the compound represented by the chemical formula HT1 (300 Å). Subsequently, an electron barrier layer was formed on the hole transport layer by vacuum deposition of the compound BH(p-type) to a thickness of 50 Å. Subsequently, an emissive layer was formed on the electron barrier layer by vacuum deposition of a mixture of the chemical formula BH(p-type) shown below and compound 1(n-type) synthesized in Production Example 1 in a 1:1 ratio as the host for the emissive layer, and the compound represented by the chemical formula BD shown below as the dopant for the emissive layer, in a weight ratio of 86:14. A hole barrier layer was formed on the emissive layer by vacuum deposition of the compound 1(n-type) synthesized in Production Example 1 to a thickness of 50 Å. Next, a compound represented by the chemical formula ET1 and a compound represented by the chemical formula LiQ were vacuum-deposited on the hole-blocking layer in a 1:1 weight ratio to form an electron injection and transport layer with a thickness of 300 Å. A negative electrode was then formed by sequentially depositing lithium fluoride (LiF) with a thickness of 10 Å and aluminum with a thickness of 800 Å on the electron injection and transport layer.

[0356] [ka]

[0357] During the process described above, the deposition rate of organic materials was maintained at 0.4-0.7 Å / sec, the deposition rate of lithium fluoride at the negative electrode was maintained at 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. The vacuum level during deposition was 2 x 10⁻¹⁰. -7 ~5x10 -6 torr (converted to 2.666 x 10) -5 ~6.665x10 -4 We fabricated an organic light-emitting element while maintaining Pa.

[0358] Examples 2 to 20 An organic light-emitting element was fabricated in the same manner as in Example 1, except that the compounds listed in Table 1 below were used as the host for the light-emitting layer instead of compound 1.

[0359] Examples 21 and 22 An organic light-emitting element was fabricated in the same manner as in Example 1, except that a compound listed in Table 1 below was used as the host for the light-emitting layer instead of compound 1, and compound 10 was used as the hole-blocking layer instead of compound 1.

[0360] [ka]

[0361] Comparative Examples 1 to 5 An organic light-emitting device was fabricated in the same manner as in Example 1, except that the compounds listed in Table 1 below were used as the host for the light-emitting layer instead of compound 1.

[0362] [ka]

[0363] When current was applied to the organic light-emitting elements fabricated in Examples 1 to 20 and Comparative Examples 1 to 5, the voltage, efficiency, and lifetime were measured (1600 nit (cd / m²). 2The criteria were used to determine the lifespan of the T90 element, and the results are shown in Table 1 below. 2 This refers to the time it takes for something to decrease from )) to 90%.

[0364] [Table 1]

[0365] In Comparative Example 1, compound BH1 was found to have significantly worse voltage, efficiency, and lifespan compared to Examples 1-20 because the benzene ring in its core structure was not substituted with a carbazole group and a silyl or aryl group.

[0366] The compound BH2 used in Comparative Example 2 has only a carbazole group substituted on the benzene ring in its core structure. While it achieves high efficiency and long lifespan, it was confirmed to have a higher voltage compared to Examples 1-20.

[0367] In Comparative Example 3, compound BH3 had only a carbazole group substituted on the benzene ring in its core structure, and the silyl group was replaced with a carbazole group. As a result, it was confirmed that the voltage, efficiency, and lifespan were significantly degraded compared to Examples 1-20.

[0368] Compounds BH4 and BH5 used in Comparative Examples 4 and 5 exhibited significantly degraded voltage, efficiency, and lifespan compared to Examples 1-20 due to their different core structures. [Explanation of Symbols]

[0369] 1 ··· Circuit board 2 ···Anode 3. Hole injection layer 4 ···Hole transport layer 5 ···Electron barrier layer 6 ···Emitting layer 7 ···Hole Barrier 8...electron transport layer 9...electron injection layer 10 ···Cathode 11 ···Electron injection and transport layer

Claims

1. The compound represented by the following chemical formula 1: [Chemical formula 1] 【Chemistry 128】 In the above chemical formula 1 X is NR; O; or S, R and at least one of R1 to R3 are a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and the remaining ones are identical or different to each other and are independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted cycloalkyl group. L1-L3 and L11-L13 are either identical or different from each other, and each is independently a directly bonded; substituted or unsubstituted allylene group; or substituted or unsubstituted divalent heterocyclic group. G1 to G3 are either identical or different from each other, and each is independently a hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group. n1 and n2 are integers from 1 to 4, and m1 and m2 are integers from 0 to 4. n3 is an integer between 1 and 3, and m3 is an integer between 0 and 3. g1 to g3 are integers from 0 to 8, When n1 to n3, m1 to m3, and g1 to g3 are each 2 or more, the substituents in parentheses are each identical or different from each other. n1 + m1 is less than or equal to 4, n2 + m2 is less than or equal to 4, and n3 + m3 is less than or equal to 3. m1 + m2 + m3 are integers greater than or equal to 1.

2. The compound according to claim 1, wherein L1 to L3 and L11 to L13 are the same or different from each other, and each is independently a directly bonded; allylene group; or divalent heterocyclic group.

3. The compound according to claim 1, wherein at least one of 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 remaining members are the same or different from each other, and each is independently hydrogen; or deuterium.

4. The compound according to claim 1, wherein m1 + m2 + m3 is 1 or 2.

5. The compound according to claim 1, wherein the chemical formula 1 is represented by any of the following chemical formulas 1-A-1 to 1-A-3: [Chemical formula 1-A-1] 【Chemistry 129】 [Chemical formula 1-A-2] 【Chemistry 130】 [Chemical formula 1-A-3] 【Chemistry 131】 In the above chemical formulas 1-A-1 to 1-A-3, The definitions of X, R1-R3, L1-L3, L11-L13, G1-G3, and g1-g3 are the same as those in Chemical Formula 1.

6. The compound according to claim 1, wherein the chemical formula 1 is represented by any of the following chemical formulas 1-B-1 to 1-B-3: [Chemical formula 1-B-1] 【Chemistry 132】 [Chemical formula 1-B-2] 【Chemistry 133】 [Chemical formula 1-B-3] 【Chemistry 134】 In the above chemical formulas 1-B-1 to 1-B-3, The definitions of X, R1-R3, L1-L3, L11-L13, G1-G3, and g1-g3 are the same as those in Chemical Formula 1.

7. At least one of R1 to R3 is a triphenylsilyl group; a phenyl group; a biphenyl group; a carbazole group; a dibenzofuran group; a dibenzothiophene group; a benzofuran dibenzofuran group; or an indolocarbazole group, and the remaining ones are identical or different to each other, and each is independently hydrogen; or deuterium. L1 to L3 and L11 to L13 are identical or different from each other, and are independently directly bonded; or are phenylene groups. The compound according to claim 1, wherein G1 to G3 are the same or different from each other, and each is independently hydrogen; or deuterium.

8. The compound according to claim 1, wherein the chemical formula 1 is represented by any of the following compounds: 【Chemistry 135】 【Transformation 136】 【Chemistry 137】 【Chemistry 138】 【Chemistry 139】 [Chemistry 140] 【Chemistry 141】 【Chemistry 142】 【Chemistry 143】 【Chemistry 144】 【Chemistry 145】 【Chemistry 146】 【Chemistry 147】 【Chemistry 148】 【Chemistry 149】 [Chemical 150] 【Chemistry 151】 【Chemistry 152】 【Chemistry 153】 【Chemistry 154】 【Chemistry 155】 【Chemistry 156】 【Chemistry 157】 【Chemistry 158】 【Chemistry 159】 [Chemical 160] 【Chemistry 161】 【Chemistry 162】 【Chemical 163】 【Chemistry 164】 【Chemistry 165】 【Chemistry 166】 【Chemistry 167】 【Chemical 168】 【Chemistry 169】 【Chemistry 170】 【Chemistry 171】 【Chemistry 172】 【Chemistry 173】 【Chemistry 174】 【Chemistry 175】 【Chemistry 176】 【Chemistry 177】 【Chemistry 178】 【Chemistry 179】 【Chemistry 180】 【Chemistry 181】 【Chemistry 182】 【Chemistry 183】 【Chemistry 184】 【Chemistry 185】 【Chemical 186】 【Chemistry 187】 【Chemical 188】 【Chemical 189】 【Chemistry 190】 【Chemistry 191】 【Chemistry 192】 【Chemistry 193】 【Chemistry 194】 【Chemistry 195】 【Chemistry 196】 【Chemistry 197】 【Chemistry 198】 【Chemistry 199】 【Chemistry 200】 【Chemical Engineering 201】 【Chemical Engineering 202】 【Chemical 203】 【Chemical 204】 【Chemical 205】 【Chemical 206】 【Chemical 207】 【Chemical 208】 [ ] Ｄ＝ｘ１～ｘ２ This means that the structure inside the parentheses contains x1 to x2 deuterium atoms, and that value is an integer.

9. An organic light-emitting element comprising an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers contain a compound according to any one of claims 1 to 8.

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

11. The organic light-emitting element according to claim 9, wherein the organic layer includes a hole-blocking layer, and the hole-blocking layer includes the compound.

12. The organic light-emitting element according to claim 9, wherein the organic layer includes a light-emitting layer and a hole-blocking layer, and the light-emitting layer and the hole-blocking layer contain the compound.

13. The organic light-emitting element according to claim 9, wherein the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.

14. The organic light-emitting element according to claim 9, wherein the organic layer includes one or more layers selected from a hole transport layer, a hole injection layer, an electron barrier layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole barrier layer, and an electron injection and transport layer.

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