Organic light emitting device

Abstract

The present specification provides an organic light-emitting device including a positive electrode, a negative electrode, and one or more organic material layers provided between the positive electrode and the negative electrode, the one or more organic material layers including a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2.

Description

Technical Field

[0001] This specification relates to organic light emitting devices.

[0002] This application claims the priority of Korean Patent Application No. 10-2023-0133469 filed with the Korean Patent Office on October 6, 2023, the entire contents of which are incorporated herein by reference. Background Art

[0003] Generally speaking, the phenomenon of organic light emitting refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light emitting device using the phenomenon of organic light emitting generally has a structure including an anode and a cathode and an organic layer located between them. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed by a multilayer structure composed of different substances, for example, it can be formed by a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. For the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons re-transition to the ground state, light is emitted.

[0004] There is a continuous demand for the development of new materials for organic light-emitting devices as described above. Summary of the invention

[0005] Technical issues

[0006] The present disclosure provides an organic light-emitting device with low driving voltage, high efficiency and / or long lifetime.

[0007] Solution to the problem

[0008] One embodiment of the present specification provides an organic light-emitting device, including: an anode, a cathode, and one or more organic layers arranged between the anode and the cathode, wherein one or more of the organic layers contains a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula 2.

[0009] [Chemical formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] X is NR, O or S,

[0013] At least one of R and R1 to R3 is a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and the others are the same as or different from 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,

[0014] L1 to L3 and L11 to L13 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0015] G1 to G3 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0016] n1 and n2 are each an integer from 1 to 4, m1 and m2 are each an integer from 0 to 4,

[0017] n3 is an integer from 1 to 3, m3 is an integer from 0 to 3,

[0018] g1 to g3 are each an integer from 0 to 8,

[0019] When the above n1 to n3, m1 to m3 and g1 to g3 are each 2 or more, the substituents in the brackets are the same or different from each other.

[0020] n1+m1 is less than 4, n2+m2 is less than 4, n3+m3 is less than 3,

[0021] m1+m2+m3 is an integer greater than 1,

[0022] [Chemical formula 2]

[0023]

[0024] In the above chemical formula 2,

[0025] Cy is a substituted or unsubstituted N-containing monocyclic ring,

[0026] T1 to T4 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0027] t1 and t4 are each an integer from 0 to 3,

[0028] t2 is an integer from 0 to 2,

[0029] t3 is an integer from 0 to 4,

[0030] When t1, t3 and t4 are each 2 or more, the substituents in the brackets are the same or different from each other.

[0031] When the above t2 is 2, the substituents in the brackets may be the same as or different from each other.

[0032] Effects of the Invention

[0033] The organic light emitting device according to an embodiment of the present invention includes the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2, thereby having the effects of low driving voltage, high efficiency, and / or long lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] Figure 1 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 stacked in this order is shown.

[0035] Figure 2 The diagram shows an example of an organic light-emitting device having 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 stacked in sequence.

[0036] Figure 3 The diagram shows an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport and injection layer 11, and a cathode 10 are sequentially stacked.

[0037] Explanation of symbols

[0038] 1: Substrate

[0039] 2: Anode

[0040] 3: Hole injection layer

[0041] 4: Hole transport layer

[0042] 5: Electron blocking layer

[0043] 6: Luminous layer

[0044] 7: Hole blocking layer

[0045] 8: Electron transport layer

[0046] 9: Electron injection layer

[0047] 10: Cathode

[0048] 11: Electron transport and injection layer DETAILED DESCRIPTION

[0049] Next, this specification is described in more detail.

[0050] In the present specification, when it is indicated that a certain part “includes / comprises” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.

[0051] In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.

[0052] In this manual, Or dotted lines indicate the position of bonding to the chemical formula or compound.

[0053] In this specification, "N% substituted by deuterium" means that N% of the available hydrogen in the corresponding structure is substituted by deuterium. For example, when it is indicated that dibenzofuran is substituted with 25% deuterium, it means that 2 of the 8 hydrogens in dibenzofuran are substituted by deuterium.

[0054] In this specification, the degree of deuteration can be determined by nuclear magnetic resonance spectroscopy ( 1 The results were confirmed by known methods such as H NMR, GC / MS, etc.

[0055] In the present specification, examples of substituents are described below, but are not limited thereto.

[0056] The term "substituted" mentioned above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.

[0057] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium, a halogen group, a nitrile group (-CN), a nitro group, a hydroxyl group, an alkyl group, a cycloalkyl group, an alkoxy group, a phosphine oxide group, an aryloxy group, an alkylthio group, Arylthio Alkylsulfonyl Arylsulfonyl The alkylene group may be substituted with one or more substituents of an alkenyl group, a silyl group, a boron group, an amine group, an aryl group, or a heterocyclic group, or may be substituted with a substituent formed by connecting two or more substituents of the substituents exemplified above, or may not have any substituent. For example, a "substituent formed by connecting two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent formed by connecting two phenyl groups.

[0058] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, an amino group, a silyl group, a boron group, an alkoxy group, an aryloxy group, an alkyl group, a cycloalkyl group, an aryl group, and a heterocyclic group, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0059] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, alkyl, aryl, and heterocyclic groups, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0060] Examples of the above substituents are described below, but are not limited thereto.

[0061] In the present specification, as examples of the halogen group, there are fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0062] In this specification, the silyl group can be represented by -SiY a Y b Y c The chemical formula of Y a , Y b and Y c Each of them can be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. The above-mentioned silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but is not limited thereto.

[0063] In this specification, the boron group can be represented by -BY d Y e The chemical formula of Y d and Y e Each of them may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, and the like, but are not limited thereto.

[0064] In the present 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 another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited thereto.

[0065] In the present specification, the above description about the alkyl group is applicable to the arylalkyl group except that the arylalkyl group is substituted with an aryl group.

[0066] In this specification, the alkoxy group may be straight chain, branched chain or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably the number of carbon atoms is 1 to 20. Specifically, it may be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentyl group, a n-hexyl group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, etc., but is not limited thereto.

[0067] The alkyl group, alkoxy group, and other substituents containing an alkyl portion described in the present specification include all of linear and branched forms.

[0068] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are 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-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, etc., but are not limited thereto.

[0069] In the present specification, the alkynyl group is a substituent containing a triple bond between carbon atoms, and may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkynyl group is 2 to 10.

[0070] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0071] In the present specification, the amino group is -NH2, and the above-mentioned alkyl, aryl, heterocyclic group, alkenyl, cycloalkyl and combinations thereof may be substituted on the above-mentioned amino group. The number of carbon atoms of the above-mentioned substituted amino group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the number of carbon atoms of the above-mentioned amino group is 1 to 20. According to one embodiment, the number of carbon atoms of the above-mentioned amino group is 1 to 10. As specific examples of substituted amino groups, there are methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9,9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthracenylamino, dibenzofuranylphenylamino, 9-methylanthrylamino, diphenylamino, phenylnaphthylamino, ditolylamino, phenyltolylamino, diphenylamino, etc., but are not limited thereto.

[0072] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms. According to one embodiment, the carbon number of the above-mentioned aryl group is 6 to 30. According to one embodiment, the carbon number of the above-mentioned aryl group is 6 to 20. The above-mentioned aryl group may be an aryl group consisting of a single ring, or a polycyclic aryl group (an aryl group with more than two rings). The aryl group consisting of a single ring may also be expressed as a monocyclic aryl group, which may refer to a phenyl group, or a group formed by connecting two or more phenyl groups. As the above-mentioned aryl group consisting of a single ring, it may be phenyl, biphenyl, terphenyl, quaterphenyl, etc., but it is not limited thereto. The polycyclic aryl group may refer to a group formed by the fusion of two or more single rings such as naphthyl and phenanthryl. As the above-mentioned polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, phenylene, fluorenyl, triphenylene, etc., but are not limited to these.

[0073] In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. In this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

[0074] When the fluorenyl group is substituted, it may be Isospirofluorenyl; (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) and the like substituted fluorenyl, but the present invention is not limited thereto.

[0075] In the present specification, the above description on the aryl group can be applied to the aryl group in the aryloxy group.

[0076] In the present specification, the above description about the alkyl group can be applied to the alkyl group in the above alkylthio group and alkylsulfonyl group.

[0077] In the present specification, the above description about the aryl group can be applied to the aryl group in the arylthio group and the arylsulfonyl group.

[0078] In the present specification, the heterocyclic group is a ring group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 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 heterocyclic group is 2 to 20. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarbazolyl, triazinyl and the like, but are not limited thereto.

[0079] In the present specification, a heteroaryl group is aromatic, and other than this, the above description about the heterocyclic group is applicable.

[0080] In the present specification, the above description about the aryl group is applicable except that the arylene group is divalent.

[0081] In the present specification, the above description on the heterocyclic group is applicable to the divalent heterocyclic group except that the divalent heterocyclic group is divalent.

[0082] In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, "ring" means a hydrocarbon ring or a heterocyclic ring.

[0083] The hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic groups, and may be selected from the examples of the cycloalkyl group or aryl group described above.

[0084] In this specification, the meaning of forming a ring by combining with adjacent groups means combining 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 above hydrocarbon ring refers to a ring consisting only of carbon and hydrogen atoms. The above heterocycle refers to a ring containing one or more elements selected from N, O, P, S, Si and Se. In this specification, the above aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle and aromatic heterocycle can be monocyclic or polycyclic.

[0085] In this specification, an aliphatic hydrocarbon ring refers to a ring that is not an aromatic ring and is composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.

[0086] In this specification, an aromatic hydrocarbon ring refers to an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenanthene, pyrene, tetracene, In the present specification, the aromatic hydrocarbon ring can be interpreted as having the same meaning as the aryl group.

[0087] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dihydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane Azoctane Thioctane etc., but not limited thereto.

[0088] In the present specification, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, Azoles, Isopropylamine Azoles, thiazoles, isothiazoles, triazoles, diazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazines, Azine, thiazine, di Olefins, triazines, tetrazines, isoquinolines, quinolines, quinones, quinazolines, quinoxalines, naphthyridines, acridines, phenanthridines, naphthyridines, triazaindene, indoles, indolizines, benzothiazoles, benzo azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phen Oxazine, indolecarbazole, indenocarbazole, etc., but are not limited to these.

[0089] Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention can be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

[0090] The organic light emitting device according to the present invention has the effects of low driving voltage, high efficiency and / or long life by simultaneously including the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 in the light emitting layer.

[0091] Specifically, by using the compound of Chemical Formula 1 together with the compound of Chemical Formula 2, the energy transfer of the exciton generated between the compound represented by Chemical Formula 1 and the p-type host to the compound represented by Chemical Formula 2 is easy, thereby having the effect of high efficiency and / or long life. In particular, the compound represented by Chemical Formula 2 has a narrow half width compared to the case of using an Ir complex as a dopant, so it is also effective in improving color purity. Therefore, the device using the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 at the same time can significantly enhance the low voltage, high efficiency and / or long life characteristics of the device due to the synergistic effect in the organic light-emitting device.

[0092] Next, Chemical Formula 1 will be described in detail.

[0093] [Chemical formula 1]

[0094]

[0095] In the above chemical formula 1,

[0096] X is NR, O or S,

[0097] At least one of R and R1 to R3 is a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and the others are the same as or different from 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,

[0098] L1 to L3 and L11 to L13 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0099] G1 to G3 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0100] n1 and n2 are each an integer from 1 to 4, m1 and m2 are each an integer from 0 to 4,

[0101] n3 is an integer from 1 to 3, m3 is an integer from 0 to 3,

[0102] g1 to g3 are each an integer from 0 to 8,

[0103] When the above n1 to n3, m1 to m3 and g1 to g3 are each 2 or more, the substituents in the brackets are the same or different from each other.

[0104] n1+m1 is less than 4, n2+m2 is less than 4, n3+m3 is less than 3,

[0105] m1+m2+m3 is an integer greater than or equal to 1.

[0106] In one embodiment of the present specification, X is NR, O or S.

[0107] In one embodiment of the present specification, X is NR.

[0108] In one embodiment of the present specification, X is O.

[0109] In one embodiment of the present specification, X is S.

[0110] In one embodiment of the present specification, R is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0111] In one embodiment of the present specification, R is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0112] In one embodiment of the present specification, R is a substituted or unsubstituted aryl group.

[0113] In one embodiment of the present specification, R is a phenyl group or a biphenyl group.

[0114] In one embodiment of the present specification, at least one of R1 to R3 is a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and the rest are the same or different from 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.

[0115] In one embodiment of the present specification, at least one of R1 to R3 is a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, and the rest are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms.

[0116] In one embodiment of the present specification, at least one of R1 to R3 is a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, and the rest are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms.

[0117] In one embodiment of the present specification, at least one of R1 to R3 is a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, and the rest are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms.

[0118] In one embodiment of the present specification, at least one of R1 to R3 is a silyl group which is substituted or unsubstituted by deuterium, an alkyl group or an aryl group; an aryl group which is substituted or unsubstituted by deuterium or an aryl group; or a heterocyclic group which is substituted or unsubstituted by deuterium or a heterocyclic group, and the rest are the same or different and are independently hydrogen or deuterium.

[0119] In one embodiment of the present specification, at least one of R1 to R3 is a silyl group which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 60 carbon atoms, or an aryl group having 6 to 60 carbon atoms; an aryl group having 6 to 60 carbon atoms which is unsubstituted or substituted by deuterium, or an aryl group having 6 to 60 carbon atoms; or a heterocyclic group having 2 to 60 carbon atoms which is unsubstituted or substituted by deuterium, or a heterocyclic group having 2 to 60 carbon atoms, and the rest are the same or different and are independently hydrogen or deuterium.

[0120] In one embodiment of the present specification, at least one of R1 to R3 is a silyl group which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted by deuterium, or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms which is unsubstituted or substituted by deuterium, or a heterocyclic group having 2 to 30 carbon atoms, and the rest are the same or different and are independently hydrogen or deuterium.

[0121] In one embodiment of the present specification, at least one of R1 to R3 is a silyl group which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted by deuterium, or an aryl group having 6 to 20 carbon atoms; or a heterocyclic group having 2 to 20 carbon atoms which is unsubstituted or substituted by deuterium, or a heterocyclic group having 2 to 20 carbon atoms, and the rest are the same or different and are independently hydrogen or deuterium.

[0122] In one embodiment of the present specification, at least one of R1 to R3 is a silyl group substituted with a phenyl group, a phenyl group, a biphenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a heterocyclic group having 2 to 60 carbon atoms and containing one or more of N and O as heteroatoms, and the rest are the same or different and are independently hydrogen or deuterium.

[0123] In one embodiment of the present specification, at least one of R1 to R3 is triphenylsilyl, phenyl, biphenyl, carbazolyl, dibenzofuranyl, dibenzothienyl, benzofuranodibenzofuranyl, or indolecarbazolyl, and the others are the same or different and are independently hydrogen or deuterium.

[0124] In one embodiment of the present specification, the benzofuranodibenzofuranyl group is a benzo[1,2-b:3,4-b′]dibenzofuranyl group.

[0125] In one embodiment of the present specification, the indolocarbazolyl group is an indolo[3,2,1-jk]carbazolyl group.

[0126] In one embodiment of the present specification, at least one of R1 to R3 is a group represented by the following structural formula, or a substituted or unsubstituted aryl group.

[0127]

[0128] In the above structural formula, P1 to P3 are substituted or unsubstituted aryl groups, Indicates the binding positions to L1 to L3.

[0129] In one embodiment of the present specification, P1 to P3 are substituted or unsubstituted aryl groups having 6 to 60 carbon atoms.

[0130] In one embodiment of the present specification, P1 to P3 are substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0131] In one embodiment of the present specification, P1 to P3 are substituted or unsubstituted aryl groups having 6 to 20 carbon atoms.

[0132] In one embodiment of the present specification, P1 to P3 are phenyl groups.

[0133] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group.

[0134] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.

[0135] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

[0136] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms.

[0137] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond, or a substituted or unsubstituted arylene group.

[0138] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond or an arylene group having 6 to 60 carbon atoms.

[0139] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond or an arylene group having 6 to 30 carbon atoms.

[0140] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond or an arylene group having 6 to 20 carbon atoms.

[0141] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond or a phenylene group.

[0142] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group.

[0143] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.

[0144] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

[0145] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms.

[0146] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and are each independently a direct bond, or a substituted or unsubstituted arylene group.

[0147] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and are each independently a direct bond or an arylene group.

[0148] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and are each independently a direct bond or an arylene group having 6 to 60 carbon atoms.

[0149] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and are each independently a direct bond or an arylene group having 6 to 30 carbon atoms.

[0150] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and are each independently a direct bond or an arylene group having 6 to 20 carbon atoms.

[0151] In one embodiment of the present specification, L11 to L13 are the same as or different from each other, and are each independently a direct bond or a phenylene group.

[0152] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0153] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

[0154] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0155] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0156] In one embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0157] In one embodiment of the present specification, G1 to G3 are hydrogen.

[0158] In one embodiment of the present specification, n1 and n2 are each an integer of 1 to 4, and m1 and m2 are each an integer of 0 to 4.

[0159] In one embodiment of the present specification, n3 is an integer from 1 to 3, and m3 is an integer from 0 to 3.

[0160] In one embodiment of the present specification, n1 is 1.

[0161] In one embodiment of the present specification, n2 is 1.

[0162] In one embodiment of the present specification, n3 is 1.

[0163] In one embodiment of the present specification, m1 is 0.

[0164] In one embodiment of the present specification, m1 is 1.

[0165] In one embodiment of the present specification, m2 is 0.

[0166] In one embodiment of the present specification, m2 is 1.

[0167] In one embodiment of the present specification, m3 is 0.

[0168] In one embodiment of the present specification, m3 is 1.

[0169] In one embodiment of the present specification, g1 to g3 are integers of 0 to 8, respectively.

[0170] In one embodiment of the present specification, g1 to g3 are 0.

[0171] In one embodiment of the present specification, g1 to g3 are 8.

[0172] In one embodiment of the present specification, n1+m1 is 4 or less, n2+m2 is 4 or less, and n3+m3 is 3 or less.

[0173] In one embodiment of the present specification, m1+m2+m3 is an integer greater than or equal to 1.

[0174] In one embodiment of the present specification, m1+m2+m3 is 1 to 3.

[0175] In one embodiment of the present specification, m1+m2+m3 is 1 or 2.

[0176] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-A-1 to 1-A-3.

[0177] [Chemical formula 1-A-1]

[0178]

[0179] [Chemical formula 1-A-2]

[0180]

[0181] [Chemical formula 1-A-3]

[0182]

[0183] In the above chemical formulas 1-A-1 to 1-A-3,

[0184] Definitions of X, R1 to R3, L1 to L3, L11 to L13, G1 to G3, and g1 to g3 are the same as those in the above Chemical Formula 1.

[0185] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-B-1 to 1-B-3.

[0186] [Chemical formula 1-B-1]

[0187]

[0188] [Chemical formula 1-B-2]

[0189]

[0190] [Chemical formula 1-B-3]

[0191]

[0192] In the above chemical formulas 1-B-1 to 1-B-3,

[0193] Definitions of X, R1 to R3, L1 to L3, L11 to L13, G1 to G3, and g1 to g3 are the same as those in the above Chemical Formula 1.

[0194] In one embodiment of the present specification, in the case of a compound of Chemical Formula 1 containing deuterium, it can be manufactured by a known deuteration reaction. In one embodiment of the present specification, the compound represented by Chemical Formula 1 can be formed by using a deuterated compound as a precursor, or deuterium can be introduced into the compound by a hydrogen-deuterium exchange reaction using a deuterated solvent in the presence of an acid catalyst.

[0195] In one embodiment of the present specification, the compound represented by the above chemical formula 1 is substituted by deuterium by more than 20%. In another embodiment, the compound represented by the above chemical formula 1 is substituted by deuterium by more than 30%. In another embodiment, the compound represented by the above chemical formula 1 is substituted by deuterium by more than 40%. In another embodiment, the compound represented by the above chemical formula 1 is substituted by deuterium by more than 50%. In another embodiment, the compound represented by the above chemical formula 1 is substituted by deuterium by more than 60%. In another embodiment, the compound represented by the above chemical formula 1 is substituted by deuterium by more than 70%. In another embodiment, the compound represented by the above chemical formula 1 is substituted by deuterium by more than 80%. In another embodiment, the compound represented by the above chemical formula 1 is substituted by deuterium by more than 90%. In another embodiment, the compound represented by the above chemical formula 1 is substituted by deuterium by 100%.

[0196] In one embodiment of the present specification, the compound represented by the above Chemical Formula 1 contains 40% to 60% deuterium. In another embodiment, the compound represented by the above Chemical Formula 1 contains 40% to 80% deuterium. In another embodiment, the compound represented by the above Chemical Formula 1 contains 60% to 80% deuterium. In another embodiment, the compound represented by the above Chemical Formula 1 contains 80% to 100% deuterium.

[0197] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following compounds.

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273] In this manual, [] D＝x1～x2 Indicates that the structure in brackets contains x1 to x2 deuteriums, which is an integer. For example, [] D＝1～41 Indicates that it contains 1 to 41 deuteriums.

[0274] The compound represented by Chemical Formula 1 according to one embodiment of the present specification can produce a core structure as shown in the following Reaction Formula 1. Substituents can be bonded by methods known in the art, and the type, position or number of substituents can be changed according to techniques known in the art.

[0275] <Reaction formula 1>

[0276]

[0277] Next, Chemical Formula 2 will be described in detail.

[0278] [Chemical formula 2]

[0279]

[0280] In the above chemical formula 2,

[0281] Cy is a substituted or unsubstituted N-containing monocyclic ring,

[0282] T1 to T4 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0283] t1 and t4 are each an integer from 0 to 3,

[0284] t2 is an integer from 0 to 2,

[0285] t3 is an integer from 0 to 4,

[0286] When t1, t3 and t4 are each 2 or more, the substituents in the brackets are the same or different from each other.

[0287] When the above t2 is 2, the substituents in the brackets may be the same as or different from each other.

[0288] In one embodiment of the present specification, the above Cy is a substituted or unsubstituted N-containing five-membered monocyclic ring, or a substituted or unsubstituted N-containing six-membered monocyclic ring.

[0289] In one embodiment of the present specification, the above Cy is a substituted or unsubstituted N-containing five-membered monocyclic ring, or a substituted or unsubstituted N-containing six-membered monocyclic ring.

[0290] In one embodiment of the present specification, the above Cy may be represented by any one of the following Cy-1 to Cy-3.

[0291] [Chemical formula Cy-1]

[0292]

[0293] [Chemical formula Cy-2]

[0294]

[0295] [Chemical formula Cy-3]

[0296]

[0297] In the above chemical formulas Cy-1 to Cy-3,

[0298] T11 to T13 and T21 to T24 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0299] The dotted line (---) indicates the position fused with the above Chemical Formula 2.

[0300] In one embodiment of the present specification, the above Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-A-1 to 2-A-3.

[0301] [Chemical formula 2-A-1]

[0302]

[0303] [Chemical formula 2-A-2]

[0304]

[0305] [Chemical formula 2-A-3]

[0306]

[0307] In the above chemical formulas 2-A-1 to 2-A-3,

[0308] The definitions of T1 to T4 and t1 to t4 are the same as those in the above Chemical Formula 2,

[0309] T11 to T13 and T21 to T24 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0310] In one embodiment of the present specification, T1 to T4 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0311] In one embodiment of the present specification, T1 to T4 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted ring having 2 to 60 carbon atoms.

[0312] In one embodiment of the present specification, T1 to T4 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

[0313] In one embodiment of the present specification, T1 to T4 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted ring having 2 to 20 carbon atoms.

[0314] In one embodiment of the present specification, T1 to T4 are the same as or different from each other, and are independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with adjacent groups to form a dibenzofuran ring or a dibenzothiophene ring.

[0315] In one embodiment of the present specification, T1 to T4 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms.

[0316] In one embodiment of the present specification, T1 to T4 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.

[0317] In one embodiment of the present specification, T1 to T4 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted heterocyclic ring having 2 to 20 carbon atoms.

[0318] In one embodiment of the present specification, T1 to T4 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, or are combined with adjacent groups to form a substituted or unsubstituted dibenzofuran ring, or a substituted or unsubstituted dibenzothiophene ring.

[0319] In one embodiment of the present specification, T1 to T4 are the same as or different from each other, and are independently hydrogen, deuterium, methyl, ethyl, propyl, butyl, phenyl, biphenyl or terphenyl, or are combined with adjacent groups to form a dibenzofuran ring or a dibenzothiophene ring.

[0320] In one embodiment of the present specification, T1 to T4 are the same as or different from each other, and are independently hydrogen, deuterium, butyl, or phenyl, or are combined with adjacent groups to form a dibenzofuran ring.

[0321] In one embodiment of the present specification, T1 and an adjacent group are bonded to each other to form a dibenzofuran ring.

[0322] In one embodiment of the present specification, T2 to T4 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0323] In one embodiment of the present specification, T2 to T4 are hydrogen.

[0324] In one embodiment of the present specification, T11 to T13 and T21 to T24 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0325] In one embodiment of the present specification, T11 to T13 and T21 to T24 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted ring having 2 to 60 carbon atoms.

[0326] In one embodiment of the present specification, T11 to T13 and T21 to T24 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

[0327] In one embodiment of the present specification, T11 to T13 and T21 to T24 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted ring having 2 to 20 carbon atoms.

[0328] In one embodiment of the present specification, T11 to T13 and T21 to T24 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0329] In one embodiment of the present specification, T11 to T13 and T21 to T24 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0330] In one embodiment of the present specification, T11 to T13 and T21 to T24 are the same as or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0331] In one embodiment of the present specification, the above Chemical Formula 2 is represented by the following Chemical Formula 2-B-1 or 2-B-2.

[0332] [Chemical formula 2-B-1]

[0333]

[0334] [Chemical formula 2-B-2]

[0335]

[0336] In the above chemical formulas 2-B-1 and 2-B-2,

[0337] The definitions of T2 to T4 and t2 to t4 are the same as those in the above Chemical Formula 2,

[0338] Y is O or S,

[0339] T11 to T13 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0340] In one embodiment of the present specification, Y is O.

[0341] In one embodiment of the present specification, Y is S.

[0342] In one embodiment of the present specification, t1 is an integer from 0 to 3.

[0343] In one embodiment of the present specification, t1 is 0.

[0344] In one embodiment of the present specification, t1 is 1.

[0345] In one embodiment of the present specification, t1 is 3.

[0346] In one embodiment of the present specification, t2 is an integer from 0 to 2.

[0347] In one embodiment of the present specification, t2 is 0.

[0348] In one embodiment of the present specification, t2 is 1.

[0349] In one embodiment of the present specification, t2 is 2.

[0350] In one embodiment of the present specification, t3 is an integer from 0 to 4.

[0351] In one embodiment of the present specification, t3 is 0.

[0352] In one embodiment of the present specification, t3 is 1.

[0353] In one embodiment of the present specification, t3 is 4.

[0354] In one embodiment of the present specification, t4 is an integer from 0 to 3.

[0355] In one embodiment of the present specification, t4 is 0.

[0356] In one embodiment of the present specification, t4 is 1.

[0357] In one embodiment of the present specification, t4 is 3.

[0358] In one embodiment of the present specification, the compound represented by the above chemical formula 2 is substituted by deuterium by more than 20%. In another embodiment, the compound represented by the above chemical formula 2 is substituted by deuterium by more than 30%. In another embodiment, the compound represented by the above chemical formula 2 is substituted by deuterium by more than 40%. In another embodiment, the compound represented by the above chemical formula 2 is substituted by deuterium by more than 50%. In another embodiment, the compound represented by the above chemical formula 2 is substituted by deuterium by more than 60%. In another embodiment, the compound represented by the above chemical formula 2 is substituted by deuterium by more than 70%. In another embodiment, the compound represented by the above chemical formula 2 is substituted by deuterium by more than 80%. In another embodiment, the compound represented by the above chemical formula 2 is substituted by deuterium by more than 90%. In another embodiment, the compound represented by the above chemical formula 2 is substituted by deuterium by 100%.

[0359] In one embodiment of the present specification, the compound represented by the above chemical formula 2 contains 40% to 60% deuterium. In another embodiment, the compound represented by the above chemical formula 2 contains 40% to 80% deuterium. In another embodiment, the compound represented by the above chemical formula 2 contains 60% to 80% deuterium. In another embodiment, the compound represented by the above chemical formula 2 contains 80% to 100% deuterium.

[0360] In one embodiment of the present specification, the above Chemical Formula 2 is represented by any one of the following compounds.

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367] The compound represented by Chemical Formula 2 according to one embodiment of the present specification can produce a core structure as shown in the following Reaction Formula 2. Substituents can be bonded by methods known in the art, and the type, position or number of substituents can be changed according to techniques known in the art.

[0368] <Reaction 2>

[0369]

[0370] In the present specification, various substituents are introduced into the core structure of the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2, respectively, so that compounds having various energy band gaps can be synthesized. In addition, in the present specification, various substituents are introduced into the core structure of the structure as described above, so that the HOMO and LUMO energy levels of the compound can also be adjusted.

[0371] Next, the organic light emitting device according to the present invention will be described.

[0372] In one embodiment of the present invention, an organic light-emitting device is provided, comprising: an anode, a cathode, and one or more organic layers arranged between the anode and the cathode, wherein one or more of the organic layers contains a compound represented by the above chemical formula 1 and a compound represented by the above chemical formula 2.

[0373] The organic light-emitting device of the present specification uses the compound of Chemical Formula 1 and the compound of Chemical Formula 2 to form an organic layer, and can also be manufactured using a common method and material for manufacturing an organic light-emitting device.

[0374] The organic layer of the organic light-emitting device of the present specification may be formed by a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and one or more of the electron transport and injection layers as organic layers. However, the structure of the organic light-emitting device of the present specification is not limited thereto and may include a smaller number or a larger number of organic layers.

[0375] 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 2 as a dopant.

[0376] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include two or more compounds represented by the chemical formula 2 as dopants.

[0377] In one embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, an electron transport and injection layer, or a hole blocking layer, and the electron injection layer, the electron transport layer, the electron transport and injection layer, or the hole blocking layer may contain the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2.

[0378] In the organic light-emitting device of the present specification, the organic layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, the electron injection layer, or the electron transport and injection layer may contain the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2.

[0379] In one embodiment of the present specification, the organic layer includes an electron adjustment layer, and the electron adjustment layer may include the compound represented by the chemical formula 1 and the compound represented by the chemical formula 2.

[0380] In one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer may include the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

[0381] In one embodiment of the present specification, the organic layer includes a hole blocking layer and a light-emitting layer, and the hole blocking layer and the light-emitting layer may include a compound represented by the chemical formula 1 and a compound represented by the chemical formula 2. In this case, the compound represented by the chemical formula 1 included in the light-emitting layer and the hole blocking layer may be the same or different, and the compound represented by the chemical formula 2 included in the light-emitting layer and the hole blocking layer may be the same or different.

[0382] 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 the chemical formula 1 and the compound represented by the chemical formula 2.

[0383] 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 main component.

[0384] 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.

[0385] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include two or more compounds represented by the chemical formula 1 as a main component.

[0386] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the chemical formula 1 as a first host, and may further include another second host.

[0387] In one embodiment of the present specification, the first host is an n-type phosphorescent host, and the second host is a p-type phosphorescent host. In this case, the weight ratio of the first host to the second host may be 2:8 to 8:2, or 4:6 to 6:4, or 5:5.

[0388] The above-mentioned n-type is a substance that can take away electrons from the matrix substance (the substance of the organic layer), and generally known substances can be used, but it is not limited to this. That is, the n-type can be defined as a substance having the property of being able to donate electrons to the LUMO (lowest unoccupied molecular orbital) energy level of the matrix. On the contrary, the p-type is a substance which, when a layer is formed only of p-type substances, receives electrons from the HOMO (highest occupied molecular orbital) energy level of a substance located in the adjacent cathode direction, thereby generating holes in the substance located in the adjacent cathode direction; or, when a p-type substance is doped in an arbitrary matrix, receives electrons from the HOMO of the matrix substance, thereby generating an equal amount of holes in the HOMO of the matrix. For this reason, when a layer is formed only of p-type substances, the closer the HOMO of the substance located in the cathode direction is to the LUMO of the p-type substance, the easier it is to take away electrons from the HOMO of the adjacent layer, thereby generating holes in the HOMO of the adjacent layer. Furthermore, when a p-type substance is doped in an arbitrary matrix, the closer the LUMO of the p-type substance is to the HOMO of the matrix, the easier it is to take away electrons, thereby generating holes in the matrix.

[0389] The p-type host may be a compound generally known in the art, for example, a structure containing a N-containing monocyclic ring, dibenzofuran, and / or a carbazole group.

[0390] In one embodiment of the present specification, the second host is a carbazole compound.

[0391] In one embodiment of the present specification, the second host is a biscarbazole compound.

[0392] In one embodiment of the present specification, the second host is a biscarbazole compound substituted with an aryl group.

[0393] In one embodiment of the present specification, the light-emitting layer includes a first host and a second host, and may further include a dopant, and the dopant may be a phosphorescent dopant.

[0394] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may be a blue light-emitting layer, a red light-emitting layer, or a green light-emitting layer.

[0395] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may be a blue light-emitting layer.

[0396] In one embodiment of the present specification, the light-emitting layer may include a host and a dopant. Specifically, the dopant may be a fluorescent dopant or a phosphorescent dopant.

[0397] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the chemical formula 2 as a dopant, and may further include another dopant.

[0398] In one embodiment of the present specification, the dopant may include an arylamine compound, a heterocyclic compound including boron and nitrogen, a metal coordination compound, a platinum coordination compound, an iridium coordination compound, an iridium-based compound, or the like.

[0399] For example, when the above-mentioned light-emitting layer emits red light, as a light-emitting dopant, phosphorescent substances such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium, bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium, bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium, tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum) or fluorescent substances such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used, but are not limited to these. When the light-emitting layer emits green light, as a light-emitting dopant, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium, face-tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinoline)aluminum) can be used, but it is not limited to these. When the light-emitting layer emits blue light, as a light-emitting dopant, phosphorescent materials such as platinum coordination compounds, (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers can be used, but it is not limited to these.

[0400] In one embodiment of the present specification, the dopant is contained in an amount of 1 to 20 parts by weight based on 100 parts by weight of the host.

[0401] In one embodiment of the present specification, the light emitting layer includes a host and a dopant in a weight ratio of 99:1 to 1:99. Specifically, the weight ratio includes 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. Within the above range, energy transfer from the host to the dopant occurs efficiently.

[0402] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the chemical formula 1 and the compound represented by the chemical formula 2, and may also include a fluorescent host, a phosphorescent host, a fluorescent dopant, or a phosphorescent dopant.

[0403] In one embodiment of the present specification, the organic layer includes two or more light-emitting layers, and one or more of the two or more light-emitting layers includes the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

[0404] In one embodiment of the present specification, the organic layer includes two or more light-emitting layers, and each of the two or more light-emitting layers includes the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2.

[0405] In one embodiment of the present specification, the organic layer includes two or more light-emitting layers, and the maximum light-emitting peaks of the two or more light-emitting layers may be different from each other. The light-emitting layer including the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2 is blue, and the light-emitting layer not including the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2 may include a blue, red or green light-emitting compound known in the technical field.

[0406] In one embodiment of the present specification, the maximum emission peak of the light-emitting layer including the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2 may be 400nm to 500nm. That is, the light-emitting layer including the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2 may emit blue light.

[0407] In one embodiment of the present specification, the organic layer includes two or more light-emitting layers, the maximum light-emitting peak of one light-emitting layer (light-emitting layer 1) is 400nm to 500nm, and the maximum light-emitting peak of another light-emitting layer (light-emitting layer 2) can show a maximum light-emitting peak of 510nm to 580nm, or 610nm to 680nm. In this case, the light-emitting layer 1 may include a compound represented by the above chemical formula 1 and a compound represented by the above chemical formula 2. In addition, the light-emitting layer 2 may include a compound represented by the above chemical formula 1 and a compound represented by the above chemical formula 2, or may include other compounds in addition thereto.

[0408] The organic light-emitting device of the present specification may also include a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and one or more organic layers among the hole injection and transport layer.

[0409] In one embodiment of the present specification, the organic light-emitting device includes an anode, a cathode, and two or more organic layers arranged between the anode and the cathode, and at least one of the two or more organic layers contains the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2.

[0410] In one embodiment of the present specification, the two or more organic layers may be selected from two or more of the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron regulating layer, and a hole blocking layer.

[0411] In one embodiment of the present specification, the organic layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound represented by the chemical formula 1 and the compound represented by the chemical formula 2. Specifically, the compound represented by the chemical formula 1 and the compound represented by the chemical formula 2 may be included in one of the two or more electron transport layers, or may be included in each of the two or more electron transport layers.

[0412] In addition, in one embodiment of the present specification, when the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 are contained in each layer of the above-mentioned two or more electron transport layers, other materials except the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 may be the same as or different from each other.

[0413] When the organic layer including the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2 is an electron transport layer, an electron injection layer, or an electron transport and injection layer, the above electron transport layer, the electron injection layer, or the electron transport and injection layer may further include an n-type dopant or an organic metal compound. The above n-type dopant or organic metal compound may use a material known in the technical field, for example, a metal or a metal complex may be used.

[0414] For example, the n-type dopant or the organometallic compound may be LiQ, but is not limited thereto. The electron transport layer, the electron injection layer, or the electron transport and injection layer including the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 may also include LiQ (Lithium Quinolate).

[0415] In one embodiment of the present specification, the organic layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2. Specifically, in one embodiment of the present specification, the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 may be included in one of the two or more hole transport layers, or may be included in each of the two or more hole transport layers.

[0416] In addition, in one embodiment of the present specification, when the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 are contained in each layer of the above two or more hole transport layers, other materials except the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 may be the same as or different from each other.

[0417] In one embodiment of the present specification, in addition to the organic layer containing the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2, the above organic layer may also include a hole injection layer or a hole transport layer, which hole injection layer or the hole transport layer contains a compound containing an aromatic amine group, a carbazole group, or a benzocarbazole group.

[0418] In one embodiment of the present specification, the thickness of the organic layer including the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 may be to or to Preferably to

[0419] In another embodiment, the organic layer may include other organic compounds, metals or metal compounds in addition to the compound represented by the chemical formula 1 and the compound represented by the chemical formula 2.

[0420] In one embodiment of the present specification, the organic light-emitting device may be a (normal type) organic light-emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

[0421] In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0422] For example, the organic light emitting device may have a stacked structure as shown below, but is not limited thereto.

[0423] (1) Anode / hole transport layer / light-emitting layer / cathode

[0424] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0425] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0426] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0427] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0428] (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0429] (7) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0430] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0431] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0432] (10) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0433] (11) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0434] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0435] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0436] (14) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0437] (15) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0438] (16) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0439] (17) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0440] (18) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0441] (19) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport and injection layer / cathode

[0442] The structure of the organic light-emitting device of the present specification may have the following Figures 1 to 3 The structure shown is not limited thereto.

[0443] Figure 1 The diagram 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 the structure shown above, the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 may be contained in the above light emitting layer 6.

[0444] Figure 2 The diagram shows 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 stacked. In the structure shown above, the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2 may be contained in the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light-emitting layer 6, the hole blocking layer 7, the electron transport layer 8, or the electron injection layer 9.

[0445] Figure 3 The diagram shows an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport and injection layer 11, and a cathode 10 are sequentially stacked. In the structure shown above, the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2 may be contained in the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light-emitting layer 6, the hole blocking layer 7, or the electron transport and injection layer 11.

[0446] In one embodiment of the present specification, the hole blocking layer and the light emitting layer may be disposed adjacent to each other. For example, the hole blocking layer and the light emitting layer may be disposed in physical contact with each other.

[0447] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that at least one of the organic layers contains the above compounds, ie, the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2.

[0448] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

[0449] For example, the organic light-emitting device according to the present specification can be manufactured as follows: using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation (e-beam evaporation), a metal or a conductive metal oxide or an alloy thereof is evaporated on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer is formed on the anode, and then a substance that can be used as a cathode is evaporated on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate.

[0450] The organic layer may further include one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole injection and transport layer.

[0451] The organic layer may be a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc., but is not limited thereto and may also be a single layer structure. In addition, the organic layer may be made of various polymer materials and by a solvent process other than evaporation, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer to form a smaller number of layers.

[0452] In addition, the compound of the above chemical formula 1 or the compound of the above chemical formula 2 can be used not only by vacuum evaporation method but also by solution coating method to form an organic layer when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating method, dip coating method, blade coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited thereto.

[0453] In addition to the above method, an organic light-emitting device may also be manufactured by sequentially vapor-depositing a cathode material, an organic layer, and an anode material on a substrate. However, the manufacturing method is not limited thereto.

[0454] The anode is an electrode for injecting holes. As the anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), indium zinc oxide (IZO, Indium Zinc Oxide); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0455] The cathode is an electrode for injecting electrons. In order to facilitate the electron injection into the organic layer, the cathode material is preferably a material with a small work function. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0456] The hole injection layer is a layer that receives holes from the electrode. The hole injection material is preferably a material that has the ability to transport holes, has the effect of receiving holes from the anode, and has an excellent hole injection effect on the light-emitting layer or the light-emitting material. In addition, it is preferably a material that has an excellent ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. Moreover, it is preferably a material with excellent thin film forming ability. In addition, it is preferred 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. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, and arylamine-based organics; hexanitrile hexaazatriphenylene-based organics; quinacridone-based organics; perylene-based organics; anthraquinone, polyaniline, and polythiophene-based conductive polymers, etc., but are not limited to these.

[0457] In one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-1, but the present invention is not limited thereto.

[0458] [Chemical formula HI-1]

[0459]

[0460] In the above chemical formula HI-1,

[0461] R315 to R317 are the same as or different from each other, and are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0462] r315 is an integer from 1 to 5. When the above r315 is 2 or more, the two or more R315 are the same or different from each other.

[0463] r316 is an integer of 1 to 5. When the number of r316 is 2 or more, two or more R316 are the same as or different from each other.

[0464] In one embodiment of the present specification, the above R317 is any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0465] In one embodiment of the present specification, the above R317 is any one selected from the group consisting of a carbazolyl group, a phenyl group, a biphenyl group, a triphenylene group, and a combination thereof.

[0466] In one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are independently a substituted or unsubstituted aryl group, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0467] In one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are independently a phenyl group or a biphenyl group, or are combined with adjacent groups to form an indene substituted with a methyl group.

[0468] In one embodiment of the present specification, the chemical formula HI-1 is represented by any one of the following compounds.

[0469]

[0470] In one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-2, but the present invention is not limited thereto.

[0471] [Chemical formula HI-2]

[0472]

[0473] In the above chemical formula HI-2,

[0474] R401 to R403 are the same as or different from each other and are each independently a halogen group,

[0475] R401 to R403 are 4.

[0476] In one embodiment of the present specification, R401 to R403 are F.

[0477] In one embodiment of the present specification, the chemical formula HI-2 is represented by the following compound.

[0478]

[0479] In one embodiment of the present specification, the hole injection layer includes the chemical formulas HI-1 and HI-2.

[0480] In one embodiment of the present specification, the hole injection layer includes the chemical formula HI-1 and HI-2 at a weight ratio of 1:99 to 99:1.

[0481] The thickness of the hole injection layer can be 1 nm to 150 nm. When the thickness of the hole injection layer is 1 nm or more, it has the advantage of preventing the hole injection characteristics from being reduced, and when it is 150 nm or less, it has the advantage of preventing the driving voltage from rising in order to improve the movement of holes when the thickness of the hole injection layer is too thick.

[0482] In one embodiment of the present specification, the hole injection layer may include an arylamine compound containing a carbazole group and a p-type dopant. According to an example, the amine compound is shown as Het101-L101-N(Ar101)(Ar102), Het101 is a substituted or unsubstituted carbazole group, L101 is a directly bonded, or substituted or unsubstituted arylene group, Ar101 and Ar102 are the same or different from each other, and each independently can be a substituted or unsubstituted aryl group. The amine compound and the p-type dopant may be included in a suitable molar ratio. According to an example, the amine compound and the p-type dopant may be included in a molar ratio of 99.9:0.1 to 90:10.

[0483] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, preferably a material with a large mobility for holes. As specific examples, there are arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited thereto.

[0484] In one embodiment of the present specification, the hole transport layer may include a carbazole group-containing arylamine compound.

[0485] In one embodiment of the present specification, the hole transport layer includes the compound represented by the chemical formula HI-1, but is not limited thereto.

[0486] The hole injection and transport layer is a layer that transports holes to the light-emitting layer. The substances exemplified in the hole transport layer and the hole injection layer can be used, but are not limited thereto.

[0487] A hole buffer layer may be further disposed between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.

[0488] 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 above-mentioned compounds or materials known in the art.

[0489] The electron blocking layer is a layer that prevents the electrons injected from the electron injection layer from entering the hole injection layer through the light-emitting layer, thereby improving the life and efficiency of the device. Known materials can be used without restriction, and the substances exemplified in the description of the hole injection layer can be used, but are not limited thereto. The electron blocking layer can be formed between the light-emitting layer and the hole transport layer, between the light-emitting layer and the hole injection layer, or between the light-emitting layer and the layer that simultaneously performs hole injection and hole transport.

[0490] In one embodiment of the present specification, the electron blocking layer includes a compound represented by the following chemical formula EB-1, but the present invention is not limited thereto.

[0491] [Chemical formula EB-1]

[0492]

[0493] In the above chemical formula EB-1,

[0494] T1 to T14 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0495] t13 is an integer of 1 to 3. When the above t13 is 2 or more, the above two or more t13s are the same as or different from each other.

[0496] In one embodiment of the present specification, the above T1 to T14 are the same as or different from each other, and are each independently hydrogen, deuterium, or a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0497] In one embodiment of the present specification, the above T1 to T14 are the same as or different from each other, and are each independently hydrogen, deuterium, or a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms.

[0498] In one embodiment of the present specification, the above T1 to T14 are the same as or different from each other, and are each independently hydrogen, deuterium, phenyl, biphenyl or naphthyl.

[0499] In one embodiment of the present specification, the above T1 to T13 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0500] In one embodiment of the present specification, the above-mentioned T14 is a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0501] In one embodiment of the present specification, the above-mentioned T14 is a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms.

[0502] In one embodiment of the present specification, the above-mentioned T14 is a phenyl group, a biphenyl group or a naphthyl group.

[0503] In one embodiment of the present specification, the chemical formula EB-1 may include the following compounds, but is not limited thereto.

[0504]

[0505] In one embodiment of the present specification, the chemical formula EB-1 can also be used as a second host material of the light-emitting layer.

[0506] The above-mentioned light-emitting layer can emit red, green or blue light, and can be formed of a phosphorescent material or a fluorescent material. The above-mentioned light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. As specific examples, there are 8-hydroxy-quinoline aluminum complexes (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo Compounds of the oxazole, benzothiazole and benzimidazole series; poly(p-phenylene vinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0507] The above-mentioned light-emitting layer may include a host material and a dopant material. When the organic light-emitting device according to one embodiment of the present specification includes another light-emitting layer in addition to the light-emitting layer including the above-mentioned chemical formula 1, the host material includes an aromatic condensed ring derivative or a heterocyclic compound. Specifically, as the aromatic condensed ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as the heterocyclic compound, there are dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0508] As the dopant material, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, Indoxypyrene, etc. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamine. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but not limited thereto. In one embodiment of the present specification, the above-mentioned light-emitting layer may include the compound represented by Chemical Formula 1 of the present invention as the phosphorescent host in the light-emitting layer.

[0509] In one embodiment of the present specification, the light-emitting layer may include the compound represented by Chemical Formula 2 of the present invention as a phosphorescent dopant in the light-emitting layer.

[0510] According to one example, the host and the dopant may be included in a suitable weight ratio, and according to one example, the host and the dopant may be included in a weight ratio of 100:1 to 100:10.

[0511] The hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed using the same conditions as the electron injection layer. When the organic light-emitting device according to one embodiment of the present specification includes another hole blocking layer in addition to the hole blocking layer comprising the above chemical formula 1, specifically, Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

[0512] 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.

[0513] In one embodiment of the present specification, the hole blocking layer may include a compound including an N-containing heterocyclic group and a fluorene ring.

[0514] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, preferably a material with a large mobility for electrons. As a specific example, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to this. The electron transport layer can be used together with any desired cathode material as used in the prior art. In particular, a suitable cathode material is a common material having a low work function and accompanied by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, etc., in each case accompanied by an aluminum layer or a silver layer.

[0515] The thickness of the electron transport layer can be 1 nm to 50 nm. When the thickness of the electron transport layer is 1 nm or more, it has the advantage of preventing the electron transport characteristics from being reduced, and when the thickness is 50 nm or less, it has the advantage of preventing the driving voltage from increasing in order to improve the movement of electrons when the thickness of the electron transport layer is too thick.

[0516] In one embodiment of the present specification, the electron transport layer may include a compound containing two N-containing heterocyclic groups, and may also include an n-type dopant or an organic metal compound. According to an example, the n-type dopant or the organic metal compound may be LiQ, and the compound containing two N-containing heterocyclic groups and the n-type dopant (or organic metal compound) may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.

[0517] The electron injection layer is a layer that receives electrons from the electrode. As the electron injection material, the following materials are preferred: materials that have excellent ability to transport electrons, have the effect of receiving electrons from the second electrode, and have excellent electron injection effect on the light-emitting layer or the light-emitting material. In addition, materials that prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer and have excellent thin film forming ability are preferred. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0518] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

[0519] In one embodiment of the present specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. The substances exemplified in the electron transport layer and the electron injection layer can be used, but are not limited thereto.

[0520] In one embodiment of the present specification, the electron injection and transport layer includes a compound represented by the following chemical formula ET-1, but is not limited thereto.

[0521] [Chemical formula ET-1]

[0522]

[0523] In the above chemical formula ET-1,

[0524] At least one of Z11 to Z13 is N, and the rest are CH,

[0525] At least one of Z21 to Z23 is N, and the others are CH,

[0526] L601 and L602 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0527] Ar601 to Ar604 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0528] In one embodiment of the present specification, L601 and L602 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0529] In one embodiment of the present specification, L601 and L602 are phenylene groups.

[0530] In one embodiment of the present specification, Ar601 to Ar604 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0531] In one embodiment of the present specification, Ar601 to Ar604 are phenyl groups.

[0532] In one embodiment of the present specification, the chemical formula ET-1 is represented by the following compound.

[0533]

[0534] In one embodiment of the present specification, the electron injection and transport layer may further include a metal coordination compound. The metal coordination compound is as described above.

[0535] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0536] The organic light-emitting device according to the present specification can be used in a variety of electronic devices. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0537] Below, in order to specifically describe this specification, an embodiment will be cited to describe in detail. However, the embodiments according to this specification can be deformed into various different forms, and it is not interpreted that the scope of this application is limited to the embodiments described in detail below. The embodiments of this application are provided to more completely describe this specification to those skilled in the art.

[0538] <Production Example 1>

[0539] Preparation Example of Compound 1

[0540]

[0541] Synthesis of intermediate 1

[0542] Under a nitrogen atmosphere, 24 g of the starting material 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 then heated and stirred at 160°C for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and after adding water and ethyl acetate to separate the liquid, it was treated with MgSO4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 28 g of intermediate 1. (Yield 70%, Mass (Mass) [M + ]=663)

[0543] Synthesis of intermediate 2

[0544] Under nitrogen atmosphere, 28 g of intermediate 1, 7.0 g of 2-hydroxyphenylboronic acid, 27 g of potassium phosphate, 320 mL of dihydrogen phosphate were added. After adding 0.4 g of bis(tri-tert-butylphosphine)palladium(0)]Pd(PtBu3)2 to 80 mL of oxane and water, the mixture was heated at 120°C and stirred for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, separated by adding water and toluene, and then treated with MgSO4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 23 g of intermediate 2. (Yield 76%, mass [M + ]=721)

[0545] Synthesis of compound 1

[0546] Under a nitrogen atmosphere, in a flask containing 23 g of intermediate 2 dissolved in 300 mL of toluene (anhydrous) cooled to 0°C, 47 mL of t-butyllithium [t-Butyllithium, 1.7 M hexane solution] was slowly added dropwise, and then stirred at 70°C for 5 hours. When the lithium halogen exchange reaction was completed, it was cooled to 0°C again, 9.2 mL of boron tribromide [borontribromide] was slowly added dropwise, and then the temperature was raised to 70°C and stirred for 10 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water and NH4Cl solution (aq. NH4Cl) were added, and after separation, it was treated with MgSO4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified twice by recrystallization (toluene / hexane) to obtain 3.8 g of compound 1. (Yield 17%, mass [M + ]=694)

[0547] Preparation Example of Compound 2

[0548]

[0549] Synthesis of intermediate 3

[0550] The intermediate 3 was prepared by the same method as the method for preparing the intermediate 1 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 the intermediate 3 was obtained. (Yield 57%, mass [M + ]=815)

[0551] Synthesis of intermediate 4

[0552] The intermediate 2 of Synthesis Example 1 was prepared by the same method as that of Synthesis Example 1 except that 23 g of the intermediate 3 was used instead of the intermediate 1, thereby obtaining 18 g of the intermediate 4. (Yield 73%, mass [M + ]=873)

[0553] Synthesis of compound 2

[0554] The same method as the method for producing compound 1 in Synthesis Example 1 was used to produce 2.7 g of compound 2, except that 18 g of intermediate 4 was used instead of intermediate 2. (Yield 15%, mass [M+] = 846)

[0555] Preparation Example of Compound 3

[0556]

[0557] Synthesis of intermediate 5

[0558] The intermediate 5 was prepared by the same method as the method for preparing the intermediate 1 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, thereby obtaining 28 g of the intermediate 5. (Yield 74%, mass [M + ]=525)

[0559] Synthesis of intermediate 6

[0560] Under a nitrogen atmosphere, 28 g of intermediate 5, 18 g of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 22 g of potassium carbonate, 400 mL of tetrahydrofuran and 100 mL of water were added, and then 0.6 g of tetrakis(triphenylphosphine)palladium(0)[Tetrakis(triphenylphosphine)palladium(0)]Pd(PPh3)4 was added, and the mixture was heated and stirred at 80°C for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and water and toluene were added to separate the liquids, and then treated with MgSO4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 22 g of intermediate 6. (Yield 69%, mass [M + ]=599)

[0561] Synthesis of intermediate 7

[0562] The intermediate 7 (24 g) was obtained by the same method as that of the intermediate 2 in Synthesis Example 1 except that 22 g of the intermediate 6 was used instead of the intermediate 1. (Yield 74%, mass [M + ]=656)

[0563] Synthesis of compound 3

[0564] In a nitrogen atmosphere, 17 g of boron triiodide was added to a flask containing 15 g of intermediate 7 dissolved in 500 mL of 1,2-dichlorobenzene (DCB), and the mixture was stirred at 120°C for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, separated by adding water and sodium thiosulfate solution, and then treated with MgSO4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 4.7 g of compound 3. (Yield 31%, mass [M + ]=664)

[0565] Preparation Example of Compound 4

[0566]

[0567] Synthesis of intermediate 8

[0568] The intermediate 8 was prepared by the same method as that of the intermediate 1 of 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 to obtain 21 g of the intermediate 8. (Yield 78%, mass [M + ]=284)

[0569] Synthesis of intermediate 9

[0570] 23 g of Intermediate 9 was produced by the same method as the method for producing 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. (Yield 70%, mass [M + ]=446)

[0571] Synthesis of intermediate 10

[0572] Under nitrogen atmosphere, 23 g of intermediate 9, 16 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane), 15 g of potassium acetate, 400 mL of distilled water were added. After 0.23 g of palladium acetate (∥) [palladium acetate (0)] Pd (OAc) 2 and 0.58 g of tricyclohexylphosphine [Tricyclohexylphosphine] PCy 3 were added, and the mixture was heated at 120 ° C for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water and toluene were added to separate the liquid, and then treated with MgSO 4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 20 g of intermediate 10. (Yield 72%, mass [M + ]=538)

[0573] Synthesis of intermediate 11

[0574] Under a nitrogen atmosphere, 20 g of intermediate 10, 9.3 g of 2-bromo-5-chlorophenol, 24 g of potassium phosphate, 280 mL of tetrahydrofuran and 70 mL of water were added, and then 0.19 g of bis(tri-tert-butylphosphine)palladium(0)Pd(PtBu3)2 was added, followed by heating at 100°C for 6 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and after separation by adding water and toluene, it was treated with MgSO4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane), thereby obtaining 16 g of intermediate 11. (Yield 80%, mass [M + ]=539)

[0575] Synthesis of intermediate 12

[0576] The intermediate 12 was prepared by the same method as the method for preparing compound 3 in Synthesis Example 3 except that 16 g of intermediate 11 was used instead of intermediate 7, thereby obtaining 8.2 g of intermediate 12. (Yield 51%, mass [M + ]=546)

[0577] Synthesis of compound 4

[0578] 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 dioxaborolane were added. After adding 14 mL of oxane and 14 mL of water, 0.07 g of bis(tri-tert-butylphosphine)palladium(0)Pd(PtBu3)2 was added, and the mixture was heated and stirred at 130°C for 14 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and water and toluene were added to separate the liquids, and then treated with MgSO4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane), thereby obtaining 3.8 g of compound 4. (Yield 78%, mass [M + ]=664)

[0579] Preparation Example of Compound 5

[0580]

[0581] The same method as the method for producing compound 4 in Synthesis Example 4 was used to produce 4.1 g of compound 5, 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. (Yield 74%, mass [M + ]=753)

[0582] Preparation Example of Compound 6

[0583]

[0584] Synthesis of intermediate 13

[0585] The intermediate 13 was prepared by the same method as that of the intermediate 1 of 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-chlorobenzene was used instead of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole. (Yield 78%, mass [M + ]=449)

[0586] Synthesis of intermediate 14

[0587] 23 g of Intermediate 14 was produced by the same method 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. (Yield 77%, mass [M + ]=537)

[0588] Synthesis of intermediate 15

[0589] The intermediate 15 (19 g) was obtained by the same method as that of the intermediate 2 in Synthesis Example 1 except that 23 g of the intermediate 14 was used instead of the intermediate 1. (Yield 75%, mass [M + ]=594)

[0590] Synthesis of compound 6

[0591] The same method as the method for producing compound 3 in Synthesis Example 3 was used to produce 4.2 g of compound 6, except that 10 g of intermediate 15 was used instead of intermediate 7. (Yield 41%, mass [M + ]=602)

[0592] Preparation Example of Compound 7

[0593]

[0594] Synthesis of intermediate 16

[0595] 10 g of Intermediate 16 was produced by the same method as the method for producing 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. (Yield 76%, mass [M + ]=689)

[0596] Synthesis of intermediate 17

[0597] The intermediate 17 was obtained by the same method as that of the intermediate 2 in Synthesis Example 1 except that 10 g of the intermediate 16 was used instead of the intermediate 1. (Yield 70%, mass [M + ]=746)

[0598] Synthesis of compound 7

[0599] The same method as the method for producing compound 3 in Synthesis Example 3 was used to produce 3.1 g of compound 7, except that 7.6 g of intermediate 17 was used instead of intermediate 7. (Yield 40%, mass [M + ]=754)

[0600] Preparation Example of Compound 8

[0601]

[0602] Synthesis of intermediate 18

[0603] Under a nitrogen atmosphere, 15 g of intermediate 8, 21 g of 9H-3,9'-biscarbazole, 34 g of potassium phosphate, and 500 mL of xylene were added, followed by addition of 0.97 g of tris(dibenzylideneacetone)dipalladium(0)Pd2(dba)3 and 1.2 g of 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene[Xantphos], and the mixture was heated and stirred at 160°C for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, separated by adding water and toluene, and then treated with MgSO4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to obtain 24 g of intermediate 18. (Yield 85%, mass [M + ]=536)

[0604] Synthesis of intermediate 19

[0605] The intermediate 19 (21 g) was obtained by the same method as that for the intermediate 10 in Synthesis Example 4 except that 24 g of the intermediate 18 was used instead of the intermediate 9. (Yield 75%, mass [M + ]=627)

[0606] Synthesis of intermediate 20

[0607] The intermediate 20 (16 g) was obtained by the same method as that of the intermediate 11 in Synthesis Example 4 except that 21 g of the intermediate 19 was used instead of the intermediate 10. (Yield 76%, mass [M + ]=628)

[0608] Synthesis of intermediate 21

[0609] The intermediate 21 was prepared by the same method as the method for preparing compound 3 in Synthesis Example 3 except that 16 g of intermediate 20 was used instead of intermediate 7, thereby obtaining 7.1 g of intermediate 21. (Yield 44%, mass [M + ]=635)

[0610] Synthesis of compound 8

[0611] The same method as the method for producing compound 4 in Synthesis Example 4 was used to produce 3.5 g of compound 8, 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. (Yield 75%, mass [M + ]=843)

[0612] Preparation Example of Compound 9

[0613]

[0614] Synthesis of intermediate 22

[0615] The intermediate 22 (26 g) was obtained by the same method as that of the intermediate 18 in Synthesis Example 8 except that 20 g of the intermediate 13 was used instead of the intermediate 8. (Yield 83%, mass [M + ]=701)

[0616] Synthesis of intermediate 23

[0617] The intermediate 23 (22 g) was obtained by the same method as that of the intermediate 2 in Synthesis Example 1 except that 26 g of the intermediate 22 was used instead of the intermediate 1. (Yield 78%, mass [M + ]=758)

[0618] Synthesis of compound 9

[0619] The same method as the method for producing compound 3 in Synthesis Example 3 was used to produce 3.2 g of compound 9, except that 10 g of intermediate 23 was used instead of intermediate 7. (Yield 32%, mass [M + ]=766)

[0620] Preparation Example of Compound 10

[0621]

[0622] Synthesis of intermediate 24

[0623] The intermediate 24 (20 g) was obtained by the same method as that of the intermediate 18 in Synthesis Example 8 except that 20 g of the intermediate 13 was used instead of the intermediate 8 and 9.0 g of carbazole was used instead of 9H-3,9'-biscarbazole. (Yield 84%, mass [M +]=536)

[0624] Synthesis of intermediate 25

[0625] The intermediate 25 (17 g) was obtained by the same method as the method for producing the intermediate 2 in Synthesis Example 1 except that 20 g of the intermediate 24 was used instead of the intermediate 1. (Yield 77%, mass [M + ]=593)

[0626] Synthesis of compound 10

[0627] The same method as the method for producing compound 3 in Synthesis Example 3 was used to produce 4.3 g of compound H10, except that 10 g of intermediate 25 was used instead of intermediate 7. (Yield 42%, mass [M + ]=601)

[0628] Preparation Example of Compound 11

[0629]

[0630] Synthesis of intermediate 26

[0631] 21 g of Intermediate 26 was produced by the same method as the method for producing 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. (Yield 77%, mass [M + ]=612)

[0632] Synthesis of intermediate 27

[0633] The intermediate 27 (17 g) was obtained by the same method as that of the intermediate 2 in Synthesis Example 1 except that 21 g of the intermediate 26 was used instead of the intermediate 1. (Yield 74%, mass [M + ]=669)

[0634] Synthesis of compound 11

[0635] The same method as the method for producing compound 3 in Synthesis Example 3 was used to produce 3.8 g of compound 11, except that 10 g of intermediate 27 was used instead of intermediate 7. (Yield 38%, mass [M + ]=677)

[0636] Preparation Example of Compound 12

[0637]

[0638] Synthesis of intermediate 28

[0639] The intermediate 28 (19 g) was obtained by the same method as the method for producing the intermediate 1 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. (Yield 76%, mass [M + ]=525)

[0640] Synthesis of intermediate 29

[0641] 16 g of Intermediate 29 was prepared by the same method as the method for preparing 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-dioxaboralane. (Yield 63%, mass [M + ]=703)

[0642] Synthesis of intermediate 30

[0643] The intermediate 29 (16 g) was used instead of the intermediate 1, and the intermediate 30 (12 g) was obtained by the same method as the method for producing the intermediate 2 in Synthesis Example 1. (Yield 69%, mass [M + ]=760)

[0644] Synthesis of compound 12

[0645] The same method as the method for producing compound 3 in Synthesis Example 3 was used to produce 3.1 g of compound H12, except that 8.0 g of intermediate 30 was used instead of intermediate 7. (Yield 38%, mass [M + ]=768)

[0646] Preparation Example of Compound 13

[0647]

[0648] Synthesis of intermediate 31

[0649] The intermediate 31 was prepared by the same method as the method for preparing the intermediate 1 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. (Yield 74%, mass [M + ]=525)

[0650] Synthesis of intermediate 32

[0651] 26 g of Intermediate 32 was produced by the same method as the method for producing 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)indolo[3,2,1-jk]carbazole was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan. (Yield 71%, mass [M + ]=689)

[0652] Synthesis of intermediate 33

[0653] The intermediate 33 (20 g) was obtained by the same method as that of the intermediate 2 in Synthesis Example 1 except that 26 g of the intermediate 32 was used instead of the intermediate 1. (Yield 71%, mass [M + ]=743)

[0654] Synthesis of compound 13

[0655] The same method as the method for producing compound 3 in Synthesis Example 3 was used to produce 3.2 g of compound 13, except that 10 g of intermediate 33 was used instead of intermediate 7. (Yield 32%, mass [M + ]=751)

[0656] Preparation Example of Compound 14

[0657]

[0658] Synthesis of intermediate 34

[0659] The intermediate 34 (16 g) was obtained by the same method as that of the intermediate 19 in Synthesis Example 8 except that 20 g of the intermediate 26 was used instead of the intermediate 18. (Yield 70%, mass [M + ]=703)

[0660] Synthesis of intermediate 35

[0661] The intermediate 35 (12 g) was obtained by the same method as that of the intermediate 11 in Synthesis Example 4 except that 16 g of the intermediate 34 was used instead of the intermediate 10. (Yield 75%, mass [M + ]=704)

[0662] Synthesis of intermediate 36

[0663] The intermediate 36 was obtained by the same method as the method for producing compound 3 in Synthesis Example 3 except that 12 g of intermediate 35 was used instead of intermediate 7. (Yield 40%, mass [M + ]=712)

[0664] Synthesis of compound 14

[0665] The intermediate 36 of 4.8 g was used instead of the 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, except that the above was performed by the same method as the method for producing the compound 4 in Synthesis Example 4, thereby obtaining 4.3 g of the compound 14. (yield 69%, mass [M+] = 918)

[0666] Preparation Example of Compound 15

[0667]

[0668] Synthesis of intermediate 37

[0669] The intermediate 37 (16 g) was obtained by the same method as the method for producing the intermediate 1 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. (Yield 72%, mass [M + ]=739)

[0670] Synthesis of intermediate 38

[0671] The intermediate 38 (12 g) was obtained by the same method as the method for producing the intermediate 2 in Synthesis Example 1 except that 16 g of the intermediate 37 was used instead of the intermediate 1 and 5.5 g of 2-(phenylamino)phenyl)boronic acid was used instead of 2-hydroxyphenylboronic acid. (Yield 64%, mass [M + ]=872)

[0672] Synthesis of compound 15

[0673] The same method as the method for producing compound 1 in Synthesis Example 1 was used to produce 2.3 g of compound 15, except that 12 g of intermediate 38 was used instead of intermediate 2. (Yield 20%, mass [M + ]=845)

[0674] Preparation Example of Compound 16

[0675]

[0676] Synthesis of intermediate 39

[0677] The intermediate 39 (10 g) was obtained by the same method as the method for producing the intermediate 11 in Synthesis Example 4 except that 15 g of the intermediate 10 and 7.5 g of 2-bromo-5-chlorophenol were used instead of 2-bromo-5-chlorophenol. (Yield 65%, mass [M + ]=555)

[0678] Synthesis of intermediate 40

[0679] The intermediate 40 (3.5 g) was obtained by the same method as the method for producing compound 3 in Synthesis Example 3 except that 10 g of intermediate 39 was used instead of intermediate 7. (Yield 35%, mass [M + ]=562)

[0680] Synthesis of compound 16

[0681] The same method as the method for producing compound 4 in Synthesis Example 4 was used to produce 3.4 g of compound 16, 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. (Yield 79%, mass [M + ]=694)

[0682] Preparation Example of Compound 17

[0683]

[0684] Synthesis of intermediate 41

[0685] The intermediate 41 was prepared by the same method as that of the intermediate 1 in Synthesis Example 1, except that 15 g of 2'-(tri(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-carbazolyl-1,2,3,4,5,6,7,8-d8 was used instead of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole. (Yield 70%, mass [M + ]=770)

[0686] Synthesis of intermediate 42

[0687] The intermediate 42 (13 g) was obtained by the same method as that of the intermediate 2 in Synthesis Example 1 except that 16 g of the intermediate 41 was used instead of the intermediate 1. (Yield 75%, mass [M + ]=832)

[0688] Synthesis of compound 17

[0689] The same method as the method for producing compound 1 in Synthesis Example 1 was used to produce 2.2 g of compound 17, except that 13 g of intermediate 42 was used instead of intermediate 2. (Yield 18%, mass [M + ]=804)

[0690] Preparation Example of Compound 18

[0691]

[0692] Synthesis of intermediate 43

[0693] The intermediate 43 (18 g) was obtained by the same method as the method for producing the intermediate 1 in Synthesis Example 1 except that 14 g of 4-(9H-carbazole-9-yl-d8)phenyl-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. (Yield 82%, mass [M + ]=461)

[0694] Synthesis of intermediate 44

[0695] The intermediate 44 (17 g) was obtained by the same method as the method for producing the intermediate 18 in Synthesis Example 8 except that 18 g of the intermediate 43 was used instead of the intermediate 8 and 8.2 g of 9H-carbazolyl-1,2,3,4,5,6,7,8-d8 was used instead of 9H-3,9'-biscarbazole. (Yield 78%, mass [M + ]=556)

[0696] Synthesis of intermediate 45

[0697] The intermediate 45 (13 g) was obtained by the same method as the method for producing the intermediate 2 in Synthesis Example 1 except that 18 g of the intermediate 44 was used instead of the intermediate 1. (Yield 69%, mass [M + ]=613)

[0698] Synthesis of compound 18

[0699] The same method as the method for producing compound 3 in Synthesis Example 3 was used to produce 3.5 g of compound H18, except that 8.0 g of intermediate 45 was used instead of intermediate 7. (Yield 43%, mass [M + ]=620)

[0700] Preparation Example of Compound 19

[0701]

[0702] Synthesis of intermediate 46

[0703] The intermediate 46 (20 g) was obtained by the same method as the method for producing the intermediate 1 in Synthesis Example 1, except that 18 g of 2'-(9H-carbazole-9-yl-d8)-[1,1'-biphenyl]-2,3',4,4',5,5',6,6'-d8-3-ol was used instead of the starting material 3-(triphenylsilyl)phenol and 10 g of 1-bromo-3-chloro-5-fluorobenzene was used instead of 9-(3,4-dichloro-5-fluorophenyl)-9H-carbazole. (Yield 78%, mass [M + ]=540)

[0704] Synthesis of intermediate 47

[0705] 20 g of Intermediate 47 was produced by the same method as the method for producing 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-carbazolyl-1,2,3,4,5,6,7,8-d8 was used instead of 2-([1,1'-biphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan. (Yield 76%, mass [M + ]=715)

[0706] Synthesis of intermediate 48

[0707] The intermediate 48 (16 g) was obtained by the same method as the method for producing the intermediate 2 in Synthesis Example 1 except that 20 g of the intermediate 47 was used instead of the intermediate 1. (Yield 74%, mass [M + ]=777)

[0708] Synthesis of compound 19

[0709] The same method as the method for producing compound 3 in Synthesis Example 3 was used to produce 3.6 g of compound 19, except that 8.0 g of intermediate 48 was used instead of intermediate 7. (Yield 45%, mass [M + ]=784)

[0710] Preparation Example of Compound 20

[0711]

[0712] Synthesis of intermediate 49

[0713] 13 g of Intermediate 49 was prepared by the same method as the method for preparing 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. (Yield 74%, mass [M + ]=635)

[0714] Synthesis of intermediate 50

[0715] The intermediate 50 (11 g) was obtained by the same method as that of the intermediate 2 in Synthesis Example 1 except that 13 g of the intermediate 49 was used instead of the intermediate 1. (Yield 78%, mass [M + ]=692)

[0716] Synthesis of compound 20

[0717] The same method as the method for producing compound 3 in Synthesis Example 3 was used to produce 4.4 g of compound 20, except that 11 g of intermediate 50 was used instead of intermediate 7. (Yield 40%, mass [M + ]=700)

[0718] <Production Example 2>

[0719] Preparation Example of Compound D1

[0720]

[0721] Synthesis of intermediate 51

[0722] Under a nitrogen atmosphere, 20 g of 1-(3-bromophenyl)-1H-benzo[d]imidazole, 23 g of 9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazyl-2-ol, 31 g of potassium phosphate, 1.4 g of copper iodide (CuI), 1.8 g of picolinic acid, and 500 mL of dimethyl sulfoxide (DMSO) were added, and then heated at 150°C and stirred for 72 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the liquids, and then treated with MgSO4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by column chromatography (ethyl acetate / hexane) to obtain 30 g of intermediate 51. (Yield 81%, mass [M + ]=509)

[0723] Synthesis of intermediate 52

[0724] Under a nitrogen atmosphere, 15 g of intermediate 5-1, 11.2 g of 1,3-di-tert-butyl-5-iodobenzene and 200 mL of toluene were added, and the mixture was heated and stirred at 100°C for 50 hours. After the reaction was completed, the reaction solution was cooled to room temperature, the generated solid was filtered and washed with diethyl ether. 200 mL of methanol and 20 mL of water were added to the obtained solid, stirred and dissolved. And 7.2 g of ammonium hexafluorophosphate (NH4PF6) was added and stirred at room temperature for 3 days. After the reaction was completed, water was added, filtered and washed with diethyl ether. The washed solid was dried to obtain 10 g of intermediate 52. (Yield 49%, mass [M + ]=698)

[0725] Synthesis of compound D1

[0726] Under a nitrogen atmosphere, 10 g of intermediate 5-2, 3.5 g of sodium acetate, 5.9 g of dichloro(1,5-cyclooctadiene)platinum (Pt(COD)Cl2), and 100 mL of dimethylformamide (DMF) were added, and the mixture was heated and stirred at 120°C for 72 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and water and ethyl acetate were added to separate the liquids, and then treated with MgSO4 (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by column chromatography (ethyl acetate / hexane) to obtain 1.1 g of compound D1. (Yield 9%, mass [M + ]=891)

[0727] Preparation Example of Compound D2

[0728]

[0729] Synthesis of intermediate 53

[0730] The intermediate 53 (10 g) was obtained by the same method as the method for producing the intermediate 52 of Synthesis Example 21 except that 15 g of 2'-bromo-1,1':3',1"-terphenyl-2,2",3,3",4,4',4",5,5',5",6,6',6"-d13 was used instead of the starting material 1,3-di-tert-butyl-5-iodobenzene. (Yield 45%, mass [M + ]=752)

[0731] Synthesis of compound D2

[0732] The same method as the method for producing compound D1 in Synthesis Example 21 was used to produce 1.0 g of compound D2, except that 10 g of intermediate 53 was used instead of the starting material intermediate 52. (Yield 8%, mass [M + ]=944)

[0733] Preparation Example of Compound D3

[0734]

[0735] Synthesis of intermediate 54

[0736] The intermediate 54 was prepared by the same method as that of the intermediate 51 of Synthesis Example 21, except that 29 g of 9-(4-(tert-butyl)pyridin-2-yl)-6-phenyl-9H-carbazol-2-ol was used instead of the starting material 9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazol-2-ol, to obtain 35 g of the intermediate 54. (Yield 82%, mass [M + ]=585)

[0737] Synthesis of intermediate 55

[0738] The intermediate 54 was 35 g instead of the intermediate 51, and 23 g of 4-(tert-butyl)-2'-chloro-1,1':3',1"-terphenyl-2",3",4",5",6"-d5 was used instead of 1,3-di-tert-butyl-5-iodobenzene. The intermediate 55 was prepared by the same method as the method for preparing the compound intermediate 52 in Synthesis Example 21, thereby obtaining 21 g of the intermediate 55. (Yield 40%, mass [M + ]=876)

[0739] Synthesis of compound D3

[0740] The same method as the method for producing compound D1 in Synthesis Example 21 was used to produce 1.1 g of compound D3, except that 10 g of intermediate 55 was used instead of intermediate 52. (Yield 9%, mass [M + ]=1068)

[0741] <Examples and Comparative Examples>

[0742] Example 1

[0743] ITO (indium tin oxide) is used The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0744] On the ITO transparent electrode prepared as the anode, the following compound HT1 and the following compound HI1 were mixed in a ratio of 98:2 (molar ratio) and A hole injection layer is formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, a compound represented by the following chemical formula HT1 is deposited Then, a film with a thickness of 1000 nm was deposited on the hole transport layer. The BH (p-type) compound was vacuum-deposited to form an electron blocking layer. Next, on the electron blocking layer, a compound of the following chemical formula BH (p-type) as the main body of the light-emitting layer and the above-mentioned compound 1 was mixed in a ratio of 1:1 and a dopant compound represented by compound D1 was vacuum-deposited in a weight ratio of 88:12 to form a light-emitting layer. On the light-emitting layer, a film thickness of The compound 1 is vacuum-deposited to form a hole blocking layer. Next, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ are vacuum-deposited on the hole blocking layer at a weight ratio of 1:1, thereby forming a hole blocking layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A thickness of is evaporated to form a cathode.

[0745]

[0746] In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 2x10. -7 ~5ⅹ10 -6 A support is provided to produce an organic light-emitting device.

[0747] Example 2 to Example 30

[0748] An organic light-emitting device was produced by the same method as in Example 1, except that the compounds listed in Table 1 below were used instead of the host compound 1 and the dopant compound D1 of the light-emitting layer.

[0749] Example 31 and Example 32

[0750] In the above Example 1, an organic light-emitting device was prepared by the same method as in the above Example 1, except that the compounds listed in the following Table 1 were used instead of the main compound 1 and the dopant compound D1 of the light-emitting layer, and the compound H5 was used as the hole blocking layer instead of the above compound H1.

[0751] [Example Compounds]

[0752]

[0753]

[0754] Comparative Examples 1 to 7

[0755] In Example 1, an organic light-emitting device was produced by the same method as in Example 1, except that the compounds listed in Table 1 below were used instead of the host compound 1 and the dopant compound D1 of the light-emitting layer.

[0756] [Comparative Example Compound]

[0757]

[0758] When current was applied to the organic light-emitting devices prepared in Examples 1 to 32 and Comparative Examples 1 to 7, voltage, efficiency, and lifetime (1600 nits reference) were measured, and the results are shown in the following Table 1. The lifetime T90 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 90%.

[0759]

Table 1

[0760]

[0761]

[0762] In Comparative Examples 1 and 2, the compound BD1 used as a dopant is Ir(dFppy)3, and it can be confirmed that since the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 are not used simultaneously, no synergistic effect in the organic light-emitting device is exhibited.

[0763] It was confirmed that the compound BH1 used as the host in Comparative Example 3 had no carbazole group and silyl group or aryl group substituted on the benzene ring included in the core structure, and therefore, the voltage, efficiency and life were significantly deteriorated compared with Examples 1 to 32.

[0764] It was confirmed that the compound BH2 used as the main body in Comparative Example 4 had only carbazole groups substituted on the benzene ring included in the core structure, and the voltage, efficiency and life were significantly deteriorated compared with Examples 1 to 32.

[0765] It can be confirmed that the compound BH3 used as the main body in Comparative Example 5 is substituted with only a carbazole group on the benzene ring included in the core structure, and a silyl group on the carbazole group, and therefore, the voltage, efficiency and life are significantly deteriorated compared with Examples 1 to 32.

[0766] It was confirmed that the core structures of Compound BH4 and Compound BH5 used as hosts in Comparative Examples 6 and 7 were different, and therefore, the voltage, efficiency, and life were significantly deteriorated compared with Examples 1 to 32.

Claims

1. An organic light-emitting device, comprising: anode, cathode, and One or more organic layers are provided between the anode and the cathode, One or more of the organic layers includes a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2: [Chemical formula 1] In the chemical formula 1, X is NR, O or S, At least one of R and R1 to R3 is a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and the others are the same as or different from 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 to L3 and L11 to L13 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group, G1 to G3 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, n1 and n2 are each an integer from 1 to 4, m1 and m2 are each an integer from 0 to 4, n3 is an integer from 1 to 3, m3 is an integer from 0 to 3, g1 to g3 are each an integer from 0 to 8, When n1 to n3, m1 to m3 and g1 to g3 are each 2 or more, the substituents in the brackets are the same or different from each other. n1+m1 is less than 4, n2+m2 is less than 4, n3+m3 is less than 3, m1+m2+m3 is an integer greater than 1, [Chemical formula 2] In the chemical formula 2, Cy is a substituted or unsubstituted N-containing monocyclic ring, T1 to T4 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring, t1 and t4 are each an integer from 0 to 3, t2 is an integer from 0 to 2, t3 is an integer from 0 to 4, When t1, t3 and t4 are each 2 or more, the substituents in the brackets are the same or different from each other. When t2 is 2, the substituents in the brackets are the same as or different from each other.

2. The organic light emitting device according to claim 1, wherein: The L1 to L3 and L11 to L13 are the same as or different from each other, and are each independently a direct bond, an arylene group or a divalent heterocyclic group.

3. The organic light emitting device according to claim 1, wherein: At least one of R1 to R3 is a silyl group which is substituted or unsubstituted by deuterium, an alkyl group or an aryl group; an aryl group which is substituted or unsubstituted by deuterium or an aryl group; or a heterocyclic group which is substituted or unsubstituted by deuterium or a heterocyclic group, and the others are the same or different and are independently hydrogen or deuterium.

4. The organic light emitting device according to claim 1, wherein: The m1+m2+m3 is 1 or 2.

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

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

7. The organic light emitting device according to claim 1, wherein: At least one of R1 to R3 is triphenylsilyl, phenyl, biphenyl, carbazolyl, dibenzofuranyl, dibenzothienyl, benzofuranodibenzofuranyl, or indolecarbazolyl, and the others are the same or different and are independently hydrogen or deuterium, The L1 to L3 and L11 to L13 are the same as or different from each other, and are each independently a direct bond or a phenylene group, G1 to G3 are the same as or different from each other, and are each independently hydrogen or deuterium.

8. The organic light emitting device according to claim 1, wherein: The chemical formula 2 is represented by any one of the following chemical formulas 2-A-1 to 2-A-3: [Chemical formula 2-A-1] [Chemical formula 2-A-2] [Chemical formula 2-A-3] In the chemical formulae 2-A-1 to 2-A-3, The definitions of T1 to T4 and t1 to t4 are the same as those in the chemical formula 2, T11 to T13 and T21 to T24 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

9. The organic light emitting device according to claim 1, wherein: The T1 to T4 are the same as or different from each other, and are independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, or are combined with adjacent groups to form a dibenzofuran ring or a dibenzothiophene ring.

10. The organic light emitting device according to claim 8, wherein: The T11 to T13 and T21 to T24 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

11. The organic light emitting device according to claim 1, wherein: The chemical formula 1 is represented by any one of the following compounds: [] D＝x1～x2 It means that the structure in brackets contains x1 to x2 deuteriums, where the value is an integer.

12. The organic light emitting device according to claim 1, wherein: The chemical formula 2 is represented by any one of the following compounds:

13. The organic light emitting device according to claim 1, wherein: The organic layer includes a light emitting layer including the compound represented by the Chemical Formula 1 and the compound represented by the Chemical Formula 2.

14. The organic light emitting device according to claim 13, wherein: The light emitting layer includes the compound represented by the Chemical Formula 1 as a host, and includes the compound represented by the Chemical Formula 2 as a dopant.

15. The organic light emitting device according to claim 13, wherein: The organic layer further includes one or more of a hole transport layer, a hole injection layer, an electron blocking layer, a hole injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer.

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