Compound and organic light-emitting device comprising same

Abstract

The present specification provides a compound represented by chemical formula 11 and an organic light-emitting device comprising the same.

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2024-0002624, filed with the Korean Patent Office on January 8, 2024, the entire content of which is incorporated herein by reference.

[0002] This specification relates to a compound and an organic light-emitting device including the same. Background Art

[0003] Generally, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light-emitting device using the organic light-emitting phenomenon typically has a structure including an anode and a cathode and an organic layer located therebetween. Here, in order to improve the efficiency and stability of the organic light-emitting device, the organic layer is mostly formed of a multilayer structure formed of different substances respectively. For example, it may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. For such a structure of the organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons return to the ground state again.

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

[0005] Prior Art Documents

[0006] Patent Documents

[0007] (Patent Document 1) Korean Patent Publication No. 2000-0051826 Summary of the Invention

[0008] Technical Problem

[0009] This specification provides a compound and an organic light-emitting device including the same.

[0010] Solution to the Problem

[0011] One embodiment of this specification provides a compound represented by the following Chemical Formula 11.

[0012] [Chemical Formula 11]

[0013]

[0014] In Chemical Formula 11 above,

[0015] Y11 and Y21 are each independently O, S, or CRR'.

[0016] L11 is a directly bonded, substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

[0017] l11 is an integer from 0 to 3. When l11 is 2 or more, two or more L11s are the same as or different from each other,

[0018] n21 is an integer from 0 to 6 or an integer from 0 to 8,

[0019] n22 is an integer from 0 to 4,

[0020] m11 is an integer from 0 to 10,

[0021] When m11, n21, and n22 are each 2 or more, two or more substituents within parentheses are the same as or different from each other,

[0022] p is an integer of 0 or 1,

[0023] When p is 0, n21 is an integer from 0 to 8, Ar11 is a substituted or unsubstituted alkyl group, -SiR”R”'R””, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group with three or more rings, a substituted or unsubstituted heteroaryl group with two or more rings containing N, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing O or S. When Ar11 is a heteroaryl group, L is not directly bonded.

[0024] When p is 1, n21 is an integer from 0 to 6, Ar11 is a substituted or unsubstituted alkyl group, -SiR”R”'R””, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group with two or more rings containing N, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing O or S. When Ar11 is an unsubstituted phenyl group, L is not directly bonded.

[0025] R, R', R”, R”', R””, R11, R21, and R22 are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0026] However, it does not include the structure represented by the above chemical formula 11 as and the case where the structure represented by is represented by chemical formula A',

[0027] However, it does not include the case where the structure represented by the above chemical formula 11 as and the structure represented by are both represented by chemical formula C,

[0028] [Chemical formula A']

[0029]

[0030] [Chemical formula C]

[0031]

[0032] Y is the above Y11 or Y21,

[0033] indicating the part connected to the nuclear structure.

[0034] In addition, an embodiment of the present specification provides an organic light-emitting device, which includes: an anode, a cathode, and one or more organic layers disposed between the above anode and the above cathode, and one or more of the above organic layers contain the compound represented by the above Chemical formula 11.

[0035] Advantages of the Invention

[0036] The compounds described in the present specification can be used as materials for the organic layers of organic light-emitting devices. The compounds according to at least one embodiment can achieve an improvement in efficiency, a lower driving voltage, and / or an improvement in lifetime characteristics in organic light-emitting devices. In particular, the compounds described in the present specification can be used as materials for hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection. In addition, compared with existing organic light-emitting devices, it has the effects of low driving voltage, high efficiency, and / or long lifetime. Description of the Drawings

[0037] Figure 1 An example of an organic light-emitting device in which a substrate 1, an anode 2, an organic layer 12, and a cathode 10 are sequentially stacked is illustrated.

[0038] Figure 2 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 is illustrated.

[0039] Figure 3 An example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 11, and a cathode 10 are sequentially stacked is illustrated.

[0040] Symbol Explanation

[0041] 1: Substrate

[0042] 2: Anode

[0043] 3: Hole injection layer

[0044] 4: Hole transport layer

[0045] 5: Electron blocking layer

[0046] 6: Light emitting layer

[0047] 7: Hole blocking layer

[0048] 8: Electron transport layer

[0049] 9: Electron injection layer

[0050] 10: Cathode

[0051] 11: Electron injection and transport layer

[0052] 12: Organic layer Detailed implementation manners

[0053] Next, this specification will be described in more detail.

[0054] In this specification, when it is indicated that a certain part "contains / includes" a certain component, unless there is a particularly contrary record, it means that other components can be further included, rather than excluding other components.

[0055] In this specification, when it is indicated that a certain component is "on" another component, it includes not only the case where a certain component is in contact with another component, but also the case where there are other components between the two components.

[0056] In this specification, the deuterium substitution rate of a compound can be determined by the following methods: a method using TLC-MS (Thin-Layer Chromatography / Mass Spectrometry) and calculating the substitution rate based on the maximum (max.) value of the distribution formed by the molecular weight at the end of the reaction; or a quantitative analysis method using NMR, adding DMF as an internal standard, and calculating the D-substitution rate from the integration ratio on 1H NMR and the integrated amount of the total peak (peak).

[0057] In this specification, "energy level" refers to the magnitude of energy. Therefore, the energy level is interpreted as representing the absolute value of the energy value. For example, a low or deep energy level means an increase in the absolute value in the negative direction from the vacuum energy level.

[0058] In this specification, HOMO (highest occupied molecular orbital) refers to the molecular orbital function (highest occupied molecular orbital) of the electron in the region with the highest energy in the region that can participate in the bonding, LUMO (lowest unoccupied molecular orbital) refers to the molecular orbital function (lowest unoccupied molecular orbital) of the electron in the antibonding region with the lowest energy, and the HOMO energy level refers to the distance from the vacuum energy level to the HOMO. In addition, the LUMO energy level refers to the distance from the vacuum energy level to the LUMO.

[0059] In this specification, the band gap refers to the difference between the HOMO energy level and the LUMO energy level, that is, the HOMO-LUMO energy gap (Gap).

[0060] In this specification, the HOMO level can be measured by using a photoelectron spectrometer (AC3 manufactured by Riken Keiki Co., Ltd.) under atmospheric pressure, and the LUMO level can be calculated using a wavelength value measured by photoluminescence (PL).

[0061] In the present specification, the term "a combination thereof" included in the expression of Markush form means a mixture or combination of one or more components selected from the expression of Markush form, and means that one or more components selected from the above components are included.

[0062] In the present specification, examples of substituents are described below, but are not limited thereto.

[0063] The term "substituted" mentioned above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by 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.

[0064] In one embodiment of 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 Substituted with one or more substituents selected from alkenyl, silyl, boron, amino, aryl, or heterocyclic group, or substituted with a substituent formed by linking two or more of the above-exemplified substituents, or having no substituent. For example, the "substituent formed by linking two or more substituents" may be a biphenyl group. That is, a biphenyl group may be an aryl group or may be interpreted as a substituent formed by linking two phenyl groups.

[0065] In one embodiment of the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, halogen group, nitrile group, nitro group, hydroxyl group, amino group, silyl group, boron group, alkoxy group, aryloxy group, alkyl group, cycloalkyl group, aryl group, and heterocyclic group, or substituted with a substituent formed by linking two or more of the above-exemplified substituents, or having no substituent.

[0066] In one embodiment of the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, alkyl group, aryl group, and heterocyclic group, or substituted with a substituent formed by linking two or more of the above-exemplified substituents, or having no substituent.

[0067] In the present specification, being substituted with deuterium by N% means that N% of the available hydrogen in the corresponding structure is substituted with deuterium. For example, in dibenzofuran, when it is indicated that it is substituted with deuterium by 25%, it means that 2 out of 8 hydrogens of dibenzofuran are substituted with deuterium.

[0068] Examples of the above substituents are described below, but are not limited thereto.

[0069] In the present specification, examples of the halogen group include a fluorine group (-F), a chlorine group (-Cl), a bromine group (-Br), or an iodine group (-I).

[0070] In the present specification, a silyl group may be represented by the chemical formula -SiY a Y b Y c wherein each of the above Y a 、Y b and Y c may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the silyl group include triphenylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0071] In the present specification, a boron group may be represented by -BY d Y eThe chemical formula of the above-mentioned Y d and Y e each may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the above-mentioned boron group include, but are not limited to, trimethylboron group, triethylboron group, tert-butyldimethylboron group, triphenylboron group, phenylboron group, etc.

[0072] In this specification, the above-mentioned alkyl group may be straight-chain or branched-chain, 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 above-mentioned alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the above-mentioned alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned alkyl group is 1 to 10. Specific examples of the alkyl group include, but are not limited to, 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.

[0073] In this specification, for arylalkyl groups, except for being substituted by an aryl group, the above description regarding alkyl groups can be applied.

[0074] In this specification, the above-mentioned 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 methoxy, ethoxy, n-propoxy, isopropoxy, isopropyl oxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but are not limited to this.

[0075] The alkyl groups, alkoxy groups and other substituents containing an alkyl moiety described in this specification include all straight-chain or branched-chain forms.

[0076] In this specification, the alkenyl group may be straight-chain 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 of the above-mentioned alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above-mentioned alkenyl group is 2 to 6. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthalen-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, styryl, etc.

[0077] In this specification, the above-mentioned alkynyl group is a substituent containing a triple bond between carbon atoms, which can 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 above-mentioned alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned alkynyl group is 2 to 10.

[0078] In this 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 number of carbon atoms of the above-mentioned cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is 3 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is 3 to 6. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc., but are not limited thereto.

[0079] In this specification, the amino group is -NH2, and the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and their combinations can 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. Specific examples of the substituted amino group include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9,9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthrylamino, dibenzofuranylphenylamino, 9-methylanthrylamino, diphenylamino, phenylnaphthylamino, xylenylamino, phenyltolylamino, diphenylamino, etc., but are not limited thereto.

[0080] In this specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and can be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the above-mentioned aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the above-mentioned aryl group is 6 to 20. According to one embodiment, the number of carbon atoms of the above-mentioned monocyclic aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the above-mentioned monocyclic aryl group is 6 to 20. Regarding the above-mentioned aryl group, as the monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, quaterphenyl, etc., but is not limited thereto. According to one embodiment, the number of carbon atoms of the above-mentioned polycyclic aryl group is 10 to 30. According to one embodiment, the number of carbon atoms of the above-mentioned polycyclic aryl group is 10 to 20. As the above-mentioned polycyclic aryl group, it can be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, triphenyl, yl, fluorenyl, triphenylene, etc., but is not limited thereto.

[0081] In this specification, the substituted aryl may include a structure in which an aliphatic hydrocarbon ring is fused to the aryl. According to one embodiment, the above-mentioned substituted aryl may include tetrahydronaphthyl, and more specifically, may include (1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl), but is not limited thereto.

[0082] In this specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. At this time, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

[0083] When the above-mentioned fluorenyl group is substituted, it may be and other spirofluorenyl groups; (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) and other substituted fluorenyl groups. But is not limited thereto.

[0084] In this specification, the aryl group in the aryloxy group may be applied to the above description of the aryl group.

[0085] In this specification, the alkyl group in the above-mentioned alkylthio group and alkylsulfonyl group may be applied to the above description of the alkyl group.

[0086] In this specification, the aryl group in the above-mentioned arylthio group and arylsulfonyl group may be applied to the above description of the aryl group.

[0087] In this specification, the heterocyclic group is a cyclic 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 of the above-mentioned heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms of the above-mentioned heterocyclic group is 2 to 20. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidinyl, quinolinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothiophenyl, indolocarbazolyl, triazinyl, etc., but are not limited thereto.

[0088] In this specification, the heteroaryl group is aromatic, and in addition, the above description of the heterocyclic group may be applied.

[0089] In this specification, the above-mentioned arylene group, except that it is divalent, may be applied to the description of the above-mentioned aryl group.

[0090] In this specification, the divalent heterocyclic group, except that it is divalent, may be applied to the description of the above-mentioned heterocyclic group.

[0091] In this specification, in a substituted or unsubstituted ring formed by binding adjacent groups to each other, the "ring" refers to a hydrocarbon ring or a heterocyclic ring.

[0092] The above hydrocarbon rings can be aromatic, aliphatic, or fused rings of aromatic and aliphatic, and can be selected from the examples of the above cycloalkyl or aryl groups.

[0093] In this specification, the meaning of combining with adjacent groups to form a ring 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 heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or their fused rings. The above hydrocarbon rings refer to rings composed only of carbon and hydrogen atoms. The above heterocyclic rings refer to rings containing one or more elements selected from elements such as N, O, P, S, Si, and Se. In this specification, the above aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocyclic rings, and aromatic heterocyclic rings can be monocyclic or polycyclic.

[0094] In this specification, the aliphatic hydrocarbon ring, as a non-aromatic ring, refers to a ring composed only of carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc., but are not limited thereto.

[0095] In this specification, the aromatic hydrocarbon ring refers to an aromatic ring composed only of carbon and hydrogen atoms. Examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, etc., but are not limited thereto. In this specification, the aromatic hydrocarbon ring can be interpreted to have the same meaning as the aryl group.

[0096] In this specification, the aliphatic heterocyclic ring refers to an aliphatic ring containing one or more heteroatoms. Examples of the aliphatic heterocyclic ring include oxirane, tetrahydrofuran, 1,4-di oxane (1,4-dioxane), pyrrolidine, piperidine, morpholine, oxepane azocane thiazocane etc., but are not limited thereto.

[0097] In this specification, the aromatic heterocyclic ring refers to an aromatic ring containing one or more heteroatoms. Examples of the aromatic heterocyclic ring include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, oxazole, iso oxazole, thiazole, isothiazole, triazole, diazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, azine, thiazine, di Alkenes, triazines, tetrazines, isoquinolines, quinolines, quinones, quinazolines, quinoxalines, naphthyridines, acridines, phenanthridines, phthalazines, triazaindenes, indoles, indolizines, benzothiazoles, benzo azoles, benzimidazoles, benzothiophenes, benzofurans, dibenzothiophenes, dibenzofurans, carbazoles, benzocarbazoles, dibenzocarbazoles, phenazines, imidazopyridines, phen azines, indolocarbazoles, indacarbazoles, etc., but are not limited thereto.

[0098] Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention can be deformed into various forms, and the scope of the present invention is not limited to the embodiments described below.

[0099] The compound represented by Chemical Formula 11 according to the present invention has high efficiency, low voltage and / or long life characteristics by enhancing hole transport characteristics through the connection of carbazole and / or carbazole derivatives on the triazine nucleus.

[0100] In particular, by introducing a heteroaryl group into Ar11, the distance between the LUMO of the triazine nucleus and other molecules can be adjusted, thereby adjusting the electron transport characteristics. When the heteroaryl group is bonded through a phenylene linking group at the meta position of the triazine, the orbital distance between the triazine nucleus and the heteroaryl group represented by Ar11 is ensured, thereby obtaining a compound having a high triplet energy (T1). In addition, when the compound represented by Chemical Formula 11 of the present invention contains deuterium, the efficiency and life of the device are improved. Specifically, when hydrogen is replaced by deuterium, the chemical properties of the compound are almost unchanged, but the physical properties of the deuterated compound are changed and the vibrational energy level is lowered. The deuterium-substituted compound can prevent the reduction of the van der Waals force between molecules or the reduction of the quantum efficiency due to the collision caused by the vibration between molecules. In addition, the C-D bond can improve the stability of the compound.

[0101] Therefore, when the compound represented by the above Chemical Formula 11 is applied to an organic light-emitting device, an organic light-emitting device having high efficiency, low voltage and / or long life characteristics can be obtained.

[0102] Hereinafter, the compound represented by Chemical Formula 11 will be described in detail.

[0103] [Chemical Formula 11]

[0104]

[0105] In the above Chemical Formula 11,

[0106] Y11 and Y21 are each independently O, S or CRR',

[0107] L11 is a directly bonded, substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

[0108] l11 is an integer from 0 to 3. When the above l11 is 2 or more, two or more L11s are the same as or different from each other,

[0109] n21 is an integer from 0 to 6 or an integer from 0 to 8,

[0110] n22 is an integer from 0 to 4,

[0111] m11 is an integer from 0 to 10,

[0112] When the above m11, n21, and n22 are each 2 or more, two or more substituents within the parentheses are the same as or different from each other,

[0113] p is an integer of 0 or 1,

[0114] When p is 0, n21 is an integer from 0 to 8, Ar11 is a substituted or unsubstituted alkyl group, -SiR”R”'R””, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group having three or more rings, a substituted or unsubstituted heteroaryl group having two or more rings containing N, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing O or S, and when Ar11 is a heteroaryl group, L is not directly bonded,

[0115] When p is 1, n21 is an integer from 0 to 6, Ar11 is a substituted or unsubstituted alkyl group, -SiR”R”'R””, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having two or more rings containing N, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing O or S, and when Ar11 is an unsubstituted phenyl group, L is not directly bonded,

[0116] R, R', R”, R”', R””, R11, R21, and R22 are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0117] However, it does not include the structure represented by the above Chemical Formula 11 as and the case where the structure represented by is represented by Chemical Formula A',

[0118] However, it does not include the case where the structure represented by the above Chemical Formula 11 as and the structure represented by are both represented by Chemical Formula C,

[0119] [Chemical Formula A']

[0120]

[0121] [Chemical formula C]

[0122]

[0123] Y is the above-mentioned Y11 or Y21,

[0124] representing the part connected to the nuclear structure.

[0125] In one embodiment of this specification, the above chemical formula 11 is a compound represented by the following chemical formula 1 or chemical formula 2.

[0126] [Chemical formula 1]

[0127]

[0128] [Chemical formula 2]

[0129]

[0130] In the above chemical formula 1 or chemical formula 2,

[0131] Y1 is O, S or CRR',

[0132] Y1' and Y2 are each independently O, S,

[0133] L is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

[0134] l is an integer from 0 to 3. When the above l is 2 or more, two or more Ls are the same or different from each other,

[0135] Ar is a substituted or unsubstituted alkyl group, -SiR”R”'R””, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group with three or more rings, a substituted or unsubstituted heteroaryl group with two or more rings containing N, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing O or S,

[0136] When Ar is a heteroaryl group, L is not directly bonded,

[0137] Ar' is a substituted or unsubstituted alkyl group, -SiR”R”'R””, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group with two or more rings containing N, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing O or S,

[0138] When Ar' is an unsubstituted phenyl group, L is not directly bonded,

[0139] R, R', R'', R''', R'''', R1 and R2 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0140] n is an integer from 0 to 8, and m and n' are each an integer from 0 to 10.

[0141] When each of m, n, and n' is 2 or more, the substituents in two or more parentheses are the same as or different from each other.

[0142] However, it does not include the structure represented by the following in Chemical Formula 1: and the structure represented by the following in Chemical Formula 2: and the case where the structure represented by is represented by Chemical Formula A'.

[0143] However, it does not include the case where the structure represented by the following in Chemical Formula 2: and the structure represented by are both represented by Chemical Formula C.

[0144] [Chemical Formula A']

[0145]

[0146] [Chemical Formula C]

[0147]

[0148] Y is the above Y1, Y1' or Y2,

[0149] representing the part connected to the nuclear structure.

[0150] In one embodiment of this specification, at least one of the structure represented by the following in Chemical Formula 1: and the structure represented by the following in Chemical Formula 2: is a compound represented by any one of the following Chemical Formulas A to C.

[0151] [Chemical Formula A]

[0152]

[0153] [Chemical Formula B]

[0154]

[0155] [Chemical Formula C]

[0156]

[0157] In the above Chemical Formulas A to C,

[0158] Y is the above Y1 or Y1',

[0159] representing the part connected to the nuclear structure.

[0160] In one embodiment of the present specification, when at least one of the above Y1' and Y2 is S, the representation of the above Chemical Formula 2 is the structure and the representation is at least one of the structures is represented by any one of the above Chemical Formulas A to C.

[0161] In one embodiment of the present specification, the above L is a direct bond; a substituted or unsubstituted arylene having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene containing O, S or N having 2 to 60 carbon atoms.

[0162] In one embodiment of the present specification, the above L is a direct bond; a substituted or unsubstituted arylene having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene containing O, S or N having 2 to 30 carbon atoms.

[0163] In one embodiment of the present specification, the above L is a direct bond; a substituted or unsubstituted arylene having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene containing O, S or N having 2 to 20 carbon atoms.

[0164] In one embodiment of the present specification, the above L is a direct bond; a substituted or unsubstituted arylene having 6 to 12 carbon atoms; or a substituted or unsubstituted heteroarylene containing O, S or N having 2 to 12 carbon atoms.

[0165] In one embodiment of the present specification, the above L is a direct bond; a substituted or unsubstituted arylene having 6 to 10 carbon atoms; or a substituted or unsubstituted heteroarylene containing O, S or N having 2 to 10 carbon atoms.

[0166] In one embodiment of the present specification, the above L is a direct bond, or a substituted or unsubstituted arylene having 6 to 60 carbon atoms.

[0167] In one embodiment of the present specification, the above L is a direct bond, or a substituted or unsubstituted arylene having 6 to 30 carbon atoms.

[0168] In one embodiment of the present specification, the above L is a direct bond, or a substituted or unsubstituted arylene having 6 to 20 carbon atoms.

[0169] In one embodiment of the present specification, the above L is a direct bond, or a substituted or unsubstituted arylene having 6 to 12 carbon atoms.

[0170] In one embodiment of the present specification, the above-mentioned L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.

[0171] In one embodiment of the present specification, the above-mentioned L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, which may be substituted by deuterium.

[0172] In one embodiment of the present specification, the above-mentioned L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, which may be substituted by deuterium.

[0173] In one embodiment of the present specification, the above-mentioned L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, which may be substituted by deuterium.

[0174] In one embodiment of the present specification, the above-mentioned L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, which may be substituted by deuterium.

[0175] In one embodiment of the present specification, the above-mentioned L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 10 carbon atoms, which may be substituted by deuterium.

[0176] In one embodiment of the present specification, the above-mentioned L is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene group.

[0177] In one embodiment of the present specification, the above-mentioned L is a direct bond, a substituted or unsubstituted phenylene group.

[0178] In one embodiment of the present specification, the above-mentioned L is a direct bond, a phenylene group which may be substituted or unsubstituted by deuterium, a biphenylene group which may be substituted or unsubstituted by deuterium, a terphenylene group which may be substituted or unsubstituted by deuterium, or a naphthylene group which may be substituted or unsubstituted by deuterium.

[0179] In one embodiment of the present specification, the above-mentioned L is a direct bond, a phenylene group which may be substituted or unsubstituted by deuterium.

[0180] In one embodiment of the present specification, the above-mentioned L is a direct bond, a phenylene group.

[0181] In one embodiment of the present specification, the above-mentioned L is a phenylene group.

[0182] In one embodiment of the present specification, l is an integer from 0 to 3.

[0183] In one embodiment of the present specification, l is 0.

[0184] In one embodiment of the present specification, l is 1.

[0185] In one embodiment of the present specification, l is 2.

[0186] In one embodiment of the present specification, l is 3.

[0187] In one embodiment of the present specification, Ar is a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 12 to 60 carbon atoms with three or more rings, a substituted or unsubstituted heteroaryl group having two or more rings containing N, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms with a single or multiple rings containing O or S.

[0188] In one embodiment of the present specification, Ar is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 12 to 30 carbon atoms with three or more rings, a substituted or unsubstituted heteroaryl group having two or more rings containing N, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms with a single or multiple rings containing O or S.

[0189] In one embodiment of the present specification, Ar is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 12 to 20 carbon atoms with three or more rings, a substituted or unsubstituted heteroaryl group having two or more rings containing N and having 2 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms with a single or multiple rings containing O or S.

[0190] In one embodiment of the present specification, Ar is a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 12 to 20 carbon atoms with three or more rings, a substituted or unsubstituted heteroaryl group having two or more rings containing N and having 2 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms with a single or multiple rings containing O or S.

[0191] In one embodiment of the present specification, Ar is a deuterium-substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a deuterium-substituted or unsubstituted silyl group, a deuterium-substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a deuterium-substituted or unsubstituted aryl group having 12 to 60 carbon atoms with three or more rings, a deuterium-substituted or unsubstituted heteroaryl group having two or more rings containing N, or a deuterium-substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms with a single or multiple rings containing O or S.

[0192] In one embodiment of the present specification, Ar is an alkyl group having 1 to 30 carbon atoms which may or may not be substituted with deuterium, a silyl group which may or may not be substituted with deuterium, a cycloalkyl group having 3 to 30 carbon atoms which may or may not be substituted with deuterium, an aryl group having 12 to 30 carbon atoms with three or more rings which may or may not be substituted with deuterium, a heteroaryl group having two or more rings containing N which may or may not be substituted with deuterium, or a heteroaryl group having a single or multiple rings containing O or S and having 2 to 30 carbon atoms which may or may not be substituted with deuterium.

[0193] In one embodiment of the present specification, Ar is an alkyl group having 1 to 20 carbon atoms which may or may not be substituted with deuterium, a silyl group which may or may not be substituted with deuterium, a cycloalkyl group having 3 to 20 carbon atoms which may or may not be substituted with deuterium, an aryl group having 12 to 20 carbon atoms with three or more rings which may or may not be substituted with deuterium, a heteroaryl group having two or more rings containing N and having 2 to 20 carbon atoms which may or may not be substituted with deuterium, or a heteroaryl group having a single or multiple rings containing O or S and having 2 to 20 carbon atoms which may or may not be substituted with deuterium.

[0194] In one embodiment of the present specification, Ar is an alkyl group having 1 to 12 carbon atoms which may or may not be substituted with deuterium, a silyl group which may or may not be substituted with deuterium, a cycloalkyl group having 3 to 12 carbon atoms which may or may not be substituted with deuterium, an aryl group having 12 to 20 carbon atoms with three or more rings which may or may not be substituted with deuterium, a heteroaryl group having two or more rings containing N and having 2 to 20 carbon atoms which may or may not be substituted with deuterium, or a heteroaryl group having a single or multiple rings containing O or S and having 2 to 20 carbon atoms which may or may not be substituted with deuterium.

[0195] In one embodiment of the present specification, Ar is a silyl group which may or may not be substituted, a heteroaryl group having two or more rings containing N and having 2 to 30 carbon atoms which may or may not be substituted, or a heteroaryl group having a single or multiple rings containing O or S and having 2 to 30 carbon atoms which may or may not be substituted.

[0196] In one embodiment of the present specification, Ar is a silyl group which may or may not be substituted, a heteroaryl group having two or more rings containing N and having 2 to 20 carbon atoms which may or may not be substituted, or a heteroaryl group having a single or multiple rings containing O or S and having 2 to 20 carbon atoms which may or may not be substituted.

[0197] In one embodiment of the present specification, Ar is a silyl group which may or may not be substituted with deuterium, a heteroaryl group having two or more rings containing N and having 2 to 30 carbon atoms which may or may not be substituted with deuterium, or a heteroaryl group having a single or multiple rings containing O or S and having 2 to 30 carbon atoms which may or may not be substituted with deuterium.

[0198] In one embodiment of the present specification, Ar is a triphenylsilyl group which may or may not be deuterium-substituted, a bicyclic or higher heteroaryl group containing N with 2 to 20 carbon atoms which may or may not be deuterium-substituted, or a monocyclic or polycyclic heteroaryl group containing O or S with 2 to 20 carbon atoms which may or may not be deuterium-substituted.

[0199] In one embodiment of the present specification, Ar is a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0200] In one embodiment of the present specification, Ar is a triphenylsilyl group which may or may not be deuterium-substituted, a carbazolyl group which may or may not be deuterium-substituted, a dibenzofuranyl group which may or may not be deuterium-substituted, or a dibenzothiophenyl group which may or may not be deuterium-substituted.

[0201] In one embodiment of the present specification, Ar' is a substituted or unsubstituted alkyl group with 1 to 60 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group with 3 to 60 carbon atoms, a substituted or unsubstituted aryl group with 6 to 60 carbon atoms, a substituted or unsubstituted bicyclic or higher heteroaryl group containing N, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing O or S with 2 to 60 carbon atoms.

[0202] In one embodiment of the present specification, Ar' is a substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group with 3 to 30 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, a substituted or unsubstituted bicyclic or higher heteroaryl group containing N, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing O or S with 2 to 30 carbon atoms.

[0203] In one embodiment of the present specification, Ar' is a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 20 carbon atoms, a substituted or unsubstituted bicyclic or higher heterocyclic aryl group containing N with 2 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic aryl group containing O or S with 2 to 20 carbon atoms.

[0204] In one embodiment of the present specification, Ar' is a substituted or unsubstituted alkyl group with 1 to 12 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted cycloalkyl group with 3 to 12 carbon atoms, a substituted or unsubstituted aryl group with 6 to 20 carbon atoms, a substituted or unsubstituted bicyclic or higher heterocyclic aryl group containing N with 2 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic aryl group containing O or S with 2 to 20 carbon atoms.

[0205] In one embodiment of the present specification, Ar' is an alkyl group having 1 to 60 carbon atoms which may or may not be substituted with deuterium, a silyl group which may or may not be substituted with deuterium, a cycloalkyl group having 3 to 60 carbon atoms which may or may not be substituted with deuterium, an aryl group having 6 to 60 carbon atoms which may or may not be substituted with deuterium, a polycyclic heteroaryl group having two or more rings containing N which may or may not be substituted with deuterium, or a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms containing O or S which may or may not be substituted with deuterium.

[0206] In one embodiment of the present specification, Ar' is an alkyl group having 1 to 30 carbon atoms which may or may not be substituted with deuterium, a silyl group which may or may not be substituted with deuterium, a cycloalkyl group having 3 to 30 carbon atoms which may or may not be substituted with deuterium, an aryl group having 6 to 30 carbon atoms which may or may not be substituted with deuterium, a polycyclic heteroaryl group having two or more rings containing N which may or may not be substituted with deuterium, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms containing O or S which may or may not be substituted with deuterium.

[0207] In one embodiment of the present specification, Ar' is an alkyl group having 1 to 20 carbon atoms which may or may not be substituted with deuterium, a silyl group which may or may not be substituted with deuterium, a cycloalkyl group having 3 to 20 carbon atoms which may or may not be substituted with deuterium, an aryl group having 6 to 20 carbon atoms which may or may not be substituted with deuterium, a polycyclic heteroaryl group having two or more rings containing N and having 2 to 20 carbon atoms which may or may not be substituted with deuterium, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms containing O or S which may or may not be substituted with deuterium.

[0208] In one embodiment of the present specification, Ar' is an alkyl group having 1 to 12 carbon atoms which may or may not be substituted with deuterium, a silyl group which may or may not be substituted with deuterium, a cycloalkyl group having 3 to 12 carbon atoms which may or may not be substituted with deuterium, an aryl group having 6 to 20 carbon atoms which may or may not be substituted with deuterium, a polycyclic heteroaryl group having two or more rings containing N and having 2 to 20 carbon atoms which may or may not be substituted with deuterium, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms containing O or S which may or may not be substituted with deuterium.

[0209] In one embodiment of the present specification, Ar' is an aryl group having 6 to 30 carbon atoms which may or may not be substituted, a silyl group which may or may not be substituted, a polycyclic heteroaryl group having two or more rings containing N and having 2 to 30 carbon atoms which may or may not be substituted, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms containing O or S which may or may not be substituted.

[0210] In one embodiment of the present specification, Ar' is an aryl group having 6 to 20 carbon atoms which may or may not be substituted, a silyl group which may or may not be substituted, a polycyclic heteroaryl group having two or more rings containing N and having 2 to 20 carbon atoms which may or may not be substituted, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms containing O or S which may or may not be substituted.

[0211] In one embodiment of the present specification, Ar' is an aryl group having 6 to 30 carbon atoms which may or may not be substituted with deuterium, a triphenylsilyl group which may or may not be substituted with deuterium, a polycyclic heteroaryl group having 2 to 30 carbon atoms containing N which may or may not be substituted with deuterium, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms containing O or S which may or may not be substituted with deuterium.

[0212] In one embodiment of the present specification, Ar' is an aryl group having 6 to 20 carbon atoms which may or may not be substituted with deuterium, a triphenylsilyl group which may or may not be substituted with deuterium, a polycyclic heteroaryl group having 2 to 20 carbon atoms containing N which may or may not be substituted with deuterium, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms containing O or S which may or may not be substituted with deuterium.

[0213] In one embodiment of the present specification, Ar' is an aryl group having 6 to 12 carbon atoms which may or may not be substituted with deuterium, a triphenylsilyl group which may or may not be substituted with deuterium, a polycyclic heteroaryl group having 2 to 20 carbon atoms containing N which may or may not be substituted with deuterium, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms containing O or S which may or may not be substituted with deuterium.

[0214] In one embodiment of the present specification, Ar' is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0215] In one embodiment of the present specification, Ar' is a phenyl group which may or may not be substituted with deuterium, a biphenyl group which may or may not be substituted with deuterium, a triphenylsilyl group which may or may not be substituted with deuterium, a carbazolyl group which may or may not be substituted with deuterium, a dibenzofuranyl group which may or may not be substituted with deuterium, or a dibenzothiophenyl group which may or may not be substituted with deuterium.

[0216] In one embodiment of the present specification, R”, R”' and R”” are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0217] In one embodiment of the present specification, R”, R”' and R”” are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0218] In one embodiment of the present specification, R”, R”' and R”” are the same as or different from each other, and each independently is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0219] In one embodiment of the present specification, R″, R″′, and R″″ are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group.

[0220] In one embodiment of the present specification, R″, R″′, and R″″ are the same as or different from each other, and each independently is a phenyl group which is substituted or unsubstituted with deuterium.

[0221] In one embodiment of the present specification, R″, R″′, and R″″ are phenyl groups.

[0222] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0223] In one embodiment of the present specification, R, R′, R″, R″′, R″″, R1, and R2 are the same as or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0224] In one embodiment of the present specification, R, R′, R″, R″′, R″″, R1, and R2 are the same as or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0225] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently is hydrogen or deuterium.

[0226] In one embodiment of the present specification, R1 and R2 are hydrogen.

[0227] In one embodiment of the present specification, n is an integer from 0 to 8.

[0228] In one embodiment of the present specification, n is 0.

[0229] In one embodiment of the present specification, n is 1.

[0230] In one embodiment of the present specification, n is 2.

[0231] In one embodiment of the present specification, n is 3.

[0232] In one embodiment of the present specification, n is 4.

[0233] In one embodiment of the present specification, n is 5.

[0234] In one embodiment of the present specification, n is 6.

[0235] In one embodiment of the present specification, n is 7.

[0236] In one embodiment of the present specification, n is 8.

[0237] In one embodiment of the present specification, m and n' are each integers from 0 to 10.

[0238] In one embodiment of the present specification, m is 0.

[0239] In one embodiment of the present specification, m is 1.

[0240] In one embodiment of the present specification, m is 2.

[0241] In one embodiment of the present specification, m is 3.

[0242] In one embodiment of the present specification, m is 4.

[0243] In one embodiment of the present specification, m is 5.

[0244] In one embodiment of the present specification, m is 6.

[0245] In one embodiment of the present specification, m is 7.

[0246] In one embodiment of the present specification, m is 8.

[0247] In one embodiment of the present specification, m is 9.

[0248] In one embodiment of the present specification, m is 10.

[0249] In one embodiment of the present specification, n' is 0.

[0250] In one embodiment of the present specification, n' is 1.

[0251] In one embodiment of the present specification, n' is 2.

[0252] In one embodiment of the present specification, n' is 3.

[0253] In one embodiment of the present specification, n' is 4.

[0254] In one embodiment of the present specification, n' is 5.

[0255] In one embodiment of the present specification, n' is 6.

[0256] In one embodiment of the present specification, n' is 7.

[0257] In one embodiment of the present specification, n' is 8.

[0258] In one embodiment of the present specification, the compound represented by the above Chemical Formula 11 is deuterium-substituted by at least 40%. In another embodiment, the compound represented by the above Chemical Formula 11 is deuterium-substituted by more than 50%. In another embodiment, the compound represented by the above Chemical Formula 11 is deuterium-substituted by more than 60%. In another embodiment, the compound represented by the above Chemical Formula 11 is deuterium-substituted by more than 70%. In another embodiment, the compound represented by the above Chemical Formula 11 is deuterium-substituted by more than 80%. In another embodiment, the compound represented by the above Chemical Formula 11 is deuterium-substituted by more than 90%. In another embodiment, the compound represented by the above Chemical Formula 11 is deuterium-substituted by 100%.

[0259] In one embodiment of the present specification, the compound represented by the above Chemical Formula 11 contains 40% to 60% of deuterium. In another embodiment, the compound represented by the above Chemical Formula 11 contains 40% to 80% of deuterium. In another embodiment, the compound represented by the above Chemical Formula 11 contains 60% to 80% of deuterium. In another embodiment, the compound represented by the above Chemical Formula 11 contains 80% to 100% of deuterium.

[0260] In one embodiment of the present specification, the above Rs are the same as or different from each other and each independently may be deuterium-substituted.

[0261] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following compounds.

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275] In one embodiment of the present specification, the above chemical formula 2 is represented by any one of the following compounds.

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313] According to an embodiment of the present specification, the compound represented by Chemical Formula 11 can produce a nuclear structure by the method of the following synthesis example. The substituents can be combined by methods known in the art, and the type, position, or number of substituents can be changed according to techniques known in the art.

[0314] In the present specification, by introducing various substituents into the nuclear structure of the compound represented by Chemical Formula 11, compounds with various band gaps can be synthesized. In addition, in the present specification, by introducing various substituents into the nuclear structure of the above-described structure, the HOMO and LUMO energy levels of the compound can also be adjusted.

[0315] In addition, the present specification provides an organic light-emitting device including the above-mentioned compound.

[0316] The organic light-emitting device according to the present specification is characterized by including: an anode, a cathode, and one or more organic layers provided between the anode and the cathode, and one or more of the organic layers contain the compound represented by Chemical Formula 11.

[0317] The organic light-emitting device of this specification forms an organic layer using the compound of Chemical Formula 1 described above. In addition, it can be manufactured using the manufacturing methods and materials of ordinary organic light-emitting devices.

[0318] When manufacturing the organic light-emitting device, the above-mentioned compound can be formed into an organic layer not only by vacuum evaporation but also by solution coating. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

[0319] The organic layer of the organic light-emitting device of this specification can be formed in a single-layer structure or a multilayer structure with two or more stacked organic layers. For example, the organic light-emitting device of the present invention can have a structure including one or more of a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as the organic layer. However, the structure of the organic light-emitting device of this specification is not limited thereto and can include a smaller or larger number of organic layers.

[0320] In the organic light-emitting device of this specification, the above-mentioned organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may contain the compound represented by Chemical Formula 11 above.

[0321] In the organic light-emitting device of this specification, the above-mentioned organic layer includes a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may contain the compound represented by Chemical Formula 11 above.

[0322] In one embodiment of this specification, the above-mentioned organic layer includes an electron injection layer, an electron transport layer, an electron injection and transport layer, or a hole blocking layer, and the electron injection layer, the electron transport layer, the electron injection and transport layer, or the hole blocking layer may contain the compound represented by Chemical Formula 11 above.

[0323] In the organic light-emitting device of this specification, the above-mentioned 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 Chemical Formula 11 above.

[0324] In one embodiment of this specification, the above-mentioned organic layer includes an electron adjustment layer, and the electron adjustment layer may contain the compound represented by Chemical Formula 11 above.

[0325] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound represented by Chemical Formula 11 above.

[0326] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound represented by Chemical Formula 11 above as a host.

[0327] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound represented by Chemical Formula 11 above as a blue host.

[0328] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound represented by Chemical Formula 11 above as a dopant.

[0329] In one embodiment of the present specification, the organic light-emitting device is a green organic light-emitting device in which the light-emitting layer contains the compound represented by Chemical Formula 11 above as a host.

[0330] According to one embodiment of the present specification, the organic light-emitting device is a red organic light-emitting device in which the light-emitting layer contains the compound represented by Chemical Formula 11 above as a host.

[0331] In another embodiment, the organic light-emitting device is a blue organic light-emitting device in which the light-emitting layer contains the compound represented by Chemical Formula 11 above as a host.

[0332] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer contains the compound represented by Chemical Formula 11 above as a host, and may further contain a dopant. At this time, based on 100 parts by weight of the host, the content of the dopant may include 1 part by weight to 60 parts by weight, preferably, 1 part by weight to 10 parts by weight.

[0333] At this time, as the dopant, a phosphorescent substance such as (4,6-F2ppy)2Irpic can be used; or a fluorescent substance such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymer, PPV-based polymer, anthracene-based compound, pyrene-based compound, boron-based compound, etc., but not limited thereto.

[0334] In another embodiment, in addition to the compound represented by Chemical Formula 11 above, the organic layer may further contain other organic compounds, metals or metal compounds.

[0335] In an organic light-emitting device according to an embodiment of the present specification, the light-emitting layer further includes a fluorescent dopant or a phosphorescent dopant. At this time, relative to 100 parts by weight of the host, the dopant in the light-emitting layer contains 1 part by weight to 50 parts by weight.

[0336] In an embodiment of the present specification, the thickness of the organic layer containing the compound represented by Chemical Formula 11 is to According to one example, it is to According to another example, it is to

[0337] In an organic light-emitting device according to an embodiment of the present specification, the maximum emission peak of the organic layer is 400 nm to 500 nm. In another embodiment, the maximum emission peak of the organic layer is 400 nm to 470 nm.

[0338] As another example, the organic layer includes a light-emitting layer, the light-emitting layer contains the compound represented by Chemical Formula 11 as a host, and may further include another host.

[0339] According to an embodiment of the present specification, the dopant is a metal coordination compound.

[0340] According to an embodiment of the present specification, the dopant is a platinum coordination compound.

[0341] According to an embodiment of the present specification, the dopant is an iridium coordination compound.

[0342] According to an embodiment of the present specification, the dopant is the following Chemical Formula D-1 or D-2, but is not limited thereto.

[0343] [Chemical Formula D-1]

[0344]

[0345] [Chemical Formula D-2]

[0346]

[0347] In Chemical Formulas D-1 and D-2 above,

[0348] M is a transition metal,

[0349] A1, A3, A5, A6, K1, K2, and K3 are the same as or different from each other, and each independently is a direct bond, O, S, a divalent ester group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted divalent alkenyl group, a substituted or unsubstituted divalent allyl group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0350] A2 and A4 are the same as or different from each other, and each independently is a direct bond, N, a substituted or unsubstituted trivalent alkylene group, a substituted or unsubstituted trivalent aryl group, or a substituted or unsubstituted trivalent heteroaryl group.

[0351] n is 1 or 2. When n is 2, the structures in the parentheses are the same as or different from each other.

[0352] According to an embodiment of this specification, M above is iridium or platinum.

[0353] According to an embodiment of this specification, the above dopant can be selected from the following structural formulas, but is not limited thereto.

[0354]

[0355]

[0356]

[0357]

[0358] In an embodiment of this specification, the light-emitting layer containing the compound represented by the above Chemical Formula 11 is blue.

[0359] According to an example, based on 100 parts by weight of the sum of the host and dopant of the light-emitting layer, the content of the compound represented by the above Chemical Formula 11 is 70 to 99.99 parts by weight, preferably 80 to 99.9 parts by weight, and more preferably 90 to 99.5 parts by weight.

[0360] In an embodiment of this specification, the above organic layer contains the above compound, and the band gap energy of the above compound is 2.9 eV or more.

[0361] The organic light-emitting device of this specification may further include one or more organic layers such as 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 transport and injection layer.

[0362] In an embodiment of this specification, the above organic light-emitting device may further include one or more of an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer between the cathode and the light-emitting layer.

[0363] In one embodiment of the present specification, the above-described organic light-emitting device includes an anode, a cathode, and two or more organic layers disposed between the anode and the cathode, and at least one of the two or more organic layers contains a compound represented by Chemical Formula 11.

[0364] In one embodiment of the present specification, two or more of the above-described organic layers may be selected from the group consisting of a light-emitting layer, a hole-transporting layer, a hole-injecting layer, a hole-transporting and injecting layer, and an electron-blocking layer.

[0365] In one embodiment of the present specification, two or more of the above-described organic layers may be selected from the group consisting of a light-emitting layer, an electron-transporting layer, an electron-injecting layer, an electron-transporting and injecting layer, an electron-modulating layer, and a hole-blocking layer.

[0366] In one embodiment of the present specification, the above-described organic layer includes two or more light-emitting layers, and at least one of the two or more light-emitting layers contains a compound represented by Chemical Formula 11. Specifically, in one embodiment of the present specification, the compound represented by Chemical Formula 11 may be contained in one of the two or more light-emitting layers or in each of the two or more light-emitting layers.

[0367] In one embodiment of the present specification, the above-described organic layer includes two or more electron-transporting layers, and at least one of the two or more electron-transporting layers contains a compound represented by Chemical Formula 11. Specifically, in one embodiment of the present specification, the compound represented by Chemical Formula 11 may be contained in one of the two or more electron-transporting layers or in each of the two or more electron-transporting layers.

[0368] In addition, in one embodiment of the present specification, when the above-described compound is contained in each of the two or more electron-transporting layers, materials other than the compound represented by Chemical Formula 11 may be the same as or different from each other.

[0369] When the organic layer containing the compound represented by Chemical Formula 11 is an electron-transporting layer, the electron-transporting layer may further contain an n-type dopant. The n-type dopant may be a material known in the art. For example, a metal or a metal complex may be used. For example, the electron-transporting layer containing the compound represented by Chemical Formula 11 may further contain LiQ (Lithium Quinolate).

[0370] 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 contains the compound represented by Chemical Formula 11. Specifically, in one embodiment of the present specification, the compound represented by Chemical Formula 11 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.

[0371] In addition, in one embodiment of the present specification, when the compound represented by Chemical Formula 11 is included in each of the two or more hole transport layers, the other materials except the compound represented by Chemical Formula 11 may be the same or different from each other.

[0372] In one embodiment of the present specification, in addition to the organic layer containing the compound represented by Chemical Formula 11, the organic layer may further include a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer contains a compound containing an arylamino group, a carbazolyl group, or a benzocarbazolyl group.

[0373] In one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0374] In one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device having an inverted structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0375] In the organic light-emitting device of the present invention, the organic layer may include an electron blocking layer, and the electron blocking layer may use materials known in the art.

[0376] For example, the organic light-emitting device may have a stacked structure as shown below, but is not limited thereto.

[0377] (1) Anode / Hole Transport Layer / Light-Emitting Layer / Cathode

[0378] (2) Anode / Hole Injection Layer / Hole Transport Layer / Light-Emitting Layer / Cathode

[0379] (3) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light-Emitting Layer / Cathode

[0380] (4) Anode / Hole Transport Layer / Light-Emitting Layer / Electron Transport Layer / Cathode

[0381] (5) Anode / Hole Transport Layer / Light-Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0382] (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0383] (7) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0384] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0385] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0386] (10) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0387] (11) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0388] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0389] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0390] (14) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0391] (15) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0392] (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0393] (17) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0394] (18) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0395] The structure of the organic light-emitting device described in this specification may have a structure as Figures 1 to 3 shown, but is not limited thereto.

[0396] Figure 1 An example of an organic light-emitting device in which a substrate 1, an anode 2, an organic layer 12, and a cathode 10 are sequentially stacked is illustrated. In the structure described above, the above compound may be included in the above organic layer 12.

[0397] Figure 2 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 stacked in sequence is illustrated. In the structure described above, the above compound may be included in the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light-emitting layer 6, the hole blocking layer 7, the electron transport layer 8, or the electron injection layer 9.

[0398] Figure 3 An example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 11, and a cathode 10 are stacked in sequence is illustrated. In the structure described above, the above compound may be included in the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light-emitting layer 6, the hole blocking layer 7, or the electron injection and transport layer 11.

[0399] For example, an organic light-emitting device according to this specification can be manufactured as follows: using a PVD (physical vapor deposition) method such as sputtering or 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, an electron 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 for manufacturing. 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.

[0400] The above 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 transport and injection layer.

[0401] The above organic layer may be a multilayer structure including a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, a light-emitting layer, and an electron transport layer, an electron injection layer, an electron injection and transport layer, etc., but is not limited thereto, and may also be a single-layer structure. In addition, the above organic layer may use various polymer materials and be manufactured into a smaller number of layers by a solvent process other than the evaporation method, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer printing.

[0402] The above-mentioned anode is a hole-injecting electrode. As the anode material, generally, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferred. Specific examples of the anode material 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 zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but not limited thereto.

[0403] The above-mentioned cathode is an electron-injecting electrode. As the cathode material, generally, in order to enable electrons to be easily injected into the organic layer, a material with a small work function is preferred. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but not limited thereto.

[0404] The above-mentioned hole injection layer is a layer that plays a role in facilitating the injection of holes from the anode to the light-emitting layer. The hole injection material is a material that can well receive holes from the anode at a low voltage. 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. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic compounds, hexanitrile hexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinone, and conductive polymers such as polyaniline and polythiophene, etc., but not limited thereto. The thickness of the hole injection layer can be from 1 nm to 150 nm. When the thickness of the above-mentioned hole injection layer is 1 nm or more, it has the advantage of preventing the reduction of hole injection characteristics. When it is 150 nm or less, it has the advantage of preventing the driving voltage from rising in order to improve the hole migration when the thickness of the hole injection layer is too thick.

[0405] In one embodiment of the present specification, the above-mentioned hole injection layer may contain one or more of the following compounds: an N-containing polycyclic compound containing a cyano group or an amine compound containing a carbazolyl group. At this time, the above-mentioned N-containing polycyclic compound may be 1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (HATCN). According to an example, the hole transport layer may contain the above-mentioned compound alone, or may contain two or more of the above-mentioned compounds. According to another example, the above-mentioned HATCN may be vapor-deposited to be used as the first hole transport layer, and on the above-mentioned first hole transport layer, the above-mentioned amine compound containing a carbazolyl group may be vapor-deposited to be used as the second hole transport layer.

[0406] The above-mentioned hole transport layer can play a role in facilitating the transport of holes. A 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, and a material with a large hole mobility is suitable. As specific examples, there are arylamine-based organic compounds, conductive polymers, and block copolymers having both a conjugated part and a non-conjugated part, etc., but not limited thereto.

[0407] In one embodiment of the present specification, the above-mentioned hole transport layer may contain an amine compound containing a carbazolyl group.

[0408] A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, and may contain materials known in the art for hole injection or transport.

[0409] The above-mentioned electron blocking layer is a layer that adjusts the overall performance of the device by preventing electrons from the light-emitting layer from flowing into the anode and regulating the flow of holes flowing into the light-emitting layer. As the above-mentioned electron blocking material, a compound is preferably used: a compound that prevents the inflow of electrons from the light-emitting layer to the anode and has the ability to regulate the flow of the injected holes for the light-emitting layer or the light-emitting material. In one embodiment, an arylamine-based organic compound may be used as the electron blocking layer, but it is not limited thereto.

[0410] In one embodiment of the present specification, the above-mentioned electron blocking layer may contain an amine compound containing a carbazolyl group. According to an example, the above-mentioned compound may be a compound in which a carbazolyl group and an amino group are connected by an o-biphenylene group.

[0411] The above-mentioned light-emitting layer can emit red, green, or blue light and can be formed of a phosphorescent substance or a fluorescent substance. The above-mentioned light-emitting substance is a substance capable of receiving holes and electrons from a hole transport layer and an electron transport layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having a high quantum efficiency for fluorescence or phosphorescence. As a specific example, there is the compound of Chemical Formula 1 described above; tris(8-hydroxyquinoline)aluminum (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo azole, benzothiazole, and benzimidazole-based compounds; poly(p-phenylene vinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited thereto.

[0412] As the host material of the light-emitting layer, there are aromatic condensed ring derivatives or heterocyclic-containing compounds, etc. Specifically, as the aromatic condensed ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as the heterocyclic-containing compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds pyrimidine derivatives, etc., but are not limited thereto.

[0413] When the light-emitting layer emits red light, as the light-emitting dopant, phosphorescent materials such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), etc. can be used; or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum), etc., but not limited thereto. When the light-emitting layer emits green light, as the light-emitting dopant, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium), etc. or fluorescent materials such as Alq3(tris(8-hydroxyquinoline)aluminum), etc. can be used, but not limited thereto. When the light-emitting layer emits blue light, as the light-emitting dopant, phosphorescent materials such as (4,6-F2ppy)2Irpic, etc. can be used; or fluorescent materials such as spiro-DPVBi, spiro-6P, divinylbenzene(DSB), divinylarylene(DSA), PFO-based polymer, PPV-based polymer, etc., but not limited thereto.

[0414] In one embodiment of the present specification, the above light-emitting layer contains the compound according to the present invention as the host, and may contain a pyrene compound substituted with an amino group or a polycyclic compound containing boron as the dopant. The above host and dopant may be contained in a suitable weight ratio. According to an example, the above host and dopant may each be contained in a weight ratio of 100:1 to 100:10.

[0415] The above hole blocking layer is a layer that adjusts the overall performance of the device by blocking the holes from the light-emitting layer from flowing into the cathode and adjusting the electrons flowing into the light-emitting layer. As the hole blocking material, the following compounds are preferably used: compounds that prevent the inflow of holes from the light-emitting layer to the cathode and have the ability to adjust the injected electrons for the light-emitting layer or the light-emitting material. As the hole blocking material, a suitable material can be used according to the composition of the organic substances used in the device. Specifically, there are diazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., but not limited thereto.

[0416] In one embodiment of the present specification, the above-mentioned hole blocking layer may include a compound as described below: a compound in which a nitrogen-containing ring structure is directly or through a linking group connected to a spirofluorene xanthene (spiro[fluorene-9,9'-xanthene]) structure.

[0417] The above-mentioned electron transport layer can play a role in facilitating the transport of electrons. The electron transport material is a material that can receive electrons well from the cathode and transfer them to the light-emitting layer, and a material with a large electron mobility is suitable. As specific examples, there are the compounds mentioned above or an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic radical compound, a hydroxyflavone-metal complex, etc., but not limited thereto. 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 reduction of electron transport characteristics. When it is 50 nm or less, it has the advantage of preventing the driving voltage from rising for improving the electron migration when the thickness of the electron transport layer is too thick.

[0418] In one embodiment of the present specification, the above-mentioned electron transport layer may include a compound containing a nitrogen-containing ring and CN, and may also include an n-type dopant or an organometallic compound. According to an example, the above-mentioned n-type dopant or organometallic compound may be LiQ, and may contain the compound represented by Chemical Formula 11 of the present invention and the above-mentioned n-type dopant (or organometallic compound) in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.

[0419] The above-mentioned electron injection layer can play a role in facilitating the injection of electrons. As the electron injection material, preferably the following compounds: having the ability to transport electrons, having the effect of injecting electrons from the cathode, having an excellent electron injection effect on the light-emitting layer or the light-emitting material, preventing excitons generated in the light-emitting layer from migrating to the hole injection layer, and having excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, biphenylquinone, thiopyran dioxide, oxazole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluoreneylidene methane, anthrone, etc. and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, etc., but not limited thereto.

[0420] In one embodiment of the present specification, the above-mentioned electron injection layer may include lithium fluoride (LiF).

[0421] Examples of the above metal coordination compounds include lithium 8-hydroxyquinolate, zinc bis(8-hydroxyquinolate), copper bis(8-hydroxyquinolate), manganese bis(8-hydroxyquinolate), aluminum tris(8-hydroxyquinolate), aluminum tris(2-methyl-8-hydroxyquinolate), gallium tris(8-hydroxyquinolate), beryllium bis(10-hydroxybenzo[h]quinolate), zinc bis(10-hydroxybenzo[h]quinolate), gallium bis(2-methyl-8-quinolate) chloride, gallium bis(2-methyl-8-quinolate)(o-cresol), aluminum bis(2-methyl-8-quinolate)(1-naphthol), gallium bis(2-methyl-8-quinolate)(2-naphthol), etc., but are not limited thereto.

[0422] Depending on the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a bi-directional emitting type.

[0423] The organic light-emitting device according to the present specification can be used by being included in various electronic devices. For example, the above electronic devices can be a display panel, a touch panel, a solar module, a lighting device, etc., but are not limited thereto.

[0424] Hereinafter, in order to specifically describe the present specification, examples will be given and described in detail. However, the examples according to the present specification can be deformed into various different forms, and the scope of the present application is not construed as being limited to the examples described in detail below. The examples of the present application are provided to more completely describe the present specification to those skilled in the art.

[0425] Synthesis Example 1: Synthesis of Compound 2

[0426] Step 1) Synthesis of Intermediate 1-1

[0427]

[0428] Under a nitrogen atmosphere, 5H-benzofuro[3,2-c]carbazole-1,2,3,4,6,7,8,9,10,11-d10 (15 g, 56.1 mmol) and 9-(4,6-dichloro-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (21.8 g, 67.3 mmol) were added to 300 ml of dimethylacetamide and stirred. Then, potassium carbonate (23.3 g, 168.3 mmol) was added and stirred at 50 °C. After reacting for 2 hours, it was cooled to room temperature. After the organic layer was filtered to remove salts, the filtered organic layer was distilled. It was redissolved by adding it again to 311 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a yellow solid compound 1-1 (23 g, 74%, MS: [M+H] + = 555.1).

[0429] Step 2) Synthesis of Compound 1

[0430]

[0431] Under a nitrogen atmosphere, 1-1 (20 g, 36.1 mmol) and 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl-3,4,5,6-d4)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (13.8 g, 36.1 mmol) were added to 400 ml of tetrahydrofuran, and the mixture was stirred and refluxed. Then, potassium carbonate (15 g, 108.3 mmol) was dissolved in 45 ml of water and added. After thorough stirring, tetrakis(triphenylphosphine)palladium (1.3 g, 1.1 mmol) was added. After reacting for 6 hours, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 558 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 1 (18.7 g, 67%, MS: [M+H] + = 774).

[0432] Synthesis Example 2: Synthesis of Compound 2

[0433] Step 1) Synthesis of Intermediate 2-1

[0434]

[0435] Under a nitrogen atmosphere, 12H-benzofuro[3,2-a]carbazole (15 g, 58.3 mmol) and 9-(4,6-dichloro-1,3,5-triazin-2-yl)-9H-carbazole (22 g, 70 mmol) were added to 300 ml of dimethylacetamide and stirred. Then, potassium carbonate (24.2 g, 174.9 mmol) was added and stirred at 50 °C. After reacting for 1 hour, the reaction mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. It was dissolved again in 312 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a yellow solid compound 2-1 (21.6 g, 69%, MS: [M+H] + = 537).

[0436] Step 2) Synthesis of Compound 2

[0437]

[0438] Under a nitrogen atmosphere, 2-1 (20 g, 37.3 mmol) and 2-(3-(dibenzo[b,d]furan-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13.8 g, 37.3 mmol

[0439] ) were added to 400 ml of tetrahydrofuran, and the mixture was stirred and refluxed. Then, potassium carbonate (15.5 g, 111.9 mmol) was dissolved in 45 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (1.3 g, 1.1 mmol) was added. After reacting for 8 hours, it was cooled to room temperature, and the resulting solid was filtered. The solid was added to 555 mL of chloroform to dissolve it, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 2 (16.7 g, 60%, MS: [M+H] + = 744.8).

[0440] Synthesis Example 3: Synthesis of Compound 3

[0441] Step 1) Synthesis of Intermediate 3-1

[0442]

[0443] Under a nitrogen atmosphere, 7H-benzo[4,5]thieno[2,3-b]carbazole (15 g, 54.9 mmol) and 9-(4,6-dichloro-1,3,5-triazin-2-yl)-9H-carbazole (20.8 g, 65.8 mmol) were added to 300 ml of dimethylacetamide and stirred. Then, potassium carbonate (22.8 g, 164.6 mmol) was added and stirred at 50 °C. After reacting for 1 hour, it was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. It was added again to 303 mL of chloroform to dissolve it, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a yellow solid compound 3-1 (18.2 g, 60%, MS: [M+H]+ = 553.1).

[0444] Step 2) Synthesis of Compound 3

[0445]

[0446] Under a nitrogen atmosphere, 3-1 (20 g, 36.2 mmol) and 2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (14 g, 36.2 mmol) were added to 400 ml of tetrahydrofuran, and the mixture was stirred and refluxed. Then, potassium carbonate (15 g, 108.7 mmol) was dissolved in 45 ml of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium (1.3 g, 1.1 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 562 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give a white solid compound 3 (14.9 g, 53%, MS: [M+H] + = 777).

[0447] Synthesis Example 4: Synthesis of Compound 4

[0448] Step 1) Synthesis of Intermediate 4-1

[0449]

[0450] Under a nitrogen atmosphere, 5H-benzo[f]chromeno[3,2-c]carbazole (15 g, 58.3 mmol) and 9-(4,6-dichloro-1,3,5-triazin-2-yl)-9H-carbazole (22 g, 70 mmol) were added to 300 ml of dimethylacetamide and stirred. Then, potassium carbonate (24.2 g, 174.9 mmol) was added and stirred at 50 °C. After reacting for 1 hour, the reaction mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. It was redissolved in 312 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to give a yellow solid compound 4-1 (16.2 g, 52%, MS: [M+H] + = 537).

[0451] Step 2) Synthesis of Compound 4

[0452]

[0453] Under a nitrogen atmosphere, 4-1 (20 g, 37.3 mmol) and triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (17.3 g, 37.3 mmol) were added to 400 ml of tetrahydrofuran, and the mixture was stirred and refluxed. Then, potassium carbonate (15.5 g, 111.9 mmol) was dissolved in 45 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (1.3 g, 1.1 mmol) was added. After reacting for 10 hours, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 624 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 4 (17.8 g, 57%, MS: [M+H] + = 837).

[0454] Synthesis Example 5: Synthesis of Compound 5

[0455] Step 1) Synthesis of Intermediate 5-1

[0456]

[0457] Under a nitrogen atmosphere, 7H-benzofuro[2,3-b]carbazole (15 g, 58.3 mmol) and 9-(4,6-dichloro-1,3,5-triazin-2-yl)-9H-carbazole (22 g, 70 mmol) were added to 300 ml of dimethylacetamide and stirred. Then, potassium carbonate (24.2 g, 174.9 mmol) was added and stirred at 50 °C. After reacting for 4 hours, the reaction mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. It was redissolved in 10 times 312 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a yellow solid compound 5-1 (15.6 g, 50%, MS: [M+H] + = 537).

[0458] Step 2) Synthesis of Compound 5

[0459]

[0460] Under a nitrogen atmosphere, 5-1 (20 g, 37.3 mmol) and 2-([1,1':3',1”-terphenyl]-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13.3 g, 37.3 mmol) were added to 400 ml of tetrahydrofuran, and the mixture was stirred and refluxed. Then, potassium carbonate (15.5 g, 111.9 mmol) was dissolved in 45 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (1.3 g, 1.1 mmol) was added. After reacting for 9 hours, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 545 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 5 (18.8 g, 69%, MS: [M+H] + = 730.8).

[0461] Synthesis Example 6: Synthesis of Compound 6

[0462] Step 1) Synthesis of Intermediate 6-1

[0463]

[0464] Under a nitrogen atmosphere, 5H-benzofuro[3,2-c]carbazole-1,2,3,4,6,7,8,9,10,11-d10 (15 g, 56.1 mmol) and 5-(4,6-dichloro-1,3,5-triazin-2-yl)-5H-benzofuro[3,2-c]carbazole-1,2,3,4,6,7,8,9,10,11-d10 (28 g, 67.3 mmol) were added to 300 ml of dimethylacetamide and stirred. Then, potassium carbonate (23.3 g, 168.3 mmol) was added and stirred at 50 °C. After reacting for 4 hours, it was cooled to room temperature. The organic layer was filtered to remove salts, and then the filtered organic layer was distilled. It was redissolved in 363 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a yellow solid compound 6-1 (22.1 g, 61%, MS: [M+H] + = 647.2).

[0465] Step 2) Synthesis of Compound 6

[0466]

[0467] Under a nitrogen atmosphere, 6-1 (20 g, 31 mmol) and 2-(3-(dibenz o[b,d]thiophen-4-yl-d7)phenyl-2,4,5,6-d4)-4,4,5,5-tetramethyl-1,3,2-dioxabor olane (12.3 g, 31 mmol) were added to 400 ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (12.8 g, 92.9 mmol) was dissolved in 40 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (1.1 g, 0.9 mmol) was added. After reacting for 10 hours, it was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 545 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 6 (17.2 g, 63%, MS: [M+H] += 882.2).

[0468] Synthesis Example 7: Synthesis of Compound 7

[0469] Step 1) Synthesis of Intermediate 7-1

[0470]

[0471] Under a nitrogen atmosphere, 7H-benzo[f]chromeno[3,2-b]carbazole (15 g, 58.3 mmol) and 7-(4,6-dichloro-1,3,5-triazin-2-yl)-7H-benzo[4,5]thieno[2,3-b]carbazole (29.5 g, 70 mmol) were added to 300 ml of dimethylacetamide and stirred. Then, potassium carbonate (24.2 g, 174.9 mmol) was added and stirred at 50 °C. After reacting for 4 hours, it was cooled to room temperature. After the organic layer was filtered to remove salts, the filtered organic layer was distilled. It was redissolved in 374 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a yellow solid compound 7-1 (28.8 g, 77%, MS: [M+H] + = 643.1).

[0472] Step 2) Synthesis of Compound 7

[0473]

[0474] Under a nitrogen atmosphere, 7-1 (20 g, 31.1 mmol) and triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (14.4 g, 31.1 mmol) were added to 400 ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (12.9 g, 93.4 mmol) was dissolved in 40 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (1.1 g, 0.9 mmol) was added. After reacting for 9 hours, it was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 587 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 7 (17 g, 58%, MS: [M+H] + = 943.2).

[0475] Synthesis Example 8: Synthesis of Compound 8

[0476] Step 1) Synthesis of intermediate 8-1

[0477]

[0478] Under nitrogen atmosphere, 12H-benzofurano[3,2-a]carbazole (15 g, 58.3 mmol) and 12-(4,6-dichloro-1,3,5-triazin-2-yl)-12H-benzo[4,5]thieno[3,2-a]carbazole (29.5 g, 70 mmol) were added to 300 ml of dimethylacetamide and stirred. Then, potassium carbonate (24.2 g, 174.9 mmol) was added and stirred at 50°C. After reacting for 1 hour, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. The mixture was again put into 374 mL of chloroform to dissolve, washed with water twice, and then the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a yellow solid compound 8-1 (25.1 g, 67%, MS: [M+H] + =643.1).

[0479] Step 2) Synthesis of Compound 8

[0480]

[0481] Under a nitrogen atmosphere, 8-1 (20 g, 31.1 mmol) and 2-(2-(dibenzo[b,d]thiophen-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (12 g, 31.1 mmol) were added to 400 ml of tetrahydrofuran, and the mixture was stirred and refluxed. Then, potassium carbonate (12.9 g, 93.4 mmol) was dissolved in 40 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (1.1 g, 0.9 mmol) was added. After reacting for 7 hours, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 539 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 8 (20 g, 74%, MS: [M+H] + = 867).

[0482] Synthesis Example 9: Synthesis of Compound 9

[0483] Step 1) Synthesis of Intermediate 9-1

[0484]

[0485] Under a nitrogen atmosphere, 5H-benzofuro[3,2-c]carbazole (15 g, 58.3 mmol) and 9-(4,6-dichloro-1,3,5-triazin-2-yl)-9H-carbazole (22 g, 70 mmol) were added to 300 ml of dimethylacetamide and stirred. Then, potassium carbonate (23.3 g, 168.3 mmol) was added and stirred at 50 °C. After reacting for 2 hours, the reaction mixture was cooled to room temperature, the organic layer was filtered to remove salts, and the filtered organic layer was distilled. It was redissolved in 311 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a yellow solid compound 9-1 (22.5 g, 72%, MS: [M+H] + = 537).

[0486] Step 2) Synthesis of Compound 9

[0487]

[0488] Under a nitrogen atmosphere, 9-1 (20 g, 37.3 mmol) and 9-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (13.8 g, 37.3 mmol) were added to 400 ml of tetrahydrofuran, and the mixture was stirred and refluxed. Then, potassium carbonate (15.5 g, 111.9 mmol) was dissolved in 45 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (1.3 g, 1.1 mmol) was added. After reacting for 6 hours, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 558 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 9 (19.7 g, 71%, MS: [M+H] + = 743.8).

[0489] Example 1-1

[0490] An ITO (indium tin oxide) glass substrate coated with a thin film with a thickness of was placed in distilled water containing a detergent and washed using ultrasonic waves. At this time, the detergent used was a product of Fischer Co., and the distilled water used was distilled water filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed with solvents of isopropanol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, using oxygen plasma, the above substrate was cleaned for 5 minutes, and then the substrate was transported to a vacuum evaporator.

[0491] On the thus-prepared ITO transparent electrode as the anode, the following compounds HT1 and the following compound HI1 were thermally vacuum-evaporated in a ratio of 98:2 (molar ratio) to form a hole injection layer with a thickness of . On the above hole injection layer, the compound represented by the following chemical formula HT1 was vacuum-evaporated to form a hole transport layer. Then, on the above hole transport layer, with a film thickness of The compound of BH (p-type) is vacuum-evaporated to form an electron blocking layer. Then, on the above electron blocking layer, a compound obtained by mixing the following chemical formula BH (p-type), which is the host of the light-emitting layer, and the compound represented by Compound 1 synthesized in the above Synthesis Example 1 (n-type) at a ratio of 1:1, and a compound represented by the following chemical formula BD, which is a dopant of the light-emitting layer, are vacuum-evaporated at a weight ratio of 88:12 to form a light-emitting layer. On the above light-emitting layer, a hole blocking layer is formed by evaporating the compound represented by the following chemical formula HB1. Then, on the above hole blocking layer, the compound represented by the following chemical formula ET1 and the compound represented by the following chemical formula LiQ are vacuum-evaporated at a weight ratio of 1:1, so as to form an electron injection and transport layer with a thickness of The compound represented by the following chemical formula HB1 is evaporated to form a hole blocking layer. Then, on the above hole blocking layer, the compound represented by the following chemical formula ET1 and the compound represented by the following chemical formula LiQ are vacuum-evaporated at a weight ratio of 1:1, so as to form an electron injection and transport layer with a thickness of On the above electron injection and transport layer, lithium fluoride (LiF) is successively evaporated with a thickness of and aluminum is evaporated with a thickness of

[0492]

[0493] to form a cathode. In the above process, the evaporation rate of the organic matter is maintained The evaporation rate of lithium fluoride for the cathode is maintained and the evaporation rate of aluminum is maintained -7 ~5×10 -6 Torr, and thus an organic light-emitting device is fabricated.

[0494] Examples 1-2 to 1-9

[0495] Using the compounds described in the above Synthesis Examples 2 to 9 to replace the above Compound 1, an organic light-emitting device was fabricated by the same method as in the above Example 1-1 except for this.

[0496] Comparative Examples 1-1 to 1-5

[0497] Using the compounds described in Table 1 below to replace the above Compound 1, an organic light-emitting device was fabricated by the same method as in the above Example 1-1 except for this. The compounds BH1 to BH5 used in Table 1 below are as follows.

[0498]

[0499] Experimental Example

[0500] When a current was applied to the organic light-emitting devices fabricated in the above Examples and Comparative Examples, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T90 It refers to the time required for the brightness to decrease from the initial brightness (1000 nits) to 90%.

[0501]

Table 1

[0502]

[0503] As shown in Table 1 above, the organic light-emitting devices of Examples 1-1 to 1-9 using a triazine compound having a polycyclic carbazolyl group fused with heteroaryl and substituted with various Ars as the N-type host in the hole transport region and the light-emitting layer showed excellent characteristics in terms of the efficiency, driving voltage, and stability of the organic light-emitting device.

[0504] On the contrary, the compounds of Comparative Examples 1-1 to 1-5 are in the form of carbazole derivatives of Formulas 1 and 2 having the structure of Formula A' (BH1, BH2), or L-Ar is phenyl (BH4, BH5), or Ar' is pyridine (BH3). The organic light-emitting devices using the above compounds showed results of increased voltage, decreased efficiency, and decreased stability (lifetime) compared to the organic light-emitting devices of Examples 1-1 to 1-9 using the compound of Formula 1 according to the present application.

Claims

1. A compound represented by the following Chemical Formula 11: [Chemical Formula 11] In the Chemical Formula 11, Y11 and Y21 are each independently O, S, or CRR', L11 is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene, l11 is an integer from 0 to 3, and when l11 is 2 or more, two or more L11s are the same or different from each other, n21 is an integer from 0 to 6 or an integer from 0 to 8, n22 is an integer from 0 to 4, m11 is an integer from 0 to 10, when each of m11, n21, and n22 is 2 or more, two or more substituents within parentheses are the same or different from each other, p is an integer of 0 or 1, when p is 0, n21 is an integer from 0 to 8, Ar11 is a substituted or unsubstituted alkyl group, -SiR”R”'R””, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group having three or more rings, a substituted or unsubstituted heteroaryl group having two or more rings containing N, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing O or S. When Ar11 is a heteroaryl group, L is not directly bonded. When p is 1, n21 is an integer from 0 to 6, Ar11 is a substituted or unsubstituted alkyl group, -SiR”R”'R””, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having two or more rings containing N, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing O or S. When Ar11 is an unsubstituted phenyl group, L is not directly bonded. R, R', R”, R”', R””, R11, R21, and R22 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, However, it does not include the case where the structure represented by and the structure represented by are represented by chemical formula A', and the structure represented by ​ However, it does not include the case where the structure represented by and the structure represented by are both represented by chemical formula C, where the structure represented by and the structure represented by are both represented by chemical formula C, and the structure represented by are both represented by chemical formula C. [Chemical Formula A'] [Chemical Formula C] Y is the Y11 or Y21, Indicates the part connected to the nuclear structure.

2. A compound represented by the following Chemical Formula 1 or Chemical Formula 2: [Chemical Formula 1] [Chemical Formula 2] In the Chemical Formula 1 or Chemical Formula 2, Y1 is O, S, or CRR', Y1' and Y2 are each independently O, S, L is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene, l is an integer from 0 to 3, and when l is 2 or more, two or more Ls are the same or different from each other, Ar is a substituted or unsubstituted alkyl group, -SiR”R”'R””, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group having three or more rings, a substituted or unsubstituted heteroaryl group having two or more rings containing N, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing O or S, when Ar is a heteroaryl group, L is not directly bonded, Ar' is a substituted or unsubstituted alkyl group, -SiR”R”'R””, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group having two or more rings containing N, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing O or S, when Ar' is an unsubstituted phenyl group, L is not directly bonded. R, R', R”, R”', R1, and R2 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, n is an integer from 0 to 8, and m and n' are each an integer from 0 to 10. When each of m, n, and n' is 2 or more, the substituents in two or more parentheses are the same as or different from each other. However, it does not include the structure represented by the chemical formula 1 as , the structure represented by the chemical formula 2 as , and the case where the structure represented by is represented by the chemical formula A'. However, it does not include the case where the structure represented by and the structure represented by are both represented by chemical formula C, and the structure represented by are both represented by chemical formula C. [Chemical formula A'] Y is the aforementioned Y1, Y1', or Y2. [Chemical formula C] Indicates the part connected to the nuclear structure.

3. The compound according to claim 2, wherein The representation of Chemical Formula 1 is and the structure of the representation of Chemical Formula 2 is At least one of the structures is represented by any one of the following Chemical Formulas A to C: [Chemical formula A] [Chemical formula B] [Chemical formula C] In the aforementioned Chemical formulas A to C, Y is the aforementioned Y1 or Y1'. Indicates the part connected to the nuclear structure.

4. The compound according to claim 3, wherein When at least one of Y1' and Y2 is S, the representation of Chemical Formula 2 is The structure and the representation are At least one of the structures is represented by any one of Chemical Formulas A to C.

5. The compound according to claim 2, wherein, L is a direct bond, or an arylene group having 6 to 30 carbon atoms which may be substituted with deuterium or unsubstituted.

6. The compound according to claim 2, wherein L is a direct bond, or a phenylene group which may be substituted with deuterium or unsubstituted.

7. The compound according to claim 2, wherein, Ar is a substituted or unsubstituted silyl group, a substituted or unsubstituted polycyclic heteroaryl group having 2 to 30 carbon atoms and containing N in two or more rings, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms and containing O or S.

8. The compound according to claim 2, wherein, Ar is a triphenylsilyl group which may be substituted with deuterium or unsubstituted, a carbazolyl group which may be substituted with deuterium or unsubstituted, a dibenzofuranyl group which may be substituted with deuterium or unsubstituted, or a dibenzothiophenyl group which may be substituted with deuterium or unsubstituted.

9. The compound according to claim 2, wherein, Ar' is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted polycyclic heteroaryl group having 2 to 30 carbon atoms and containing N in two or more rings, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms and containing O or S.

10. The compound according to claim 2, wherein, Ar' is a phenyl group which may be substituted with deuterium or unsubstituted, a biphenyl group which may be substituted with deuterium or unsubstituted, a triphenylsilyl group which may be substituted with deuterium or unsubstituted, a carbazolyl group which may be substituted with deuterium or unsubstituted, a dibenzofuranyl group which may be substituted with deuterium or unsubstituted, or a dibenzothiophenyl group which may be substituted with deuterium or unsubstituted.

11. The compound according to claim 2, wherein R1 and R2 are the same as or different from each other, and are each independently hydrogen or deuterium.

12. The compound according to claim 2, wherein The aforementioned Chemical formula 1 is represented by any one of the following compounds:

13. The compound according to claim 2, wherein, The aforementioned Chemical formula 2 is represented by any one of the following compounds:

14. An organic light emitting device, comprising: An anode, a cathode, and one or more organic layers provided between the anode and the cathode, and one or more of the organic layers contain the compound according to any one of claims 1 to 13.

15. The organic light emitting device according to claim 14, wherein, The organic layer includes a light-emitting layer, and the light-emitting layer contains the compound.

16. The organic light emitting device according to claim 15, wherein, The light-emitting layer contains the compound as a host and also contains a dopant.

17. The organic light emitting device according to claim 14, wherein, The organic layer includes one or more of an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer between the cathode and the light-emitting layer.

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