Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound of Chemical Formula 1 and an organic light-emitting device comprising the same.

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2022-0166812 filed with the Korean Patent Office on December 2, 2022, the entire contents of which are incorporated into this specification.

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

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

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

[0005] Technical issues

[0006] The present application provides a compound and an organic light-emitting device comprising the same.

[0007] Solution to the problem

[0008] One embodiment of the present specification provides a compound of the following Chemical Formula 1:

[0009] [Chemical formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] B is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0013] R1 to R16, R25 and R26 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, d is an integer from 0 to 2,

[0014] R21 to R24 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0015] Another embodiment of the present specification provides an organic light-emitting device, comprising: an anode, a cathode, and at least one organic layer disposed between the anode and the cathode, wherein at least one of the organic layers contains the compound.

[0016] Effects of the Invention

[0017] The compound according to one embodiment of the present invention may be used as a material for an organic layer of an organic light-emitting device.

[0018] The compound according to a specific embodiment of the present invention can be used as a light-emitting layer material of an organic light-emitting device.

[0019] The compound according to one embodiment of the present invention is included in an organic light-emitting device to improve device characteristics, such as low driving voltage, excellent efficiency characteristics, or excellent lifespan characteristics. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] Figures 1 to 3 Examples of organic light emitting devices according to several embodiments of the present invention are illustrated.

[0021] 1: Substrate

[0022] 2: Anode

[0023] 3: Luminous layer

[0024] 4: Cathode

[0025] 5: Hole injection layer

[0026] 6: Hole transport layer

[0027] 7: Luminous layer

[0028] 8: Electron transport layer

[0029] 9: Electron blocking layer

[0030] 10: Hole blocking layer

[0031] 11: Electron injection and transport layer DETAILED DESCRIPTION

[0032] Next, this specification is described in more detail.

[0033] In the present specification, when it is indicated that a certain part “includes / comprises” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.

[0034] In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.

[0035] In the present specification, the deuterium substitution rate of the compound can be determined by the following methods: a method of calculating the substitution rate based on the maximum value of the distribution formed by the molecular weight at the end of the reaction using TLC-MS (Thin-Layer Chromatography / Mass Spectrometry); or a method of calculating the D-substitution rate from the integrated amount of the total peak by adding DMF as an internal standard and using the integration ratio on 1H NMR by a quantitative analysis method using NMR.

[0036] In the present specification, "..." and "*" respectively represent a site to be connected to other substituents or a linking part.

[0037] 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.

[0038] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium, a halogen group, a nitrile group (-CN), a nitro group, a hydroxyl group, an alkyl group, a cycloalkyl group, an alkoxy group, a phosphine oxide group, an aryloxy group, an alkylthio group, Arylthio Alkylsulfonyl Arylsulfonyl The alkylene group may be substituted with one or more substituents selected from the group consisting of alkenyl, silyl, boronyl, amine, aryl and heterocyclic groups, or may be substituted with a substituent formed by connecting two or more substituents selected from the group consisting of the above-mentioned substituents, or may not have any substituent. For example, a "substituent formed by connecting two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent formed by connecting two phenyl groups.

[0039] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an aryloxy group, an alkyl group, an aryl group, and a heterocyclic group, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0040] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, alkyl, aryl, and heterocyclic groups, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0041] Examples of the above substituents are described below, but are not limited thereto.

[0042] In the present specification, as examples of the halogen group, there are fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0043] In the present specification, the silyl group can be represented by the chemical formula -SiYaYbYc, wherein Ya, Yb and Yc can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but is not limited thereto.

[0044] In this specification, the boron group can be represented by the chemical formula -BYdYe, and the above-mentioned Yd and Ye can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The above-mentioned boron group specifically includes dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, phenylboryl, etc., but is not limited thereto.

[0045] In the present specification, the alkyl group may be a linear or branched group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited thereto.

[0046] In this specification, the alkoxy group can be straight chain, branched 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 can be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, an isopropyloxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentyl group, a n-hexyl group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, etc., but it is not limited thereto.

[0047] The alkyl group, alkoxy group, and other substituents containing an alkyl portion described in the present specification include all of linear and branched forms.

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

[0049] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0050] In the present specification, the amino group is -NH2, and the above-mentioned amino group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms of the above-mentioned substituted amino group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the number of carbon atoms of the above-mentioned amino group is 1 to 20. According to one embodiment, the number of carbon atoms of the above-mentioned amino group is 1 to 10. As specific examples of substituted amino groups, there are methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9,9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthracenylamino, dibenzofuranylphenylamino, 9-methylanthrylamino, diphenylamino, phenylnaphthylamino, ditolylamino, phenyltolylamino, diphenylamino, etc., but are not limited thereto.

[0051] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, quaterphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, phenylene, fluorenyl, triphenylene, etc., but are not limited to these.

[0052] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

[0053] When the fluorenyl group is substituted, it may be Isospirofluorenyl; (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) and the like substituted fluorenyl, but the present invention is not limited thereto.

[0054] In the present specification, the above description on the aryl group can be applied to the aryl group in the aryloxy group.

[0055] In the present specification, the heterocyclic group is a ring group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 20. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarbazolyl, triazinyl and the like, but are not limited thereto.

[0056] In the present specification, a heteroaryl group is aromatic, and other than this, the above description about the heterocyclic group is applicable.

[0057] In the present specification, the description of the above-mentioned aryl group is applicable to the above-mentioned arylene group except that the above-mentioned arylene group is divalent.

[0058] In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, "ring" means a hydrocarbon ring or a heterocyclic ring.

[0059] The hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic groups, and may be selected from the examples of the cycloalkyl group or aryl group described above.

[0060] In this specification, the meaning of forming a ring by combining with adjacent groups means combining with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle, or a condensed ring thereof. The above hydrocarbon ring refers to a ring consisting only of carbon and hydrogen atoms. The above heterocycle refers to a ring containing one or more heteroatoms selected from N, O, P, S, Si and Se. In this specification, the above aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle and aromatic heterocycle can be monocyclic or polycyclic.

[0061] In this specification, an aliphatic hydrocarbon ring refers to a ring that is not an aromatic ring and is composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.

[0062] In this specification, an aromatic hydrocarbon ring refers to an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenanthene, pyrene, tetracene, In the present specification, the aromatic hydrocarbon ring can be interpreted as having the same meaning as the aryl group.

[0063] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dihydrofuran, Examples of the present invention include, but are not limited to, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azacyclooctane, and thiocane.

[0064] In the present specification, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, Azoles, Isopropylamine Azoles, thiazoles, isothiazoles, triazoles, diazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazines, Azine, thiazine, di Olefins, triazines, tetrazines, isoquinolines, quinolines, quinones, quinazolines, quinoxalines, naphthyridines, acridines, phenanthridines, naphthyridines, triazaindene, indoles, indolizines, benzothiazoles, benzo azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phen Oxazine, indolecarbazole, indenocarbazole, etc., but are not limited to these.

[0065] Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention can be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

[0066] The compound according to one embodiment of the present specification is represented by the above-mentioned Chemical Formula 1. The compound of the above-mentioned Chemical Formula 1 is characterized in that biphenyl and B substituted by dibenzofuran are substituted on carbons 9 and 10 of anthracene, respectively, wherein the dibenzofuran is characterized in that it is bonded to the ortho position of the biphenyl. Due to the structural characteristics as described above, when the above-mentioned compound is applied to an organic light-emitting device, the effects of low voltage, high efficiency and / or long life can be exhibited.

[0067] According to one embodiment of the present specification, the above Chemical Formula 1 may be represented by any one of the following Chemical Formulas 21 to 23.

[0068] [Chemical formula 21]

[0069]

[0070] [Chemical formula 22]

[0071]

[0072] [Chemical formula 23]

[0073]

[0074] In the above Chemical Formulae 21 to 23, the description of the substituents is the same as defined in the above Chemical Formula 1.

[0075] According to one embodiment of the present specification, R21 to R26 are hydrogen or deuterium.

[0076] According to one embodiment of the present specification, B is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a group of the following Chemical Formula 11.

[0077] [Chemical formula 11]

[0078]

[0079] In the above chemical formula 11,

[0080] X is O or S,

[0081] R17 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0082] a and b are each 0 or 1, c is an integer from 0 to 12,

[0083] * is a site bonded to Chemical Formula 1.

[0084] According to one embodiment of the present specification, the above-mentioned B is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted naphthobenzothienyl group.

[0085] According to one embodiment of the present specification, the deuterium substitution rate of B is 0%.

[0086] According to one embodiment of the present specification, the deuterium substitution rate of B is 10% to 100%.

[0087] According to one embodiment of the present specification, the deuterium substitution rate of B is 20% to 100%.

[0088] According to one embodiment of the present specification, the deuterium substitution rate of B is 50% to 100%.

[0089] According to one embodiment of the present specification, B is any one of the following structures or a structure in which two or more of them are connected, and the following structure may be substituted with deuterium.

[0090]

[0091]

[0092] In the above structure, ... is a portion bonded to the above Chemical Formula 1.

[0093] According to one embodiment of the present specification, each of R1 to R16 is hydrogen or deuterium.

[0094] According to one embodiment of the present specification, R1 to R8 are hydrogen.

[0095] According to one embodiment of the present specification, R1 to R8 are deuterium.

[0096] According to one embodiment of the present specification, R9 to R16 are hydrogen.

[0097] According to one embodiment of the present specification, R9 to R16 are deuterium.

[0098] According to one embodiment of the present specification, the deuterium substitution rate of the compound of the above Chemical Formula 1 is 0%.

[0099] According to one embodiment of the present specification, the deuterium substitution rate of the compound of Chemical Formula 1 is 10% to 100%.

[0100] According to one embodiment of the present specification, the deuterium substitution rate of the compound of Chemical Formula 1 is 20% to 100%.

[0101] According to one embodiment of the present specification, the deuterium substitution rate of the compound of Chemical Formula 1 is 50% to 100%.

[0102] According to one embodiment of the present specification, the compound is any one selected from the following structures.

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116] One embodiment of the present specification provides an organic light-emitting device including: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers contains the compound.

[0117] Specifically, the organic light-emitting device includes: an anode, a cathode, and at least one organic layer including a light-emitting layer disposed between the anode and the cathode, and at least one of the organic layers includes the compound of Chemical Formula 1.

[0118] The organic light-emitting device of the present specification may form one or more organic layers using the above-mentioned compounds, and may be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0119] According to one embodiment of the present specification, the thickness of the organic layer containing the compound of the above Chemical Formula 1 is to Preferably to More preferably to

[0120] The above compounds can be used to form an organic layer by vacuum evaporation or solution coating when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited to these.

[0121] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking an anode, an organic layer and a cathode on a substrate. In this case, it can be manufactured as follows: a physical vapor deposition method (PVD: physical Vapor Deposition) such as sputtering or electron beam evaporation is used to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer to manufacture. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode substance, an organic layer and an anode substance on a substrate. In addition, the compound of the above chemical formula 1 can be used not only by vacuum evaporation method but also by solution coating method to form an organic layer when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited to this.

[0122] According to one embodiment of the present specification, the organic layer may be formed of a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. When the organic light-emitting device includes a plurality of organic layers, for example, the organic layer may be a multi-layer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number or a larger number of organic layers.

[0123] The organic layer can be formed of the same substance or different substances. In addition, the organic layer can be made of various polymer materials and made into a smaller number of layers by a solvent process other than evaporation, such as spin coating, dip coating, scraper coating, screen printing, inkjet printing, or thermal transfer.

[0124] According to one embodiment of the present specification, the organic layer including the compound of Chemical Formula 1 may be a light-emitting layer.

[0125] The light-emitting layer including the compound of the above chemical formula 1 may include only a single substance, or may include another substance. For example, the compound of the above chemical formula 1 may play a role as a host in the light-emitting layer, and may also include another dopant.

[0126] According to one embodiment of the present specification, the light-emitting layer further includes a fluorescent dopant or a phosphorescent dopant.

[0127] At this time, as the above-mentioned dopant, phosphorescent materials such as (4,6-F2ppy)2Irpic; or fluorescent materials such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, PPV-based polymers, anthracene-based compounds, pyrene-based compounds, and boron-based compounds can be used, but are not limited to these.

[0128] According to one embodiment of the present specification, the dopant in the light-emitting layer includes 1 part by weight to 50 parts by weight relative to 100 parts by weight of the host.

[0129] According to one embodiment of the present specification, the organic layer includes a hole blocking layer, an electron transport layer or an electron injection layer. In this case, the hole blocking layer, the electron transport layer or the electron injection layer may or may not include the compound.

[0130] According to one embodiment of the present specification, the organic layer includes a hole injection layer, a hole transport layer or an electron blocking layer. In this case, the hole injection layer, the hole transport layer or the electron blocking layer may or may not include the compound.

[0131] According to one embodiment of the present specification, the organic light-emitting device includes: an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, and further includes a single organic layer between the light-emitting layer and the anode, and the light-emitting layer includes the compound.

[0132] According to one embodiment of the present specification, the organic light-emitting device includes: an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, and further includes multiple organic layers between the light-emitting layer and the anode, and the light-emitting layer contains the compound.

[0133] According to one embodiment of the present specification, the organic light-emitting device includes: an anode, a cathode, and a light-emitting layer arranged between the anode and the cathode, and between the light-emitting layer and the anode, there is also one or more of a hole injection layer, a hole transport layer and an electron blocking layer, and the light-emitting layer contains the compound.

[0134] According to one embodiment of the present specification, the organic light-emitting device includes: an anode, a cathode, and a light-emitting layer arranged between the anode and the cathode, and a hole injection layer, a hole transport layer and an electron blocking layer are included between the anode and the light-emitting layer, and the light-emitting layer contains the above-mentioned compound.

[0135] According to one embodiment of the present specification, the organic light-emitting device is a structure in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer and a cathode are sequentially provided, and the light-emitting layer contains the compound. In this case, another organic layer may be provided between the layers.

[0136] According to one embodiment of the present specification, the organic light-emitting device includes: an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, and further includes a single organic layer between the light-emitting layer and the cathode, and the light-emitting layer includes the compound.

[0137] According to one embodiment of the present specification, the organic light-emitting device includes: an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, and further includes multiple organic layers between the light-emitting layer and the cathode, and the light-emitting layer contains the compound.

[0138] According to one embodiment of the present specification, the organic light-emitting device includes: an anode, a cathode, and a light-emitting layer arranged between the anode and the cathode, and between the cathode and the light-emitting layer there is also a hole blocking layer, an electron injection layer, an electron transport layer, and one or more of the electron injection and transport layers, and the light-emitting layer contains the above-mentioned compound.

[0139] According to one embodiment of the present specification, the organic light-emitting device includes: an anode, a cathode, and a light-emitting layer arranged between the anode and the cathode, and a hole blocking layer and an electron injection and transport layer are included between the cathode and the light-emitting layer, and the light-emitting layer contains the above-mentioned compound.

[0140] According to one embodiment of the present specification, the organic light-emitting device is a structure in which an anode, a light-emitting layer, a hole blocking layer, an electron injection and transport layer, and a cathode are sequentially provided, and the light-emitting layer contains the compound. In this case, another organic layer may be provided between the layers.

[0141] According to one embodiment of the present specification, the organic light-emitting device is a structure in which an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron injection and transport layer, and a cathode are stacked in sequence, and the light-emitting layer contains the above-mentioned compound.

[0142] For example, the structure of the organic light-emitting device of the present specification may have the following Figures 1 to 3 The structure shown is not limited thereto.

[0143] Figure 1 An example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a light-emitting layer 3 , and a cathode 4 is shown.

[0144] Figure 2The diagram shows an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a hole injection layer 5 , a hole transport layer 6 , a light-emitting layer 7 , an electron transport layer 8 , and a cathode 4 .

[0145] Figure 3 An example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light-emitting layer 7, a hole blocking layer 10, an electron injection and transport layer 11, and a cathode 4 is shown.

[0146] Specifically, the organic light-emitting device may have a stacked structure as shown below, for example, in addition to the structure explicitly shown in the above drawings, but is not limited thereto.

[0147] (1) Anode / hole transport layer / light-emitting layer / cathode

[0148] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0149] (3) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0150] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0151] (5) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0152] (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0153] (7) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0154] (8) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0155] (9) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0156] (10) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0157] (11) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0158] (12) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0159] (13) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0160] (14) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0161] (15) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0162] According to one embodiment of the present specification, the above-mentioned "electron transport layer / electron injection layer" may be replaced by "electron injection and transport layer" or "a layer that performs both electron injection and electron transport layer". For example, the above-mentioned (15) may be an organic light-emitting device having a stacking sequence of "anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron injection and transport layer / cathode".

[0163] According to one embodiment of the present specification, the above-mentioned "hole injection layer / hole transport layer" may be replaced by "hole injection and transport layer" or "layer that simultaneously performs hole injection and hole transport". For example, the above-mentioned (15) may be an organic light-emitting device having a stacking sequence of "anode / hole injection and transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode".

[0164] The anode is an electrode for injecting holes. As the anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), indium zinc oxide (IZO, Indium Zinc Oxide); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0165] The cathode is an electrode for injecting electrons. As the cathode material, in order to facilitate the injection of electrons into the organic layer, a material with a small work function is preferably used. Specific examples of cathode materials that can be used in the present invention include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0166] The hole injection layer can play a role in making the injection of holes from the anode to the light-emitting layer smooth. The hole injection material is a material that can well receive holes from the anode at a low voltage, and the HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrines, oligothiophenes, arylamine compounds, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, perylene compounds, benzonitrile compounds, anthraquinone and polyaniline and polythiophene conductive polymers, but are not limited to these.

[0167] Specifically, the hole injection layer may use an arylamine compound and a benzonitrile compound, and more specifically, an arylamine compound substituted with a carbazole group and a benzonitrile compound substituted with a halogen group, but the present invention is not limited thereto.

[0168] The thickness of the hole injection layer can be 1nm to 150nm. When the thickness of the hole injection layer is more than 1nm, it has the advantage of preventing the hole injection characteristics from being reduced, and when it is less than 150nm, it has the advantage of preventing the driving voltage from rising in order to improve the migration of holes when the thickness of the hole injection layer is too thick.

[0169] According to one embodiment of the present specification, the hole injection layer includes a compound of the following chemical formula HI-1.

[0170] [Chemical formula HI-1]

[0171]

[0172] In the above chemical formula HI-1,

[0173] L101 is a direct bond, or a substituted or unsubstituted arylene group,

[0174] R101 to R103 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

[0175] According to one embodiment of the present specification, L101 is a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0176] According to one embodiment of the present specification, the above-mentioned L101 is a direct bond, or a substituted or unsubstituted phenylene group.

[0177] According to one embodiment of the present specification, the above-mentioned L101 is a direct bond or a phenylene group.

[0178] According to one embodiment of the present specification, R101 to R103 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group, or a substituted or unsubstituted polycyclic aryl group.

[0179] According to one embodiment of the present specification, the above-mentioned R101 to R103 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted fluorenyl group.

[0180] According to one embodiment of the present specification, R101 to R103 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted fluorenyl group.

[0181] According to one embodiment of the present specification, R101 to R103 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, or a fluorenyl group substituted with an alkyl group.

[0182] According to one embodiment of the present specification, the chemical formula HI-1 is any one of the following structures.

[0183]

[0184] According to one embodiment of the present specification, the hole injection layer includes a compound of the following chemical formula HI-2.

[0185] [Chemical formula HI-2]

[0186]

[0187] In the above chemical formula HI-2,

[0188] R111 to R113 are the same as or different from each other, and are each independently hydrogen, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0189] a111 to a113 are each an integer from 1 to 5,

[0190] When a111 is 2 or more, the two or more R111 are the same or different from each other.

[0191] When a112 is 2 or more, the two or more R112 are the same or different from each other.

[0192] When a113 is 2 or more, two or more R113s may be the same as or different from each other.

[0193] According to one embodiment of the present specification, the above R111 to R113 are the same as or different from each other, and each is a halogen group or a nitrile group.

[0194] According to one embodiment of the present specification, R111 to R113 are the same as or different from each other, and are each a fluorine group or a nitrile group.

[0195] According to one embodiment of the present specification, the chemical formula HI-2 is the following structure.

[0196]

[0197] According to one embodiment of the present specification, the hole injection layer includes the compound of the chemical formula HI-1 and the compound of the chemical formula HI-2.

[0198] The hole transport layer can play a role in making the hole transport smooth. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and is suitable for materials with large hole mobility. Specific examples of hole transport materials include arylamine organics, carbazole compounds, conductive polymers, and block copolymers with both conjugated and non-conjugated parts, but are not limited to these. Specifically, carbazole compounds substituted with arylamine groups can be used in the hole transport layer, but are not limited to these.

[0199] According to one embodiment of the present specification, the hole transport layer includes a compound of the following chemical formula HT-1.

[0200] [Chemical formula HT-1]

[0201]

[0202] In the above chemical formula HT-1,

[0203] L201 and L202 are the same or different from each other, and are each independently a directly bonded, substituted or unsubstituted arylene group,

[0204] R200 is a substituted or unsubstituted aryl group,

[0205] R201 to R204 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0206] According to one embodiment of the present specification, L201 and L202 are the same as or different from each other, and are each independently a substituted or unsubstituted arylene group.

[0207] According to one embodiment of the present specification, L201 and L202 are the same as or different from each other, and are each independently a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0208] According to one embodiment of the present specification, L201 and L202 are the same as or different from each other, and are each independently a substituted or unsubstituted phenylene group.

[0209] According to one embodiment of the present specification, each of L201 and L202 is a phenylene group.

[0210] According to one embodiment of the present specification, the above R200 is a substituted or unsubstituted monocyclic aryl group, or a substituted or unsubstituted polycyclic aryl group.

[0211] According to one embodiment of the present specification, the above R200 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted fluorenyl group.

[0212] According to one embodiment of the present specification, the above R200 is a substituted or unsubstituted naphthyl group.

[0213] According to one embodiment of the present specification, R201 to R204 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

[0214] According to one embodiment of the present specification, R201 to R204 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group, or a substituted or unsubstituted polycyclic aryl group.

[0215] According to one embodiment of the present specification, the above-mentioned R201 to R204 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted fluorenyl group.

[0216] According to one embodiment of the present specification, R201 to R204 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group.

[0217] According to one embodiment of the present specification, each of R201 to R204 is a phenyl group.

[0218] According to one embodiment of the present specification, the chemical formula HT-1 is the following structure.

[0219]

[0220] A hole buffer layer may be further disposed between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the technical field.

[0221] An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may include the above-mentioned compounds or materials known in the art. Specifically, a carbazole compound may be used in the electron blocking layer.

[0222] According to one embodiment of the present specification, the electron blocking layer includes a compound of the following chemical formula EB-1.

[0223] [Chemical formula EB-1]

[0224]

[0225] In the above chemical formula EB-1,

[0226] L301 is a substituted or unsubstituted arylene group,

[0227] R301 and R302 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

[0228] According to one embodiment of the present specification, the above L301 is a monocyclic or polycyclic arylene group.

[0229] According to one embodiment of the present specification, the L301 is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0230] According to one embodiment of the present specification, the above-mentioned L301 is a biphenylene group.

[0231] According to one embodiment of the present specification, the above-mentioned R301 and R302 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted fluorenyl group.

[0232] According to one embodiment of the present specification, R301 and R302 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0233] According to one embodiment of the present specification, R301 and R302 are the same as or different from each other, and are each independently a biphenyl group which may be substituted with an aryl group or not.

[0234] According to one embodiment of the present specification, the chemical formula EB-1 is the following structure.

[0235]

[0236] The above-mentioned light-emitting layer can emit red, green or blue light, and can be composed of a phosphorescent material or a fluorescent material. The above-mentioned light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. For example, as the above-mentioned light-emitting material, there are 8-hydroxy-quinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo azole, benzothiazole and benzimidazole compounds; poly(p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorene; rubrene, etc., but are not limited thereto.

[0237] As the main material of the light-emitting layer, there are aromatic fused ring derivatives or heterocyclic compounds. For example, as aromatic fused ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but not limited thereto. Specifically, as the host of the light-emitting layer, the compound of Chemical Formula 1 of the present invention can be used, but not limited thereto.

[0238] When the light-emitting layer emits red light, as a light-emitting dopant, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium, bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium, bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium, tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum) or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used, but are not limited to these. When the light-emitting layer emits green light, as a light-emitting dopant, phosphorescent materials such as Ir(ppy)3(tris(2-phenylpyridine)iridium, tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinoline)aluminum) can be used, but are not limited to these. When the light-emitting layer emits blue light, as a light-emitting dopant, phosphorescent materials such as (4,6-F2ppy)2Irpic can be used; or fluorescent materials such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyrylbenzene (DSB), distyrylarylene (DSA), pyrene-based compounds, PFO-based polymers, PPV-based polymers can be used, but are not limited to these. Specifically, as the above-mentioned dopant, a pyrene-based compound can be used, but is not limited to this.

[0239] According to one embodiment of the present specification, the dopant includes a compound of the following chemical formula D.

[0240] [Chemical formula D]

[0241]

[0242] In the above chemical formula D,

[0243] X1 and X2 are the same as or different from each other, and are independently CR' or NR", at least one of X1 and X2 is NR",

[0244] R401 to R403, R' and R" are the same as or different from each other, and are independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0245] R401 and R403 are each an integer of 0 to 4, R402 is an integer of 0 to 3, and when R401 to R403 are each 2 or more, the substituents in the brackets are the same as or different from each other.

[0246] According to one embodiment of the present specification, R401 to R403 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0247] According to one embodiment of the present specification, R401 to R403 are the same as or different from each other, and are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group.

[0248] According to one embodiment of the present specification, R401 to R403 are the same as or different from each other, and are each independently hydrogen, deuterium, or a linear or branched alkyl group.

[0249] According to one embodiment of the present specification, R401 to R403 are the same as or different from each other, and are each independently hydrogen, deuterium, a linear alkyl group having 1 to 30 carbon atoms, or a branched alkyl group having 4 to 30 carbon atoms.

[0250] According to one embodiment of the present specification, R401 to R403 are the same as or different from each other, and are each independently hydrogen, deuterium, or a branched alkyl group having 4 to 30 carbon atoms.

[0251] According to one embodiment of the present specification, X1 and X2 are the same or different from each other, and are independently NR", and R" is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0252] According to one embodiment of the present specification, X1 and X2 are the same as or different from each other, and are independently NR", and R" is a substituted or unsubstituted aryl group.

[0253] According to one embodiment of the present specification, X1 and X2 are the same as or different from each other, and are independently NR", and R" is an aryl group substituted by an alkyl group.

[0254] According to one embodiment of the present specification, the chemical formula D is the following structure.

[0255]

[0256] According to one embodiment of the present specification, the light-emitting layer includes the compound of Chemical Formula 1 as a host of the light-emitting layer, and includes the compound of Chemical Formula D as a dopant of the light-emitting layer.

[0257] According to one embodiment of the present invention, in the light-emitting layer, the weight ratio of the compound of Chemical Formula 1 to the compound of Chemical Formula D is 100:1 to 1:1, specifically, 70:1 to 2:1 or 50:1 to 3:1.

[0258] A hole blocking layer may be provided between the cathode and the light-emitting layer. The hole blocking layer is a layer that blocks holes from reaching the cathode and can be formed under the same conditions as the hole injection layer. Specific examples of hole blocking materials include Oxadiazole derivatives or triazole derivatives, triazine derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but not limited thereto. Specifically, triazine derivatives can be used, but not limited thereto.

[0259] According to one embodiment of the present specification, the hole blocking layer includes a compound of the following chemical formula HB-1.

[0260] [Chemical formula HB-1]

[0261]

[0262] In the above chemical formula HB-1,

[0263] L501 to L503 are the same as or different from each other, and are each independently a directly bonded, substituted or unsubstituted arylene group,

[0264] R501 to R504 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0265] According to one embodiment of the present specification, L501 to L503 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

[0266] According to one embodiment of the present specification, L501 to L503 are the same as or different from each other, and are each independently a directly bonded, or substituted or unsubstituted biphenylene group.

[0267] According to one embodiment of the present specification, L501 and L502 are the same as or different from each other, and are each independently a direct bond.

[0268] According to one embodiment of the present specification, the L503 is a substituted or unsubstituted biphenylene group.

[0269] According to one embodiment of the present specification, the above-mentioned L503 is a biphenylene group.

[0270] According to one embodiment of the present specification, R501 to R504 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

[0271] According to one embodiment of the present specification, R501 to R504 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group, or a substituted or unsubstituted polycyclic aryl group.

[0272] According to one embodiment of the present specification, the above-mentioned R501 to R504 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted fluorenyl group.

[0273] According to one embodiment of the present specification, R501 to R504 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0274] According to one embodiment of the present specification, R501 to R504 are the same as or different from each other, and are each independently a phenyl group which may be substituted or unsubstituted by a naphthyl group.

[0275] According to one embodiment of the present specification, the chemical formula HB-1 is any one of the following structures.

[0276]

[0277] The above-mentioned electron transport layer can play a role in making the transmission of electrons smooth. The electron transport material is a material that can receive electrons well from the cathode and transfer them to the light-emitting layer, and is suitable for materials with high electron mobility. For example, as the above-mentioned electron transport material, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to this. The thickness of the electron transport layer can be 1nm to 50nm. When the thickness of the electron transport layer is more than 1nm, it has the advantage of preventing the electron transport characteristics from being reduced. When it is less than 50nm, it has the advantage of preventing the driving voltage from rising in order to improve the migration of electrons when the thickness of the electron transport layer is too thick.

[0278] The electron injection layer can play a role in facilitating the injection of electrons. As the electron injection material, the following compounds are preferred: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have excellent thin film forming ability. For example, the electron injection material includes fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0279] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

[0280] The electron transport layer and the electron injection layer may be formed of a single layer. For example, the electron injection and transport layers may be formed by vacuum evaporating an electron injection substance and an electron transport substance at the same time, or by vacuum evaporating a substance that exhibits both electron injection and transport effects.

[0281] The electron injection and transport layer may further include a metal complex. Examples of the metal complex include, but are not limited to, Al complexes of 8-hydroxyquinoline (Alq3), LiQ, metal coordination compounds, etc. For example, the electron injection and transport layer may use triazine derivatives and lithium quinoline (LiQ), but are not limited to these.

[0282] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0283] In addition, the organic light-emitting device according to the present specification can be included in various electronic devices for use. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0284] Modes for Carrying Out the Invention

[0285] Below, in order to specifically illustrate this specification, experimental examples will be cited for detailed description. However, the embodiments according to this specification can be deformed into various different forms, and it is not interpreted that the scope of this application is limited to the embodiments described in detail below. The embodiments of this application are provided to more completely illustrate this specification to those skilled in the art.

[0286] <Production Example 1> Synthesis of Compound 1

[0287]

[0288] Under nitrogen atmosphere, in a 500 mL round-bottom flask, 9-bromo-10-(naphthalen-1-yl)anthracene (6.50 g, 16.97 mmol) and compound a-1 (8.33 g, 18.67 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2 M potassium carbonate aqueous solution (120 mL) was added. After adding tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.59 g, 0.51 mmol), the mixture was heated and stirred for 2 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 mL of toluene to produce compound 1 (5.99 g, yield: 57%). MS [M+H] + =623

[0289] <Production Example 2> Synthesis of Compound 2

[0290]

[0291] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-bromo-10-(naphthalen-2-yl) anthracene (6.50 g, 16.97 mmol) and compound a-2 (8.33 g, 18.67 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added. After adding tetrakis(triphenylphosphine)palladium (0.59 g, 0.51 mmol), heating and stirring were performed for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 310 mL of toluene to produce compound 2 (6.23 g, yield: 59%). MS [M+H] + =623

[0292] <Production Example 3> Synthesis of Compound 3

[0293]

[0294] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-bromo-10-(phenanthren-9-yl) anthracene (6.50 g, 16.51 mmol) and compound a-3 (9.26 g, 18.67 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added. After adding tetrakis(triphenylphosphine)palladium (0.59 g, 0.51 mmol), heating and stirring were performed for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 mL of toluene to produce compound 3 (6.44 g, yield: 56%). MS [M+H] + =673

[0295] <Production Example 4> Synthesis of Compound 4

[0296]

[0297] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-bromo-10-phenylanthracene-1,2,3,4,5,6,7,8-d8 (6.50 g, 19.06 mmol) and compound a-1 (9.35 g, 20.97 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added. After adding tetrakis(triphenylphosphine)palladium (0.66 g, 0.57 mmol), heating and stirring were performed for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 mL of toluene to produce compound 4 (6.51 g, yield: 59%). MS [M+H] + =581

[0298] <Production Example 5> Synthesis of Compound 5

[0299]

[0300] Under a nitrogen atmosphere, in a 500-mL round-bottom flask, compound 9-([1,1'-biphenyl]-4-yl)-10-bromoanthracene-1,2,3,4,5,6,7,8-d8) (6.50 g, 15.85 mmol) and compound a-2 (7.78 g, 17.44 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added. After adding tetrakis(triphenylphosphine)palladium (0.55 g, 0.48 mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 mL of toluene to produce compound 5 (7.06 g, yield: 68%). MS [M+H] + =657

[0301] <Production Example 6> Synthesis of Compound 6

[0302]

[0303] Under nitrogen atmosphere, in a 500-mL round-bottom flask, compound 9-([1,1'-biphenyl]-3-yl)-10-bromoanthracene-1,2,3,4,5,6,7,8-d8) (6.50 g, 15.85 mmol) and compound a-3 (7.78 g, 17.44 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added. After adding tetrakis(triphenylphosphine)palladium (0.55 g, 0.48 mmol), the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 mL of toluene to produce compound 6 (7.34 g, yield: 70%). MS [M+H] + =657

[0304] <Production Example 7> Synthesis of Compound 7

[0305]

[0306] Under a nitrogen atmosphere, in a 500-mL round-bottom flask, 9-([1,1'-biphenyl]-2-yl-d9)-10-bromoanthracene-1,2,3,4,5,6,7,8-d8 (6.50 g, 15.26 mmol) and compound a-4 (7.74 g, 16.78 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then a 2M aqueous potassium carbonate solution (120 mL) was added. After adding tetrakis(triphenylphosphine)palladium (0.53 g, 0.46 mmol), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 mL of toluene to produce compound 7 (6.89 g, yield: 66%). MS [M+H] + =682

[0307] <Production Example 8> Synthesis of Compound 8

[0308]

[0309] Under nitrogen atmosphere, in a 500-mL round-bottom flask, compound 3-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d]furan-1,2,4,6,7,8,9-d7 (3-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d]furan-1,2,4,6,7,8,9-d7) (6.50 g, 14.84 mmol) and compound a-1 (7.28 g, 16.32 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, followed by addition of tetrakis(triphenylphosphine)palladium (0.51 g, 0.45 mmol) and heating with stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 270 mL of toluene to produce compound 8 (6.13 g, yield: 61%). MS [M+H] + =678

[0310] <Production Example 9> Synthesis of Compound 9

[0311]

[0312] Under nitrogen atmosphere, in a 500-mL round-bottom flask, compound 7-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8)naphtho[1,2-b]benzofuran-1,2,3,4,5,6,8,10-d8) (6.50 g, 13.29 mmol) and compound a-2 (6.52 g, 14.62 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis(triphenylphosphine)palladium (0.46 g, 0.40 mmol) was added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 mL of toluene to produce compound 9 (6.75 g, yield: 70%). MS [M+H] + =729

[0313] <Production Example 10> Synthesis of Compound 10

[0314]

[0315] Under nitrogen atmosphere, in a 500 mL round-bottom flask, 9-bromo-10-(4-(naphthalen-2-yl-d7)phen yl-2,3,5,6-d4)anthracene-1,2,3,4,5,6,7,8-d8) (6.50 g, 13.60 mmol) and compound a-3 (6.67 g, 14.96 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, followed by addition of tetrakis(triphenylphosphine)palladium (0.47 g, 0.41 mmol) and heating with stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 260 mL of toluene to produce compound 10 (6.31 g, yield: 64%). MS [M+H] + =723

[0316] <Production Example 11> Synthesis of Compound 11

[0317]

[0318] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-bromo-10-(4-(naphthalen-1-yl-d7)phenyl-2,3,5,6-d4)anthracene-1,2,3,4,5,6,7,8-d8) (5.50 g, 16.13 mmol) and compound a-5 (8.45 g, 17.74 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, followed by addition of tetrakis(triphenylphosphine)palladium (0.56 g, 0.48 mmol) and heating with stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 mL of toluene to produce compound 11 (6.17 g, yield: 63%). MS [M+H] + =734

[0319] <Production Example 12> Synthesis of Compound 12

[0320]

[0321] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8)phenanthrene-1,2,3,4,5,6,7,8,10-d9) (6.50 g, 14.44 mmol) and compound a-2 (7.09 g, 15.89 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis(triphenylphosphine)palladium (0.50 g, 0.43 mmol) was added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 mL of toluene to produce compound 12 (6.51 g, yield: 65%). MS [M+H] + =690

[0322] Example 1-1.

[0323] ITO (indium tin oxide) The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0324] On the ITO transparent electrode prepared as the anode, the following compound HI1 and the following compound HI2 were mixed in a ratio of 98:2 (molar ratio) and A hole injection layer is formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, a compound represented by the following chemical formula HT1 is deposited Then, a film with a thickness of 1000 nm was deposited on the hole transport layer. The EB1 compound is vacuum-deposited to form an electron blocking layer. Next, a film having a thickness of Compound 1 synthesized in the above-mentioned Preparation Example 1 and the compound represented by the following chemical formula BD were vacuum-deposited at a weight ratio of 25:1 to form a light-emitting layer. The compound of HB1 was vacuum-deposited to form a hole blocking layer. Next, on the hole blocking layer, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-deposited at a weight ratio of 1:1, thereby forming a hole blocking layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A cathode is formed by evaporation with a thickness of .

[0325]

[0326] In the above process, the evaporation rate of organic matter is maintained to Lithium fluoride at the cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 2×10 -7 Up to 5×10 -6 A support is provided to produce an organic light-emitting device.

[0327] Example 1-2 to Example 1-12.

[0328] An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the compounds described in Table 1 below were used instead of Compound 1.

[0329] Comparative Examples 1-1 to 1-8.

[0330] In the above Example 1-1, an organic light-emitting device was manufactured by the same method as in the above Example 1-1, except that the compounds described in the following Table 1 were used instead of Compound 1. The compounds BH1 to BH8 used in the following Table 1 are shown below.

[0331]

[0332] Experimental example.

[0333] When current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in the following Table 1. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.

[0334] [Table 1]

[0335]

[0336]

[0337] As shown in Table 1 above, an organic light-emitting device using the compound of the present invention as a light-emitting layer exhibits excellent characteristics in terms of efficiency, driving voltage and stability of the organic light-emitting device.

[0338] Specifically, the organic light-emitting devices (Examples 1-1 to 1-12) using the compounds of the present invention exhibited low voltage, high efficiency, and long life compared to the organic light-emitting devices of Comparative Examples 1-1 to 1-8 manufactured using compounds BH1 to BH8.

[0339] The above content describes the preferred embodiment (light-emitting layer) of the present invention, but the present invention is not limited thereto and can be implemented in various forms within the scope of protection claimed by the present invention and the scope of the detailed description of the invention, which also belongs to the scope of the present invention.

Claims

1. A compound of the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, B is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, R1 to R16, R25 and R26 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, d is an integer from 0 to 2, R21 to R24 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

2. The compound according to claim 1, wherein The chemical formula 1 is represented by any one of the following chemical formulas 21 to 23: [Chemical formula 21] [Chemical formula 22] [Chemical formula 23] In the Chemical Formulae 21 to 23, the substituents are the same as those defined in the Chemical Formula 1.

3. The compound according to claim 2, wherein The R21 to R24 are hydrogen or deuterium.

4. The compound according to claim 2, wherein The R25 and R26 are hydrogen or deuterium.

5. The compound according to claim 1, wherein B is a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a group of the following chemical formula 11: [Chemical formula 11] In the chemical formula 11, X is O or S, R17 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, a and b are each 0 or 1, c is an integer from 0 to 12, * is a site bonded to Chemical Formula 1.

6. The compound according to claim 1, wherein The B is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted naphthobenzothienyl group.

7. The compound according to claim 1, wherein B is any one of the following structures or a structure formed by connecting two or more of them, and the following structures are substituted or unsubstituted with deuterium: In the structure, ... is a portion bonded to the chemical formula 1.

8. The compound according to claim 1, wherein The R1 to R16 are each hydrogen or deuterium.

9. The compound according to claim 1, wherein The compound is any one selected from the following structures:

10. An organic light-emitting device, wherein: include: anode, cathode, and One or more organic layers are provided between the anode and the cathode, One or more of the organic layers contains the compound according to any one of claims 1 to 9.

11. The organic light emitting device according to claim 10, wherein: The organic layer containing the compound is a light-emitting layer.

12. The organic light emitting device according to claim 11, wherein: The light-emitting layer further comprises a compound of the following chemical formula D: [Chemical formula D] In the chemical formula D, X1 and X2 are the same as or different from each other, and are independently CR' or NR", at least one of X1 and X2 is NR", R401 to R403, R' and R" are the same as or different from each other, and are independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with adjacent groups to form a substituted or unsubstituted ring, R401 and R403 are each an integer of 0 to 4, R402 is an integer of 0 to 3, and when R401 to R403 are each 2 or more, the substituents in the brackets are the same as or different from each other.

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