Organic light emitting device, composition for organic material layer of organic light emitting device, and method for manufacturing organic light emitting device

Abstract

SOLUTION: Provided are: an organic light emitting device including a heterocyclic compound represented by the chemical formula A and a heterocyclic compound represented by the chemical formula B in the figure; a composition for an organic material layer of the organic light emitting device; and a method for manufacturing the organic light emitting device.EFFECT: The organic light emitting device, the composition for an organic material layer of the organic light emitting device, and the method for manufacturing the organic light emitting device can reduce the driving voltage of the device, improve the light emitting efficiency, and improve the service life characteristics of the device.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present specification relates to an organic light-emitting device, a composition for an organic layer of an organic light-emitting device, and a method for producing an organic light-emitting device. This application claims the benefit of the filing dates of Korean Patent Applications Nos. 10-2024-0012153 and 10-2024-0154120, filed with the Korean Intellectual Property Office on January 26, 2024 and November 4, 2024, respectively, the entire contents of which are incorporated herein by reference. [Background technology]

[0002] The light-emitting element is a type of self-luminous display element, and has the advantages of a wide viewing angle, excellent contrast, and fast response speed. An organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an organic light-emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs, and then annihilate, emitting light. The organic thin film may be configured as a single layer or multiple layers as needed.

[0003] The material of the organic thin film may have a light-emitting function as needed. For example, the material of the organic thin film may be a compound that can constitute an emitting layer by itself, or a compound that can function as a host or dopant in a host-dopant emitting layer. In addition, the material of the organic thin film may be a compound that can function as a hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, etc. To improve the performance, lifetime, or efficiency of organic light-emitting devices, there is a continuing need to develop materials for organic thin films. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] U.S. Patent No. 4,356,429 Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present specification is to provide an organic light-emitting device, a composition for an organic material layer of the organic light-emitting device, and a method for producing the organic light-emitting device. [Means for solving the problem]

[0006] One embodiment of the present specification provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a heterocyclic compound represented by the following chemical formula A; and a heterocyclic compound represented by the following chemical formula B: [ka] In the above chemical formulas A and B, L1 to L4 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; Ar1 to Ar3 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a combination thereof; Ar4 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a substituted or unsubstituted amine group; R1 and R2 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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; R3 and R4 are the same or different and each independently represent hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms, 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, or two or more adjacent groups bond to each other to form a substituted or unsubstituted ring, l1 to l4 are the same or different and each independently represents an integer of 1 to 3, and when each of l1 to l4 is an integer of 2 or more, the types of substituents in parentheses are the same or different, r1 is an integer from 0 to 6, Each of r2 to r4 is an integer between 0 and 4, The sum of r1 and r2 is 8, The sum of r3 and r4 is 6, When each of l1 to l4 and r1 to r4 is an integer of 2 or more, the substituents in the parentheses may be the same or different. N-Het1 is represented by the following chemical formula N: [ka] In the above chemical formula N, [ka] means the portion linked to L3, Y1 to Y5 are the same or different and each independently represent CRa or N, and at least one is N; Ra is 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.

[0007] Another embodiment of the present specification provides a composition for an organic layer of an organic light-emitting device, comprising: a heterocyclic compound represented by the chemical formula A; and a heterocyclic compound represented by the chemical formula B.

[0008] Another embodiment of the present specification provides a method for manufacturing an organic light-emitting device, comprising the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layers, wherein the step of forming the organic material layers comprises forming one or more organic material layers using the composition for an organic material layer of the organic light-emitting device described above. [Effects of the Invention]

[0009] An organic light-emitting device according to one embodiment of the present application includes an organic material layer, and the organic material layer contains a heterocyclic compound represented by chemical formula A and a heterocyclic compound represented by chemical formula B. Furthermore, a composition for an organic material layer of an organic light-emitting device according to one embodiment of the present application can use the heterocyclic compound represented by chemical formula A and the heterocyclic compound represented by chemical formula B as materials for the organic material layer of the organic light-emitting device. More specifically, the organic material layer of the organic light-emitting device and the composition for an organic material layer of the organic light-emitting device are characterized in that they each contain the heterocyclic compound represented by chemical formula A as a P-type host material and the heterocyclic compound represented by chemical formula B as an N-type host material.

[0010] When a heterocyclic compound represented by Chemical Formula A, which can be used as a unipolar P-type host material with excellent hole mobility, and a compound represented by Chemical Formula B, which can be used as a unipolar N-type host material with excellent electron mobility, are mixed in the appropriate ratio and used as device materials, it is easy to balance the number of holes and electrons in the light-emitting layer, thereby maximizing hole transport and electron transport properties, resulting in increased exciton generation efficiency and improved device efficiency and lifetime. This is because, compared to using a single bipolar host or other combinations such as a premix of two or more types, it is easy to control the charge density by adjusting the ratio, making it possible to combine various p-type and n-type hosts, which allows the development of many mixed host systems and is advantageous for improving device characteristics.

[0011] Therefore, when the composition for organic material layer is used in an organic light emitting device or when an organic light emitting device is manufactured, the driving voltage of the device can be reduced, the light efficiency can be improved, the thermal stability of the compound can be improved, and the life characteristics of the device can be improved. [Brief explanation of the drawings]

[0012] [Figure 1] 1 is a diagram illustrating an example of a stacked structure of an organic light-emitting device according to an embodiment of the present specification. [Figure 2] 1 is a diagram illustrating an example of a stacked structure of an organic light-emitting device according to an embodiment of the present specification. [Figure 3] 1 is a diagram illustrating an example of a stacked structure of an organic light-emitting device according to an embodiment of the present specification. DETAILED DESCRIPTION OF THE INVENTION

[0013] The present specification will be explained in more detail below. In this specification, unless otherwise specified, when a part "comprises" a certain component, it does not mean that it may further include other components, but does not exclude other components.

[0014] In this specification, the chemical formula [ka] means the binding position.

[0015] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different.

[0016] In this specification, the term "substituted or unsubstituted" means being substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; an alkyl group having 1 to 60 carbon atoms; an alkenyl group having 2 to 60 carbon atoms; an alkynyl group having 2 to 60 carbon atoms; a cycloalkyl group having 3 to 60 carbon atoms; a heterocycloalkyl group having 2 to 60 carbon atoms; an aryl group having 6 to 60 carbon atoms; a heteroaryl group having 2 to 60 carbon atoms; a silyl group; a phosphine oxide group; and an amine group, or with a substituent in which two or more substituents selected from the above-mentioned exemplary substituents are linked together.

[0017] In this specification, when "no substituent is shown in the chemical formula or compound structure," it means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 H, Deuterium) or tritium are isotopes of hydrogen, so unless they are specifically excluded, they can be interpreted as concepts included in hydrogen.

[0018] That is, in this application, according to Chem.Commun., 2014, 50, 14870, deuterium exhibits equivalent effects or improved effects in some evaluation criteria in terms of driving voltage, luminous efficiency, and lifespan compared to hydrogen, and falls within the range that a person of ordinary skill in the art would predict to have equivalent effects without specific experiments. Therefore, deuterium, which is an isotope of hydrogen, is interpreted as a concept included in hydrogen unless it is explicitly excluded.

[0019] According to one embodiment of the present specification, "when no substituent is shown in the chemical formula or compound structure," may mean that all positions available as a substituent are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be deuterium, which is an isotope of hydrogen, and in this case, the content of deuterium may be 0% to 100%.

[0020] According to one embodiment of the present specification, in the case where "substituents are not displayed in the chemical formula or structure of a compound," if deuterium is not clearly excluded, such as when the deuterium content is 0%, the hydrogen content is 100%, or all substituents are hydrogen, hydrogen and deuterium may be used together in the compound.

[0021] According to one embodiment of the present specification, deuterium is one of the isotopes of hydrogen, and is an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, and may be represented by hydrogen-2, and its atomic symbol is D or 2 It may also be written as H.

[0022] According to one embodiment of the present specification, isotopes, which refer to atoms with the same atomic number (Z) but different mass numbers (A), can be interpreted as elements with the same number of protons but different numbers of neutrons.

[0023] According to one embodiment of the present specification, the content T% of a specific substituent can be defined as T2 / T1×100=T%, where T1 is the total number of substituents that the base compound may have and T2 is the number of specific substituents among the total number of substituents.

[0024] That is, [ka] Taking the phenyl group represented by the formula below as an example, a deuterium content of 20% can be expressed as 20% when the total number of substituents that the phenyl group can have is 5 (T1 in the formula), of which the number of deuterium is 1 (T2 in the formula). That is, a phenyl group with a deuterium content of 20% may be represented by the following structural formula. [ka]

[0025] Furthermore, according to one embodiment of the present specification, a "phenyl group having a deuterium content of 0%" may refer to a phenyl group that does not contain a deuterium atom, i.e., a phenyl group that has five hydrogen atoms.

[0026] As used herein, the halogen may be fluorine, chlorine, bromine, or iodine.

[0027] In this specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms and may be further substituted with other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, more specifically 1 to 20. Specific examples include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl ... Examples of alkyl groups include, but are not limited to, butyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl groups.

[0028] In this specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms and may be further substituted with other substituents. The number of carbon atoms in the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group.

[0029] In this specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The alkynyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms.

[0030] In this specification, the alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably has 1 to 20 carbon atoms. Specific examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, and p-methylbenzyloxy.

[0031] In this specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms and may be further substituted with other substituents. Here, "polycyclic" refers to a group in which a cycloalkyl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be a cycloalkyl group, but may also be other types of cyclic groups, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0032] In this specification, the heterocycloalkyl group contains O, S, Se, N, or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, which may be further substituted with other substituents. Here, the term "polycyclic" refers to a group in which a heterocycloalkyl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be a heterocycloalkyl group, but may also be other types of cyclic groups, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 20. In this specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic ring means a group in which an aryl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be an aryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or a heteroaryl group. The aryl group includes a spiro group. The number of carbon atoms in the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and fused ring groups thereof.

[0033] In this specification, the terphenyl group may be selected from the following structures: [ka]

[0034] As used herein, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a substituted or unsubstituted ring.

[0035] When the fluorenyl group is substituted, it may be selected from the following structures, but is not limited thereto. [ka]

[0036] In this specification, the heteroaryl group contains S, O, Se, N, or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, which may be further substituted with other substituents. Here, the polycyclic ring refers to a group in which the heteroaryl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be a heteroaryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or an aryl group. The number of carbon atoms in the heteroaryl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 25.Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, a a quinolyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, a quinozolyl group, a naphthyridyl group, an acridinyl group, a phenanthridinyl group, an imidazopyridinyl group, a diazanaphthalenyl group, a triazaindene group, an indolyl group, an indolizinyl group, a benzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiophene group, a benzofuran group, a dibenzothiophene group, a dibenzofuran group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazo ... aryl group, phenazinyl group, dibenzosilole group, spirobi(dibenzosilole) group, dihydrophenazinyl group, phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiathiazinyl group, phthalazinyl group, naphthyridinyl group , phenanthrolinyl group, benzo[c][1,2,5]thiadiazolyl group, 2,3-dihydrobenzo[b]thiophene group, 2,3-dihydrobenzofuran group, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl group, pyrazolo[1,5-c]quinazolinyl group, pyrido[1,2-b]indazolyl group, pyrido[1,2-a]imidazo[1,2-e]indolinyl group, 5,11-dihydroindeno[1,2-b]carbazolyl group, and the like.

[0037] In this specification, when a substituent is a carbazole group, it means that it is bonded to the nitrogen or carbon of the carbazole.

[0038] As used herein, when the carbazole group is substituted, additional substituents may be substituted on the nitrogen or carbon of the carbazole.

[0039] As used herein, a benzocarbazole group may have any one of the following structures: [ka]

[0040] As used herein, a dibenzocarbazole group may have any one of the following structures: [ka]

[0041] As used herein, a naphthobenzofuran group may have any one of the following structures: [ka]

[0042] As used herein, a naphthobenzothiophene group may have any one of the following structures: [ka]

[0043] In this specification, the silyl group is a substituent that contains Si and is directly linked to the Si atom as a radical, and is represented by -Si(R101)(R102)(R103), where R101 to R103 may be the same or different and each independently represent at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, and a heteroaryl group.

[0044] Specific examples of the silyl group include: [ka] These include, but are not limited to:

[0045] In this specification, the phosphine oxide group is represented by -P(=O)(R104)(R105), where R104 and R105 may be the same or different and each independently represent at least one substituent selected from the group consisting of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, and a heteroaryl group. Specifically, the phosphine oxide group may be substituted with an alkyl group or an aryl group, and the alkyl group and aryl group may be as exemplified above. For example, the phosphine oxide group may include, but is not limited to, a dimethylphosphine oxide group, a diphenylphosphine oxide group, and a dinaphthylphosphine oxide group.

[0046] In this specification, the amine group is represented by -N(R106)(R107), where R106 and R107 may be the same or different and each independently represent at least one substituent selected from the group consisting of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, and a heteroaryl group. The amine group may be selected from the group consisting of -NH2, a monoalkylamine group, a monoarylamine group, a monoheteroarylamine group, a dialkylamine group, a diarylamine group, a diheteroarylamine group, an alkylarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group. The number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group.

[0047] In this specification, the arylene group may be any of the examples of the aryl group described above, except that the arylene group is a divalent group.

[0048] In this specification, the heteroarylene group may be any of the examples of the heteroaryl group described above, except that the heteroarylene group is a divalent group.

[0049] As used herein, the term "adjacent" groups may refer to a substituent substituted on an atom directly linked to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring can be interpreted as groups "adjacent" to each other.

[0050] The hydrocarbon rings and hetero rings that can form adjacent groups include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic hetero rings, and aromatic hetero rings, and the structures exemplified above as the cycloalkyl group, aryl group, heterocycloalkyl group, and heteroaryl group, respectively, may be applied, except that the rings are not monovalent groups. In one embodiment of the present specification, a group not represented by a substituent or a group represented by hydrogen can be substituted with deuterium. That is, hydrogen (H) and deuterium (D) can be substituted with each other.

[0051] In general, there is a difference in thermodynamic behavior between hydrogen-bonded compounds and deuterium-substituted compounds. This is because the mass of a deuterium atom is twice as large as that of hydrogen, and due to the difference in atomic mass, deuterium has the characteristic of having lower vibrational energy.

[0052] In addition, the bond dissociation energy between carbon and deuterium is higher than that between carbon and hydrogen, so the deuterium-substituted structure increases the thermal stability of the molecule, improving the lifespan of devices using it.

[0053] When a compound is deposited on a silicon wafer, substances containing deuterium tend to be packed closer together with tighter intermolecular distances. Also, when observing the thin film surface with an atomic force microscope (AFM), it can be seen that thin films made from compounds containing deuterium are deposited on a more uniform surface without any aggregates.

[0054] <Organic light-emitting element> The organic light-emitting device according to the present specification will be described below. The organic material layer of the organic light-emitting device according to one embodiment of the present specification contains a heterocyclic compound represented by the following chemical formula A. [ka] In the above chemical formula A, the explanation of each substituent is as described above.

[0055] The heterocyclic compound represented by the chemical formula A is a 2-substituted naphthobenzofuran, [ka] acts as a donor unit to increase the electron density of the aromatic unit, shift the HOMO energy level toward the vacuum level, and enhance the hole-generating properties. [ka] is substituted at various positions on the core skeleton, which changes the thermal properties of the material, such as the glass transition temperature and thermal decomposition temperature, thereby increasing thermal stability, and by changing the length of the conjugated structure and molecular orientation, the hole properties are improved, resulting in an overall display of excellent electron and hole transport properties.

[0056] When a heterocyclic compound represented by chemical formula A, which has excellent hole transport properties, is used together with a heterocyclic compound represented by chemical formula B, which has fast electron transport properties, it acts as a P-type host material, making it easy to balance the number of holes and electrons in the organic layer (especially the light-emitting layer (EML)), thereby maximizing hole transport properties and electron transport properties. As a result, charge balance occurs within the organic layer, preventing degradation caused by the accumulation of electrons and holes. As a result, exciton generation efficiency increases, resulting in high efficiency and long life.

[0057] The organic material layer of the organic light-emitting device according to one embodiment of the present specification contains a heterocyclic compound represented by the following chemical formula B. [ka] In the above chemical formula B, the explanation of each substituent is as described above.

[0058] The compound represented by the chemical formula B is a 2-substituted oxygen-containing condensed heterocycle (dibenzofuran) having three or more rings, and the first substituent [ka] The N-Het1 (represented by the structural formula N, which corresponds to triazine, etc.) acts as an acceptor unit to lower the electron density of the aromatic unit and deepen the LUMO energy level, thereby enhancing the electron transfer properties. [ka] The Ar4 is substituted at various positions in the core skeleton, which changes the thermal properties of the material, such as the glass transition temperature and thermal decomposition temperature, thereby increasing thermal stability, and by changing the length of the conjugated structure and molecular orientation, the hole properties are improved, resulting in excellent electron and hole transport properties and high efficiency overall.

[0059] When a heterocyclic compound represented by formula B, which has fast electron transfer properties, is used together with a heterocyclic compound represented by formula A, which has excellent hole transfer properties, it acts as an N-type host material, and in the organic layer (especially the light-emitting layer (EML)), the large difference between the HOMO and LUMO between the two hosts generates excitons between the two hosts, forming an excited charge-transfer complex, exhibiting exciplex properties. This has the effect of lowering the driving voltage due to strong hole and electron transport properties, and the formation of an exciplex between the two hosts allows the energy transfer process to dominate the light-emitting process. When the two compounds are used in combination, charge balance is maintained and electron injection and transfer are facilitated, resulting in high efficiency and low driving voltage, while also demonstrating excellent lifespan characteristics.

[0060] When used in an organic light emitting device, the compound according to the above embodiment may have low driving voltage, high luminous efficiency, and / or long life characteristics.

[0061] According to one embodiment of the present specification, the chemical formula A may be represented by the following chemical formula A-1. [ka] In the above chemical formula A-1, Each of L1, L2, Ar1 to Ar3, R1, R2, l1, l2, r1, and r2 is defined as in Chemical Formula A above.

[0062] According to one embodiment of the present specification, the chemical formula A may be represented by any one of the following chemical formulae A-101 to A-108. [ka] [ka] In the chemical formulas A-101 to A-108, L1, L2, Ar1 to Ar3, R1, R2, l1, l2, r1, and r2 are defined as in Chemical Formula A above, r1' is an integer from 0 to 5, r2' is an integer from 0 to 3, When each of r1' and r2' is an integer of 2 or more, the types of the substituents in the parentheses are the same or different.

[0063] According to one embodiment of the present specification, the chemical formula B may be represented by either one of the following chemical formulas B-1 and B-2. [ka] In the chemical formulas B-1 and B-2, The definitions of L3, L4, Ar4, N-Het1, R3, R4, l3, l4, and r4 are the same as those in Chemical Formula B above; r3' is an integer of 0 to 3, and when r3' is an integer of 2 or more, R3's are the same or different from each other; r3" is an integer of 0 to 2, and when r3" is 2, R3 are the same or different from each other; r4' is an integer of 0 to 3, and when r4' is an integer of 2 or more, R4's are the same or different from each other.

[0064] According to one embodiment of the present specification, the chemical formula B may be represented by the following chemical formula B-11 or B-12. [ka] In the chemical formulas B-11 and B-12, The definitions of L3, L4, Ar4, N-Het1, r3, r4, l3, and l4 are the same as those in Chemical Formula B above; R3', R4', and R5 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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; r4" is an integer of 0 to 2, and when r4" is 2, R4' are the same or different from each other; r5 is an integer of 0 to 4, and when r5 is an integer of 2 or more, R5s are the same or different.

[0065] According to one embodiment of the present specification, the chemical formula B may be represented by any one of the following chemical formulas B-101 to B-115. [ka] [ka] [ka] [ka] In the chemical formulas B-101 to B-115, The definitions of L3, L4, Ar4, N-Het1, r3, r4, l3, and l4 are the same as those in Chemical Formula B above; R3', R4', and R5 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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; r3' is an integer of 0 to 3, and when r3' is an integer of 2 or more, R3' are the same or different from each other; r3" is an integer of 0 to 2, and when r3" is 2, R3' are the same or different from each other; r4' is an integer of 0 to 3, and when r4' is an integer of 2 or more, R4' are the same or different from each other; r4" is an integer of 0 to 2, and when r4" is 2, R4' are the same or different from each other; r5 is an integer of 0 to 4, and when r5 is an integer of 2 or more, R5s are the same or different.

[0066] According to one embodiment of the present specification, L1 to L4 are the same or different and may each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

[0067] According to one embodiment of the present specification, L1 to L4 may be the same or different and each independently represent a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0068] According to one embodiment of the present specification, L1 to L4 may be the same or different and each independently represent a direct bond; or an arylene group having 6 to 30 carbon atoms and which is unsubstituted or substituted with deuterium.

[0069] According to one embodiment of the present specification, L1 to L4 may be the same or different and each independently represent a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0070] According to one embodiment of the present specification, L1 to L4 may be the same or different and each independently represent a direct bond; a deuterium-substituted or unsubstituted phenylene group; a deuterium-substituted or unsubstituted biphenylene group; or a deuterium-substituted or unsubstituted naphthylene group.

[0071] According to one embodiment of the present specification, Ar1 to Ar3 may be the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms; or a combination thereof.

[0072] According to one embodiment of the present specification, Ar1 to Ar3 may be the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; or a combination thereof.

[0073] According to one embodiment of the present specification, Ar1 to Ar3 may be the same or different and each independently represent an aryl group having 6 to 30 carbon atoms and substituted or unsubstituted with a substituent selected from the group consisting of deuterium, an alkyl group, and an aryl group; a heteroaryl group having 2 to 30 carbon atoms and substituted or unsubstituted with a substituent selected from the group consisting of deuterium, an alkyl group, and an aryl group; or a combination thereof.

[0074] According to one embodiment of the present specification, Ar1 to Ar3 are the same or different and each independently represent a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a fluorenyl group; a spirobifluorenyl group; a phenanthrenyl group; a dibenzofuranyl group; a dibenzothiophenyl group; a naphthobenzofuranyl group; a naphthobenzothiophenyl group; a carbazole group; or a combination thereof, each independently of the other, which may be substituted or unsubstituted with a substituent selected from the group consisting of deuterium, a halogen group, an alkyl group, and an aryl group.

[0075] According to one embodiment of the present specification, Ar4 may be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms; or a substituted or unsubstituted amine group.

[0076] According to one embodiment of the present specification, Ar4 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; or -NRbRc, where Rb and Rc may be the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms; 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.

[0077] According to one embodiment of the present specification, Ar4 is an aryl group having 6 to 30 carbon atoms and substituted or unsubstituted with deuterium or an aryl group; a heteroaryl group having 2 to 30 carbon atoms and substituted or unsubstituted with deuterium or an aryl group; or -NRbRc, where Rb and Rc may be the same or different and each independently represent hydrogen; deuterium; an aryl group having 6 to 30 carbon atoms and substituted or unsubstituted with deuterium or an aryl group; or a heteroaryl group having 2 to 30 carbon atoms and substituted or unsubstituted with deuterium or an aryl group.

[0078] According to one embodiment of the present specification, Ar4 is an aryl group having 6 to 20 carbon atoms and substituted or unsubstituted with deuterium or an aryl group; a heteroaryl group having 2 to 20 carbon atoms and substituted or unsubstituted with deuterium or an aryl group; or -NRbRc, where Rb and Rc may be the same or different and each independently represent hydrogen; deuterium; an aryl group having 6 to 20 carbon atoms and substituted or unsubstituted with deuterium or an aryl group; or a heteroaryl group having 2 to 20 carbon atoms and substituted or unsubstituted with deuterium or an aryl group.

[0079] According to one embodiment of the present specification, Ar4 may be a phenyl group; a biphenyl group; a naphthyl group; a dibenzofuranyl group; a dibenzothiophenyl group; a 9-carbazole group; a 9-benzocarbazole group; or -NRbRc, wherein the phenyl group; the biphenyl group; the naphthyl group; the dibenzofuranyl group; the dibenzothiophenyl group; the 9-carbazole group; and the 9-benzocarbazole group may each independently be substituted or unsubstituted with deuterium, a phenyl group, or a naphthyl group, and Rb and Rc may be the same or different and each independently be hydrogen; deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a dibenzofuranyl group substituted or unsubstituted with deuterium; or a dibenzothiophenyl group substituted or unsubstituted with deuterium.

[0080] According to one embodiment of the present specification, R1 and R2 are the same or different and may each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 40 carbon atoms; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0081] According to one embodiment of the present specification, R1 and R2 are the same or different and may each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms; 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.

[0082] According to one embodiment of the present specification, R1 and R2 are the same or different and may each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms; 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.

[0083] According to one embodiment of the present specification, R1 and R2 may be the same or different and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; or a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms.

[0084] According to one embodiment of the present specification, R1 and R2 may be the same or different and may each independently be hydrogen; or deuterium.

[0085] According to one embodiment of the present specification, R3 and R4 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 40 carbon atoms; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted ring.

[0086] According to one embodiment of the present specification, R3 and R4 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms; 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, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms.

[0087] According to one embodiment of the present specification, R3 and R4 are the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

[0088] According to one embodiment of the present specification, R3 and R4 are the same or different and each independently represent hydrogen or deuterium, or two or more adjacent groups may be bonded to each other to form a benzene ring substituted or unsubstituted with deuterium.

[0089] In one embodiment of the present application, the chemical formula N may be selected from the following structural formulas: [ka] In the structural formula: [ka] The definitions of Y1 to Y5 are the same as those in the chemical formula N.

[0090] According to one embodiment of the present specification, Y1 to Y5 are the same or different and each independently represent CRa or N, and two or more groups may be N. In other words, the structural formula N may be any one of the following structures: [ka] In the structural formula: [ka] The definitions of Y1 to Y5 are the same as those in the chemical formula N.

[0091] According to one embodiment of the present specification, Y1 to Y5 are the same or different and each independently represent CRa or N, and three groups may be N. In other words, the structural formula N may be any one of the following structures: [ka]

[0092] Preferably, the structural formula N is: [ka] may be.

[0093] In the structural formula: [ka] The definitions of Y2 to Y5 are the same as those in the chemical formula N.

[0094] According to one embodiment of the present specification, Ra may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; or a combination thereof.

[0095] According to one embodiment of the present specification, Ra may be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; or a combination thereof.

[0096] According to one embodiment of the present specification, Ra may be an aryl group having 6 to 20 carbon atoms and substituted or unsubstituted with a substituent selected from the group consisting of deuterium and an aryl group; a heteroaryl group having 2 to 20 carbon atoms and substituted or unsubstituted with deuterium; or a combination thereof.

[0097] According to one embodiment of the present specification, Ra may be a phenyl group substituted or unsubstituted with deuterium, a phenyl group, or a naphthyl group; a naphthyl group substituted or unsubstituted with deuterium or a phenyl group; a phenanthrenyl group substituted or unsubstituted with deuterium; a dibenzofuranyl group substituted or unsubstituted with deuterium; a dibenzothiophenyl group substituted or unsubstituted with deuterium; or a combination thereof.

[0098] According to one embodiment of the present specification, the heterocyclic compound represented by chemical formula A and the heterocyclic compound represented by chemical formula B may have the same or different deuterium contents, and each may independently be 0% or 1% to 100%.

[0099] According to one embodiment of the present specification, the deuterium contents of the heterocyclic compound represented by chemical formula A and the heterocyclic compound represented by chemical formula B may be the same or different, and each may independently be 0% or 10% to 100%.

[0100] According to one embodiment of the present specification, the heterocyclic compound represented by chemical formula A and the heterocyclic compound represented by chemical formula B may have the same or different deuterium contents, and each may independently be 0% or 20% to 100%.

[0101] According to one embodiment of the present specification, the heterocyclic compound represented by chemical formula A and the heterocyclic compound represented by chemical formula B may have the same or different deuterium contents, and each may independently be 0% or 30% to 100%.

[0102] According to one embodiment of the present specification, the heterocyclic compound represented by chemical formula A and the heterocyclic compound represented by chemical formula B may have the same or different deuterium contents, and each may independently be 0% or 60% to 100%.

[0103] According to one embodiment of the present specification, the heterocyclic compound represented by chemical formula A and the heterocyclic compound represented by chemical formula B may have the same or different deuterium contents, and each may independently be 0% or 80% to 100%.

[0104] According to one embodiment of the present specification, the heterocyclic compound represented by chemical formula A and the heterocyclic compound represented by chemical formula B may have the same or different deuterium contents, and each may independently be 0% or 90% to 100%.

[0105] The formula A may be represented by any one of the following heterocyclic compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

change

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[0106] According to one embodiment of the present specification, the chemical formula B may be represented by any one of the following heterocyclic compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0107] By introducing various substituents into the structure represented by Chemical Formula A and / or B, it is possible to synthesize compounds having the specific properties of the introduced substituents. For example, by introducing into the core structure substituents that are mainly used in hole injection layer materials, hole transport layer materials, hole transport assist layer materials, light emitting layer materials, electron transport layer materials, electron transport assist layer materials, and charge generation layer materials used in the manufacture of organic light emitting devices, it is possible to synthesize materials that satisfy the requirements for each organic layer.

[0108] In addition, by introducing various substituents into the structure of the chemical formula A and / or B, the energy band gap can be finely adjusted, and the properties at the interface between organic materials can be improved, thereby diversifying the uses of the material.

[0109] According to one embodiment of the present specification, the organic layer may further include an emission layer, and the emission layer may include a heterocyclic compound represented by the chemical formula A; and a heterocyclic compound represented by the chemical formula B.

[0110] In another embodiment of the present specification, the light-emitting layer may contain the heterocyclic compound represented by the chemical formula A and the heterocyclic compound represented by the chemical formula B as hosts, respectively.

[0111] According to one embodiment of the present specification, the light-emitting layer may contain, as red hosts, the heterocyclic compound represented by the chemical formula A and the heterocyclic compound represented by the chemical formula B.

[0112] According to one embodiment of the present specification, the light-emitting layer may contain the heterocyclic compound represented by the chemical formula A and the heterocyclic compound represented by the chemical formula B as green hosts.

[0113] According to one embodiment of the present specification, the light-emitting layer may contain, as blue hosts, the heterocyclic compound represented by the chemical formula A and the heterocyclic compound represented by the chemical formula B.

[0114] According to one embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

[0115] According to one embodiment of the present specification, the first electrode may be a cathode, and the second electrode may be an anode.

[0116] According to one embodiment of the present specification, the organic light-emitting element may be a blue organic light-emitting element, and the heterocyclic compound represented by chemical formula A and the heterocyclic compound represented by chemical formula B may each be used as a material for the blue organic light-emitting element.

[0117] According to one embodiment of the present specification, the organic light-emitting element may be a green organic light-emitting element, and the heterocyclic compound represented by chemical formula A and the heterocyclic compound represented by chemical formula B may each be used as a material for the green organic light-emitting element.

[0118] According to one embodiment of the present specification, the organic light-emitting element may be a red organic light-emitting element, and the heterocyclic compound represented by chemical formula A and the heterocyclic compound represented by chemical formula B may each be used as a material for the red organic light-emitting element.

[0119] The organic material layer of the organic light-emitting device of the present specification may have a single-layer structure or a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present specification may have a structure including a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a fewer or greater number of organic material layers.

[0120] According to one embodiment of the present specification, the organic layer may contain an iridium-based dopant.

[0121] According to one embodiment of the present specification, the iridium-based dopant may be Ir(ppy)3, which is a green phosphorescent dopant, but is not limited thereto.

[0122] According to one embodiment of the present specification, the iridium-based dopant may be a red phosphorescent dopant, (piq)2(Ir)(acac), but is not limited thereto.

[0123] In the organic light-emitting device of the present specification, the anode material may be a material with a relatively large work function, such as a transparent conductive oxide, a metal, or a conductive polymer. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0124] In the organic light-emitting device of the present specification, the cathode material may be a material with a relatively low work function, such as a metal, a metal oxide, or a conductive polymer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and materials with a multilayer structure such as LiF / Al or LiO / Al.

[0125] In the organic light-emitting device of the present specification, the hole injection material may be a known hole injection material, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429, or a starburst-type amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], for example, tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), or a soluble conductive polymer, polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic acid). Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), Polyaniline / Camphor sulfonic acid, or Polyaniline / Poly(4-styrenesulfonate) may also be used.

[0126] In the organic light-emitting device of this specification, the hole transport material may be a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, or the like, or a low-molecular or high-molecular material.

[0127] In the organic light-emitting device of the present specification, examples of the electron transport material that can be used include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, and metal complexes of 8-hydroxyquinoline and derivatives thereof. Not only low-molecular-weight substances but also high-molecular-weight substances can be used.

[0128] In the organic light-emitting device of the present specification, for example, LiF is typically used as the electron injection material in the art, but the present specification is not limited thereto.

[0129] In the organic light-emitting device of the present specification, a red, green, or blue light-emitting material may be further used as the light-emitting material, and two or more light-emitting materials may be mixed as needed. In this case, two or more light-emitting materials may be deposited as separate supply sources or may be premixed and deposited as a single supply source. The light-emitting material may be a fluorescent material or a phosphorescent material. The light-emitting material may be a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, or a material in which both the host material and the dopant material contribute to light emission.

[0130] When a mixture of hosts for the light-emitting material is used, the mixture may be of the same type or different types. For example, two or more N-type host materials or P-type host materials may be selected and used as the host material for the light-emitting layer.

[0131] The organic light emitting device according to an embodiment of the present specification may be top-emitting, bottom-emitting, or dual-sided emitting, depending on the materials used.

[0132] The heterocyclic compound according to an embodiment of the present specification can also function in organic electronic devices such as organic solar cells, organic photoreceptors, and organic transistors based on the same principle as that applied to organic light-emitting devices.

[0133] The organic light-emitting device of the present specification may further include one or more layers selected from the group consisting of an emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0134] 1 to 3 illustrate examples of the stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present specification. However, these drawings are not intended to limit the scope of the present application, and structures of organic light-emitting devices known in the technical field may be applied to the present application.

[0135] 1 shows an organic light-emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, the present invention is not limited to this structure, and an organic light-emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be realized as shown in FIG. 2. The composition for the organic light-emitting device may be included in the organic material layer 300, and the organic material layer 300 may be one or more layers.

[0136] 3 illustrates an example in which the organic material layer has multiple layers. The organic light-emitting device of FIG. 3 includes a hole injection layer 301, a hole transport layer 302, an electron blocking layer 303, an emitting layer 304, a hole blocking layer 305, an electron transport layer 306, and an electron injection layer 307. The composition for the organic light-emitting device may be included in the emitting layer 304. However, such a layered structure does not limit the scope of the present application. If necessary, the remaining layers except for the emitting layer may be omitted, and other necessary functional layers may be further added.

[0137] An organic light-emitting device according to one embodiment of the present specification includes a first electrode; a first stack provided on the first electrode and including a first light-emitting layer; a charge generation layer provided on the first stack; a second stack provided on the charge generation layer and including a second light-emitting layer; and a second electrode provided on the second stack.

[0138] When the organic light-emitting device according to an embodiment of the present specification has the above-described two-stack structure, one or more of the first light-emitting layer (first stack light-emitting layer) and the second light-emitting layer (second stack light-emitting layer) may contain the heterocyclic compound represented by the chemical formula A; and the heterocyclic compound represented by the chemical formula B.

[0139] The first stack and the second stack may each independently further include one or more of the above-mentioned hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer, and the like.

[0140] The heterocyclic compound represented by the chemical formula A and the heterocyclic compound represented by the chemical formula B can be used when forming an organic layer of an organic light-emitting device, and are particularly preferably used as light-emitting layer materials.

[0141] The heterocyclic compound represented by the chemical formula A and the heterocyclic compound represented by the chemical formula B may be in a premixed form, or powdered materials may be mixed before forming the organic layer of the organic light-emitting device, or compounds that are in a liquid state at an appropriate temperature or higher may be mixed. The composition is in a solid state below the melting point of each material, and can be maintained in a liquid state by adjusting the temperature.

[0142] The heterocyclic compound represented by the chemical formula A and the heterocyclic compound represented by the chemical formula B may further contain materials known in the technical field, such as a solvent and an additive.

[0143] <Composition for organic layer of organic light-emitting device> Hereinafter, the composition for the organic layer of the organic light-emitting device according to the present specification will be described.

[0144] Another embodiment of the present specification is a composition for an organic layer of an organic light-emitting device, characterized in that it contains a heterocyclic compound represented by the chemical formula A and a heterocyclic compound represented by the chemical formula B. The chemical formula A and the chemical formula B contained in the composition for an organic layer of the organic light-emitting device have been described above.

[0145] According to one embodiment of the present specification, the weight ratio of the heterocyclic compound represented by the chemical formula A to the heterocyclic compound represented by the chemical formula B may be 1:10 to 10:1.

[0146] According to one embodiment of the present specification, the weight ratio of the heterocyclic compound represented by the chemical formula A to the heterocyclic compound represented by the chemical formula B may be 1:5 to 5:1.

[0147] According to one embodiment of the present specification, the weight ratio of the heterocyclic compound represented by the chemical formula A to the heterocyclic compound represented by the chemical formula B may be 1:3 to 3:1.

[0148] In addition, the composition for an organic layer containing the heterocyclic compound of Formula A and the heterocyclic compound of Formula B provides excellent thermal stability when used in an organic light emitting device. This thermal stability not only provides driving stability to future organic light emitting devices but also improves their lifespan characteristics.

[0149] <Method of manufacturing organic light-emitting element> One embodiment of the present specification provides a method for manufacturing an organic light-emitting device, comprising the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layers, wherein the step of forming the organic material layers comprises forming one or more organic material layers using the composition for an organic material layer of the organic light-emitting device described above.

[0150] In one embodiment of the present specification, the step of forming the organic layer may be performed by pre-mixing the heterocyclic compound of Formula A and the heterocyclic compound of Formula B and forming the organic layer using a thermal vacuum deposition method.

[0151] The term "pre-mixed" means that the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 are mixed in a single source before being deposited on an organic layer.

[0152] The premixed materials may be referred to as an organic layer composition according to one embodiment of the present application.

[0153] The organic light emitting device according to an embodiment of the present specification may be manufactured using a conventional method and material for manufacturing an organic light emitting device, except that the organic material layer is formed using the composition for the organic material layer of the organic light emitting device described above.

[0154] Specifically, in the method for forming the organic material layer, the heterocyclic compound of Formula A and the heterocyclic compound of Formula B may be formed into the organic material layer by a solution coating method as well as a vacuum deposition method during the manufacture of the organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc. [Example]

[0155] The present specification will be described in more detail below with reference to examples, but these are merely for the purpose of illustrating the present application and are not intended to limit the scope of the present application.

[0156] Manufacturing example [Production Example 1] Production of Compound A-5 [ka] 1) Preparation of Compound A-5-1 A-5-2 (A) (20 g, 0.060 mol, 1 eq), phenylboronic acid (B) (8.04 g, 0.066 mol, 1.1 eq), K2CO3 (20.8 g, 0.151 mol, 2.5 eq), and Pd(PPh3)4 (3.38 g, 0.003 mol, 0.05 eq) were added to 1,4-dioxane (250 ml) and water (50 ml) and stirred at 100 °C for 6 hours. After the reaction was terminated by adding water, the mixture was extracted with MC (methylene chloride) and water. The water was then removed with MgSO4. Compound A-5-1 (15.8 g) was obtained in 80% yield after separation on a silica gel column.

[0157] 2) Preparation of Compound A-5 A mixture of A-5-1 (6 g, 0.018 mol, 1 eq), N-phenyldibenzo[b,d]furan-4-amine (C) (6.5 g, 0.020 mol, 1.1 eq), NaOt-Bu (2.6 g, 0.028 mol, 1.5 eq), Pd2(dba)3 (0.84 g, 0.0009 mol, 0.05 eq), and XPhos (0.84 g, 0.0018 mol, 0.1 eq) in toluene (120 ml) was stirred at 100 °C for 8 h. The reaction was terminated by adding water, and the mixture was extracted with MC and water. The water was then removed with MgSO4. The mixture was separated using a silica gel column, yielding 7 g of compound A-5 in 79% yield.

[0158] [Production Example 2] Production of Compound A-341 [ka] 1) Preparation of Compound A-341 A mixture of A-5-1 (5 g, 0.015 mol, 1 eq) from Preparation Example 1, N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (D) (6.8 g, 0.018 mol, 1.2 eq), NaOH (1.5 g, 0.038 mol, 2.5 eq), Pd2(dba)3 (0.7 g, 0.0008 mol, 0.05 eq), and XPhos (0.7 g, 0.0015 mol, 0.1 eq) was added to 1,4-dioxane (50 mL) and water (10 mL) and stirred at 100°C for 8 hours. The reaction was terminated by adding water, and the mixture was extracted with MC and water. The water was then removed with MgSO4. Separation was carried out on a silica gel column to obtain 5.5 g of compound A-341 in a 67% yield.

[0159] [Production Example 3] Production of other compound A Compound A was synthesized in the same manner as in Preparation Example 1 or 2, except that intermediates A, B, C, and D in Table 1 below were used in place of intermediates (A), (B), (C), and (D) described in Preparation Example 1 or 2.

[0160] [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4]

[0161] [Production Example 4] Production of Compound B-1 [ka] 1) Preparation of Compound B-1-2 B-1-3(E) (20 g, 0.060 mol, 1 eq), phenylboronic acid (F) (8.09 g, 0.066 mol, 1.1 eq), K2CO3 (20.8 g, 0.151 mol, 2.5 eq), Pd(PPh3)4 (3.38 g, 0.003 mol, 0.05 eq) were added to 1,4-dioxane (250 ml) and water (50 ml) and stirred at 100 °C for 6 hours. After the reaction was terminated by adding water, the mixture was extracted with MC and water. The water was then removed with MgSO4. The mixture was separated using a silica gel column, yielding 17 g of compound B-1-2 in 86% yield.

[0162] 2) Preparation of Compound B-1-1 1,4-Dioxane (200 ml) was added to the B-1-2 (17 g, 0.052 mol, 1 eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (26 g, 0.103 mol, 2 eq), KOAc (15 g, 0.155 mol, 3 eq), Pd2(dba)3 (2.37 g, 0.0026 mol, 0.05 eq), and XPhos (2.46 g, 0.0052 mol, 0.1 eq) and stirred at 100 °C for 8 hours. After adding water to terminate the reaction, the mixture was extracted with MC and water. Then, water was removed with MgSO4. The mixture was separated using a silica gel column to obtain 15 g of compound B-1-1 with a yield of 69%.

[0163] 3) Preparation of Compound B-1 The B-1-1 (10 g, 0.024 mol, 1.05 eq), 2-chloro-4,6-diphenyl-1,3,5-triazine (G) (6.1 g, 0.023 mol, 1 eq), K2CO3 (6.27 g, 0.045 mol, 2 eq), and Pd(PPh3)4 (1.3 g, 0.001 mol, 0.05 eq) were added to 1,4-dioxane (100 mL) and water (20 mL) and stirred at 100 °C for 8 hours. After the reaction was terminated by adding water, the mixture was extracted with MC and water. The water was then removed with MgSO4. Separation was carried out on a silica gel column to obtain 9 g of compound B-1 in 75% yield.

[0164] [Production Example 5] Production of other compound B Compound B was synthesized in the same manner as in Preparation Example 4, except that intermediates E, F, and G in Table 2 below were used in place of intermediates (E), (F), and (G).

[0165] [Table 2-1] [Table 2-2] [Table 2-3]

[0166] [Production Example 6] Production of Compound A-323 [ka] 1) Preparation of Compound A-323 Compound A-369 (10 g, 0.016 mol, 1 eq), TfOH (3.7 g, 0.024 mol, 1.5 eq), and D6-benzene (100 ml) were added and stirred at 100°C for 8 hours. Water was added to terminate the reaction, and the mixture was extracted with MC and water. Water was then removed with MgSO4. Compound A-323 was separated using a silica gel column, yielding 8.2 g in 78% yield.

[0167] [Production Example 7] Production of Compound B-242 [ka] 1) Preparation of Compound B-242-2 B-242-3(E) (10 g, 0.035 mmol, 1 eq), 5H-Benzo[b]carbazole(H) (7.72 g, 0.035 mmol, 1 eq), NaOt-Bu (6.83 g, 0.071 mmol, 2 eq), Xphos (1.69 g, 0.0035 mmol, 0.1 eq), and Pd2(dba)3 (1.3 g, 0.0014 mmol, 0.04 eq) were added to toluene (100 mL) and stirred at 100 °C for 3 h. The reaction was terminated by adding water, and the mixture was extracted with MC and water. The water was then removed with MgSO4. The mixture was separated on a silica gel column, affording 14 g of compound B-242-2 in 94% yield.

[0168] 2) Preparation of Compound B-242-1 The B-242-2 (14 g, 0.034 mol, 1 eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (17 g, 0.067 mol, 2 eq), KOAc (9.66 g, 0.100 mol, 3 eq), Pd2(dba)3 (1.53 g, 0.0017 mol, 0.05 eq), and XPhos (1.6 g, 0.0034 mol, 0.1 eq) were added to 1,4-dioxane (150 ml) and stirred at 100 °C for 8 hours. After the reaction was terminated by adding water, the mixture was extracted with MC and water. The water was then removed with MgSO4. The mixture was separated using a silica gel column to obtain 15 g of compound B-242-1 with a yield of 87%.

[0169] 3) Preparation of Compound B-242 The B-242-1 (15 g, 0.029 mol, 1.05 eq), 2-chloro-4,6-diphenyl-1,3,5-triazine (G) (7.51 g, 0.028 mol, 1 eq), K2CO3 (5.95 g, 0.056 mol, 2 eq), and Pd(PPh3)4 (1.62 g, 0.0014 mol, 0.05 eq) were added to 1,4-dioxane (150 mL) and water (30 mL) and stirred at 100 °C for 8 hours. After the reaction was terminated by adding water, the mixture was extracted with MC and water. The water was then removed with MgSO4. The mixture was separated using a silica gel column, yielding 15 g of compound B-242 in 86% yield.

[0170] The compounds were prepared according to the same methods as in the above Preparation Examples, and the synthesis confirmation results are shown in Tables 3 and 4 below. 1 The values are measured by H NMR (CDCl3, 200 MHz), and Table 4 below shows the values measured by FD-MS (Field desorption mass spectrometry).

[0171] [Table 3-1] [Table 3-2] [Table 3-3]

[0172] [Table 4]

[0173] Experimental Example <Experimental Example 1> Fabrication of organic light-emitting element A glass substrate coated with a 1,500Å thick indium tin oxide (ITO) thin film was ultrasonically cleaned in distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) for 5 minutes using UV in a UV (Ultraviolet) cleaning machine. The substrate was then transferred to a plasma cleaning machine (PT) and plasma treated in a vacuum to remove the ITO work function and residual film, before being transferred to a thermal evaporation system for organic deposition.

[0174] On the ITO transparent electrode (anode), a hole injection layer 2-TNATA (4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine), a hole transport layer NPB (N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), and an electron blocking layer TAPC (cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine]) were formed as common layers. An emitting layer was then formed thereon by thermal vacuum deposition as follows. The emitting layer consisted of a red host The compound compositions (two compounds) listed in Table 5 below were deposited as a single source. (piq)2(Ir)(acac) was used as a red phosphorescent dopant, and the host was doped with 3 wt% Ir compound to a thickness of 400 Å. Next, Bphen (Bathophenanthroline) was deposited to a thickness of 30 Å as a hole-blocking layer, and TPBI (2,2',2''-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole) was deposited to a thickness of 250 Å as an electron-transporting layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron-transporting layer to form an electron-injecting layer. An aluminum (Al) cathode was then deposited to a thickness of 1,200 Å on the electron-injecting layer to form a cathode, completing the fabrication of an organic light-emitting device.

[0175] On the other hand, all the organic compounds required for manufacturing OLED elements are 10 -8 ~10 -6 The organic light-emitting device thus fabricated was subjected to vacuum sublimation purification under torr and used for fabricating an OLED. The electroluminescence (EL) characteristics of the organic light-emitting device fabricated as described above were measured using a Mac Science M7000. Using the measurement results, a reference luminance of 6,000 cd / m was measured using a Mac Science M6000 lifetime measurement device. 2 (cd / A) when 90 The driving voltage, luminous efficiency, color coordinate (CIE), and lifespan of the organic light emitting device manufactured according to the present invention were measured, and the results are shown in Table 5 below.

[0176] [Table 5-1] [Table 5-2]

[0177] The structures of the compounds used in Comparative Examples 3 to 8 are as follows: [ka]

[0178] As can be seen from the results in Table 5, when the heterocyclic compound of the present invention is used as a P-type host and mixed with an N-type host and vapor-deposited, the operation, efficiency, and lifetime of the organic light-emitting device are improved. When a donor with good hole-transporting ability (p-host, a compound in Group A represented by P) and an acceptor with good electron-transporting ability (n-host, a compound in Group B represented by N) are used as the host in the light-emitting layer, holes are injected into the p-host and electrons are injected into the n-host due to the exciplex phenomenon between the N-type host material and the P-type host material, thereby achieving charge balance within the device. This indicates that combining an N-type host compound with suitable electron-transporting properties and a P-type host compound with suitable hole-transporting properties in the appropriate ratio can help improve operation efficiency and lifetime.

[0179] In contrast, in the comparative example compounds used in Comparative Examples 3 to 8, H1 is 1-substituted naphthobenzofuran and is compared to the heterocyclic compound represented by chemical formula A, which corresponds to the P-type host compound; H2 is 1-substituted benzofuran and is compared to the heterocyclic compound represented by chemical formula B, which corresponds to the N-type host compound; and H3 simultaneously has the substituents (amine group and triazine group) described in the P-type host compound (chemical formula A) and the N-type host compound (chemical formula B), respectively, and may be configured to be compared to a combination of the heterocyclic compound represented by chemical formula A and the heterocyclic compound represented by chemical formula B.

[0180] Table 5 shows that Comparative Examples 3 and 4, which used H1 and H2 alone, exhibited very high driving voltages, very low efficiencies, and very short lifetimes. Comparative Example 5, which combined H1 and H2, and Comparative Example 8, which used H3 alone, showed slight improvements in device characteristics compared to Comparative Examples 1 and 2, but the improvements were weaker than those of the Examples. Comparative Examples 6 and 7, which satisfied only some of the conditions of the present invention (including one of Formula A or B) but did not, showed slight improvements in device characteristics, but still showed differences compared to the Examples. Furthermore, Comparative Examples 1, 2, 9, 10, and 11, which did not satisfy the conditions (the combination of a heterocyclic compound of Formula A and a heterocyclic compound of Formula B) and contained one heterocyclic compound of Formula A or B, showed deterioration in device characteristics to the same level as Comparative Examples 3 and 4. This confirms that the mixed deposition of a heterocyclic compound represented by Formula A of the present invention as a P-type host and a heterocyclic compound represented by Formula B as an N-type host improves the driving, efficiency, and lifetime of organic light-emitting devices.

[0181] The present invention is not limited to the above-described embodiments, and can be manufactured in various different forms, and a person skilled in the art to which the present invention pertains can understand that the present invention can be embodied in other specific forms without changing the technical idea or essential features of the present invention. Therefore, it should be understood that the above-described embodiments are illustrative in all respects and are not limiting. [Explanation of symbols]

[0182] 100... Substrate 200...Anode 300...organic layer 301 Hole injection layer 302 Hole transport layer 303...electron blocking layer 304 Light-emitting layer 305 Hole blocking layer 306 ···Electron transport layer 307 ···Electron injection layer 400 ···cathode

Claims

1. An organic light-emitting device including: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, At least one layer of the organic material layers includes a heterocyclic compound represented by the following chemical formula A; and a heterocyclic compound represented by the following chemical formula B. 【Chemical 1】 In the above chemical formulas A and B, L1 to L4 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; Ar1 to Ar3 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a combination thereof; Ar4 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a substituted or unsubstituted amine group; R1 and R2 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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; R3 and R4 are the same or different and each independently represent hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms, 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, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted ring, l1 to l4 are the same or different and each independently represents an integer of 1 to 3, and when each of l1 to l4 is an integer of 2 or more, the types of the substituents in the parentheses are the same or different, r1 is an integer from 0 to 6, Each of r2 to r4 is an integer from 0 to 4, The sum of r1 and r2 is 8, The sum of r3 and r4 is 6, When each of l1 to l4 and r1 to r4 is an integer of 2 or more, the substituents in the parentheses may be the same or different. N-Het1 is represented by the following chemical formula N: 【Chemistry 2】 In the above chemical formula N, 【Chemistry 3】 means the portion linked to L3, Y1 to Y5 are the same or different and each independently represent CRa or N, and at least one is N; Ra is 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.

2. The organic light-emitting device according to claim 1, wherein the chemical formula A is represented by the following chemical formula A-1: 【Chemistry 4】 In the above chemical formula A-1, Each of L1, L2, Ar1 to Ar3, R1, R2, l1, l2, r1, and r2 is defined as in Chemical Formula A above.

3. The organic light-emitting device according to claim 1, wherein the chemical formula B is represented by the following chemical formula B-1 or B-2: 【Chemistry 5】 In the chemical formulas B-1 and B-2, The definitions of L3, L4, Ar4, N-Het1, R3, R4, l3, l4, and r4 are the same as those in Chemical Formula B. r3' is an integer of 0 to 3, and when r3' is an integer of 2 or more, R3's are the same or different from each other; r3" is an integer of 0 to 2, and when r3" is 2, R3's are the same or different from each other; r4' is an integer of 0 to 3, and when r4' is an integer of 2 or more, R4's are the same or different from each other.

4. The organic light-emitting device according to claim 1, wherein the chemical formula A is represented by any one of the following chemical formulas A-101 to A-108: 【Chemistry 6-1】 【Chemistry 6-2】 In the chemical formulas A-101 to A-108, L1, L2, Ar1 to Ar3, R1, R2, l1, l2, r1, and r2 are defined as in Chemical Formula A above, r1' is an integer from 0 to 5, r2' is an integer of 0 to 3, When each of r1' and r2' is an integer of 2 or more, the types of the substituents in the parentheses may be the same or different.

5. The organic light-emitting device according to claim 1, wherein the chemical formula B is represented by any one of the following chemical formulas B-101 to B-115: 【Chemistry 7-1】 【Chemistry 7-2】 【Chemistry 7-3】 In the chemical formulas B-101 to B-115, The definitions of L3, L4, Ar4, N-Het1, r3, r4, l3, and l4 are the same as those in Chemical Formula B. R3', R4', and R5 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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; r3' is an integer of 0 to 3, and when r3' is an integer of 2 or more, R3' are the same or different from each other; r3" is an integer of 0 to 2, and when r3" is 2, R3' are the same or different from each other; r4' is an integer of 0 to 3, and when r4' is an integer of 2 or more, R4' are the same or different from each other; r5 is an integer of 0 to 4, and when r5 is an integer of 2 or more, R5s may be the same or different.

6. 2. The organic light-emitting device according to claim 1, wherein L1 to L4 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

7. 2. The organic light-emitting element according to claim 1, wherein Ar1 to Ar3 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; or a combination thereof.

8. Ar4 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; or -NRbRc; 2. The organic light-emitting element according to claim 1, wherein Rb and Rc are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms; 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.

9. 2. The organic light-emitting device according to claim 1, wherein R1 and R2 are the same or different and each independently represent hydrogen or deuterium.

10. 2. The organic light-emitting element according to claim 1, wherein R3 and R4 are the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

11. 2. The organic light-emitting device according to claim 1, wherein the heterocyclic compound represented by chemical formula A and the heterocyclic compound represented by chemical formula B each have a deuterium content that is the same or different from each other and is independently 0% or 1% to 100%.

12. The organic light emitting device according to claim 1 , wherein the chemical formula A is represented by any one of the following formulas: 【Chemistry 8-1】 【Chemistry 8-2】 【Chemistry 8-3】 【Chemistry 8-4】 【Chemistry 8-5】 【Chemistry 8-6】 【Chemistry 8-7】 【Hua 8-8】 【Chemistry 8-9】 【Chemistry 8-10】 【Chemistry 8-11】 【Chemistry 8-12】 【Chemistry 8-13】 【Chemistry 8-14】 【Chemistry 8-15】 【Chemistry 8-16】 【Chemistry 8-17】 【Chemistry 8-18】 【Chemistry 8-19】 【Chemistry 8-20】 【Chemistry 8-21】 【Chemistry 8-22】

13. The organic light-emitting device according to claim 1 , wherein the chemical formula B is represented by any one of the following formulas: 【Chemistry 9-1】 【Chemistry 9-2】 【Chemistry 9-3】 【Chemistry 9-4】 【Chemistry 9-5】 【Chemistry 9-6】 【Chemistry 9-7】 【Chemistry 9-8】 【Hua 9-9】 【Chemistry 9-10】 【9-11】 【Chemistry 9-12】 【Chemistry 9-13】 【Chemistry 9-14】 【Chemistry 9-15】 【Chemistry 9-16】 【Chemistry 9-17】 【Chemistry 9-18】

14. The organic light-emitting device according to claim 1 , wherein the organic material layer further comprises an emission layer, and the emission layer comprises the heterocyclic compound represented by the chemical formula A; and the heterocyclic compound represented by the chemical formula B.

15. 2. The organic light-emitting device according to claim 1, further comprising one or more layers selected from the group consisting of an emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

16. A composition for an organic material layer of an organic light-emitting device, comprising a heterocyclic compound represented by the following chemical formula A; and a heterocyclic compound represented by the following chemical formula B: 【Chemistry 10】 In the above chemical formulas A and B, L1 to L4 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; Ar1 to Ar3 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a combination thereof; Ar4 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a substituted or unsubstituted amine group; R1 and R2 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; 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; R3 and R4 are the same or different and each independently represent hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms, 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, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted ring, l1 to l4 are the same or different and each independently represents an integer of 1 to 3, and when each of l1 to l4 is an integer of 2 or more, the types of the substituents in the parentheses are the same or different, r1 is an integer from 0 to 6, Each of r2 to r4 is an integer from 0 to 4, The sum of r1 and r2 is 8, The sum of r3 and r4 is 6, When each of l1 to l4 and r1 to r4 is an integer of 2 or more, the substituents in the parentheses may be the same or different. N-Het1 is represented by the following chemical formula N: 【Chemistry 11】 In the above chemical formula N, 【Chemistry 12】 means the portion linked to L3, Y1 to Y5 are the same or different and each independently represent CRa or N, and at least one is N; Ra is 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.

17. The composition for an organic material layer of an organic light-emitting device according to claim 16, wherein the weight ratio of the heterocyclic compound represented by chemical formula A to the heterocyclic compound represented by chemical formula B is 1:10 to 10:

1.

18. providing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer; Including, The method for manufacturing an organic light emitting device, wherein the forming of the organic material layer comprises forming one or more organic material layers using the composition for an organic material layer of an organic light emitting device according to claim 16.

19. 20. The method of claim 18, wherein the forming of the organic material layer comprises pre-mixing the heterocyclic compound of Formula A and the heterocyclic compound of Formula B and forming the organic material layer using a thermal vacuum deposition method.

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