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

Abstract

The present specification provides an organic light-emitting device comprising a heterocyclic compound represented by Formula A and a heterocyclic compound represented by Formula B, a composition for an organic layer of the organic light-emitting device, and a method for manufacturing the organic light-emitting device. The organic light-emitting device, the composition for the organic layer of the organic light-emitting device, and the method for manufacturing the organic light-emitting device described in this specification can lower the driving voltage of the device, improve the luminous efficiency, and improve the lifespan characteristics of the device.

Description

Technology Field

[0001] This specification relates to an organic light-emitting device, a composition for an organic layer of an organic light-emitting device, and a method for manufacturing an organic light-emitting device.

[0002] This application claims the benefit of the filing date of Korean Patent Application No. 10-2024-0012153 filed with the Korean Intellectual Property Office on January 26, 2024, the entire contents of which are incorporated herein. Background Technology

[0003] Light-emitting elements are a type of self-emissive display element that has the advantages of a wide viewing angle, excellent contrast, and fast response speed.

[0004] An organic light-emitting diode has a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting diode with 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 can be composed of a single layer or multiple layers as needed.

[0005] The materials of organic thin films may possess luminescence capabilities as needed. For example, compounds capable of independently constituting an emissive layer may be used as organic thin film materials, or compounds capable of acting as a host or dopant in a host-dopant emissive layer may be used. Furthermore, compounds capable of performing functions such as hole injection, hole transport, electron blocking, electron transport, and electron injection may also be used as organic thin film materials.

[0006] To improve the performance, lifespan, or efficiency of organic light-emitting diodes, the development of organic thin film materials is continuously required. Prior art literature

[0007] U.S. Patent No. 4,356,429 The problem to be solved

[0008] The present specification aims to provide an organic light-emitting device, a composition for an organic layer of an organic light-emitting device, and a method for manufacturing an organic light-emitting device. means of solving the problem

[0009] One embodiment of the present specification provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a heterocyclic compound represented by the following chemical formula A; and a heterocyclic compound represented by the following chemical formula B.

[0010] [Chemical Formula A]

[0011]

[0012] [Chemical Formula B]

[0013]

[0014] In the above chemical formulas A and B,

[0015] L1 to L4 are identical or different from one another and are each independently directly bonded; 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, and

[0016] Ar1 to Ar3 are identical or different from one another and are each independently substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; or a combination thereof,

[0017] 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, and

[0018] R1 and R2 are identical or different from each other and are each independently 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.

[0019] R3 and R4 are identical or different from each other and are each independently 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, and

[0020] l1 to l4 are identical or different from each other and are each independently integers from 1 to 3, and where l1 to l4 are each integers of 2 or more, the types of substituents inside the parentheses are identical or different from each other,

[0021] r1 is an integer from 0 to 6, and

[0022] Each of r2 to r4 is an integer from 0 to 4, and

[0023] The sum of r1 and r2 is 8, and

[0024] The sum of r3 and r4 is 6, and

[0025] Where each of l1 to l4 and r1 to r4 is an integer of 2 or more, the substituents inside the parentheses are identical or different from each other, and

[0026] N-Het1 is represented by the following chemical formula N, and

[0027] [Chemical Formula N]

[0028]

[0029] In the above chemical formula N,

[0030] refers to the part connected to L3, and

[0031] Y1 to Y5 are identical or different from each other, and each is independently CRa or N, at least one being N, and

[0032] 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.

[0033] 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 formula A; and a heterocyclic compound represented by the formula B.

[0034] The last 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 layers on the first electrode; and forming a second electrode on the organic layers, wherein the step of forming the organic layers includes forming one or more organic layers using the composition for the organic layer of the organic light-emitting device described above. Effects of the invention

[0035] An organic light-emitting device according to one embodiment of the present application comprises an organic layer, wherein the organic layer comprises a heterocyclic compound represented by Formula A and a heterocyclic compound represented by Formula B. Furthermore, a composition for the organic layer of an organic light-emitting device according to one embodiment of the present application may use the heterocyclic compound represented by Formula A and the heterocyclic compound represented by Formula B as organic layer materials for the organic light-emitting device. More specifically, the organic layer of the organic light-emitting device and the composition for the organic layer of the organic light-emitting device are each characterized by comprising a heterocyclic compound represented by Formula A as a P-type host material and a heterocyclic compound represented by Formula B as an N-type host material.

[0036] 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 appropriate proportions and used as a device material, it is easy to balance the number of holes and electrons in the emissive layer. This allows for the maximization of hole transport characteristics and electron transport characteristics, and consequently, it can be confirmed that the exciton generation efficiency increases, thereby improving the efficiency and lifespan of the device. Since it is easier to control charge density through ratio adjustment compared to using a bipolar type host alone or other combinations such as two or more premixed compositions, various combinations of p-type and n-type hosts are possible. This enables the development of many mixed host systems, which is advantageous for improving device characteristics.

[0037] Thus, when the above-mentioned composition for the organic layer is used in an organic light-emitting device or when manufacturing an organic light-emitting device, the driving voltage of the device can be lowered, the light efficiency improved, the thermal stability of the compound improved, and the lifespan characteristics of the device improved. Brief explanation of the drawing

[0038] FIGS. 1 to 3 are drawings illustrating exemplary stacked structures of organic light-emitting diodes according to one embodiment of the present specification. Specific details for implementing the invention

[0039] The present specification will be described in more detail below.

[0040] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0041] In this specification, of the chemical formula means the position where it is combined.

[0042] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, any site where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0043] In this specification, “substituted or unsubstituted” means one or more substituents selected from the group consisting of deuterium; halogen group; cyano group; alkyl group having 1 to 60 carbon atoms; alkenyl group having 2 to 60 carbon atoms; alkynyl group having 2 to 60 carbon atoms; cycloalkyl group having 3 to 60 carbon atoms; heterocycloalkyl group having 2 to 60 carbon atoms; aryl group having 6 to 60 carbon atoms; heteroaryl group having 2 to 60 carbon atoms; silyl group; phosphine oxide group; and amine group, or one or more substituents selected from the exemplified substituents connected to a substituent.

[0044] In this specification, “where no substituent is indicated in the chemical formula or compound structure” means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 Since H (Deuterium) or tritium corresponds to isotopes of hydrogen, it can be interpreted as a concept included in hydrogen unless explicitly excluded.

[0045] That is, in this application, deuterium is defined as having an equivalent effect or an improved effect in some evaluation criteria compared to hydrogen in terms of driving voltage, luminous efficiency, and lifespan, in accordance with Chem. Commun., 2014, 50, 14870. Since it falls within a range where a person skilled in the art can predict that it has an equivalent effect even without specific experiments, deuterium, which is an isotope of hydrogen, is interpreted as being included in hydrogen unless explicitly excluded.

[0046] According to one embodiment of the present specification, “where no substituents are indicated in the chemical formula or compound structure” may mean that all positions where substituents may be present are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be deuterium isotopes, and in this case, the content of deuterium may be 0% to 100%.

[0047] According to one embodiment of the present specification, in the case where “substituents are not indicated in the chemical formula or compound structure,” the deuterium content is 0%, the hydrogen content is 100%, and all substituents do not explicitly exclude hydrogen or other deuterium, hydrogen and deuterium may be used in a mixture in the compound.

[0048] According to one embodiment of this specification, deuterium is one of the isotopes of hydrogen, an element having a deuteron as its nucleus, consisting of one proton and one neutron, and can be represented as hydrogen-2, and its element symbol is D or 2 It can also be written as H.

[0049] According to one embodiment of the present specification, an isotope, which means an atom having the same atomic number (Z) but different mass numbers (A), can also be interpreted as an element having the same number of protons but different numbers of neutrons.

[0050] According to one embodiment of the present specification, the meaning of the content T% of a specific substituent can be defined as T2 / T1 × 100 = T% when the total number of substituents that a basic compound may have is defined as T1 and the number of specific substituents among them is defined as T2.

[0051] in other words, Taking the phenyl group represented by as an example, the deuterium content of 20% here can be expressed as 20% when the total number of substituents the phenyl group can have is 5 (T1 in the formula) and the number of deuteriums among them is 1 (T2 in the formula). That is, a deuterium content of 20% in the phenyl group can be represented by the following structural formula.

[0052]

[0053] In addition, according to one embodiment of the present specification, “phenyl group with 0% deuterium content” may mean a phenyl group that does not contain deuterium atoms, i.e., has five hydrogen atoms.

[0054] In this specification, the halogen may be fluorine, chlorine, bromine, or iodine.

[0055] In this specification, the alkyl group comprises a straight or branched chain having 1 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, more specifically 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, There are 2,2-dimethylheptyl groups, 1-ethyl-propyl groups, 1,1-dimethyl-propyl groups, isohexyl groups, 2-methylpentyl groups, 4-methylhexyl groups, 5-methylhexyl groups, etc., but are not limited to these.

[0056] In this specification, the alkenyl group comprises a straight chain or a branched chain having 2 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically 2 to 20. Specific examples include vinyl groups, 1-propenyl groups, isopropenyl groups, 1-butenyl groups, 2-butenyl groups, 3-butenyl groups, 1-pentenyl groups, 2-pentenyl groups, 3-pentenyl groups, 3-methyl-1-butenyl groups, 1,3-butadienyl groups, allyl groups, 1-phenylvinyl-1-yl groups, 2-phenylvinyl-1-yl groups, 2,2-diphenylvinyl-1-yl groups, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl groups, 2,2-bis(diphenyl-1-yl)vinyl-1-yl groups, stilbenyl groups, styrenyl groups, etc., but are not limited to these.

[0057] In this specification, the alkynyl group comprises a straight or branched chain having 2 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, more specifically 2 to 20.

[0058] In this specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferred to have 1 to 20 carbon atoms. Specifically, it may be 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, p-methylbenzyloxy, etc., but is not limited thereto.

[0059] In this specification, the cycloalkyl group comprises a monocyclic or polycyclic group having 3 to 60 carbon atoms and may be further substituted by other substituents. Here, polycyclic means a group in which the cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be other types of ring groups, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specifically, there are cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, 3-methylcyclopentyl groups, 2,3-dimethylcyclopentyl groups, cyclohexyl groups, 3-methylcyclohexyl groups, 4-methylcyclohexyl groups, 2,3-dimethylcyclohexyl groups, 3,4,5-trimethylcyclohexyl groups, 4-tert-butylcyclohexyl groups, cycloheptyl groups, cyclooctyl groups, etc., but are not limited to these.

[0060] In this specification, the heterocycloalkyl group comprises O, S, Se, N, or Si as a heteroatom, comprises a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, polycyclic means a group in which the heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be other types of ring groups, such as a cycloalkyl group, an aryl group, a heteroaryl group, etc. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0061] In this specification, the aryl group comprises a monocyclic or polycyclic group having 6 to 60 carbon atoms and may be further substituted by other substituents. Here, polycyclic means a group in which the aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be other types of ring groups, such as cycloalkyl groups, heterocycloalkyl groups, heteroaryl groups, etc. The aryl group comprises a spiro group. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the above aryl groups include, but are not limited to, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, anthryl groups, chrysenyl groups, phenanthrenyl groups, perylenyl groups, fluoranthenyl groups, triphenylenyl groups, phenalenyl groups, pyrenyl groups, tetracenyl groups, pentacenyl groups, fluorenyl groups, indenyl groups, acenaphthylenyl groups, benzofluorenyl groups, spirobifluorenyl groups, 2,3-dihydro-1H-indenyl groups, and condensation rings thereof.

[0062] In this specification, the terphenyl group may be selected from the following structures.

[0063]

[0064] In this specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a substituted or unsubstituted ring.

[0065] When the above fluorenyl group is substituted, it may be selected from the following structures, but is not limited thereto.

[0066]

[0067] In this specification, the heteroaryl group comprises S, O, Se, N, or Si as a heteroatom and comprises a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic group means a group in which the heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be a different type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25.Specific examples of the above heteroaryl groups include pyridyl group, pyrrolyl group, pyrimidyl group, pyridazolyl group, furanyl group, thiophene group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazolyl group, oxazolyl group, thiazolyl group, deoxynyl group, triazolyl group, tetrazolyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozoliryl group, naphthalidyl group, acrridinyl group, phenanthridinyl group, imidazopyridinyl group, diazanaphthalenyl group, Triazindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophen group, benzofuran group, dibenzothiophen group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzocazolyl group, dibenzocazolyl group, phenazinyl group, dibenzosilol group, dihydrophenazinyl group, phenoxazinyl group, phenantridyl 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, phenantrazinyl group, phenothiathiazinyl group, Examples include phthalazinyl group, naphthylidinyl 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]azacillinyl 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, but are not limited to these.

[0068] In this specification, when a substituent is a carbazole group, it means bonding to the nitrogen or carbon of carbazole.

[0069] In this specification, when a carbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole.

[0070] In this specification, the benzocarbazole group may be any one of the following structures.

[0071]

[0072] In this specification, the dibenzocarbazole group may be any one of the following structures.

[0073]

[0074] In this specification, the naphthobenzofuran group may be any one of the following structures.

[0075]

[0076] In this specification, the naphthobenzothiophene group may be any one of the following structures.

[0077]

[0078] In the present specification, the silyl group is a substituent comprising Si and said Si atom directly connected as a radical, and is represented as -Si(R101)(R102)(R103), where R101 to R103 are identical or different from each other and may each be a substituent consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group.

[0079] Specific examples of silyl groups include (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group), etc., are included, but are not limited to these.

[0080] In this specification, the phosphine oxide group is represented as -P(=O)(R104)(R105), and R104 and R105 are identical or different from each other and may each be a substituent consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group. Specifically, it may be substituted with an alkyl group or an aryl group, and the alkyl group and aryl group may be applied according to the examples described above. For example, the phosphine oxide group may include a dimethylphosphine oxide group, a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, etc., but is not limited thereto.

[0081] In this specification, the amine group is represented as -N(R106)(R107), and R106 and R107 are identical or different from each other and may each be a substituent consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group. The amine group may be selected from the group consisting of -NH2; monoalkylamine group; monoarylamine group; monoheteroarylamine group; dialkylamine group; diarylamine group; diheteroarylamine group; alkylarylamine group; alkylheteroarylamine group; and arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the above amine groups include, but are not limited to, methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, dibiphenylamine, anthracenylamine, 9-methyl-anthracenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, triphenylamine, biphenylnaphthylamine, phenylbiphenylamine, biphenylfluorenylamine, phenyltriphenyllenylamine, biphenyltriphenyllenylamine, etc.

[0082] In this specification, the examples of aryl groups described above may be applied, except that the arylene group is a divalent group.

[0083] In this specification, the examples of the aforementioned heteroaryl groups may be applied, except that the heteroarylen group is a divalent group.

[0084] In this specification, "adjacent" groups may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the atom on which the substituent is substituted, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

[0085] The hydrocarbon rings and heterocycles that can be formed by adjacent groups include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles, and except that the rings are not monovalent groups, structures exemplified by the aforementioned cycloalkyl groups, aryl groups, heterocycloalkyl groups, and heteroaryl groups may be applied.

[0086] In one embodiment of the present specification, a group not represented as a substituent; or a group represented as hydrogen, may all mean that they are interchangeable with deuterium. That is, hydrogen (H); or deuterium (D) may indicate that they are interchangeable with one another.

[0087] In general, compounds bonded with hydrogen and compounds substituted with deuterium show differences in thermodynamic behavior. This is because the mass of a deuterium atom is twice that of hydrogen, and due to this difference in atomic mass, deuterium has the characteristic of having lower vibrational energy.

[0088] Furthermore, the single bond dissociation energy between carbon and deuterium is higher than that between carbon and hydrogen. Therefore, structures substituted with deuterium increase the thermal stability of the molecule, which has the effect of improving the lifespan of devices utilizing it.

[0089] When compounds are deposited on a silicon wafer, materials containing deuterium tend to be packed with tighter intermolecular distances. Furthermore, observation of the thin film surface using an Atomic Force Microscope (AFM) confirms that thin films fabricated with deuterium-containing compounds are deposited as a more uniform surface without any areas of aggregation.

[0090] Organic light-emitting diodes

[0091] Hereinafter, an organic light-emitting device according to the present specification will be described.

[0092] An organic layer of an organic light-emitting device according to one embodiment of the present specification comprises a heterocyclic compound represented by the following chemical formula A.

[0093] [Chemical Formula A]

[0094]

[0095] In the above chemical formula A, the description of each substituent is as described above.

[0096] The heterocyclic compound represented by the above chemical formula A is a 2-substituted naphthobenzofuran, wherein the first substituent ( ) as a donor unit increases the electron density of the aromatic unit, shifts the HOMO energy level toward the vacuum level, and enhances hole generation characteristics, and the second substituent ( ) can be substituted at various positions in the core framework to change the thermal properties of the material, such as glass transition temperature and thermal decomposition temperature, thereby increasing thermal stability and changing the length and molecular orientation of the conjugated structure to improve hole properties, so that the overall electron and hole transport characteristics can be excellent.

[0097] When a heterocyclic compound represented by chemical formula A, which has excellent hole transport characteristics, is used together with a heterocyclic compound represented by chemical formula B, which has fast electron transport characteristics, it acts as a P-type host material. This makes it easy to balance the number of holes and electrons within the organic layer (especially the emissive layer (EML layer)), thereby maximizing hole transport and electron transport characteristics. Consequently, charge balance occurs within the organic layer, preventing degradation caused by the accumulation of electrons and holes. As a result, exciton generation efficiency increases, leading to high efficiency and long lifespan characteristics.

[0098] An organic layer of an organic light-emitting device according to one embodiment of the present specification comprises a heterocyclic compound represented by the following chemical formula B.

[0099] [Chemical Formula B]

[0100]

[0101] In the above chemical formula B, the description of each substituent is as described above.

[0102] The compound represented by the above chemical formula B is 2-substituted as an oxygen-containing fused heterocyclic ring (dibenzofuran) of 3 or more rings, and the first substituent ( In ), N-Het1 (represented by structural formula N, corresponding to triazine, etc.) acts as an acceptor unit to lower the electron density of the aromatic unit, thereby deepening the LUMO energy level and enhancing electron transport characteristics, and the second substituent ( Ar4 of ) is substituted at various positions in the core framework, thereby changing the thermal properties of the material such as glass transition temperature and thermal decomposition temperature, which increases thermal stability, and changes the length and molecular orientation of the conjugated structure to improve hole properties, so that the overall electron and hole transport characteristics are excellent and high efficiency can be achieved.

[0103] When a heterocyclic compound represented by chemical formula B, which exhibits fast electron transport characteristics, is used in combination with a heterocyclic compound represented by chemical formula A, which exhibits excellent hole transport characteristics, it acts as an N-type host material. Due to the large HOMO and LUMO difference between the two hosts within the organic layer (particularly the emitting layer (EML layer)), excitons are generated between the two hosts, and excitons exhibit exciplex characteristics that form a charge transport complex in the excited state. Consequently, the driving voltage is lowered due to strong hole and electron transport characteristics, and because an exciplex is formed between the two hosts, the energy transfer process becomes dominant during the luminescence process. When the two compounds are used in combination, charge balance is maintained, and electron injection and transport are facilitated, allowing for the simultaneous realization of high efficiency and low driving voltage, as well as excellent lifespan characteristics.

[0104] When the compound according to the above embodiment is used in an organic light-emitting device, it may have low driving voltage, high luminous efficiency, and / or long lifespan characteristics.

[0105] According to one embodiment of the present specification, the formula A can be represented by the following formula A-1.

[0106] [Chemical Formula A-1]

[0107]

[0108] In the above chemical formula A-1,

[0109] Each of L1, L2, Ar1 to Ar3, R1, R2, l1, l2, r1 and r2It is as defined in the above chemical formula A.

[0110] According to one embodiment of the present specification, the formula A may be represented by any one of the following formulas A-101 to A-108.

[0111] [Chemical Formula A-101]

[0112]

[0113] [Chemical Formula A-102]

[0114]

[0115] [Chemical Formula A-103]

[0116]

[0117] [Chemical Formula A-104]

[0118]

[0119] [Chemical Formula A-105]

[0120]

[0121] [Chemical Formula A-106]

[0122]

[0123] [Chemical Formula A-107]

[0124]

[0125] [Chemical Formula A-108]

[0126]

[0127] In the above chemical formulas A-101 to A-108,

[0128] Each of L1, L2, Ar1 to Ar3, R1, R2, l1, l2, r1 and r2 is as defined in the above chemical formula A, and

[0129] r1' is an integer from 0 to 5, and

[0130] r2' is an integer from 0 to 3, and

[0131] If each r1' and r2' is an integer greater than or equal to 2, the types of substituents inside the parentheses are the same or different.

[0132] According to one embodiment of the present specification, the formula B may be represented as either the following formula B-1 or B-2.

[0133] [Chemical Formula B-1]

[0134]

[0135] [Chemical Formula B-2]

[0136]

[0137] In the above chemical formulas B-1 and B-2,

[0138] The definitions of each of L3, L4, Ar4, N-Het1, R3, R4, l3, l4, and r4 are as defined in the above chemical formula B, and

[0139] r3' is an integer from 0 to 3, and if r3' is an integer greater than or equal to 2, R3 are identical or different from each other, and

[0140] r3" is an integer from 0 to 2, and when r3" is 2, R3 are identical or different from each other, and

[0141] r4' is an integer from 0 to 3, and if r4' is an integer greater than or equal to 2, R4 are identical or different.

[0142] According to one embodiment of the present specification, the formula B may be represented by the following formula B-11 or B-12.

[0143] [Chemical Formula B-11]

[0144]

[0145] [Chemical Formula B-12]

[0146]

[0147] In the above chemical formulas B-11 and B-12,

[0148] The definitions of each of L3, L4, Ar4, N-Het1, r3, r4, l3 and l4 are as defined in the above chemical formula B, and

[0149] R3', R4' and R5 are identical or different from one another and are each independently 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, and

[0150] r4" is an integer from 0 to 2, and if r4" is 2, R4' are the same or different from each other, and

[0151] r5 is an integer from 0 to 4, and if r5 is an integer greater than or equal to 2, R5 are the same or different from each other.

[0152] According to one embodiment of the present specification, the formula B may be represented by any one of the following formulas B-101 to B-115.

[0153] [Chemical Formula B-101]

[0154]

[0155] [Chemical Formula B-102]

[0156]

[0157] [Chemical Formula B-103]

[0158]

[0159] [Chemical Formula B-104]

[0160]

[0161] [Chemical Formula B-105]

[0162]

[0163] [Chemical Formula B-106]

[0164]

[0165] [Chemical Formula B-107]

[0166]

[0167] [Chemical Formula B-108]

[0168]

[0169] [Chemical Formula B-109]

[0170]

[0171] [Chemical Formula B-110]

[0172]

[0173] [Chemical Formula B-111]

[0174]

[0175] [Chemical Formula B-112]

[0176]

[0177] [Chemical Formula B-113]

[0178]

[0179] [Chemical Formula B-114]

[0180]

[0181] [Chemical Formula B-115]

[0182]

[0183] In the above chemical formulas B-101 to B-115,

[0184] The definitions of each of L3, L4, Ar4, N-Het1, r3, r4, l3 and l4 are as defined in the above chemical formula B, and

[0185] R3', R4' and R5 are identical or different from one another and are each independently 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, and

[0186] r3' is an integer from 0 to 3, and if r3' is an integer greater than or equal to 2, R3' are identical or different from each other, and

[0187] r3" is an integer from 0 to 2, and if r3" is 2, R3' are the same or different from each other, and

[0188] r4' is an integer from 0 to 3, and if r4' is an integer greater than or equal to 2, R4' are identical or different from each other, and

[0189] r4" is an integer from 0 to 2, and if r4" is 2, R4' are the same or different from each other, and

[0190] r5 is an integer from 0 to 4, and if r5 is an integer greater than or equal to 2, R5 are the same or different from each other.

[0191] According to one embodiment of the present specification, L1 to L4 may be identical or different from one another and each independently directly bonded; 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.

[0192] According to one embodiment of the present specification, L1 to L4 may be identical or different from each other and each independently directly bonded; or may be substituted or unsubstituted arylene groups having 6 to 30 carbon atoms.

[0193] According to one embodiment of the present specification, L1 to L4 may be identical or different from each other and each independently directly bonded; or may be arylene groups having 6 to 30 carbon atoms substituted or unsubstituted with deuterium.

[0194] According to one embodiment of the present specification, L1 to L4 may be identical or different from one another and each independently directly bonded; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0195] According to one embodiment of the present specification, L1 to L4 may be identical or different from one another and each independently directly bonded; a phenylene group substituted or unsubstituted with deuterium; a biphenylene group substituted or unsubstituted with deuterium; or a naphthylene group substituted or unsubstituted with deuterium.

[0196] According to one embodiment of the present specification, Ar1 to Ar3 may be identical or different from one another and each independently substituted or unsubstituted aryl group having 6 to 40 carbon atoms; substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms; or a combination thereof.

[0197] According to one embodiment of the present specification, Ar1 to Ar3 may be identical or different from one another and each independently substituted or unsubstituted aryl group having 6 to 30 carbon atoms; substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; or a combination thereof.

[0198] According to one embodiment of the present specification, Ar1 to Ar3 may be identical or different from one another and each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a substituent selected from the group consisting of deuterium, alkyl groups and aryl groups; a heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a substituent selected from the group consisting of deuterium, alkyl groups and aryl groups; or a combination thereof.

[0199] According to one embodiment of the present specification, Ar1 to Ar3 may be identical or different from one another and may each independently be 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, and each may be independently substituted or unsubstituted with a substituent selected from the group consisting of deuterium, a halogen group, an alkyl group and an aryl group.

[0200] 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.

[0201] 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, and Rb and Rc are the same or different from each other and each independently may be 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.

[0202] According to one embodiment of the present specification, Ar4 is an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium or an aryl group; a heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium or an aryl group; or -NRbRc, where Rb and Rc are the same or different from each other and may each independently be hydrogen; deuterium; an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium or an aryl group; or a heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium or an aryl group.

[0203] According to one embodiment of the present specification, Ar4 is an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium or an aryl group; a heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium or an aryl group; or -NRbRc, wherein Rb and Rc are the same or different from each other and may each independently be hydrogen; deuterium; an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium or an aryl group; or a heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium or an aryl group.

[0204] 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, and the phenyl group; a biphenyl group; a naphthyl group; a dibenzofuranyl group; a dibenzothiophenyl group; a 9-carbazole group; and a 9-benzocarbazole group may each be independently substituted or unsubstituted with a deuterium, a phenyl group, or a naphthyl group, and Rb and Rc may be the same or different from each other and may each be independently hydrogen; a deuterium; a phenyl group substituted or unsubstituted with a deuterium; a biphenyl group substituted or unsubstituted with a deuterium; a naphthyl group substituted or unsubstituted with a deuterium; a dibenzofuranyl group substituted or unsubstituted with a deuterium; or a dibenzothiophenyl group substituted or unsubstituted with a deuterium.

[0205] According to one embodiment of the present specification, R1 and R2 may be identical or different from each other and may each independently be 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.

[0206] According to one embodiment of the present specification, R1 and R2 may be identical or different from each other and may each independently be 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.

[0207] According to one embodiment of the present specification, R1 and R2 may be identical or different from each other and may each independently be 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.

[0208] According to one embodiment of the present specification, R1 and R2 may be the same or different from each other and may each independently be 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.

[0209] According to one embodiment of the present specification, R1 and R2 may be the same or different from each other and may each independently be hydrogen; or deuterium.

[0210] According to one embodiment of the present specification, R3 and R4 are identical or different from each other and are each independently 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 combined to form a substituted or unsubstituted ring.

[0211] According to one embodiment of the present specification, R3 and R4 may be identical or different from each other and each independently 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 combined to form a substituted or unsubstituted aromatic ring having 6 to 30 carbon atoms.

[0212] According to one embodiment of the present specification, R3 and R4 may be identical or different from each other and each independently be hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or two or more adjacent groups may be combined to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

[0213] According to one embodiment of the present specification, R3 and R4 may be identical or different from each other and each independently hydrogen; or deuterium, or two or more adjacent groups may combine to form a benzene ring that is substituted or unsubstituted with deuterium.

[0214] In the embodiment of the present application date, the chemical formula N may be selected from the following structural formulas.

[0215]

[0216] In the above structural formula,

[0217] and the definitions of Y1 to Y5 are as defined in the chemical formula N.

[0218] According to one embodiment of the present specification, Y1 to Y5 are identical or different from each other and are each independently 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.

[0219]

[0220]

[0221] In the above structural formula, and the definitions of Y1 to Y5 are as defined in the chemical formula N.

[0222] According to one embodiment of the present specification, Y1 to Y5 are identical or different from each other and are each independently CRa or N, and three groups may be N. In other words, the structural formula N may be any one of the following structures.

[0223]

[0224] Preferably, the above structural formula N is It could be.

[0225] In the above structural formula, and the definitions of Y2 to Y5 are as defined in the chemical formula N.

[0226] 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.

[0227] 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.

[0228] According to one embodiment of the present specification, Ra may be an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a substituent selected from the group consisting of deuterium and aryl groups; a heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium; or a combination thereof.

[0229] 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.

[0230] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the formula A; and the heterocyclic compound represented by the formula B may be the same or different from each other, and may each be independently 0% or 1% to 100%.

[0231] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the formula A; and the heterocyclic compound represented by the formula B may be the same or different from each other, and may each be independently 0% or 10% to 100%.

[0232] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the formula A; and the heterocyclic compound represented by the formula B may be the same or different from each other, and may each independently be 0% or 20% to 100%.

[0233] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the formula A; and the heterocyclic compound represented by the formula B may be the same or different from each other, and may each independently be 0% or 30% to 100%.

[0234] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the formula A; and the heterocyclic compound represented by the formula B may be the same or different from each other, and may each independently be 0% or 60% to 100%.

[0235] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the formula A; and the heterocyclic compound represented by the formula B may be the same or different from each other, and may each independently be 0% or 80% to 100%.

[0236] According to one embodiment of the present specification, the deuterium content of the heterocyclic compound represented by the formula A; and the heterocyclic compound represented by the formula B may be the same or different from each other, and may each independently be 0% or 90% to 100%.

[0237] The above chemical formula A can be represented as any one of the following heterocyclic compounds.

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260] According to one embodiment of the present specification, the formula B may be represented as any one of the following heterocyclic compounds.

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279] By introducing various substituents into the structure represented by the above chemical formulas A and / or B, compounds having the unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport layer materials, hole transport auxiliary layer materials, light-emitting layer materials, electron transport layer materials, electron transport auxiliary layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, materials that satisfy the conditions required for each organic layer can be synthesized.

[0280] In addition, by introducing various substituents into the structure of the above chemical formulas A and / or B, the energy band gap can be finely tuned, while simultaneously improving the properties at the interface between organic materials and diversifying the applications of the material.

[0281] According to one embodiment of the present specification, the organic layer further comprises an emission layer, and the emission layer may comprise a heterocyclic compound represented by the formula A; and a heterocyclic compound represented by the formula B.

[0282] In another embodiment of the present specification, the light-emitting layer may each include a heterocyclic compound represented by the formula A and a heterocyclic compound represented by the formula B as a host.

[0283] According to one embodiment of the present specification, the light-emitting layer may each include a heterocyclic compound represented by the formula A and a heterocyclic compound represented by the formula B as a red host.

[0284] According to one embodiment of the present specification, the light-emitting layer may each include a heterocyclic compound represented by the formula A and a heterocyclic compound represented by the formula B as a green host.

[0285] According to one embodiment of the present specification, the light-emitting layer may each include a heterocyclic compound represented by the formula A and a heterocyclic compound represented by the formula B as a blue host.

[0286] According to one embodiment of the present specification, the first electrode may be an anode and the second electrode may be a cathode.

[0287] According to one embodiment of the present specification, the first electrode may be a negative electrode and the second electrode may be a positive electrode.

[0288] 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 the chemical formula A; and the heterocyclic compound represented by the chemical formula B may each be used as a material for the blue organic light-emitting element.

[0289] According to one embodiment of the present specification, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by the chemical formula A; and the heterocyclic compound represented by the chemical formula B may each be used as a material for the green organic light-emitting device.

[0290] 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 the chemical formula A; and the heterocyclic compound represented by the chemical formula B may each be used as a material for the red organic light-emitting element.

[0291] The organic layer of the organic light-emitting device of the present specification may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic 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, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller or larger number of organic layers.

[0292] According to one embodiment of the present specification, the organic layer may include an iridium-based dopant.

[0293] According to one embodiment of the present specification, the iridium-based dopant may be a green phosphorescent dopant Ir(ppy)3, but is not limited thereto.

[0294] According to one embodiment of the present specification, the red phosphorescent dopant (piq)2(Ir)(acac) may be used as the iridium-based dopant, but is not limited thereto.

[0295] In the organic light-emitting device of the present specification, materials with a relatively large work function may be used as the anode material, and transparent conductive oxides, metals, or conductive polymers may be used. Specific examples of the anode material include 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 SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0296] In the organic light-emitting device of the present specification, materials with a relatively low work function may be used as the cathode material, and metals, metal oxides, or conductive polymers may be used. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structural materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0297] In the organic light-emitting device of this specification, known hole injection materials may be used as the hole injection material, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or starburst-type amine derivatives described in the document [Advanced Material, 6, p. 677 (1994)], such as 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 polyaniline / dodecylbenzenesulfonic acid, which is a soluble conductive polymer. Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), Polyaniline / Camphor sulfonic acid, or Polyaniline / Poly(4-styrene-sulfonate) can be used.

[0298] In the organic light-emitting device of the present specification, the hole transport material may be a pyrazolin derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, etc., and may also be a low-molecular-weight or high-molecular-weight material.

[0299] In the organic light-emitting device of the present specification, the electron transport material may be an oxadiazole derivative, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, and may be a polymer material as well as a low molecular weight material.

[0300] In the organic light-emitting diode of this specification, for example, LiF is typically used as an electron injection material in the industry, but this specification is not limited thereto.

[0301] In the organic light-emitting device of the present specification, red, green, or blue light-emitting materials may be additionally used as light-emitting materials, and if necessary, two or more light-emitting materials may be mixed and used. In this case, two or more light-emitting materials may be deposited and used as individual sources, or they may be pre-mixed and deposited as a single source. Additionally, fluorescent materials may be used as light-emitting materials, but phosphorescent materials may also be used. As light-emitting materials, a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, may be used alone, but materials in which a host material and a dopant material participate in light emission together may also be used.

[0302] When using a mixture of hosts for light-emitting materials, hosts of the same series may be mixed, or hosts of different series may be mixed. For example, two or more types of materials, such as N-Type host materials or P-Type host materials, may be selected and used as the host material for the light-emitting layer.

[0303] An organic light-emitting device according to one embodiment of the present specification may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0304] A heterocyclic compound according to one embodiment of the present specification can operate in organic electronic devices, including organic solar cells, organic photosensitive materials, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.

[0305] The organic light-emitting device of the present specification may further include one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport assist layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0306] FIGS. 1 to 3 illustrate the stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present specification. However, the scope of the present application is not intended to be limited by these figures, and structures of organic light-emitting devices known in the art may be applied to the present application.

[0307] According to FIG. 1, an organic light-emitting device is illustrated in which an anode (200), an organic layer (300), and a cathode (400) are sequentially stacked on a substrate (100). However, the structure is not limited to this, and an organic light-emitting device may be implemented in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate as shown in FIG. 2. The composition for the organic light-emitting device may be included in the organic layer (300), and the organic layer (300) may be one or more layers.

[0308] FIG. 3 illustrates a case where the organic layer is multilayer. The organic light-emitting device according to FIG. 3 includes a hole injection layer (301), a hole transport layer (302), an electron blocking layer (303), a light-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 light-emitting layer (304). However, the scope of the present application is not limited by such a stacked structure, and, if necessary, the remaining layers excluding the light-emitting layer may be omitted, or other necessary functional layers may be added.

[0309] An organic light-emitting device according to one embodiment of the present specification comprises: a first electrode; a first stack provided on the first electrode and including a first light-emitting layer; a charge generating layer provided on the first stack; a second stack provided on the charge generating layer and including a second light-emitting layer; and a second electrode provided on the second stack.

[0310] An organic light-emitting device according to one embodiment of the present specification may, when having a 2-stack structure as described above, include at least one layer among the first light-emitting layer (first stack light-emitting layer) and the second light-emitting layer (second stack light-emitting layer) a heterocyclic compound represented by the chemical formula A; and a heterocyclic compound represented by the chemical formula B.

[0311] In addition, the first stack and the second stack may each independently include one or more of the aforementioned hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer, etc.

[0312] The heterocyclic compound represented by the above chemical formula A; and the heterocyclic compound represented by the above chemical formula B can be used when forming an organic layer of an organic light-emitting device, and can be used more preferably as a light-emitting layer material.

[0313] The heterocyclic compound represented by the above chemical formula A; and the heterocyclic compound represented by the above chemical formula B may be in a pre-mixed form, and the materials in powder form may be mixed before forming the organic layer of the organic light-emitting diode, or the 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.

[0314] The heterocyclic compound represented by the above chemical formula A; and the heterocyclic compound represented by the above chemical formula B may additionally include materials known in the art, such as solvents and additives.

[0315] <Composition for the Organic Layer of an Organic Light-Emitting Device>

[0316] Hereinafter, a composition for an organic layer of an organic light-emitting device according to the present specification will be described.

[0317] Another embodiment of the present specification is a composition for an organic layer of an organic light-emitting device, characterized by comprising a heterocyclic compound represented by Formula A and a heterocyclic compound represented by Formula B. Furthermore, the description of each of Formula A and Formula B included in the composition for the organic layer of the organic light-emitting device is as described above.

[0318] According to one embodiment of the present specification, the weight ratio of the heterocyclic compound represented by formula A and the heterocyclic compound represented by formula B may be 1:10 to 10:1.

[0319] According to one embodiment of the present specification, the weight ratio of the heterocyclic compound represented by Formula A and the heterocyclic compound represented by Formula B may be 1:5 to 5:1.

[0320] According to one embodiment of the present specification, the weight ratio of the heterocyclic compound represented by Formula A and the heterocyclic compound represented by Formula B may be 1:3 to 3:1.

[0321] In addition, the composition for an organic layer comprising 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, and this thermal stability not only provides driving stability to the organic light-emitting device in the future but can also improve lifespan characteristics.

[0322] Method for manufacturing an organic light-emitting diode

[0323] 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 layers on the first electrode; and forming a second electrode on the organic layers, wherein the step of forming the organic layers includes forming one or more organic layers using a composition for an organic layer of an organic light-emitting device described above.

[0324] In one embodiment of the present specification, the step of forming the organic layer may be formed by pre-mixing the heterocyclic compound of Formula A and the heterocyclic compound of Formula B and using a thermal vacuum deposition method.

[0325] The above pre-mixed means mixing the materials first and placing them in a container to mix the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 before depositing them on an organic layer.

[0326] The pre-mixed material may be referred to as a composition for an organic layer according to one embodiment of the present application.

[0327] An organic light-emitting device according to one embodiment of the present specification can be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except that the organic layer is formed using the composition for the organic layer of the organic light-emitting device described above.

[0328] Specifically, regarding the method of forming an organic layer, the heterocyclic compound of Formula A and the heterocyclic compound of Formula B can be formed by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the term solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0329] In the following, the present specification is explained in more detail through examples, but these are for illustrative purposes only and are not intended to limit the scope of the present application.

[0330] Preparation Example.

[0331] [Preparation Example 1] Preparation of Compound A-5

[0332]

[0333] 1) Preparation of Compound A-5-1

[0334] 1,4-Dioxane (250 ml) and Water (50 ml) were added to 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), and stirred at 100°C for 6 hours. After stopping the reaction by adding water, extraction was performed using MC (Methylene chloride) and water. Subsequently, moisture was removed with MgSO4. By separation using a silica gel column, 15.8 g of compound A-5-1 was obtained with an 80% yield.

[0335] 2) Preparation of Compound A-5

[0336] Toluene (120 ml) was added to 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), and stirred at 100°C for 8 hours. After terminating the reaction with water, extraction was performed using MC and water. Subsequently, moisture was removed with MgSO4. By separation using a silica gel column, 7 g of compound A-5 was obtained with a yield of 79%.

[0337] [Preparation Example 2] Preparation of Compound A-341

[0338]

[0339] 1) Preparation of Compound A-341

[0340] 1,4-Dioxane (50 ml) and Water (10 ml) were added to A-5-1 (5 g, 0.015 mol, 1 eq) of 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), and stirred at 100°C for 8 hours. After stopping the reaction by adding water, extraction was performed using MC and water. Subsequently, moisture was removed with MgSO4. 5.5 g of compound A-341 was obtained in a yield of 67% by separation using a silica gel column.

[0341] [Preparation Example 3] Preparation of Other Compound A

[0342] Compound A was synthesized in the same way using intermediates A, B, C, and D of Table 1 below instead of intermediates (A), (B), (C), and (D) described in Preparation Example 1 or 2 above.

[0343]

[0344]

[0345]

[0346]

[0347]

[0348] [Preparation Example 4] Preparation of Compound B-1

[0349]

[0350] 1) Preparation of Compound B-1-2

[0351] 1,4-dioxane (250 ml) and water (50 ml) were added to 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), and Pd(PPh3)4 (3.38 g, 0.003 mol, 0.05 eq), and stirred at 100°C for 6 hours. After stopping the reaction by adding water, extraction was performed using MC and water. Subsequently, moisture was removed with MgSO4. By separation using a silica gel column, 17 g of compound B-1-2 was obtained with a yield of 86%.

[0352] 2) Preparation of Compound B-1-1

[0353] 1,4-Dioxane (200 ml) was added to the above 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 stopping the reaction by adding water, extraction was performed using MC and water. Subsequently, moisture was removed with MgSO4. 15g of compound B-1-1 was obtained in a yield of 69% by separation using a silica gel column.

[0354] 3) Preparation of Compound B-1

[0355] 1,4-Dioxane (100 ml) and Water (20 ml) were added to the above 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), and stirred at 100°C for 8 hours. After terminating the reaction with the addition of water, extraction was performed using MC and water. Subsequently, moisture was removed with MgSO4. By separation using a silica gel column, 9 g of compound B-1 was obtained with a yield of 75%.

[0356] [Preparation Example 5] Preparation of Other Compound B

[0357] Compound B was synthesized in the same way using intermediates E, F, and G of Table 2 below instead of intermediates (E), (F), and (G) described in Preparation Example 4 above.

[0358]

[0359]

[0360]

[0361]

[0362] [Preparation Example 6] Preparation of Compound A-323

[0363]

[0364] 1) Preparation of Compound A-323

[0365] 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 the mixture was stirred at 100°C for 8 hours. After stopping the reaction by adding water, extraction was performed using MC and water. Subsequently, moisture was removed with MgSO4. By separation using a silica gel column, 8.2 g of Compound A-323 was obtained with a yield of 78%.

[0366] [Preparation Example 7] Preparation of Compound B-242

[0367]

[0368] 1) Preparation of Compound B-242-2

[0369] Toluene (100 mL) was added to 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), and stirred at 100°C for 3 hours. After stopping the reaction with water, extraction was performed using MC and water. Subsequently, moisture was removed with MgSO4. By separation using a silica gel column, 14 g of compound B-242-2 was obtained in a 94% yield.

[0370] 2) Preparation of Compound B-242-1

[0371] 1,4-Dioxane (150 ml) was added to the above 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), and stirred at 100°C for 8 hours. After stopping the reaction by adding water, extraction was performed using MC and water. Subsequently, moisture was removed with MgSO4. 15 g of compound B-242-1 was obtained in 87% yield by separation using a silica gel column.

[0372] 3) Preparation of Compound B-242

[0373] 1,4-Dioxane (150 ml) and Water (30 ml) were added to the above 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), and stirred at 100°C for 8 hours. After terminating the reaction with the addition of water, extraction was performed using MC and water. Subsequently, moisture was removed with MgSO4. By separation using a silica gel column, 15 g of compound B-242 was obtained with a yield of 86%.

[0375] Compounds were prepared in the same manner as the above preparation examples, and the results of their synthesis confirmation are shown in Tables 3 and 4 below, respectively. Table 3 below is 1The H NMR (CDCl3, 200 MHz) measurement is shown, and Table 4 below shows the FD-mass spectrometry (FD-MS: Field desorption mass spectrometry) measurement.

[0376]

[0377]

[0378]

[0379]

[0380] Experimental Example.

[0381] <Experimental Example 1> Fabrication of an Organic Light-Emitting Device

[0382] A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 Å was cleaned with distilled water ultrasonics. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) using UV light for 5 minutes in an Ultraviolet (UV) cleaner. Subsequently, the substrate was transferred to a plasma cleaner (PT), subjected to plasma treatment under vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.

[0383] On the above ITO transparent electrode (anode), a common layer consisting of 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]) was formed. A light-emitting layer was then thermally vacuum deposited on top of this as follows. For the light-emitting layer, a compound composition (two types of compounds) listed in Table 5 below was deposited from a single source as the red host, and (piq)2(Ir)(acac) was used as the red phosphorescent dopant to deposit a 3 wt% Ir compound onto the host to a thickness of 400 Å. Subsequently, Bphen (Bathophenanthroline) was deposited as a hole blocking layer of 30 Å. An organic light-emitting diode was fabricated by depositing a thickness of 2,2',2''-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole) as an electron transport layer of 250 Å on top of it. Finally, an electron injection layer was formed by depositing lithium fluoride (LiF) to a thickness of 10 Å on the electron transport layer, and then forming a cathode by depositing an aluminum (Al) cathode to a thickness of 1,200 Å on the electron injection layer.

[0384] Meanwhile, all organic compounds required for OLED device fabrication are 10 each for each material -8 ~10 -6 It was purified by vacuum sublimation under torr and used for OLED fabrication. The electroluminescence (EL) characteristics of the organic light-emitting diode fabricated as described above were measured using MaxScience's M7000, and as a result of the measurement, the reference brightness was 6,000 cd / m² using a lifetime measurement device (M6000) manufactured by MaxScience. 2 When (cd / A), lifetime (T 90) was measured. The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the organic light-emitting diode manufactured according to the present invention are as shown in Table 5 below.

[0385] No. Compound composition (P:N) Weight ratio (P:N) Driving voltage (V) Luminous efficiency (cd / A) CIE(x, y) Lifespan (T 90 ) Example 1 A-123:B-86 1:1 4.51 58.0 (0.68, 0.32) 147 Example 2 A-227:B-176 1:1 4.52 59.2 (0.68, 0.32) 142 Example 3 A-308:B-150 1:1 4.52 60.2 (0.68, 0.32) 148 Example 4 A-1:B-21 3:1 4.42 66.0 (0.68, 0.32) 159 Example 5 A-1:B-21 2:1 4.41 65.8 (0.68, 0.32) 151 Example 6 A-1:B-21 1:1 4.43 64.0 (0.68, 0.32) 158 Example 7 A-1:B-21 1:2 4.44 67.7 (0.68, 0.32) 156 Example 8 A-1:B-21 1:3 4.41 65.6 (0.68, 0.32) 158 Example 9 A-34:B-45 1:1 4.47 64.5 (0.68, 0.32) 152 Example 10 A-161:B-21 1:1 4.40 64.8 (0.68, 0.32) 159 Example 11 A-253:B-62 1:1 4.40 62.9 (0.68, 0.32) 155 Example 12 A-383:B-287 1:1 4.42 65.8 (0.68, 0.32) 160 Example 13 A-432:B-307 1:1 4.41 66.2 (0.68, 0.32) 161 Example 14 A-254:B-313 1:1 4.41 65.8 (0.68, 0.32) 161 Example 15 A-90:B-1 1:1 4.30 71.0 (0.68, 0.32) 169 Example 16 A-116:B-217 1:1 4.31 71.1 (0.68, 0.32) 169 Example 17 A-214:B-217 1:1 4.30 70.5 (0.68, 0.32) 169 Example 18 A-289:B-134 1:1 4.30 72.2 (0.68, 0.32) 170 Example 19 A-355:B-86 1:1 4.37 71.3 (0.68, 0.32) 168 Example 20 A-369:B-176 1:1 4.31 73.2 (0.68, 0.32) 170 Example 21 A-64:B-62 1:1 4.21 77.7 (0.68, 0.32) 185 Example 22 A-45:B-150 1:1 4.27 77.8 (0.68, 0.32) 183 Example 23 A-183:B-114 1:1 4.27 77.7 (0.68, 0.32) 181 Example 24 A-263:B-225 1:1 4.22 77.9 (0.68, 0.32) 181 Example 25 A-365:B-346 1:1 4.22 78.0 (0.68, 0.32) 188 Example 26 A-402:B-172 1:1 4.19 81.0 (0.68, 0.32) 195 Example 27 A-46:B-242 1:1 4.11 81.1 (0.68, 0.32) 195 Example 28 A-408:B-170 1:1 4.13 82.2 (0.68, 0.32) 197 Example 29 A-339:B-258 1:1 4.05 88.3 (0.68, 0.32) 208 Example 30 A-340:B-257 1:1 4.02 88.4 (0.68, 0.32) 210 Comparative Example 1 A-64 - 8.31 8.9 (0.68, 0.32) 6 Comparative Example 2 B-86 - 8.25 8.8 (0.68, 0.32) 5 Comparative Example 3 H1 - 8.32 8.8 (0.68, 0.32) 5 Comparative Example 4 H2 - 8.41 8.7 (0.68, 0.32) 5 Comparative Example 5 H1:H2 1:1 5.19 47.2 (0.68, 0.32) 131 Comparative Example 6 H1:B-134 1:1 4.95 49.6 (0.68, 0.32) 138 Comparative Example 7 A-289:H2 1:1 4.84 48.0 (0.68, 0.32) 134 Comparative Example 8 H3 - 6.50 38.3 (0.68, 0.32) 115 Comparative Example 9 B-281 - 8.51 8.8 (0.68, 0.32) 6 Comparative Example 10 A-381 - 8.46 8.7 (0.68, 0.32) 5 Comparative Example 11 B-282 - 8.57 8.6 (0.68, 0.32) 5

[0386] The structures of the compounds used in Comparative Examples 3 to 8 are as follows.

[0387]

[0388] As can be seen from the results in Table 5 above, it was confirmed that when the heterocyclic compound of the present invention is used as a P-type host and deposited mixed with an N-type host, the driving performance, efficiency, and lifespan of the organic light-emitting device are improved. When a donor with good hole transport capability (p-host, the compound of Group A represented by P above) and an acceptor with good electron transport capability (n-host, the compound of Group B represented by N above) are used as hosts for the emissive layer, the exciplex phenomenon between the N-type host material and the P-type host material causes holes to be injected into the p-host and electrons to be injected into the n-host, thereby enabling charge balance within the device. This indicates that combining an N-type host compound with appropriate electron transport characteristics and a P-type host compound with appropriate hole transport characteristics in an appropriate ratio can help improve driving efficiency and lifespan.

[0389] In contrast, in the comparative example compounds used in Comparative Examples 3 to 8 above, H1 is 1-substituted naphthobenzofuran, which corresponds to the heterocyclic compound represented by Formula A corresponding to the P-type host compound; H2 is 1-substituted benzofuran, which corresponds to the heterocyclic compound represented by Formula B corresponding to the N-type host compound; and H3 is a composition that simultaneously has the substituents (amine group and triazine group) listed in each of the P-type host compound (Formula A) and the N-type host compound (Formula B), which corresponds to the combination of the heterocyclic compound represented by Formula A and the heterocyclic compound represented by Formula B.

[0390] According to Table 5 above, it was confirmed that in Comparative Examples 3 and 4, where H1 and H2 were used alone, very high driving voltage, very low efficiency, and very short lifespan were observed. In Comparative Example 5, where H1 and H2 were combined, and Comparative Example 8, where H3 was used alone, it was confirmed that while there was a slight improvement in device characteristics compared to Comparative Examples 1 and 2, it was weak compared to the example group. Furthermore, in Comparative Examples 6 and 7, where only some of the conditions of the present invention (including either Chemical Formula A or B) were satisfied and the remainder did not satisfy the conditions, it was confirmed that there was a difference compared to the example group even if there was a slight improvement in device characteristics. Additionally, Comparative Examples 1, 2, 9, 10, and 11, which include only one heterocyclic compound of Formula A or Formula B and do not satisfy the above conditions (combination of a heterocyclic compound of Formula A and a heterocyclic compound of Formula B), were found to have deteriorated device characteristics to the level of Comparative Examples 3 and 4. Thus, it was confirmed that when a heterocyclic compound represented by Formula A of the present invention is used as a P-type host and a heterocyclic compound represented by Formula B is used as an N-type host for mixed deposition, the driving, efficiency, and lifespan of the organic light-emitting device are improved.

[0391] The present invention is not limited to the above embodiments and can be manufactured in various different forms, and those skilled in the art will understand that the invention can be implemented in other specific forms without changing the technical concept or essential features of the invention. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive. Explanation of the symbols

[0392] 100: Substrate 200: Anode 300: Organic layer 301: Hole injection layer 302: Precision Transport Layer 303: Electronic blocking layer 304: Emissive layer 305: Poison blockade layer 306: Electron transport layer 307: Electron injection layer 400: Cathode

Claims

Claim 1 An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprises a heterocyclic compound represented by any one of the following chemical formulas A-101 to A-108; and a heterocyclic compound represented by any one of the following chemical formulas B-101 to B-115: [Chemical Formula A-101] [Chemical Formula A-102] [Chemical Formula A-103] [Chemical Formula A-104] [Chemical Formula A-105] [Chemical Formula A-106] [Chemical Formula A-107] [Chemical Formula A-108] [Chemical Formula B-101] [Chemical Formula B-102] [Chemical Formula B-103] [Chemical Formula B-104] [Chemical Formula B-105] [Chemical Formula B-106] [Chemical Formula B-107] [Chemical Formula B-108] [Chemical Formula B-109] [Chemical Formula B-110] [Chemical Formula B-111] [Chemical Formula B-112] [Chemical Formula B-113] [Chemical Formula B-114] [Chemical Formula B-115] In the above formulas A-101 to A-108 and formulas B-101 to B-115, L1 to L4 are identical or different from each other and are each independently directly bonded; 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 ​​and Ar2 are identical or different from each other and are each independently 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; and Ar3 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted naphthobenzofuranyl group; a substituted or unsubstituted naphthobenzothiophenyl group; or a substituted or unsubstituted carbazole group, and 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, and R1 and R2 are identical or different from each other and each independently 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, wherein R3', R4' and R5 are identical or different from each other and each independently 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 is 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 identical or different from each other and are each independently integers from 1 to 3, and when each l1 to l4 is an integer of 2 or more, the types of substituents in parentheses are identical or different from each other, r1' is an integer of 0 to 5, each r2' to r4' is an integer of 0 to 3, each r3'' and r4'' is an integer of 0 to 2, r5 is an integer of 0 to 4, and when each l1 to l4, r1' to r4', r3", r4" and r5 are integers of 2 or more, the substituents in parentheses are identical or different from each other, and N-Het1 is represented by the following chemical formula N, [Chemical Formula N]; In the above chemical formula N, ... refers to a portion connected to L3, and Y1 to Y5 are identical or different from each other and are each independently CRa or N, at least one being N, and 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, and if the organic layer comprises a compound represented by any one of the chemical formulas A-101, A-103, A-105 and A-107, it comprises a compound represented by any one of the chemical formulas B-101 and B-103 to B-115. Claim 2 delete Claim 3 delete Claim 4 delete Claim 5 delete Claim 6 An organic light-emitting device according to claim 1, wherein L1 to L4 are identical or different from each other and each independently directly bonded; or are substituted or unsubstituted arylene groups having 6 to 30 carbon atoms. Claim 7 An organic light-emitting device according to claim 1, wherein Ar1 and Ar2 are identical or different from each other and each is independently 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. Claim 8 An organic light-emitting device according to claim 1, wherein 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, and Rb and Rc are identical or different from each other and are each independently 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. Claim 9 An organic light-emitting device according to claim 1, wherein R1 and R2 are identical or different from each other and each independently is hydrogen; or deuterium. Claim 10 An organic light-emitting device according to claim 1, wherein R3', R4' and R5 are identical or different from each other and each independently is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or two or more adjacent groups are combined to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms. Claim 11 An organic light-emitting device according to claim 1, wherein the deuterium content of the heterocyclic compound represented by any one of the formulas A-101 to A-108 and the heterocyclic compound represented by any one of the formulas B-101 to B-115 are the same or different from each other, and each is independently 0% or 1% to 100%. Claim 12 An organic light-emitting device according to claim 1, wherein the heterocyclic compound represented by any one of the chemical formulas A-101 to A-108 is represented by any one of the following: . Claim 13 An organic light-emitting device according to claim 1, wherein the heterocyclic compound represented by any one of the chemical formulas B-101 to B-115 is represented by any one of the following: . Claim 14 An organic light-emitting device according to claim 1, wherein the organic layer further comprises an emission layer, and the emission layer comprises a heterocyclic compound represented by any one of the chemical formulas A-101 to A-108; and a heterocyclic compound represented by any one of the chemical formulas B-101 to B-115. Claim 15 The organic light-emitting device of claim 1, wherein the organic light-emitting device further comprises one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport assist layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. Claim 16 A composition for an organic layer of an organic light-emitting device comprising: a heterocyclic compound represented by any one of the following chemical formulas A-101 to A-108; and a heterocyclic compound represented by any one of the following chemical formulas B-101 to B-115: [Chemical Formula A-101] [Chemical Formula A-102] [Chemical Formula A-103] [Chemical Formula A-104] [Chemical Formula A-105] [Chemical Formula A-106] [Chemical Formula A-107] [Chemical Formula A-108] [Chemical Formula B-101] [Chemical Formula B-102] [Chemical Formula B-103] [Chemical Formula B-104] [Chemical Formula B-105] [Chemical Formula B-106] [Chemical Formula B-107] [Chemical Formula B-108] [Chemical Formula B-109] [Chemical Formula B-110] [Chemical Formula B-111] [Chemical Formula B-112] [Chemical Formula B-113] [Chemical Formula B-114] [Chemical Formula B-115] In the above formulas A-101 to A-108 and formulas B-101 to B-115, L1 to L4 are identical or different from each other and are each independently directly bonded; 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 ​​and Ar2 are identical or different from each other and are each independently 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; and Ar3 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted naphthobenzofuranyl group; a substituted or unsubstituted naphthobenzothiophenyl group; or a substituted or unsubstituted carbazole group, and 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, and R1 and R2 are identical or different from each other and each independently 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, wherein R3', R4' and R5 are identical or different from each other and each independently 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 is 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 identical or different from each other and are each independently integers from 1 to 3, and when each l1 to l4 is an integer of 2 or more, the types of substituents in parentheses are identical or different from each other, r1' is an integer of 0 to 5, each r2' to r4' is an integer of 0 to 3, each r3'' and r4'' is an integer of 0 to 2, r5 is an integer of 0 to 4, and when each l1 to l4, r1' to r4', r3", r4" and r5 are integers of 2 or more, the substituents in parentheses are identical or different from each other, and N-Het1 is represented by the following chemical formula N, [Chemical Formula N]; In the above chemical formula N, ... refers to a portion connected to L3, and Y1 to Y5 are identical or different from each other, and each is independently CRa or N, at least one being N, and 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, and if the composition for the organic layer comprises a compound represented by any one of the formulas A-101, A-103, A-105 and A-107, it comprises a compound represented by any one of the formulas B-101 and B-103 to B-115. Claim 17 A composition for an organic layer of an organic light-emitting device according to claim 16, wherein the weight ratio of a heterocyclic compound represented by any one of the formulas A-101 to A-108 and a heterocyclic compound represented by any one of the formulas B-101 to B-115 is 1:10 to 10:

1. Claim 18 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 layers on the first electrode; and forming a second electrode on the organic layers, wherein the step of forming the organic layers includes forming one or more organic layers using a composition for an organic layer of an organic light-emitting device according to claim 16. Claim 19 A method for manufacturing an organic light-emitting device according to claim 18, wherein the step of forming the organic layer is to pre-mix a heterocyclic compound represented by any one of the formulas A-101 to A-108 and a heterocyclic compound represented by any one of the formulas B-101 to B-115 and form the layer using a thermal vacuum deposition method.

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