Heterocyclic compound and organic light-emitting device including the same

Abstract

The present application provides a heterocyclic compound that can significantly improve the lifetime, efficiency, electrochemical stability, and thermal stability of an organic light-emitting device, and an organic light-emitting device having the heterocyclic compound contained in an organic material layer.

Description

[Technical field]

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0100204, filed with the Korean Intellectual Property Office on August 16, 2019, the entire contents of which are incorporated herein by reference.

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

[0003] An organic electroluminescent device is a type of self-luminous display device, and has the advantages of a wide viewing angle, excellent contrast, and fast response speed.

[0004] An organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an organic light-emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs, and then disappear, emitting light. The organic thin film may be configured as a single layer or multiple layers as required.

[0005] The material of the organic thin film may have a light-emitting function as necessary. For example, the organic thin film material may be a compound that can form a light-emitting layer by itself, or a compound that plays the role of a host or dopant in a host-dopant light-emitting layer. In addition, the organic thin film material may be a compound that plays the role of hole injection, hole transport, electron block, hole block, electron transport, electron injection, etc.

[0006] In order to improve the performance, lifetime or efficiency of organic light emitting devices, there is a continuing need to develop materials for organic thin films. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] U.S. Patent No. 4,356,429 Summary of the Invention [Problem to be solved by the invention]

[0008] The present specification provides a heterocyclic compound and an organic light-emitting device including the same. [Means for solving the problem]

[0009] In one embodiment of the present application, there is provided a heterocyclic compound represented by the following Chemical Formula 1: [ka]

[0010] In the above Chemical Formula 1, L1 and L2 are the same or different and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; R1 and R2 are the same or different and each independently represents a cyano group; 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 phosphine oxide group; X1 to X3 are the same or different and each independently represents hydrogen; deuterium; or a cyano group; m is an integer of 0 to 3; n is an integer of 0 to 4; and when m and n are 2 or more, the substituents in the parentheses are the same or different. p and r are integers from 0 to 4; q and s are integers from 1 to 6; When p, q, r and s are 2 or more, the substituents within the brackets are the same or different.

[0011] In addition, in one embodiment of the present application, there is provided an organic light-emitting device including a first electrode, a second electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers includes a heterocyclic compound represented by Chemical Formula 1. Effect of the Invention

[0012] The compounds described herein can be used as organic layer materials in organic light-emitting devices. The compounds can play the role of hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. in organic light-emitting devices. In particular, the compounds can be used as electron transport layer materials, hole blocking layer materials, or charge generation layer materials in organic light-emitting devices.

[0013] Specifically, when the heterocyclic compound represented by Chemical Formula 1 is used in the organic layer, the driving voltage of the device can be reduced, the light efficiency can be improved, and the life characteristics of the device can be improved. [Brief description of the drawings]

[0014] [Figure 1] 1 is a diagram illustrating an example of a layered structure of an organic light-emitting device according to an embodiment of the present application. [Diagram 2] 1 is a diagram illustrating an example of a layered structure of an organic light-emitting device according to an embodiment of the present application. [Diagram 3] 1 is a diagram illustrating an example of a layered structure of an organic light-emitting device according to an embodiment of the present application. [Figure 4] 1 is a diagram illustrating an example of a layered structure of an organic light-emitting device according to an embodiment of the present application. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0015] This specification will be explained in more detail below. In this specification, when a part "comprises" a certain component, this means that it can further include other components, not excluding other components, unless specifically stated to the contrary.

[0016] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different.

[0017] In this specification, "substituted or unsubstituted" means being substituted or unsubstituted with one or more substituents selected from the group consisting of a linear or branched alkyl group having 1 to 60 carbon atoms; a linear or branched alkenyl group having 2 to 60 carbon atoms; a linear or branched alkynyl group having 2 to 60 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 60 carbon atoms; a monocyclic or polycyclic heterocycloalkyl group having 2 to 60 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 60 carbon atoms; a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms; a silyl group; a phosphine oxide group; and an amine group, or being substituted or unsubstituted with a substituent in which two or more substituents selected from the above-mentioned exemplary substituents are linked.

[0018] More specifically, in this specification, "substituted or unsubstituted" can mean being substituted or unsubstituted with one or more substituents selected from the group consisting of monocyclic or polycyclic aryl groups having 6 to 60 carbon atoms; or monocyclic or polycyclic heteroaryl groups having 2 to 60 carbon atoms.

[0019] In this specification, when "no substituent is shown in the chemical formula or compound structure," it means that a hydrogen atom is bonded to the carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0020] In one embodiment of the present application, "when no substituent is shown in the chemical formula or compound structure", it can mean that all positions that can be substituted are hydrogen or deuterium. In other words, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be deuterium, which is an isotope, and in this case, the content of deuterium may be 0% to 100%.

[0021] In one embodiment of the present application, in the case where "substituents are not shown in the chemical formula or compound structure", if deuterium is not explicitly excluded, such as when the deuterium content is 0%, hydrogen content is 100%, or all substituents are hydrogen, hydrogen and deuterium can be used together in the compound.

[0022] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen and is an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, and may be represented as hydrogen-2, or its atomic symbol may be written as D or 2H.

[0023] In one embodiment of the present application, isotopes refer to atoms with the same atomic number (Z) but different mass numbers (A). Isotopes can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0024] In one embodiment of the present application, the content T% of a specific substituent can be defined as T2 / T1×100=T%, where T1 is the total number of substituents that the base compound may have and T2 is the number of specific substituents among the total number of substituents.

[0025] That is, in one example, [ka] In the case where the total number of substituents that the phenyl group may have is 5 (T1 in the above T% formula), of which the number of deuterium is 1 (T2 in the formula), the deuterium content of 20% in the phenyl group represented by the following structural formula may be expressed as 20%. [ka]

[0026] In addition, in one embodiment of the present application, a "phenyl group having a deuterium content of 0%" can mean a phenyl group that does not contain a deuterium atom, that is, a phenyl group that has five hydrogen atoms.

[0027] In this specification, the halogen may be fluorine, chlorine, bromine, or iodine.

[0028] In this specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be additionally substituted with other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a pent ... Examples of such alkyl groups include, but are not limited to, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0029] In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be additionally substituted with other substituents. The number of carbon atoms in the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group.

[0030] In this specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms and may be additionally substituted with other substituents. The number of carbon atoms in the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0031] In the present specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, the alkoxy group may be, but is not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc.

[0032] In this specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be additionally substituted with other substituents. Here, the polycyclic group means a group in which the cycloalkyl group is directly linked or condensed with another cyclic group. Here, the other cyclic group may be a cycloalkyl group, but may also be other types of cyclic groups, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0033] In the present specification, the heterocycloalkyl group includes O, S, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be additionally substituted with other substituents. Here, the polycyclic group means a group in which the heterocycloalkyl group is directly linked or condensed with another cyclic group. Here, the other cyclic group may be a heterocycloalkyl group, but may also be other types of cyclic groups, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0034] In this specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be additionally substituted with other substituents. Here, the polycyclic ring means a group in which the aryl group is directly linked 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 a cycloalkyl group, a heterocycloalkyl group, or a heteroaryl group. The aryl group includes 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 aryl group include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and condensed ring groups thereof, but are not limited to these.

[0035] In the present specification, the phosphine oxide group is represented by -P(=O)R101R102, where R101 and R102 may be the same or different and each may independently be a substituent consisting of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. Specific examples of the phosphine oxide group include, but are not limited to, a diphenylphosphine oxide group and a dinaphthylphosphine oxide group.

[0036] In this specification, a silyl group is a substituent that contains Si and is directly linked to the Si atom as a radical, and is represented by -SiR104R105R106, where R104 to R106 may be the same or different and each may be independently a substituent consisting of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0037] In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0038] In this specification, the spiro group may be a group containing a spiro structure and may have 15 to 60 carbon atoms. For example, the spiro group may contain a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro-bonded to a fluorenyl group. Specifically, the following spiro group may contain any one of the groups of the following structural formulas. [ka]

[0039] In this specification, the heteroaryl group includes S, O, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be additionally substituted with other substituents. Here, the polycyclic ring means a group in which the heteroaryl group is directly linked or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be other types of ring groups, 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 heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, and a triazinyl group. group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyl group, naphthyridyl group, acridinyl group, phenanthridinyl group, imidazopyridinyl group, diazanaphthalenyl group, triazaindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocathyl group, carbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilole group, spirobi(dibenzosilole), dihydrophenazinyl group, phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiazinyl group, Examples of such an alkyl group include, but are not limited to, an azinyl group, a phthalazinyl group, a naphthyridinyl group, a phenanthrolinyl group, a benzo[c][1,2,5]thiadiazolyl group, a 5,10-dihydrodibenzo[b,e][1,4]azasilinyl group, a pyrazolo[1,5-c]quinazolinyl group, a pyrido[1,2-b]indazolyl group, a pyrido[1,2-a]imidazo[1,2-e]indolinyl group, and a 5,11-dihydroindeno[1,2-b]carbazolyl group.

[0040] In the present specification, the amine group may be selected from the group consisting of a monoalkylamine group, a monoarylamine group, a monoheteroarylamine group, -NH2, a dialkylamine group, a diarylamine group, a diheteroarylamine group, an alkylarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group, but are not limited thereto.

[0041] In this specification, the arylene group means an aryl group having two bonding positions, i.e., a divalent group. The above-mentioned explanation of the aryl group is applicable to these groups, except that they are each divalent groups. In addition, the heteroarylene group means a heteroaryl group having two bonding positions, i.e., a divalent group. The above-mentioned explanation of the heteroaryl group is applicable to these groups, except that they are each divalent groups.

[0042] In this specification, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring are interpreted as "adjacent" groups to each other.

[0043] In one embodiment of the present application, there is provided a heterocyclic compound represented by the following Chemical Formula 1: [ka] In the above Chemical Formula 1, L1 and L2 are the same or different and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; R1 and R2 are the same or different and each independently represents a cyano group; 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 phosphine oxide group; X1 to X3 are the same or different and each independently represents hydrogen; deuterium; or a cyano group; m is an integer of 0 to 3; n is an integer of 0 to 4; and when m and n are 2 or more, the substituents in the parentheses are the same or different. p and r are integers from 0 to 4; q and s are integers from 1 to 6; When p, q, r and s are 2 or more, the substituents within the brackets are the same or different.

[0044] In one embodiment of the present application, the above-mentioned Chemical Formula 1 provides a heterocyclic compound represented by the following Chemical Formula 2: [ka] In Chemical Formula 2, the definitions of each substituent are the same as those in Chemical Formula 1.

[0045] In one embodiment of the present application, the above-mentioned Chemical Formula 1 provides a heterocyclic compound represented by any one of the following Chemical Formulas 3 to 6. [ka] [ka] [ka] [ka]

[0046] In Chemical Formulae 3 to 6, the definitions of the respective substituents are the same as those in Chemical Formula 1.

[0047] In one embodiment of the present application, L1 and L2 are the same or different and may each independently be a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

[0048] In another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0049] In still another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

[0050] In still another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0051] In still another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a substituted or unsubstituted monocyclic arylene group having 6 to 10 carbon atoms; or a substituted or unsubstituted polycyclic arylene group having 10 to 20 carbon atoms.

[0052] In still another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a monocyclic arylene group having 6 to 10 carbon atoms; or a polycyclic arylene group having 10 to 20 carbon atoms.

[0053] In yet another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted binaphthylene group.

[0054] In still other embodiments, L1 and L2 are the same or different and may each independently be a direct bond; a phenylene group; a biphenylene group; a naphthylene group; or a binaphthylene group.

[0055] In one embodiment of the present application, L1 and L2 may be identical to each other.

[0056] In one embodiment of the present application, L1 and L2 may be different from each other.

[0057] In one embodiment of the present application, L1 may be a direct bond, and L2 may be 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.

[0058] In one embodiment of the present application, L1 may be a direct bond, and L2 may be 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.

[0059] In one embodiment of the present application, L1 may be a direct bond, and L2 may be a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0060] In one embodiment of the present application, the L2 may be a direct bond, and the L1 may be 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.

[0061] In one embodiment of the present application, the L2 may be a direct bond, and the L1 may be 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.

[0062] In one embodiment of the present application, the L2 may be a direct bond, and the L1 may be a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0063] In one embodiment of the present application, L1 may be a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0064] In another embodiment, L1 may be a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

[0065] In still another embodiment, the L1 may be a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0066] In still other embodiments, L1 may be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted binaphthylene group.

[0067] In still other embodiments, L1 may be a direct bond; a phenylene group; a biphenylene group; a naphthylene group; or a binaphthylene group.

[0068] In still other embodiments, said L1 is a direct bond.

[0069] In yet another embodiment, L1 is a phenylene group.

[0070] In yet another embodiment, L1 is a biphenylene group.

[0071] In yet another embodiment, L1 is a naphthylene group.

[0072] In yet another embodiment, L1 is a binaphthylene group.

[0073] In one embodiment of the present application, L2 may be a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0074] In another embodiment, L2 may be a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

[0075] In still another embodiment, the L2 may be a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0076] In still other embodiments, L2 may be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted binaphthylene group.

[0077] In still other embodiments, L2 may be a direct bond; a phenylene group; a biphenylene group; a naphthylene group; or a binaphthylene group.

[0078] In still other embodiments, said L2 is a direct bond.

[0079] In yet another embodiment, L2 is a phenylene group.

[0080] In yet another embodiment, L2 is a biphenylene group.

[0081] In yet other embodiments, L2 is a naphthylene group.

[0082] In yet another embodiment, L2 is a binaphthylene group.

[0083] In one embodiment of the present application, X1 to X3 may each independently be hydrogen; deuterium; or a cyano group.

[0084] In one embodiment of the present application, X1 may be hydrogen; deuterium; or a cyano group.

[0085] In one embodiment of the present application, X1 is hydrogen.

[0086] In one embodiment of the present application, X1 is deuterium.

[0087] In one embodiment of the present application, X1 is a cyano group.

[0088] In one embodiment of the present application, X2 may be hydrogen; deuterium; or a cyano group.

[0089] In one embodiment of the present application, X2 is hydrogen.

[0090] In one embodiment of the present application, X2 is deuterium.

[0091] In one embodiment of the present application, X2 is a cyano group.

[0092] In one embodiment of the present application, X3 is hydrogen.

[0093] In one embodiment of the present application, X3 is deuterium.

[0094] In one embodiment of the present application, X3 is a cyano group.

[0095] In one embodiment of the present application, X1 to X3 are hydrogen.

[0096] In one embodiment of the present application, m is an integer of 0 to 3, n is an integer of 0 to 4, and when m and n are 2 or more, the substituents in parentheses may be the same or different from each other.

[0097] In one embodiment of the present application, m is an integer from 0 to 3.

[0098] In one embodiment of the present application, m is 3.

[0099] In one embodiment of the present application, m is 2.

[0100] In one embodiment of the present application, m is 1.

[0101] In one embodiment of the present application, m is 0.

[0102] In one embodiment of the present application, when m is 2 or greater, the substituents within the brackets are the same or different from each other.

[0103] In one embodiment of the present application, n is an integer from 0 to 4.

[0104] In one embodiment of the present application, n is 4.

[0105] In one embodiment of the present application, n is 3.

[0106] In one embodiment of the present application, n is 2.

[0107] In one embodiment of the present application, n is 1.

[0108] In one embodiment of the present application, n is 0.

[0109] In one embodiment of the present application, when n is 2 or greater, the substituents within the brackets are the same or different from each other.

[0110] In one embodiment of the present application, R1 and R2 are the same or different and may each independently be a cyano group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted phosphine oxide group.

[0111] In another embodiment, R1 and R2 may be the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms; or a substituted or unsubstituted phosphine oxide group.

[0112] In yet another embodiment, R1 and R2 are the same or different and may each independently be a cyano group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted pyridine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted triazine group; a substituted or unsubstituted 1,10-phenanthroline group; or a substituted or unsubstituted phosphine oxide group.

[0113] In still another embodiment, R1 and R2 are the same or different from each other, and each may be independently a cyano group; a phenyl group; a biphenyl group; a naphthyl group; a triphenylene group; a dibenzofuran group; a dibenzothiophene group; a pyridine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group; a pyrimidine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group; a triazine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group; a 1,10-phenanthroline group substituted or unsubstituted with a phenyl group; or a phosphine oxide group substituted or unsubstituted with a phenyl group.

[0114] In one embodiment of the present application, R1 and R2 may be the same as each other.

[0115] In one embodiment of the present application, R1 and R2 may be different from each other.

[0116] In other embodiments, R1 may be a cyano group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted phosphine oxide group.

[0117] In still another embodiment, R1 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 phosphine oxide group.

[0118] In still other embodiments, R1 may be a cyano group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted pyridine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted triazine group; a substituted or unsubstituted 1,10-phenanthroline group; or a substituted or unsubstituted phosphine oxide group.

[0119] In still other embodiments, R1 may be a cyano group; a phenyl group; a biphenyl group; a naphthyl group; a triphenylene group; a dibenzofuran group; a dibenzothiophene group; a pyridine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group; a pyrimidine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group; a triazine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group; a 1,10-phenanthroline group substituted or unsubstituted with a phenyl group; or a phosphine oxide group substituted or unsubstituted with a phenyl group.

[0120] In yet another embodiment, R1 is a cyano group.

[0121] In yet another embodiment, R1 is a phenyl group.

[0122] In yet another embodiment, R1 is a biphenyl group.

[0123] In yet another embodiment, R1 is a naphthyl group.

[0124] In yet another embodiment, R1 is a triphenylene group.

[0125] In yet other embodiments, R1 is a dibenzofuran group.

[0126] In still other embodiments, R1 is a pyridine group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group.

[0127] In yet other embodiments, R1 is a triazine group unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, biphenyl, and naphthyl groups.

[0128] In yet another embodiment, R1 is a 1,10-phenanthroline group unsubstituted or substituted with a phenyl group.

[0129] In yet another embodiment, R1 is a phosphine oxide group unsubstituted or substituted with a phenyl group.

[0130] In still other embodiments, R2 may be a cyano group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted phosphine oxide group.

[0131] In still another embodiment, R2 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 phosphine oxide group.

[0132] In still other embodiments, R2 may be a cyano group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted pyridine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted triazine group; a substituted or unsubstituted 1,10-phenanthroline group; or a substituted or unsubstituted phosphine oxide group.

[0133] In still other embodiments, R2 may be a cyano group; a phenyl group; a biphenyl group; a naphthyl group; a triphenylene group; a dibenzofuran group; a dibenzothiophene group; a pyridine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group; a pyrimidine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group; a triazine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group; a 1,10-phenanthroline group substituted or unsubstituted with a phenyl group; or a phosphine oxide group substituted or unsubstituted with a phenyl group.

[0134] In yet other embodiments, R2 is a cyano group.

[0135] In yet other embodiments, R2 is a phenyl group.

[0136] In yet other embodiments, R2 is a biphenyl group.

[0137] In yet other embodiments, R2 is a naphthyl group.

[0138] In yet other embodiments, R2 is a triphenylene group.

[0139] In yet other embodiments, R2 is a dibenzofuran group.

[0140] In still other embodiments, R2 is a pyridine group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group.

[0141] In yet other embodiments, R2 is a triazine group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group.

[0142] In yet other embodiments, R2 is a 1,10-phenanthroline group unsubstituted or substituted with a phenyl group.

[0143] In yet other embodiments, R2 is a phosphine oxide group unsubstituted or substituted with a phenyl group.

[0144] In one embodiment of the present application, at least one of R1 and R2 can include a substituted or unsubstituted N-containing heteroaryl group.

[0145] In one embodiment of the present application, the substituted or unsubstituted N-containing heteroaryl group may be a substituted or unsubstituted heteroaryl group having one or more =N- bonds.

[0146] In other embodiments, the substituted or unsubstituted N-containing heteroaryl group may be a substituted or unsubstituted heteroaryl group having from 1 to 5 =N-bonds.

[0147] In yet another embodiment, the substituted or unsubstituted N-containing heteroaryl group may be a substituted or unsubstituted heteroaryl group having from 1 to 3 =N-bonds.

[0148] In one embodiment of the present application, having one or more =N-bonds means that the compound contains an N atom and the N atom is connected by a double bond and a single bond, and specifically may be, but is not limited to, a pyridine group, a pyrimidine group, a triazine group, a benzimidazole group, a phenanthroline group, etc.

[0149] In one embodiment of the present application, the substituted or unsubstituted N-containing heteroaryl group may be a substituted or unsubstituted pyridine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted triazine group; or a substituted or unsubstituted 1,10-phenanthroline group.

[0150] In other embodiments, the substituted or unsubstituted N-containing heteroaryl group may be a pyridine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group; a pyrimidine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group; a triazine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group; or a 1,10-phenanthroline group substituted or unsubstituted with a phenyl group.

[0151] In one embodiment of the present application, the substituted or unsubstituted N-containing heteroaryl group may be represented by any one of the following chemical formulas A1 to A30.

[0152] [ka] TIFF0007671504000012.tif234165 TIFF0007671504000013.tif230165 TIFF0007671504000014.tif223165 TIFF0007671504000015.tif217165 TIFF0007671504000016.tif240165 TIFF0007671504000017.tif115165

[0153] In the above Chemical Formulae A1 to A30, the * indicates the position where the group is bonded to L1 or L2, respectively.

[0154] In one embodiment of the present application, only R1 may contain a substituted or unsubstituted N-containing heteroaryl group.Specifically, R1 may contain a substituted or unsubstituted N-containing heteroaryl group, and R2 may be a cyano group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted phosphine oxide group.

[0155] In one embodiment of the present application, only R2 may contain a substituted or unsubstituted N-containing heteroaryl group.Specifically, R2 may contain a substituted or unsubstituted N-containing heteroaryl group, and R1 may be a cyano group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted phosphine oxide group.

[0156] In one embodiment of the present application, R1 and R2 are the same or different from each other and each can independently comprise a substituted or unsubstituted N-containing heteroaryl group.

[0157] In one embodiment of the present application, the above-mentioned Chemical Formula 1 provides a heterocyclic compound represented by any one of the following compounds:

[0158] [ka] TIFF0007671504000019.tif224165 TIFF0007671504000020.tif225165 TIFF0007671504000021.tif224165 TIFF0007671504000022.tif221165 TIFF0007671504000023.tif215165 TIFF0007671504000024.tif219165 TIFF0007671504000025.tif223165 TIFF0007671504000026.tif234165 TIFF0007671504000027.tif224165 TIFF0007671504000028.tif223165 TIFF0007671504000029.tif220165 TIFF0007671504000030.tif222165 TIFF0007671504000031.tif227165 TIFF0007671504000032.tif227165 TIFF0007671504000033.tif83165 TIFF0007671504000034.tif223165 TIFF0007671504000035.tif222165 TIFF0007671504000036.tif221165 TIFF0007671504000037.tif225165 TIFF0007671504000038.tif222165 TIFF0007671504000039.tif223165 TIFF0007671504000040.tif224165 TIFF0007671504000041.tif223165 TIFF0007671504000042.tif221165 TIFF0007671504000043.tif223165 TIFF0007671504000044.tif236165

[0159] In addition, it is possible to synthesize compounds having the inherent properties of the introduced substituents by introducing various substituents into the structure of Chemical Formula 1. For example, it is possible to synthesize materials that satisfy the requirements of each organic layer by introducing into the core structure substituents that are mainly used in hole injection layer materials, hole transport layer materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light emitting devices.

[0160] Furthermore, by introducing various substituents into the structure of Chemical Formula 1, the energy band gap can be finely adjusted, while the properties at the interface between organic materials can be improved, and the applications of the material can be diversified.

[0161] Meanwhile, the heterocyclic compound has a high glass transition temperature (Tg) and is therefore excellent in thermal stability, which is an important factor in providing driving stability to a device.

[0162] The heterocyclic compound according to one embodiment of the present application can be produced by a multi-step chemical reaction. Some intermediate compounds are produced first, and the compound of Chemical Formula 1 can be produced from the intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of the present application can be produced based on the production examples described below.

[0163] Another embodiment of the present application provides an organic light emitting device including a heterocyclic compound represented by Chemical Formula 1. The "organic light emitting device" can be expressed by terms such as "organic light emitting diode," "OLED (Organic Light Emitting Diodes)," "OLED device," "organic electroluminescent device," etc.

[0164] In one embodiment of the present application, there is provided an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a heterocyclic compound represented by Chemical Formula 1.

[0165] In one embodiment of the present application, the first electrode may be an anode and the second electrode may be a cathode.

[0166] In another embodiment of the present application, the first electrode may be a cathode and the second electrode may be an anode.

[0167] In one embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound of Chemical Formula 1 can be used as a material of the blue organic light emitting device.

[0168] In another embodiment of the present application, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 can be used as a material of the green organic light emitting device.

[0169] In another embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 can be used as a material of the red organic light emitting device.

[0170] The specific details regarding the heterocyclic compound represented by Chemical Formula 1 are the same as those described above.

[0171] The organic light-emitting device of the present application can be manufactured by a typical manufacturing method and material for an organic light-emitting device, except that one or more organic layers are formed using the above-mentioned heterocyclic compound.

[0172] In the manufacture of an organic light emitting device, the heterocyclic compound is formed in an organic layer by a solution coating method as well as a vacuum deposition method, where the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0173] The organic layer of the organic light-emitting device of the present application may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention 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 the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0174] In the organic light-emitting device of the present application, the organic layer includes an electron transport layer, and the electron transport layer can include the heterocyclic compound. When the heterocyclic compound is used in the electron transport layer, the compound is not decomposed or destroyed, and electrons are efficiently transported, so that the organic light-emitting device can have excellent operation, efficiency, and life.

[0175] In another organic light-emitting device, the organic layer includes a hole-blocking layer, and the hole-blocking layer can include the heterocyclic compound. When the heterocyclic compound is used in the hole-blocking layer, the organic light-emitting device can have excellent operation, efficiency, and life.

[0176] The organic light-emitting device of the present invention 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, an electron-injection layer, an electron-transport layer, an electron-blocking layer, and a hole-blocking layer.

[0177] 1 to 3 show examples of the stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present application. However, these figures are not intended to limit the scope of the present application, and structures of organic light-emitting devices known in the art are also applicable to the present application.

[0178] 1 shows an organic light emitting device in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, the present invention is not limited to this structure, and an organic light emitting device in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate as shown in FIG.

[0179] Fig. 3 illustrates an example in which the organic layer is multi-layered. The organic light-emitting device in Fig. 3 includes a hole injection layer 301, a hole transport layer 302, an emission layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited to such a laminated structure, and the remaining layers except for the emission layer may be omitted as necessary, and other necessary functional layers may be further added.

[0180] The organic layer containing the heterocyclic compound represented by Chemical Formula 1 may further contain other materials as necessary.

[0181] Moreover, an organic light-emitting element according to one embodiment of the present application includes a first electrode, a first stack provided on the first electrode and including a first light-emitting layer, a charge generation layer provided on the first stack, a second stack provided on the charge generation layer and including a second light-emitting layer, and a second electrode provided on the second stack.

[0182] Furthermore, an organic light-emitting element according to one embodiment of the present application includes a first stack provided on the first electrode and including a first light-emitting layer, a charge generation layer provided on the first stack, a second stack provided on the charge generation layer and including a second light-emitting layer, and the second electrode provided on the second stack.

[0183] In this case, the charge generation layer may include a heterocyclic compound represented by Formula 1. When the heterocyclic compound is used in the charge generation layer, the organic light emitting device may have excellent operation, efficiency, and lifespan.

[0184] In addition, the first stack and the second stack may each independently additionally include one or more of the hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer, and the like.

[0185] The charge generating layer may be an N-type charge generating layer, and the charge generating layer may further include a dopant known in the art in addition to the heterocyclic compound represented by Formula 1.

[0186] As an organic light emitting device according to one embodiment of the present application, an organic light emitting device having a 2-stack tandem structure is exemplarily shown in FIG. 4 below.

[0187] In this case, the first electron blocking layer, the first hole blocking layer, and the second hole blocking layer shown in FIG. 4 below may be omitted in some cases.

[0188] In one embodiment of the present application, an alkali metal or an alkaline earth metal may be doped into the compound of Chemical Formula 1. In this case, the driving voltage of the organic light emitting device may be reduced due to the formation of a gap state, and the efficiency and lifespan may be further improved.

[0189] In one embodiment of the present application, there is provided a composition comprising an alkali metal or an alkaline earth metal in the compound of Chemical Formula 1. The content of the alkali metal or alkaline earth metal in the composition may be 0.01 wt% to 30 wt%, preferably 0.01 wt% to 25 wt%, and more preferably 0.01 wt% to 20 wt%, based on the weight of the entire composition.

[0190] In one embodiment of the present application, the alkali metal or alkaline earth metal may be, but is not limited to, lithium (Li), rubidium (Rb), cesium (Cs), or magnesium (Mg).

[0191] In the organic light-emitting device according to one embodiment of the present application, materials other than the compound of Chemical Formula 1 are exemplified below. However, these are merely examples and are not intended to limit the scope of the present application. They may be replaced with materials known in the art.

[0192] The anode material may be a material with a relatively large work function, such as a transparent conductive oxide, a metal, or a conductive polymer. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0193] The cathode material may be a material having a relatively low work function, such as a metal, a metal oxide, or a conductive polymer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and materials with multilayer structures such as LiF / Al or LiO2 / Al.

[0194] As the hole injection material, a known hole injection material can be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429, or a starburst type amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], for example, tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), a soluble conductive polymer polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic acid), etc. Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), Polyaniline / Camphor sulfonic acid or Polyaniline / Poly(4-styrenesulfonate), etc. can be used.

[0195] As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used, and low molecular or high molecular weight materials may also be used.

[0196] As the electron transport material, oxadiazole derivatives, 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, etc. can be used, and not only low molecular weight substances but also polymeric substances can be used.

[0197] As the electron injection material, for example, LiF is typically used in the industry, but the present application is not limited thereto.

[0198] The light-emitting material may be a red, green, or blue light-emitting material, 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 as individual supply sources, or may be premixed and deposited as one supply source. The light-emitting material may be a fluorescent material or a phosphorescent material. The light-emitting material may be a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, or a material in which both the host material and the dopant material are involved in light emission may be used.

[0199] When the hosts of the light-emitting materials are mixed, the same type of hosts may be mixed and used, or different types of hosts may be mixed and used. For example, two or more types of n-type host materials or p-type host materials may be selected and used as the host material of the light-emitting layer.

[0200] The organic light emitting device according to one embodiment of the present application may be a front-emitting type, a back-emitting type, or a dual-emitting type, depending on the materials used.

[0201] The heterocyclic compound according to an embodiment of the present application can also function in organic electronic devices, including organic solar cells, organic photoreceptors, organic transistors, etc., based on a similar principle to that applied to organic light-emitting devices. EXAMPLES

[0202] The present invention will be described in more detail with reference to the following examples, which are merely for illustrating the present application and are not intended to limit the scope of the present application.

[0203] <Example> <Production Example 1> Production of intermediate A [ka]

[0204] 1) Preparation of intermediate A-2 (2,6-dichlorophenyl)boronic acid (47.05 g, 246.56 mmol) and 2-bromonaphthalen-1-ol (50 g, 224.14 mmol) were dissolved in 500 ml of tetrahydrofuran (THF) and 100 ml of H2O, and then Pd(PPh3)4 (7.77 g, 6.72 mmol) and K2CO3 (92.94 g, 672.43 mmol) were added and the mixture was refluxed and stirred for 17 hours. After the reaction was completed, methylene chloride (MC) was added to the reaction solution to dissolve it, and then the solution was extracted with distilled water. The organic layer was dried over anhydrous MgSO4, and the solvent was removed using a rotary evaporator. The mixture was then purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain intermediate A-2 (49 g, 75%).

[0205] 2) Preparation of intermediate A-1 Intermediate A-2 (49g, 169.19mmol) was dissolved in 500ml of dimethylacetamide, and then Cs2CO3 (165.38g, 507.58mmol) was added and stirred under reflux for 4 hours. After the reaction was completed, MC was added to the reaction solution and dissolved, followed by extraction with distilled water, and the organic layer was dried over anhydrous MgSO4, after which the solvent was removed using a rotary evaporator. The mixture was purified by column chromatography using dichloromethane and hexane as the developing solvent to obtain intermediate A-1 (35g, 82%).

[0206] 3) Preparation of intermediate A Intermediate A-1 (35g, 138.50mmol) was dissolved in 350ml of dimethylformamide (DMF), and then N-Bromosuccinimide (NBS) (27.12g, 152.35mmol) was added and stirred at room temperature (25°C) for 4 hours. After the reaction was completed, MC was added to the reaction solution and dissolved, followed by extraction with distilled water, and the organic layer was dried over anhydrous MgSO4, and the solvent was removed using a rotary evaporator. The mixture was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain intermediate A (40g, 87%).

[0207] The target intermediate was produced in the same manner as in Production Example 1, except that Compound A in Table 1 below was used instead of (2,6-dichlorophenyl)boronic acid in Production Example 1.

[0208] [Table 1]

[0209] <Production Example 2> Production of compound ET-001 [ka]

[0210] 1) Preparation of compound ET-001-P2 Intermediate A (20g, 60.32mmol) and phenylboronic acid (7.72g, 63.33mmol) were dissolved in 200ml of toluene, 40ml of ethanol, and 40ml of H2O, and then Pd(PPh3)4 (3.48g, 3.02mmol) and K3PO4 (38.41g, 180.95mmol) were added and stirred under reflux for 5 hours. After the reaction was completed, MC was added to the reaction solution and dissolved, and the solution was extracted with distilled water. The organic layer was dried with anhydrous MgSO4, the solvent was removed with a rotary evaporator, and the compound ET-001-P2 (17g, 85%) was obtained by column chromatography using dichloromethane and hexane as the developing solvent.

[0211] 2) Preparation of compound ET-001-P1 Compound ET-001-P2 (17g, 51.70mmol) and Bis(pinacolato)diboron (17.07g, 67.22mmol) were dissolved in 1,4-dioxane (170ml), and then Pd(dba)2 (1.49g, 2.59mmol), Xphos (2.46g, 5.17mmol), and KOAc (15.22g, 155.11mmol) were added and refluxed for 3 hours. After the reaction was completed, MC was added to the reaction solution and dissolved, and the solution was extracted with distilled water. The organic layer was dried with anhydrous MgSO4, and the solvent was removed with a rotary evaporator. The solution was purified by column chromatography using dichloromethane and hexane as the developing solvent to obtain compound ET-001-P1 (18g, 82%).

[0212] 3) Production of compound ET-001 Compound ET-001-P1 (10 g, 23.79 mmol) and 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (9.24 g, 23.79 mmol) were dissolved in 100 ml of toluene, 20 ml of ethanol, and 20 ml of H2O, and then Pd(PPh3)4 (1.37 g, 1.19 mmol) and K3PO4 (15.15 g, 71.38 mmol) were added and the mixture was refluxed and stirred for 5 hours. After the reaction was completed, MC was added to the reaction solution to dissolve it, and then the solution was extracted with distilled water. The organic layer was dried over anhydrous MgSO4, the solvent was removed using a rotary evaporator, and the mixture was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound ET-001 (11 g, 76%).

[0213] The target compound was produced in the same manner as in Production Example 2, except that in Production Example 2, an intermediate in Table 2 below was used instead of intermediate A, compound B in Table 2 below was used instead of phenylboronic acid, and compound C in Table 2 below was used instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

[0214] [Table 2] TIFF0007671504000049.tif173161 TIFF0007671504000050.tif169161 TIFF0007671504000051.tif150161 TIFF0007671504000052.tif161161 TIFF0007671504000053.tif150161 TIFF0007671504000054.tif165161 TIFF0007671504000055.tif150161 TIFF0007671504000056.tif150161 TIFF0007671504000057.tif161161 TIFF0007671504000058.tif164161 TIFF0007671504000059.tif123161 TIFF0007671504000060.tif173161 TIFF0007671504000061.tif157161 TIFF0007671504000062.tif178161 TIFF0007671504000063.tif169161 TIFF0007671504000064.tif166161 TIFF0007671504000065.tif158161 TIFF0007671504000066.tif150161 TIFF0007671504000067.tif161161 TIFF0007671504000068.tif158161 TIFF0007671504000069.tif170161 TIFF0007671504000070.tif236161

[0215] In order to confirm the synthesis confirmation results of the compound ET-001 and the target compounds in Table 2, 1 H NMR (CDCl3, 200 Mz) and FD-MS (Field desorption mass spectrometry) were measured, and the measured values ​​are shown in Tables 3 and 4 below. Table 3 below shows the chromatograms of the compound ET-001 and the target compounds in Table 2. 1The results are measured by H NMR (CDCl3, 300 Mz), and Table 4 below shows the measured values ​​of the compound ET-001 and the target compounds in Table 2 by FD-mass spectrometry (FD-MS).

[0216] [Table 3] TIFF0007671504000072.tif238165 TIFF0007671504000073.tif238165 TIFF0007671504000074.tif238165 TIFF0007671504000075.tif238165

[0217] [Table 4] TIFF0007671504000077.tif107165

[0218] <Experimental Example 1> Manufacturing of organic light-emitting device <Comparative Examples 1-1 to 1-2 and Examples 1 to 112> 1) Manufacturing of organic light-emitting devices A transparent electrode ITO thin film obtained from glass for organic light-emitting devices (Samsung Corning) was ultrasonically cleaned in trichloroethylene, acetone, ethanol, and distilled water in that order for 5 minutes each, and then stored in isopropanol before use.

[0219] Next, the ITO substrate was placed in a substrate holder of a vacuum deposition apparatus, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell in the vacuum deposition apparatus. [ka]

[0220] Next, the vacuum in the chamber is reduced to 10 -6 After evacuating to torr, a current was applied to the cell to evaporate 2-TNATA to deposit a 600 Å thick hole injection layer on the ITO substrate.

[0221] The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell in the vacuum deposition apparatus, and a current was applied to the cell to cause evaporation, thereby depositing a hole transport layer with a thickness of 300 Å on the hole injection layer. [ka]

[0222] After the hole injection layer and the hole transport layer were formed in this way, a blue light-emitting material having the following structure was deposited thereon as an emitting layer. Specifically, in one cell of the vacuum deposition apparatus, a blue light-emitting host material H1 was vacuum-deposited to a thickness of 200 Å, and a blue light-emitting dopant material D1 was vacuum-deposited thereon at a concentration of 5% relative to the host material. [ka]

[0223] Next, the following E1 compound and LiQ were vacuum-deposited in a weight ratio of 2:1 to form an electron transport layer to a thickness of 300 Å. [ka]

[0224] Lithium fluoride (LiF) was deposited to a thickness of 10 Å as an electron injection layer, and an Al cathode was deposited to a thickness of 1,000 Å to manufacture an organic light emitting device (Comparative Example 1-1).

[0225] In addition, an organic light emitting device (Comparative Example 1-2) was manufactured in the same manner as above, except that compound E2 was used instead of compound E1.

[0226] Furthermore, organic light-emitting devices (Examples 1 to 112) were manufactured in the same manner, except that in the manufacturing process, one of the compounds ET-001 and the target compounds in Table 2 was selected and used instead of the compound E1. The compounds selected from the compounds ET-001 and the target compounds in Table 2 are shown in the compounds in Table 5 below.

[0227] On the other hand, all the organic compounds required for manufacturing organic light-emitting devices are 10 -6 ~10 -8 The product was purified by vacuum sublimation under torr and used for the manufacture of an organic light-emitting device.

[0228] 2) Driving voltage and luminous efficiency of organic light-emitting devices The electroluminescence (EL) characteristics of each of the organic light-emitting devices of Comparative Example 1-1, Comparative Example 1-2, and Examples 1 to 112 manufactured as described above were measured using a Mac Science M7000. Based on the measurement results, a reference luminance of 700 cd / m was measured using a Mac Science M6000 lifetime measurement device. 2 The time it takes for the initial brightness to reach 95% is called the lifespan T 95 (unit: h, time) was measured.

[0229] The measurement results of the electroluminescence characteristics, color coordinates and lifetime of the Comparative Example 1-1, Comparative Example 1-2 and Examples 1 to 112 are shown in Table 5 below.

[0230] [Table 5] TIFF0007671504000083.tif245165 TIFF0007671504000084.tif205165

[0231] From the results of Table 5, it was confirmed that the organic light emitting device using the electron transport layer material of the blue organic light emitting device of the present invention had a lower driving voltage and significantly improved luminous efficiency and life span compared to Comparative Example 1. In particular, it was confirmed that the organic light emitting devices of Examples 1, 5, 25, 41, 44, 55, 65, 66, 85 and 105 using the compounds ET-001, ET-005, ET-056, ET-100, ET-103, ET-149, ET-190, ET-211, ET-459 and ET-699 in the electron transport layer had further improved driving, efficiency and life span. It was confirmed that they were excellent in all respects. This is because, unlike Comparative Examples 1-2, two substituents can be introduced to adjust HOMO, LUMO, electron mobility, etc., and the balance of electrons and holes in the light emitting layer during device preparation is improved, which is expected to improve driving, efficiency and life span.

[0232] The reason for this result is believed to be that when the invented compound having suitable length, strength and flat properties is used in the electron transport layer, it receives electrons under certain conditions to form an excited state compound, and in particular, when the excited state of the hetero skeleton part of the compound is formed, the excited energy should be transferred in a stable state before the excited hetero skeleton part undergoes other reactions, and the relatively stable compound is believed to be able to efficiently transfer electrons without decomposition or destruction of the compound. For reference, it is believed that those having a stable state when excited are aryl or acene compounds or multi-membered ring hetero compounds. Therefore, it is believed that the compound of the present invention has improved electron-transport properties or improved stability, resulting in excellence in all aspects of operation, efficiency and life.

[0233] <Experimental Example 2> Manufacturing of organic light-emitting device <Comparative Example 2> 1) Manufacturing of organic light-emitting devices A transparent electrode ITO thin film obtained from glass for organic light-emitting devices (Samsung Corning) was ultrasonically cleaned in trichloroethylene, acetone, ethanol, and distilled water in that order for 5 minutes each, and then stored in isopropanol before use.

[0234] Next, the ITO substrate was placed in a substrate holder of a vacuum deposition apparatus, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was deposited in a cell in the vacuum deposition apparatus. [ka]

[0235] Next, the vacuum in the chamber is reduced to 10 -6 After evacuating to torr, a current was applied to the cell to evaporate 2-TNATA to deposit a 600 Å thick hole injection layer on the ITO substrate.

[0236] The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell in the vacuum deposition apparatus, and a current was applied to the cell to cause evaporation, thereby depositing a hole transport layer with a thickness of 300 Å on the hole injection layer. [ka]

[0237] After the hole injection layer and the hole transport layer were formed in this way, a blue light-emitting material having the following structure was deposited thereon as an emitting layer. Specifically, in one cell of the vacuum deposition apparatus, a blue light-emitting host material H1 was vacuum-deposited to a thickness of 200 Å, and a blue light-emitting dopant material D1 was vacuum-deposited thereon at a concentration of 5% relative to the host material. [ka]

[0238] Next, E1 of the following structural formula and LiQ were vacuum-deposited in a weight ratio of 2:1 to form an electron transport layer to a thickness of 300 Å. [ka]

[0239] Lithium fluoride (LiF) was deposited to a thickness of 10 Å as an electron injection layer, and an Al cathode was deposited to a thickness of 1,000 Å to manufacture an organic light emitting device (Comparative Example 2).

[0240] In addition, organic light-emitting devices (Examples 113 to 133) were manufactured in the same manner, except that in the above manufacturing process, the electron transport layer was formed to a thickness of 250 Å instead of 300 Å, and then one of the compound ET-001 and the target compounds in Table 2 was selected to form a hole blocking layer with a thickness of 50 Å. The compounds selected from the compound ET-001 and the target compounds in Table 2 are shown in the compounds in Table 6 below.

[0241] On the other hand, all the organic compounds required for manufacturing organic light-emitting devices are 10 -6 ~10 -8 The product was purified by vacuum sublimation under torr and used for the manufacture of an organic light-emitting device.

[0242] 2) Driving voltage and luminous efficiency of organic light-emitting devices The electroluminescence (EL) characteristics of each of the organic light-emitting devices of Comparative Example 2 and Examples 113 to 133 manufactured as described above were measured using M7000 manufactured by Mac Science Co., Ltd., and the measurement results were used to measure the reference luminance of 700 cd / m2 or less using a lifetime measuring device (M6000) manufactured by Mac Science Co., Ltd. 2 The time it takes for the initial brightness to reach 95% is called the lifespan T 95 (unit: h, time) was measured.

[0243] The measurement results of the electroluminescence characteristics, color coordinates and lifetime of the organic light emitting devices of Comparative Example 2 and Examples 113 to 133 are shown in Table 6 below.

[0244] [Table 6]

[0245] From the results in Table 6, it can be seen that the organic light-emitting device using the hole blocking layer material of the blue organic electroluminescent device of the present invention has a lower driving voltage and significantly improved luminous efficiency and lifetime compared to Comparative Example 2.

[0246] <Experimental Example 3> Manufacturing of organic light-emitting device <Comparative Example 3 and Examples 134 to 148> 1) Manufacturing of organic light-emitting devices A transparent electrode ITO thin film obtained from glass for organic light-emitting devices (Samsung Corning) was ultrasonically cleaned in trichloroethylene, acetone, ethanol, and distilled water in that order for 5 minutes each, and then stored in isopropanol before use.

[0247] On the ITO transparent electrode (anode), organic materials were formed in a two-stack WOLED (White Organic Light Emitting Device) structure having a first stack and a second stack structure. The first stack was formed by thermal vacuum deposition of TAPC to a thickness of 300 Å to form a hole transport layer. After forming the hole transport layer, the light emitting layer was thermal vacuum deposited thereon as follows. The light emitting layer was deposited to a thickness of 300 Å by doping 8% of FIrpic as a blue phosphorescent dopant into the host TCz1. Then, an electron transport layer was formed to a thickness of 400 Å using TmPyPB, and a charge generation layer was formed to a thickness of 100 Å by doping 20% ​​of Cs2CO3 into TBQB.

[0248] The second stack was formed by first thermal vacuum depositing MoO3 to a thickness of 50 Å to form a hole injection layer. The common layer, the hole transport layer, was formed by doping TAPC with 20% MoO3 to a thickness of 100 Å, and then depositing TAPC to a thickness of 300 Å. On top of that, the light emitting layer was formed by doping the host TCz1 with 8% green phosphorescent dopant Ir(ppy)3 to a thickness of 300 Å, and then depositing it to form an electron transport layer using TmPyPB to a thickness of 600 Å.

[0249] Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode, thereby manufacturing an organic light emitting device (Comparative Example 3).

[0250] In addition, organic light-emitting devices (Examples 134 to 148) were manufactured in the same manner, except that one of the target compounds in Table 2 was selected and used instead of TBQB in the manufacturing process. The compound selected from the target compounds in Table 2 is shown in the compounds in Table 7 below.

[0251] On the other hand, all the organic compounds required for manufacturing organic light-emitting devices are 10 -6 ~10 -8 The product was purified by vacuum sublimation under torr and used for the manufacture of an organic light-emitting device.

[0252] From the results in Table 6, it can be seen that the organic light-emitting device using the hole blocking layer material of the blue organic electroluminescent device of the present invention has a lower driving voltage and significantly improved luminous efficiency and lifetime compared to Comparative Example 2.

[0253] <Experimental Example 3> Manufacturing of organic light-emitting device <Comparative Example 3 and Examples 134 to 148> 1) Manufacturing of organic light-emitting devices A transparent electrode ITO thin film obtained from glass for organic light-emitting devices (Samsung Corning) was ultrasonically cleaned in trichloroethylene, acetone, ethanol, and distilled water in that order for 5 minutes each, and then stored in isopropanol before use.

[0254] On the ITO transparent electrode (anode), organic materials were formed in a two-stack WOLED (White Organic Light Device) structure having a first stack and a second stack structure. The first stack was formed by thermal vacuum deposition of TAPC to a thickness of 300 Å to form a hole transport layer. After the hole transport layer was formed, the light emitting layer was thermal vacuum deposited thereon as follows. The light emitting layer was deposited to a thickness of 300 Å by doping 8% of FIrpic as a blue phosphorescent dopant into the host TCz1. Then, an electron transport layer was formed to a thickness of 400 Å using TmPyPB, and a charge generation layer was formed to a thickness of 100 Å by doping 20% ​​of Cs2CO3 into TBQB.

[0255] The second stack was formed by first thermal vacuum depositing MoO3 to a thickness of 50 Å to form a hole injection layer. The common layer, the hole transport layer, was formed by doping TAPC with 20% MoO3 to a thickness of 100 Å, and then depositing TAPC to a thickness of 300 Å. On top of that, the light emitting layer was formed by doping the host TCz1 with 8% green phosphorescent dopant Ir(ppy)3 to a thickness of 300 Å, and then depositing it to form an electron transport layer using TmPyPB to a thickness of 600 Å.

[0256] Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode, thereby manufacturing an organic light emitting device (Comparative Example 3).

[0257] In addition, organic light-emitting devices (Examples 134 to 148) were manufactured in the same manner, except that one of the target compounds in Table 2 was selected and used instead of TBQB in the manufacturing process. The compound selected from the target compounds in Table 2 is shown in the following Table 7.

[0258] On the other hand, all the organic compounds required for manufacturing organic light-emitting devices are 10 -6 ~10 -8 The product was purified by vacuum sublimation under torr and used for the manufacture of an organic light-emitting device. [ka]

[0259] The driving voltage, luminous efficiency, color coordinate (CIE), and life span of the white organic light emitting device manufactured according to the present invention were measured, and the results are shown in Table 7.

[0260] [Table 7]

[0261] From the results of Table 7, it was confirmed that the organic electroluminescent device using the charge generation layer material of the organic light emitting device having the 2-stack structure of the present invention had a lower driving voltage and improved luminous efficiency compared to Comparative Example 3. The reason for this result is presumed to be that the compound of the present invention used in the N-type charge generation layer, which is composed of the inventive framework having appropriate length, strength, and flatness characteristics and an appropriate hetero compound capable of binding with metal, is doped with an alkali metal or alkaline earth metal to form a gap state in the N-type charge generation layer, and it is determined that the electrons generated from the P-type charge generation layer are easily injected into the electron transport layer due to the gap state generated in the N-type charge generation layer. Therefore, it is determined that the P-type charge generation layer can efficiently inject and transport electrons into the N-type charge generation layer, and therefore the driving voltage of the organic light emitting device is lowered and the efficiency and lifespan are improved.

Claims

1. A heterocyclic compound represented by any one of the following chemical formulas 3 to 6: 【Chemistry 25】 【Chemistry 26】 【Chemical 27】 【Chemistry 28】 In Chemical Formulae 3 to 6, L1 and L2 are the same or different and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; R1 is 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; R2 is a phenyl group; a biphenyl group; a naphthyl group; a triphenylene group; a dibenzofuran group; a dibenzothiophene group; a pyridine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group; a pyrimidine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group; a triazine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group; a 1,10-phenanthroline group substituted or unsubstituted with a phenyl group; a carbazole group; or a pyrenyl group, X1 to X3 are the same or different and each independently represents hydrogen or deuterium; m is an integer of 0 to 3; n is an integer of 0 to 4; when m and n are 2 or more, the substituents in parentheses are the same or different; one of R1 and R2 is a pyridine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group; a pyrimidine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group; a triazine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group; a phenanthroline group substituted or unsubstituted with a phenyl group, p and r are integers from 0 to 4; q and s are integers from 1 to 6; When p, q, r, and s are 2 or more, the substituents in parentheses are the same or different from each other. In Chemical Formula 4, R2 is a phenyl group; a biphenyl group; a naphthyl group; a triphenylene group; a dibenzofuran group; a dibenzothiophene group; a pyrimidine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group; a triazine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group; a carbazole group; or a pyrenyl group; In Chemical Formula 3, when R1 is a pyrenyl group, R2 is a phenyl group; a biphenyl group; a naphthyl group; a triphenylene group; a dibenzofuran group; a dibenzothiophene group; a pyridine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group; a pyrimidine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group; a triazine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a pyridine group; a carbazole group; or a pyrenyl group.

2. The "substituted or unsubstituted" means that the heterocyclic compound according to claim 1 is substituted or unsubstituted with one or more substituents selected from the group consisting of a linear or branched alkyl group having 1 to 60 carbon atoms; a linear or branched alkenyl group having 2 to 60 carbon atoms; a linear or branched alkynyl group having 2 to 60 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 60 carbon atoms; a monocyclic or polycyclic heterocycloalkyl group having 2 to 60 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 60 carbon atoms; a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms; a silyl group; a phosphine oxide group; and an amine group, or is substituted or unsubstituted with a substituent in which two or more substituents selected from the above-mentioned exemplary substituents are linked.

3. A heterocyclic compound represented by any one of the following compounds: 【Chemical Formula 29】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

4. An organic light-emitting device comprising a first electrode, a second 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 the heterocyclic compound according to any one of claims 1 to 3.

5. The organic light-emitting element according to claim 4 , wherein the organic layer includes an electron transport layer, and the electron transport layer includes the heterocyclic compound.

6. The organic light-emitting device according to claim 4 , wherein the organic layer includes one or more hole-blocking layers, and the hole-blocking layers include the heterocyclic compound.

7. The organic light-emitting element according to claim 4, comprising: a first stack provided on the first electrode and including a first light-emitting layer; a charge generation layer provided on the first stack; a second stack provided on the charge generation layer and including a second light-emitting layer; and the second electrode provided on the second stack.

8. The organic light-emitting device according to claim 7 , wherein the charge generation layer comprises the heterocyclic compound.

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