Heterocyclic compound and organic light-emitting element comprising the same

Abstract

The present specification relates to a heterocyclic compound represented by Chemical Formula 1 and an organic light emitting element including the same.

Description

Technical Field

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0130104 filed in the Korean Intellectual Property Office on October 8, 2020, the entire contents of which are incorporated herein by reference.

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

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

[0004] An organic light-emitting device (OLED) has an organic thin film interposed between two electrodes. When voltage is applied to an OLED with this structure, electrons and holes injected from the two electrodes combine to form pairs in the organic thin film. When these electrons and holes annihilate, light is emitted. The organic thin film can be formed into a single layer or multiple layers, depending on the needs.

[0005] The material of the organic thin film may, as needed, have a light-emitting function. For example, compounds capable of forming a light-emitting layer on their own can be used as the material for the organic thin film, or compounds capable of functioning as either a host or a dopant in a host-dopant light-emitting layer can be used. In addition, compounds capable of performing hole injection, hole transport, electron blocking, hole blocking, electron transport, or electron injection functions can also be used as the material for the organic thin film.

[0006] To enhance the performance, lifespan or efficiency of organic light-emitting devices, there is a constant need to develop organic thin film materials.

[0007] It is necessary to study organic light-emitting elements, which contain compounds that can meet the conditions required for materials that can be used in organic light-emitting elements (for example, meeting appropriate energy levels, electrochemical stability, thermal stability, etc.) and have chemical structures that can perform various functions required in organic light-emitting elements depending on substituents.

[0008] Prior art literature

[0009] Patent Literature

[0010] U.S. Patent No. 4,356,429 Summary of the Invention

[0011] Technical issues

[0012] The present application relates to heterocyclic compounds and organic light-emitting devices comprising the same.

[0013] Technical Solutions

[0014] One embodiment of the present application provides a heterocyclic compound represented by the following Chemical Formula 1.

[0015] [Chemical Formula 1]

[0016]

[0017] In Chemical Formula 1,

[0018] R1 and R2 are the same as or different from each other and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C2-C60 alkenyl; substituted or unsubstituted C2-C60 alkynyl; substituted or unsubstituted C1-C60 alkoxy; substituted or unsubstituted C3-C60 cycloalkyl; substituted or unsubstituted C2-C60 heterocycloalkyl; substituted or unsubstituted C6-C60 aryl; substituted or unsubstituted C2-C60 heteroaryl; -P(=O)RR'; and -SiRR'R", or two or more adjacent groups are bonded to form a substituted or unsubstituted C6-C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2-C60 aliphatic or aromatic heterocycle.

[0019] N-het is a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic group, and contains one or more N,

[0020] X is O; or S,

[0021] L1 to L3 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0022] Ar1 and Ar2 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -NR201R202; -P(=O)RR'; or -SiRR'R",

[0023] a to c are integers from 0 to 4,

[0024] m and n are integers from 0 to 3,

[0025] When a to c, m and n are 2 or more, the substituents in the parentheses are the same as or different from each other, and

[0026] R201, R202, R, R' and R" are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0027] In addition, one embodiment of the present application provides an organic light-emitting element, which includes: a first electrode; a second electrode, arranged opposite to the first electrode; and one or more organic material layers, arranged between the first electrode and the second electrode, wherein one or more layers of the organic material layers contain one or more types of the heterocyclic compounds represented by Chemical Formula 1.

[0028] Beneficial effects

[0029] The compounds described herein can be used as materials for the organic material layer of an organic light-emitting element. These compounds can function as hole-injecting materials, hole-transporting materials, luminescent materials, electron-transporting materials, electron-injecting materials, electron-blocking materials, hole-blocking materials, and the like in an organic light-emitting element. Specifically, these compounds can be used as luminescent materials in organic light-emitting elements.

[0030] The heterocyclic compound disclosed herein is a compound having a core structure of dibenzofuran or dibenzothiophene, and excellent properties as a bipolar host are obtained by replacing the 3rd position of one benzene ring of dibenzofuran or dibenzothiophene with a heterocyclic group represented by N-het and replacing the other benzene ring with an amine-based substituent.

[0031] Specifically, when the core structure of the heterocyclic compound according to the present application is substituted with amine, the heteroatom of the amine group enhances the hole injection ability of the hole transport group, which increases efficiency and lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0032] Figures 1 to 3 1 and 2 are diagrams each schematically illustrating a stacked structure of an organic light-emitting element according to one embodiment of the present application.

[0033] [Explanation of symbols]

[0034] 100:Substrate

[0035] 200: Anode

[0036] 300: organic material layer

[0037] 301: hole injection layer

[0038] 302: hole transport layer

[0039] 303: Luminous layer

[0040] 304: hole blocking layer

[0041] 305: electron transport layer

[0042] 306: electron injection layer

[0043] 400: cathode DETAILED DESCRIPTION

[0044] Hereinafter, the present application will be described in detail.

[0045] In this specification, "when no substituent is specified in a chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium ( 2 H) is an isotope of hydrogen, so some of the hydrogen atoms may be deuterium.

[0046] In one embodiment of the present application, "when no substituent is specified in a chemical formula or compound structure" may mean that all positions that can serve as substituents may be hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms may be deuterium, which is an isotope, and herein, the deuterium content may be 0% to 100%.

[0047] In one embodiment of the present application, when "no substituent is specified in a chemical formula or compound structure," when deuterium is not explicitly excluded (for example, the deuterium content is 0% or the hydrogen content is 100%), hydrogen and deuterium may be mixed in the compound. In other words, unlike a hydrogen content of 100% or a deuterium content of 0%, the expression "the substituent X is hydrogen" does not exclude deuterium and, therefore, may refer to a state in which hydrogen and deuterium are mixed.

[0048] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, is an element having a deuterium nucleus formed by one proton and one neutron, and can be represented as hydrogen-2, and the element symbol can also be written as D or 2 H.

[0049] In one embodiment of the present application, isotopes refer to atoms having the same atomic number (Z) but different mass numbers (A), and can also be interpreted as elements having the same number of protons but different numbers of neutrons.

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

[0051] In other words, in one instance, The phenyl group having a deuterium content of 20% represented by

[0014] means that the total number of substituents that the phenyl group may have is 5 (T1 in the formula), and the number of deuterium in the substituent is 1 (T2 in the formula). In other words, the phenyl group having a deuterium content of 20% can be represented by the following structural formula.

[0052]

[0053] Furthermore, in one embodiment of the present application, “the deuterium content of the phenyl group is 0%” may refer to a phenyl group that does not include a deuterium atom, that is, a phenyl group that has 5 hydrogen atoms.

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

[0055] In the present specification, the alkyl group includes a linear or branched alkyl group having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples thereof may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

[0056] In the present specification, alkenyl includes straight or branched alkenyl groups 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, and more specifically 2 to 20. Specific examples thereof may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, distyryl, styryl, but are not limited thereto.

[0057] In the present specification, the alkynyl group includes a straight chain or branched alkynyl group having 2 to 60 carbon atoms, and may be further 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.

[0058] In this specification, the alkoxy group may be a linear, branched, or cyclic alkoxy group. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20. Specific examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like.

[0059] In this specification, cycloalkyl includes monocyclic or polycyclic cycloalkyl groups having 3 to 60 carbon atoms, and may be further substituted by other substituents. In this article, polycyclic refers to a group in which a cycloalkyl group is directly connected to other cyclic groups or is fused to other cyclic groups. In this article, other cyclic groups may be cycloalkyl groups, but may also be different types of cyclic groups, such as heterocycloalkyl, aryl and heteroaryl groups. The number of carbon groups in the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0060] In this specification, heterocycloalkyl includes O, S, Se, N or Si as heteroatoms, including monocyclic or polycyclic heterocycloalkyl groups with 2 to 60 carbon atoms, and can be further substituted by other substituents. In this article, polycyclic refers to a group in which heterocycloalkyl is directly connected to other cyclic groups or is fused with other cyclic groups. In this article, other cyclic groups can be heterocycloalkyl, but can also be different types of cyclic groups, such as cycloalkyl, aryl and heteroaryl. The number of carbon atoms in heterocycloalkyl can be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0061] In this specification, aryl includes monocyclic or polycyclic aromatic groups having 6 to 60 carbon atoms, and may be further substituted by other substituents. In this article, polycyclic refers to a group in which the aryl is directly connected to other cyclic groups or fused to other cyclic groups. In this article, other cyclic groups may be aryl, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl and heteroaryl. 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 aryl groups may include phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, The present invention also includes, but is not limited to, 1,2-dihydro-1H-indenyl, 2,3 ...

[0062] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0063] When the fluorenyl group is substituted, the following structures and the like may be included, however, the structures are not limited thereto.

[0064]

[0065] In this specification, heteroaryl includes S, O, Se, N or Si as a heteroatom, including monocyclic or polycyclic heteroaryl groups having 2 to 60 carbon atoms, and may be further substituted with other substituents. In this article, polycyclic means a group in which the heteroaryl group is directly connected or fused to other cyclic groups. In this article, the other cyclic groups may be heteroaryl groups, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl and aryl groups. The number of carbon atoms in the heteroaryl group may be 2 to 60, specifically 2 to 40 and more specifically 3 to 25. Specific examples of heteroaryl groups may include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinazolinyl, isoquinazolinyl, quinozolinyl, quinolinazolinyl, quin ... group), naphthyridinyl, acridinyl, phenanthridinyl, imidazopyridinyl, naphthyridinyl, triazaindenyl, indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothiophenyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenanthrazinyl, dibenzosilolyl (dibenzosilole) group), spirobis(dibenzosilylcyclopentadienyl), dihydrophenazinyl, phenoxazinyl, phenanthridinyl, imidazopyridinyl, thienyl, indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, indolinyl, 10,11-dihydro-dibenzo[b,f]azepine, 9,10-dihydroacridinyl, phenazinyl, phenathiazinyl, phthalazinyl, naphthyridine 1,2-a]imidazo[1,2-e]dihydroindole, 5,11-dihydroindeno[1,2-b]carbazolyl, etc., but are not limited thereto.

[0066] In the present specification, the amino group can be selected from the group consisting of a monoalkylamino group, a monoarylamino group, a monoheteroarylamino group, -NH2, a dialkylamino group, a diarylamino group, a diheteroarylamino group, an alkylarylamino group, an alkylheteroarylamino group, and an arylheteroarylamino group, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 30. Specific examples of the amino group may include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, a diphenylamino group, an anthrylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, a phenylnaphthylamino group, a ditolylamino group, a phenyltolylamino group, a triphenylamino group, a biphenylnaphthylamino group, a phenylbiphenylamino group, a biphenylfluorenylamino group, a phenyltriphenyleneamino group, a biphenyltriphenyleneamino group, and the like, but are not limited thereto.

[0067] In this specification, an arylene group refers to an aryl group having two bonding sites, i.e., a divalent group. The description of the aryl group provided above applies here, except when each is a divalent group. Furthermore, a heteroarylene group refers to a heteroaryl group having two bonding sites, i.e., a divalent group. The description of the heteroaryl group provided above applies here, except when each is a divalent group.

[0068] In this specification, a phosphine oxide group is represented by -P(=O)R101R102, and R101 and R102 are the same or different and may each 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 phosphine oxides include, but are not limited to, diphenylphosphine oxide groups and dinaphthylphosphine oxide groups.

[0069] In this specification, a silyl group is a substituent containing Si, directly attached to the Si atom as a free radical, and is represented by -SiR104R105R106. R104 to R106 are the same or different and may each 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 silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.

[0070] In this specification, an "adjacent" group may refer to a substituent that replaces an atom directly attached to the atom substituted by the corresponding substituent, a substituent that is spatially located closest to the corresponding substituent, or another substituent that replaces the atom substituted by the corresponding substituent. For example, two substituents that replace ortho positions in a benzene ring, and two substituents that replace the same carbon in an aliphatic ring may be interpreted as groups that are "adjacent" to each other.

[0071] As the aliphatic or aromatic hydrocarbon ring or heterocyclic ring that can be formed by adjacent groups, the structures shown above as the cycloalkyl group, cycloheteroalkyl group, aryl group, and heteroaryl group can be used except that they are not monovalent groups.

[0072] In the present specification, 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 substitution is not limited as long as it is a position where a hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0073] In the present specification, "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of: C1 to C60 straight or branched alkyl; C2 to C60 straight or branched alkenyl; C2 to C60 straight or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P(=O)RR'; and -NRR', or unsubstituted, or substituted by a substituent connected to two or more substituents selected from the above substituents, or unsubstituted, and

[0074] R, R' and R" are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0075] One embodiment of the present application provides a compound represented by Chemical Formula 1.

[0076] In one embodiment of the present application, R1 and R2 are the same as or different from each other and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; and -SiRR'R", or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle.

[0077] In another embodiment, R1 and R2 are the same as or different from each other and may each be independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; and -SiRR'R".

[0078] In another embodiment, R1 and R2 are the same as or different from each other and may each be independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C40 alkyl; substituted or unsubstituted C2 to C40 alkenyl; substituted or unsubstituted C2 to C40 alkynyl; substituted or unsubstituted C1 to C40 alkoxy; substituted or unsubstituted C3 to C40 cycloalkyl; substituted or unsubstituted C2 to C40 heterocycloalkyl; substituted or unsubstituted C6 to C40 aryl; substituted or unsubstituted C2 to C40 heteroaryl; -P(=O)RR'; and -SiRR'R".

[0079] In another embodiment, R1 and R2 are the same as or different from each other and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C40 alkyl; substituted or unsubstituted C6 to C40 aryl; substituted or unsubstituted C2 to C40 heteroaryl; -P(=O)RR'; and -SiRR'R".

[0080] In another embodiment, R1 and R2 are the same as or different from each other and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; C1 to C40 alkyl; C6 to C40 aryl; C2 to C40 heteroaryl; -P(=O)RR'; and -SiRR'R".

[0081] In another embodiment, R1 and R2 may be hydrogen.

[0082] In one embodiment of the present application, X may be O.

[0083] In one embodiment of the present application, X may be S.

[0084] In one embodiment of the present application, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2 to 5.

[0085] [Chemical Formula 2]

[0086]

[0087] [Chemical Formula 3]

[0088]

[0089] [Chemical Formula 4]

[0090]

[0091] [Chemical Formula 5]

[0092]

[0093] In Chemical Formula 2 to Chemical Formula 5,

[0094] Each substituent has the same definition as in Chemical Formula 1.

[0095] In one embodiment of the present application, N-het may be a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic group, and contains one or more N.

[0096] In another embodiment, N-het may be a substituted or unsubstituted monocyclic or polycyclic C2-C60 heterocyclic group, and contains one or more and three or less than three N groups.

[0097] In another embodiment, N-het may be a substituted or unsubstituted monocyclic or polycyclic C2 to C40 heterocyclic group, and contains one or more and three or less than three N groups.

[0098] In another embodiment, N-het may be a substituted or unsubstituted monocyclic or polycyclic C2 to C40 heterocyclic group, and contains one or more and three or less than three N groups.

[0099] In another embodiment, N-het may be a substituted or unsubstituted monocyclic or polycyclic C2 to C40 heterocyclyl group, and contains one or more and three or less than three =N- bonds.

[0100] In another embodiment, N-het may be a substituted or unsubstituted monocyclic or polycyclic C2 to C40 heterocyclic group, and contains one or more and three or less than three N groups connected by double bonds.

[0101] In one embodiment of the present application, in another embodiment, N-het may be a monocyclic or polycyclic C2 to C40 heterocyclic group which is unsubstituted or substituted with one or more substituents selected from the group consisting of C6 to C40 aryl groups; and C2 to C40 heteroaryl groups, and contains one or more and three or less than three N groups.

[0102] In another embodiment, N-het may be a monocyclic or polycyclic C2-C40 heterocyclic group which is unsubstituted or substituted with one or more substituents selected from the group consisting of C6-C40 aryl; and C2-C40 heteroaryl, and contains one or more and three or less than three =N-bonds.

[0103] In another embodiment, N-het may be a monocyclic or polycyclic C2 to C40 heterocyclic group which is unsubstituted or substituted with one or more substituents selected from the group consisting of C6 to C40 aryl groups; and C2 to C40 heteroaryl groups, and contains one or more and three or less than three N groups connected by double bonds.

[0104] In one embodiment of the present application, N-het may be substituted or unsubstituted pyrimidinyl; substituted or unsubstituted triazinyl; substituted or unsubstituted quinazolinyl; substituted or unsubstituted benzo[4,5]thieno[3,2-d]pyrimidinyl; substituted or unsubstituted phenantholinyl; or substituted or unsubstituted quinoxalinyl.

[0105] In one embodiment of the present application, N-het may be pyrimidinyl which is unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, biphenyl, naphthyl, and dibenzofuranyl; triazinyl which is unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzothiophenyl, carbazolyl, and dibenzofuranyl; quinazolinyl which is unsubstituted or substituted with phenyl, biphenyl, or naphthyl; benzo[4,5]thieno[3,2-d]pyrimidinyl which is unsubstituted or substituted with phenyl or naphthyl; phenantholinyl which is unsubstituted or substituted with phenyl; or quinoxalinyl which is unsubstituted or substituted with phenyl.

[0106] In one embodiment of the present application, N-het may be substituted again with a naphthyl group or a carbazolyl group.

[0107] In one embodiment of the present application, N-het may be represented by any one of the following Chemical Formulas 1-1 to 1-5.

[0108] [Chemical Formula 1-1]

[0109]

[0110] [Chemical formula 1-2]

[0111]

[0112] [Chemical formula 1-3]

[0113]

[0114] [Chemical formula 1-4]

[0115]

[0116] [Chemical Formula 1-5]

[0117]

[0118] In Chemical Formula 1-1 to Chemical Formula 1-5,

[0119] refers to the position connected to Chemical Formula 1,

[0120] X1 to X3 are the same as or different from each other and are each independently N or CRa,

[0121] X4 and X5 are the same as or different from each other and are each independently N or CRa,

[0122] X6 and X7 are the same as or different from each other and are each independently N or CRa,

[0123] X8 and X9 are the same as or different from each other and are each independently N or CRa,

[0124] X10 and X11 are the same as or different from each other and are each independently N or CRa,

[0125] At least one of X1 to X3, at least one of X6 and X7, at least one of X8 and X9, and at least one of X10 and X11 are N,

[0126] Y is O; or S,

[0127] R11 to R13 are the same as or different from each other and are each independently hydrogen; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl,

[0128] R21 to R24 are the same as or different from each other and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, and

[0129] Ra is hydrogen; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0130] In one embodiment of the present application, R11 to R13 are the same as or different from each other and may each independently be hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0131] In another embodiment, R11 to R13 are the same as or different from each other, and may each independently be hydrogen; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0132] In another embodiment, R11 to R13 are the same as or different from each other, and may each independently be hydrogen; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0133] In another embodiment, R11 to R13 are the same as or different from each other and may each independently be hydrogen; C6 to C40 aryl which is unsubstituted or substituted with C1 to C40 alkyl, C6 to C40 aryl, or C2 to C40 heteroaryl; or C2 to C40 heteroaryl which is unsubstituted or substituted with C6 to C40 aryl.

[0134] In another embodiment, R11 to R13 are the same as or different from each other and are each independently a C6 to C40 aryl group which is unsubstituted or substituted with a C1 to C40 alkyl group, a C6 to C40 aryl group, or a C2 to C40 heteroaryl group; or a C2 to C40 heteroaryl group which is unsubstituted or substituted with a C6 to C20 aryl group.

[0135] In another embodiment, R11 to R13 are the same as or different from each other and may each independently be a phenyl group which is unsubstituted or substituted with a carbazolyl group or a naphthyl group; a biphenyl group; a naphthyl group; a terphenyl group; a dimethylfluorenyl group; a carbazolyl group which is unsubstituted or substituted with a phenyl group; a dibenzofuranyl group; or a dibenzothiophenyl group.

[0136] In one embodiment of the present application, R21 to R24 are the same as or different from each other and may each independently be hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

[0137] In another embodiment, R21 to R24 are the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0138] In another embodiment, R21 to R24 are the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0139] In another embodiment, R21 to R24 are the same as or different from each other, and may each independently be hydrogen; deuterium; C6 to C40 aryl; or C2 to C40 heteroaryl.

[0140] In another embodiment, R21 to R24 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0141] In one embodiment of the present application, Ra may be hydrogen.

[0142] In one embodiment of the present application, L1 to L3 are the same as or different from each other, and may be each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0143] In another embodiment, L1 to L3 are the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0144] In another embodiment, L1 to L3 are the same as or different from each other, and may be each independently a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

[0145] In another embodiment, L1 to L3 are the same as or different from each other, and may each independently be a direct bond; or a C6 to C40 arylene group.

[0146] In another embodiment, L1 to L3 are the same as or different from each other, and may each independently be a direct bond; or a monocyclic or polycyclic C6 to C40 arylene group.

[0147] In another embodiment, L1 to L3 are the same as or different from each other, and may each independently be a direct bond; a monocyclic C6 to C10 arylene group; or a polycyclic C10 to C40 arylene group.

[0148] In another embodiment, L1 to L3 are the same as or different from each other, and may each independently be a direct bond; or a phenylene group.

[0149] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other and may each independently be a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -NR201R202; -P(=O)RR'; or -SiRR'R".

[0150] In another embodiment, Ar1 and Ar2 are the same as or different from each other and are each independently a substituted or unsubstituted C6-C60 aryl group; a substituted or unsubstituted C2-C60 heteroaryl group; -NR201R202; -P(=O)RR'; or -SiRR'R".

[0151] In another embodiment, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or -NR201R202.

[0152] In another embodiment, Ar1 and Ar2 are the same as or different from each other and are each independently C6 to C40 aryl, which is unsubstituted or substituted with C1 to C40 alkyl or C6 to C40 aryl; C2 to C40 heteroaryl, which is unsubstituted or substituted with C6 to C40 aryl; or -NR201R202.

[0153] In another embodiment, Ar1 and Ar2 are the same as or different from each other and are each independently phenyl; unsubstituted or phenyl-substituted biphenyl; naphthyl; dibenzofuranyl; dibenzothiophenyl; dimethylfluorenyl; spirobifluorenyl; terphenyl; unsubstituted or phenyl-substituted carbazolyl; -NR201R202 or spiro[fluorene-9,9'-xanthene].

[0154] In one embodiment of the present application, R201 and R202 are the same as or different from each other, and are each independently a C6 to C60 aryl group; or a C2 to C60 heteroaryl group.

[0155] In another embodiment, R201 and R202 are the same as or different from each other, and are each independently a C6 to C40 aryl group; or a C2 to C40 heteroaryl group.

[0156] In another embodiment, R201 and R202 are the same as or different from each other, and are each independently a C6 to C20 aryl group; or a C2 to C20 heteroaryl group.

[0157] In another embodiment, R201 and R202 are the same as or different from each other and are each independently a phenyl group; a biphenyl group; or a naphthyl group.

[0158] In one embodiment of the present application, It can be represented by any one of the following Chemical Formulas 1-1-1 to 1-1-5.

[0159] [Chemical formula 1-1-1]

[0160]

[0161] [Chemical formula 1-1-2]

[0162]

[0163] [Chemical formula 1-1-3]

[0164]

[0165] [Chemical formula 1-1-4]

[0166]

[0167] [Chemical formula 1-1-5]

[0168]

[0169] In Chemical Formulas 1-1-1 to 1-1-5,

[0170] Ar1, L3 and c have the same definitions as in Chemical Formula 1, and means the position connected to Chemical Formula 1,

[0171] Ar12 is a substituted or unsubstituted C6 to C60 aryl group; or -NR201R202,

[0172] Y1 is O; S; or NRb,

[0173] Y2 is O; or S,

[0174] Ar21 and Ar22 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group, or two adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring,

[0175] R31 to R38 are the same as or different from each other and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl.

[0176] R201 and R202 have the same definitions as in Chemical Formula 1,

[0177] Rb is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and

[0178] p, q, and r are integers from 0 to 4.

[0179] In one embodiment of the present application, Ar12 may be a substituted or unsubstituted C6 to C60 aryl group; or -NR201R202.

[0180] In another embodiment, Ar12 may be a substituted or unsubstituted C6 to C40 aryl group; or -NR201R202.

[0181] In another embodiment, Ar12 may be a C6 to C40 aryl group which is unsubstituted or substituted with a C6 to C10 aryl group; or -NR201R202.

[0182] In another embodiment, Ar12 can be phenyl; naphthyl; unsubstituted or phenyl-substituted biphenyl; terphenyl; phenanthrenyl; or -NR201R202.

[0183] In one embodiment of the present application, Rb may be a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0184] In another embodiment, Rb may be a substituted or unsubstituted C6 to C60 aryl group.

[0185] In another embodiment, Rb may be a substituted or unsubstituted C6 to C40 aryl group.

[0186] In another embodiment, Rb may be a C6 to C40 aryl group.

[0187] In another embodiment, Rb may be a monocyclic or polycyclic C6 to C40 aryl group.

[0188] In another embodiment, Rb may be phenyl.

[0189] In one embodiment of the present application, R31 to R38 are the same as or different from each other and may be each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl.

[0190] In another embodiment, R31 to R38 may be hydrogen.

[0191] In one embodiment of the present application, Ar21 and Ar22 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group, or two adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

[0192] In another embodiment, Ar21 and Ar22 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C40 alkyl group; or a substituted or unsubstituted C6 to C40 aryl group, or two adjacent groups may be bonded to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring.

[0193] In another embodiment, Ar21 and Ar22 are the same as or different from each other and are each independently a C1 to C40 alkyl group; or a C6 to C40 aryl group, or two adjacent groups may be bonded to form a C6 to C40 aromatic hydrocarbon ring.

[0194] In another embodiment, Ar21 and Ar22 are the same as or different from each other and are each independently a methyl group or a phenyl group, or two adjacent groups may be bonded to form a fluorenyl ring.

[0195] In one embodiment of the present application, R, R' and R" are the same as or different from each other, and may each independently be a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0196] In another embodiment, R, R′, and R″ are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C60 aryl group.

[0197] In another embodiment, R, R′, and R″ are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aromatic group.

[0198] In another embodiment, R, R′ and R″ are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 monocyclic aryl group.

[0199] In another embodiment, R, R' and R" are the same as or different from each other, and are each independently a C6 to C20 monocyclic aromatic group.

[0200] In another embodiment, R, R' and R" may be phenyl.

[0201] According to one embodiment of the present application, Chemical Formula 1 can be represented by any one of the following compounds, but is not limited thereto.

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224] Furthermore, by introducing various substituents into the structure of Chemical Formula 1, compounds having unique properties of the introduced substituents can be synthesized. For example, by introducing substituents commonly used as hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, and charge generation layer materials for manufacturing organic light-emitting devices into the core structure, materials that meet the requirements of each organic material layer can be synthesized.

[0225] Furthermore, by introducing various substituents into the structure of Chemical Formula 1, the energy band gap can be precisely controlled, and at the same time, properties at the interface between organic materials can be enhanced, and material applications can become diversified.

[0226] In addition, one embodiment of the present application provides an organic light-emitting element, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contain one or more types of heterocyclic compounds according to Chemical Formula 1.

[0227] Another embodiment provides an organic light-emitting element, comprising: a first electrode; a second electrode disposed opposite the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contains a type of heterocyclic compound according to Chemical Formula 1.

[0228] Another embodiment provides an organic light-emitting element, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contains two types of heterocyclic compounds according to Chemical Formula 1.

[0229] Specific details of the heterocyclic compound represented by Chemical Formula 1 are the same as the description provided above.

[0230] In one embodiment of the present application, the first electrode may be an anode, and the second electrode may be a cathode.

[0231] In another embodiment, the first electrode may be a cathode, and the second electrode may be an anode.

[0232] In one embodiment of the present application, the organic light-emitting element may be a blue organic light-emitting element, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the blue organic light-emitting element. For example, the heterocyclic compound according to Chemical Formula 1 may be included in a host material of a blue light-emitting layer of the blue organic light-emitting element.

[0233] In one embodiment of the present application, the organic light-emitting element may be a green organic light-emitting element, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the green organic light-emitting element. For example, the heterocyclic compound according to Chemical Formula 1 may be included in a host material of a green light-emitting layer of the green organic light-emitting element.

[0234] In one embodiment of the present application, the organic light-emitting element may be a red organic light-emitting element, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the red organic light-emitting element. For example, the heterocyclic compound according to Chemical Formula 1 may be included in a host material of a red light-emitting layer of the red organic light-emitting element.

[0235] In addition to using the aforementioned heterocyclic compound to form one or more organic material layers, the organic light-emitting device of the present disclosure can be manufactured using common organic light-emitting device manufacturing methods and materials.

[0236] When manufacturing an organic light-emitting element, the heterocyclic compound can be formed into an organic material layer by a solution coating method and a vacuum deposition method. In this article, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating and the like, but is not limited thereto.

[0237] The organic material layer of the organic light-emitting element of the present disclosure may be formed into a single-layer structure, or may be formed into a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting element according to one embodiment of the present disclosure 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, and the like as organic material layers. However, the structure of the organic light-emitting element is not limited thereto, but may include a smaller number of organic material layers.

[0238] In the organic light emitting element of the present disclosure, the organic material layer may include a light emitting layer, and the light emitting layer may include a heterocyclic compound.

[0239] In another organic light-emitting element, the organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material may include a heterocyclic compound.

[0240] In another embodiment, the organic material layer including the heterocyclic compound includes the heterocyclic compound represented by Chemical Formula 1 as a host, and an iridium-based dopant may be used therewith.

[0241] In the organic light emitting element of the present disclosure, the organic material layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer may include a heterocyclic compound.

[0242] In another organic light-emitting element, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include a heterocyclic compound.

[0243] In the organic light emitting element of the present disclosure, the organic material layer includes a hole transport layer, and the hole transport layer may contain a heterocyclic compound.

[0244] The organic light-emitting device of the present disclosure may further include one, two 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.

[0245] Figures 1 to 3 The stacking sequence of electrodes and organic material layers of an organic light-emitting device according to one embodiment of the present application is shown. However, the scope of the present application is not limited to these figures, and the structure of an organic light-emitting device known in the art can also be used in the present application.

[0246] Figure 1 1 shows an organic light emitting element in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, the structure is not limited to this structure, and as Figure 2 As shown, an organic light-emitting element can also be obtained in which a cathode, an organic material layer and an anode are successively stacked on a substrate.

[0247] Figure 3 The case where the organic material layer is multi-layered is shown. Figure 3 The organic light-emitting element includes a hole injection layer 301, a hole transport layer 302, a light-emitting 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 this stacked structure, and as needed, layers other than the light-emitting layer may not be included, and other required functional layers may be further added.

[0248] The organic material layer including the compound of Chemical Formula 1 may further include other materials as needed.

[0249] In the organic light-emitting element according to one embodiment of the present application, materials other than the heterocyclic compound of Chemical Formula 1 are shown below. However, these are for illustrative purposes only and do not limit the scope of the present application, and can be replaced by materials known in the art.

[0250] As the anode material, a material having a relatively large work function can be used, and transparent conductive oxides, metals, conductive polymers, etc. can be used. Specific examples of anode materials 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; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but are not limited thereto.

[0251] As the cathode material, a material having a relatively small work function can be used, and metals, metal oxides, conductive polymers, etc. can be used. Specific examples of cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0252] As the hole injection material, a known hole injection material can be used, and for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429; or a star-shaped sudden-type amine derivative such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA) or 1,3,5-tris[4-(3-methylphenylanilino)phenyl]benzene (m-MTDAPB) described in the document [Advanced Material, 6, p. 677 (1994)], polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid or polyaniline / poly(4-styrenesulfonate) as a conductive polymer having solubility, etc. can be used.

[0253] As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used, and low molecular weight or high molecular weight materials can also be used.

[0254] As electron transport materials, metal complexes of oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethane and its derivatives, fluorenone derivatives, diphenyl dicyanoethylene and its derivatives, dibenzoquinone derivatives, 8-hydroxyquinoline and its derivatives, etc. can be used, and polymer materials and low molecular weight materials can also be used.

[0255] As an example of the electron injection material, LiF is generally used in this technology, however, the present application is not limited thereto.

[0256] As the luminescent material, red, green, or blue luminescent materials can be used, and two or more luminescent materials can be mixed and used as needed. In this article, two or more luminescent materials can be used by depositing them as separate supply sources or by pre-mixing and depositing them as a single supply source. In addition, fluorescent materials can also be used as luminescent materials, however, phosphorescent materials can also be used. As the luminescent material, a material that emits light by bonding electrons and holes injected from the anode and cathode, respectively, can be used alone, however, a material having a host material and a dopant material that both participate in luminescence can also be used.

[0257] When mixing the host of the light-emitting material, the host of the same series can be mixed, or the host of different series can be mixed. For example, any two or more materials of n-type host materials or p-type host materials can be selected and used as the host material of the light-emitting layer.

[0258] Depending on the materials used, the organic light emitting device according to one embodiment of the present application may be a top-emission type, a bottom-emission type, or a dual-emission type.

[0259] The heterocyclic compound according to one embodiment of the present application can also be used in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, etc. under similar principles as used in organic light-emitting devices.

[0260] Hereinafter, the present specification will be described in more detail with reference to examples, however these are for illustrative purposes only, and the scope of the present application is not limited thereto.

[0261] <Preparation Example 1> Preparation of Compound 6

[0262]

[0263] Preparation of intermediate 6-2

[0264] 7-Bromo-1-chlorodibenzo[b,d]furan (20.0 g, 71.0 mmol), B2pin2 (27.1 g, 107 mmol), Pd(dppf)Cl2 (5.20 g, 7.10 mmol) and KOAc (20.9 g, 213 mmol) were introduced into 1,4-dioxane (200 ml) and stirred at 100° C. for 3 hours. The result was filtered while hot and washed several times with DCM. The filtrate was concentrated in vacuo and then filtered through silica gel. The result was washed with MeOH to obtain intermediate 6-2 (16.8 g, 72%).

[0265] Preparation of intermediate 6-1

[0266] Intermediate 6-2 (16.8 g, 51.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (13.7 g, 51.1 mmol), Pd(PPh 3 ) 4 (2.95 g, 2.56 mmol) and K 2 CO 3 (21.2 g, 153 mmol) were introduced into 1,4-dioxane / H 2 O (170 ml / 50 ml) and stirred at 100° C. for 2 hours. The result was cooled to room temperature, filtered, and then washed with H 2 O and MeOH to obtain Intermediate 6-1 (20.2 g, 91%).

[0267] Preparation of compound 6

[0268] Intermediate 6-1 (7.00 g, 16.1 mmol), N-phenyl-[1,1'-biphenyl]-4-amine (4.35 g, 17.7 mmol), Pd2dba3 (0.74 g, 0.81 mmol), Xphos (0.77 g, 1.61 mmol) and t-BuONa (3.09 g, 32.0 mmol) were introduced into xylene and stirred at 150°C for 2 hours. The result was cooled to room temperature and allowed to stand for 12 hours, and the resulting solid was filtered. The result was filtered through silica gel and then concentrated in vacuo, and the resulting solid was filtered to obtain Compound 6 (8.76 g, 85%).

[0269] The following compounds were synthesized in the same manner as in the preparation of Compound 6 in Preparation Example 1, except that A and B in Table 1 below were used as intermediates.

[0270] [Table 1]

[0271]

[0272]

[0273]

[0274] <Preparation Example 2> Preparation of Compound 47

[0275]

[0276] Preparation of intermediate 47-2

[0277] 7-Bromo-1-chlorodibenzo[b,d]furan (20.0 g, 71.0 mmol), B2pin2 (27.1 g, 107 mmol), Pd(dppf)Cl2 (5.20 g, 7.10 mmol) and KOAc (20.9 g, 213 mmol) were introduced into 1,4-dioxane (200 ml) and stirred at 100° C. for 3 hours. The resultant was filtered while hot and washed several times with DCM. The filtrate was concentrated in vacuo and then filtered through silica gel. The resultant was washed with MeOH to obtain intermediate 47-2 (16.8 g, 72%).

[0278] Preparation of intermediate 47-1

[0279] Intermediate 47-2 (16.8 g, 72.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (13.7 g, 51.1 mmol), Pd(PPh 3 ) 4 (2.95 g, 2.56 mmol) and K 2 CO 3 (21.2 g, 153 mmol) were introduced into 1,4-dioxane / H 2 O (170 ml / 50 ml) and stirred at 100° C. for 2 hours. The result was cooled to room temperature, filtered, and then washed with H 2 O and MeOH to obtain Intermediate 47-1 (20.2 g, 91%).

[0280] Preparation of compound 47

[0281] Intermediate 47-1 (7.00 g, 16.1 mmol), (4-(di(naphthalen-1-yl)amino)phenyl)boronic acid (6.89 g, 17.7 mmol), Pd2dba3 (0.74 g, 0.81 mmol), Xphos (0.77 g, 1.61 mmol) and NaOH (1.28 g, 32.0 mmol) were introduced into dioxane / H2O (70 ml / 20 ml) and stirred at 150°C for 2 hours. The result was cooled to room temperature and allowed to stand for 12 hours, and the resulting solid was filtered. The result was filtered through silica gel and then concentrated in vacuo, and the resulting solid was filtered to obtain compound 47 (8.85 g, 74%).

[0282] The following compounds were synthesized in the same manner as in the preparation of Compound 47 in Preparation Example 2, except that A and B in Table 2 below were used as intermediates.

[0283] [Table 2]

[0284]

[0285] <Preparation Example 3> Preparation of Compound 127

[0286]

[0287] Preparation of intermediate 127-2

[0288] 7-Bromo-2-chlorodibenzo[b,d]furan (20.0 g, 71.0 mmol), B2pin2 (27.1 g, 107 mmol), Pd(dppf)Cl2 (5.20 g, 7.10 mmol) and KOAc (20.9 g, 213 mmol) were introduced into 1,4-dioxane (200 ml) and stirred at 100° C. for 3 hours. The resultant was filtered while hot and washed several times with DCM. The filtrate was concentrated in vacuo and then filtered through silica gel. The resultant was washed with MeOH to obtain intermediate 127-2 (15.9 g, 68%).

[0289] Preparation of intermediate 127-1

[0290] Intermediate 127-2 (15.9 g, 48.4 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (13.0 g, 48.4 mmol), Pd(PPh 3 ) 4 (2.80 g, 2.42 mmol) and K 2 CO 3 (20.0 g, 145 mmol) were introduced into 1,4-dioxane / H 2 O (160 ml / 50 ml) and stirred at 100° C. for 2 hours. The result was cooled to room temperature, filtered, and then washed with H 2 O and MeOH to obtain Intermediate 127-1 (19.8 g, 94%).

[0291] Preparation of Compound 127

[0292] Intermediate 127-1 (7.00 g, 16.1 mmol), N-phenyl-[1,1'-biphenyl]-4-amine (4.35 g, 17.7 mmol), Pd2dba3 (0.74 g, 0.81 mmol), Xphos (0.77 g, 1.61 mmol) and t-BuONa (3.09 g, 32.0 mmol) were introduced into xylene and stirred at 150°C for 2 hours. The result was cooled to room temperature and allowed to stand for 12 hours, and the resulting solid was filtered. The result was filtered through silica gel and then concentrated in vacuo, and the resulting solid was filtered to obtain Compound 127 (6.79 g, 66%).

[0293] The following compounds were synthesized in the same manner as in the preparation of Compound 127 in Preparation Example 3, except that A and B in Table 3 below were used as intermediates.

[0294] [Table 3]

[0295]

[0296] <Preparation Example 4> Preparation of Compound 162

[0297]

[0298] Preparation of intermediate 162-2

[0299] 7-Bromo-2-chlorodibenzo[b,d]furan (20.0 g, 71.0 mmol), B2pin2 (27.1 g, 107 mmol), Pd(dppf)Cl2 (5.20 g, 7.10 mmol) and KOAc (20.9 g, 213 mmol) were introduced into 1,4-dioxane (200 ml) and stirred at 100° C. for 3 hours. The resultant was filtered while hot and washed several times with DCM. The filtrate was concentrated in vacuo and then filtered through silica gel. The resultant was washed with MeOH to obtain intermediate 162-2 (15.9 g, 68%).

[0300] Preparation of intermediate 162-1

[0301] Intermediate 162-2 (16.8 g, 72.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (13.7 g, 51.1 mmol), Pd(PPh 3 ) 4 (2.95 g, 2.56 mmol) and K 2 CO 3 (21.2 g, 153 mmol) were introduced into 1,4-dioxane / H 2 O (170 ml / 50 ml) and stirred at 100° C. for 2 hours. The result was cooled to room temperature, filtered, and then washed with H 2 O and MeOH to obtain Intermediate 162-1 (19.8 g, 94%).

[0302] Preparation of Compound 162

[0303] Intermediate 162-1 (7.00 g, 16.1 mmol), (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (6.46 g, 17.7 mmol), Pd2dba3 (0.74 g, 0.81 mmol), Xphos (0.77 g, 1.61 mmol) and NaOH (1.28 g, 32.0 mmol) were introduced into dioxane / H2O (70 ml / 20 ml) and stirred at 150°C for 2 hours. The result was cooled to room temperature and allowed to stand for 12 hours, and the resulting solid was filtered. The result was filtered through silica gel and then concentrated in vacuo, and the resulting solid was filtered to obtain Compound 162 (7.95 g, 68%).

[0304] The following compounds were synthesized in the same manner as in the preparation of Compound 162 in Preparation Example 4, except that A and B in Table 4 below were used as intermediates.

[0305] [Table 4]

[0306]

[0307] <Preparation Example 5> Preparation of Compound 229

[0308]

[0309] Preparation of intermediate 229-2

[0310] 7-Bromo-3-chlorodibenzo[b,d]furan (20.0 g, 71.0 mmol), B2pin2 (27.1 g, 107 mmol), Pd(dppf)Cl2 (5.20 g, 7.10 mmol) and KOAc (20.9 g, 213 mmol) were introduced into 1,4-dioxane (200 ml) and stirred at 100° C. for 3 hours. The resultant was filtered while hot and washed several times with DCM. The filtrate was concentrated in vacuo and then filtered through silica gel. The resultant was washed with MeOH to obtain intermediate 229-2 (15.9 g, 68%).

[0311] Preparation of intermediate 229-1

[0312] Intermediate 229-2 (15.9 g, 48.4 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (13.0 g, 48.4 mmol), Pd(PPh 3 ) 4 (2.80 g, 2.42 mmol) and K 2 CO 3 (20.0 g, 145 mmol) were introduced into 1,4-dioxane / H 2 O (160 ml / 50 ml) and stirred at 100° C. for 2 hours. The result was cooled to room temperature, filtered, and then washed with H 2 O and MeOH to obtain Intermediate 229-1 (19.8 g, 94%).

[0313] Preparation of Compound 229

[0314] Intermediate 229-1 (7.00 g, 16.1 mmol), di([1,1'-biphenyl]-4-yl)amine (5.69 g, 17.7 mmol), Pd2dba3 (0.74 g, 0.81 mmol), Xphos (0.77 g, 1.61 mmol), and t-BuONa (3.09 g, 32.0 mmol) were introduced into xylene and stirred at 150°C for 2 hours. The result was cooled to room temperature and allowed to stand for 12 hours, and the resulting solid was filtered. The result was filtered through silica gel and then concentrated in vacuo, and the resulting solid was filtered to obtain Compound 229 (7.13 g, 61%).

[0315] The following compounds were synthesized in the same manner as in the preparation of Compound 229 in Preparation Example 5, except that A and B in Table 5 below were used as intermediates.

[0316] [Table 5]

[0317]

[0318] <Preparation Example 6> Preparation of Compound 259

[0319]

[0320] Preparation of intermediate 259-2

[0321] 7-Bromo-3-chlorodibenzo[b,d]furan (20.0 g, 71.0 mmol), B2pin2 (27.1 g, 107 mmol), Pd(dppf)Cl2 (5.20 g, 7.10 mmol) and KOAc (20.9 g, 213 mmol) were introduced into 1,4-dioxane (200 ml) and stirred at 100° C. for 3 hours. The resultant was filtered while hot and washed several times with DCM. The filtrate was concentrated in vacuo and then filtered through silica gel. The resultant was washed with MeOH to obtain intermediate 259-2 (15.9 g, 68%).

[0322] Preparation of intermediate 259-1

[0323] Intermediate 259-2 (16.8 g, 72.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (13.7 g, 51.1 mmol), Pd(PPh 3 ) 4 (2.95 g, 2.56 mmol) and K 2 CO 3 (21.2 g, 153 mmol) were introduced into 1,4-dioxane / H 2 O (170 ml / 50 ml) and stirred at 100° C. for 2 hours. The result was cooled to room temperature, filtered, and then washed with H 2 O and MeOH to obtain Intermediate 259-1 (19.8 g, 94%).

[0324] Preparation of compound 259

[0325] Intermediate 259-1 (7.00 g, 16.1 mmol), (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (6.46 g, 17.7 mmol), Pd2dba3 (0.74 g, 0.81 mmol), Xphos (0.77 g, 1.61 mmol) and NaOH (1.28 g, 32.0 mmol) were introduced into dioxane / H2O (70 ml / 20 ml) and stirred at 150°C for 2 hours. The result was cooled to room temperature and allowed to stand for 12 hours, and the resulting solid was filtered. The result was filtered through silica gel and then concentrated in vacuo, and the resulting solid was filtered to obtain compound 259 (7.95 g, 68%).

[0326] <Preparation Example 7> Preparation of Compound 325

[0327]

[0328] Preparation of intermediate 325-2

[0329] 7-Bromo-4-chlorodibenzo[b,d]furan (20.0 g, 71.0 mmol), B2pin2 (27.1 g, 107 mmol), Pd(dppf)Cl2 (5.20 g, 7.10 mmol) and KOAc (20.9 g, 213 mmol) were introduced into 1,4-dioxane (200 ml) and stirred at 100° C. for 3 hours. The resultant was filtered while hot and washed several times with DCM. The filtrate was concentrated in vacuo and then filtered through silica gel. The resultant was washed with MeOH to obtain intermediate 325-2 (15.9 g, 68%).

[0330] Preparation of intermediate 325-1

[0331] Intermediate 325-2 (15.9 g, 48.4 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (13.0 g, 48.4 mmol), Pd(PPh 3 ) 4 (2.80 g, 2.42 mmol) and K 2 CO 3 (20.0 g, 145 mmol) were introduced into 1,4-dioxane / H 2 O (160 ml / 50 ml) and stirred at 100° C. for 2 hours. The result was cooled to room temperature, filtered, and then washed with H 2 O and MeOH to obtain Intermediate 325-1 (19.8 g, 94%).

[0332] Preparation of compound 325

[0333] Intermediate 325-1 (7.00 g, 16.1 mmol), di([1,1'-biphenyl]-4-yl)amine (5.69 g, 17.7 mmol), Pd2dba3 (0.74 g, 0.81 mmol), Xphos (0.77 g, 1.61 mmol), and t-BuONa (3.09 g, 32.0 mmol) were introduced into xylene and stirred at 150°C for 2 hours. The result was cooled to room temperature and allowed to stand for 12 hours, and the resulting solid was filtered. The result was filtered through silica gel and then concentrated in vacuo, and the resulting solid was filtered to obtain Compound 325 (7.13 g, 61%).

[0334] The following compounds were synthesized in the same manner as in the preparation of Compound 325 in Preparation Example 7, except that A and B in Table 6 below were used as intermediates.

[0335] [Table 6]

[0336]

[0337] <Preparation Example 9> Preparation of Compound 395

[0338]

[0339] Preparation of intermediate 395-2

[0340] 7-Bromo-1-chlorodibenzo[b,d]thiophene (20.0 g, 67.2 mmol), B2pin2 (25.6 g, 101 mmol), Pd(dppf)Cl2 (4.92 g, 6.72 mmol) and KOAc (19.8 g, 202 mmol) were introduced into 1,4-dioxane (200 ml) and stirred at 100° C. for 3 hours. The resultant was filtered while hot and washed several times with DCM. The filtrate was concentrated in vacuo and then filtered through silica gel. The resultant was washed with MeOH to obtain intermediate 395-2 (19.1 g, 82%).

[0341] Preparation of intermediate 395-1

[0342] Intermediate 395-2 (19.0 g, 55.1 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (14.8 g, 55.1 mmol), Pd(PPh 3 ) 4 (3.18 g, 2.76 mmol) and K 2 CO 3 (22.8 g, 165 mmol) were introduced into 1,4-dioxane / H 2 O (190 ml / 60 ml) and stirred at 100° C. for 2 hours. The result was cooled to room temperature, filtered, and then washed with H 2 O and MeOH to obtain Intermediate 395-1 (21.3 g, 86%).

[0343] Preparation of compound 395

[0344] Intermediate 395-1 (7.00 g, 15.6 mmol), N-phenyl-[1,1'-biphenyl]-4-amine (4.02 g, 16.4 mmol), Pd2dba3 (0.71 g, 0.78 mmol), Xphos (0.74 g, 1.56 mmol) and t-BuONa (2.99 g, 31.2 mmol) were introduced into xylene and stirred at 150°C for 2 hours. The result was cooled to room temperature and allowed to stand for 12 hours, and the resulting solid was filtered. The result was filtered through silica gel and then concentrated in vacuo, and the resulting solid was filtered to obtain Compound 395 (8.50 g, 83%).

[0345] Heterocyclic compounds corresponding to Chemical Formula 1 except for the compounds described in Preparation Examples 1 to 9 and Tables 1 to 7 were also prepared in the same manner as the method described in the above Preparation Examples.

[0346] The synthetic identification data of the compounds prepared above are shown in [Table 8] and [Table 9]. Table 8 shows 1 Table 9 shows the measured values ​​of H nuclear magnetic resonance (NMR) (CDCl 3 , 200 MHz), and Table 9 shows the measured values ​​of FD-mass spectrometry (FD-MS: field desorption mass spectrometry).

[0347] [Table 8]

[0348]

[0349]

[0350] [Table 9]

[0351]

[0352]

[0353] <Experimental Example 1>-Manufacturing of Organic Light-Emitting Element

[0354] 1) Manufacturing of organic light-emitting elements

[0355] A glass substrate coated with a 1,500-angstrom thin film of indium tin oxide (ITO) was ultrasonically cleaned with distilled water. Following the distilled water rinse, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and treated with ultraviolet ozone (UVO) for 5 minutes in an ultraviolet (UV) cleaner. The substrate was then transferred to a plasma cleaner (PT) and subjected to vacuum plasma treatment to achieve the ITO work function and remove any residual film. The substrate was then transferred to a thermal deposition system for organic deposition.

[0356] On the transparent ITO electrode (anode), a hole injection layer 2-TNATA (4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) were formed as common layers.

[0357] A light-emitting layer was thermally vacuum deposited thereon as follows. Specifically, the light-emitting layer was deposited to a thickness of 500 angstroms using each of the compounds described in Examples 1 to 42 and Comparative Examples 1 to 6 in Table 10 below as a red host for the light-emitting layer, and doped with a red phosphorescent dopant (Piq)2(Ir)(acac) at 3 wt%. Thereafter, bathocuproine (hereinafter referred to as BCP) was deposited to a thickness of 60 angstroms as a hole-blocking layer, and Alq3 was deposited thereon to a thickness of 200 angstroms as an electron-transporting layer.

[0358] Finally, an electron injection layer was formed on the electron transport layer by depositing lithium fluoride (LiF) to a thickness of 10 angstroms, and then a cathode was formed on the electron injection layer by depositing an aluminum (Al) cathode to a thickness of 1,200 angstroms, and thus, an organic light emitting element was manufactured.

[0359] Meanwhile, for each material to be used in the manufacture of organic light emitting diodes (OLEDs), the total organic compounds required to manufacture OLEDs are within 10 -8 Support up to 10 -6 Purification was performed by vacuum sublimation under support.

[0360] 2) Driving voltage and luminous efficiency of organic light-emitting elements

[0361] For each of the organic light emitting elements of Examples 1 to 42 and Comparative Examples 1 to 6 manufactured as above, electroluminescent (EL) properties were measured using M7000 manufactured by McScience Inc., and using the measurement results, when the standard brightness was 6,000 candelas / m2 (cd / m 2 ), T90 was measured using a lifetime measurement system (M6000) manufactured by Maxis. T90 means lifetime (unit: h, time), that is, the time required to reach 90% of the initial luminance.

[0362] The measured properties of the organic light emitting element are shown in Table 10 below.

[0363] [Table 10]

[0364]

[0365]

[0366]

[0367] The heterocyclic compound of the present application has a suitable molecular weight and band gap for use in the light-emitting layer of an organic light-emitting device, while also exhibiting high thermal stability. The suitable molecular weight facilitates the formation of the light-emitting layer of the organic light-emitting device, while the suitable band gap prevents the loss of electrons and holes in the light-emitting layer, thereby facilitating the efficient formation of a recombination zone.

[0368] In other words, it has been found that in compounds as heterocyclic compounds according to the present application in which an arylamine group is substituted at an appropriate position, the strong hole transport (HT) properties of the arylamine group substituted at that position resolve the hole blocking (hole trapping) phenomenon that occurs in dopants. This is confirmed by the highest occupied molecular orbital (HOMO) / lowest unoccupied molecular orbital (LUMO) data shown in Tables 11 and 12 below.

[0369] [Table 11]

[0370]

[0371]

[0372] [Table 12]

[0373] <![CDATA[S1]]> <![CDATA[T1]]> dipole moment Example 1-1 2.69 2.46 1.08 Example 1-2 2.67 2.51 1.60 Examples 1-3 2.55 2.38 0.55 Examples 1-4 2.70 2.38 1.52 Examples 1-5 2.62 2.42 0.60 Comparative Example 1-1 2.76 2.61 1.20 Comparative Example 1-2 2.82 2.74 0.93

[0374] Compounds in which an electron-transporting (ET) group is substituted at an appropriate position as the heterocyclic compound according to the present application exhibit lower T1 values ​​compared to compounds in which the electron-transporting (ET) group is substituted at another position. Typical red dopants have low T1 values, and efficiency is believed to be increased by facilitating energy transfer from the host to the dopant. Furthermore, the threshold voltage can be adjusted based on the behavior of the electron-transporting (ET) group. Specifically, when the core structure of the heterocyclic compound according to the present application is substituted with an amine, the heteroatom of the amine group enhances the hole-injection capability of the hole-transporting group, thereby improving efficiency and lifetime.

[0375] It has been identified that when the core structure of the heterocyclic compound according to the present application is substituted with amine, the heteroatom of the amine group enhances the hole injection ability of the hole transport group, thereby improving efficiency and lifespan.

[0376] <Experimental Example 2>-Manufacturing of Organic Light-Emitting Element

[0377] 1) Manufacturing of organic light-emitting elements

[0378] A glass substrate coated with a 1,500 angstrom thin film of indium tin oxide (ITO) was ultrasonically cleaned with distilled water. After the distilled water rinse, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and treated with ultraviolet ozone (UVO) for 5 minutes in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and subjected to vacuum plasma treatment to achieve the ITO work function and remove any residual film. The substrate was then transferred to a thermal deposition system for organic deposition.

[0379] On the transparent ITO electrode (anode), a hole injection layer 2-TNATA (4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) were formed as common layers.

[0380] An emitting layer was thermally vacuum deposited thereon as follows. Specifically, the emitting layer was deposited to a thickness of 500 angstroms by using each of the compounds described in Examples 1 to 9 in Table 13 below as a red host for the emitting layer and doping the red phosphorescent dopant (Piq)2(Ir)(acac) at 3 wt%. Thereafter, bathocuproine (hereinafter referred to as BCP) was deposited to a thickness of 60 angstroms as a hole-blocking layer, and Alq3 was deposited thereon to a thickness of 200 angstroms as an electron-transporting layer.

[0381] Finally, an electron injection layer was formed on the electron transport layer by depositing lithium fluoride (LiF) to a thickness of 10 angstroms, and then a cathode was formed on the electron injection layer by depositing an aluminum (Al) cathode to a thickness of 1,200 angstroms, and thus, an organic light emitting element was manufactured.

[0382] At the same time, for each material that will be used in OLED manufacturing, the total organic compounds required to make OLEDs are within 10 -8 Support up to 10 -6 Purification was performed by vacuum sublimation under support.

[0383] 2) Driving voltage and luminous efficiency of organic light-emitting elements

[0384] For each of the organic light-emitting elements of Examples 1 to 9 in Table 13 manufactured as above, electroluminescence (EL) properties were measured using an M7000 manufactured by Maxims, and using the measurement results, T90 was measured using a lifetime measurement system (M6000) manufactured by Maxims at a standard luminance of 6,000 candelas / square meter. T90 means lifetime (unit: h, time), that is, the time required to reach 90% of the initial luminance.

[0385] The measured properties of the organic light emitting element are shown in Table 13 below.

[0386] [Table 13]

[0387]

[0388]

[0389] As can be seen from the results of Table 13, it was identified that when the heterocyclic compound according to the present application and the heterocyclic compounds of compounds A and B are mixed and deposited as the organic material layer of the organic light-emitting element, the threshold voltage and driving voltage can be appropriately adjusted, and the efficiency or life of the organic light-emitting element can be improved.

[0390] Specifically, it was found that when the heterocyclic compound according to the present application is combined with a specific N-type host compound (such as Compound A), the device lifetime is improved. Combining an N-type host compound with strong electron-transporting properties with a P-type host compound with strong hole-transporting properties helps achieve charge balance in the device, which significantly improves lifetime.

[0391] Furthermore, when compound 81 or 87, which weakens the electron-transporting group ability, is combined with compound 6, which has a strong electron-transporting group ability, the compound weakening the electron-transporting group ability acts as an electron blocking layer (EBL) that improves device efficiency and lifetime, and can form a suitable threshold voltage by increasing the LUMO level.

Claims

1. A heterocyclic compound represented by the following Chemical Formula 1: [Chemical Formula 1] in, In Chemical Formula 1, R1 and R2 are the same as or different from each other and are each independently selected from the group consisting of hydrogen; and deuterium; N-het is represented by any one of the following Chemical Formulas 1-1 to 1-5: [Chemical Formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] [Chemical Formula 1-5] In Chemical Formula 1-1 to Chemical Formula 1-5, means the position of connection to Chemical Formula 1; X1 to X3 are the same as or different from each other, and are each independently N or CRa; X4 and X5 are the same as or different from each other and are each independently N or CRa; X6 and X7 are the same as or different from each other and are each independently N or CRa; X8 and X9 are the same as or different from each other and are each independently N or CRa; X10 and X11 are the same as or different from each other, and are each independently N or CRa; At least two of X1 to X3, at least one of X4 and X5, at least one of X6 and X7, at least one of X8 and X9, and at least one of X10 and X11 are N; Y is O; or S; R11 and R12 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; R13 is hydrogen; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl; R21 to R24 are the same as or different from each other and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl; and Ra is hydrogen; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl; X is O; or S; L1 and L2 are the same as or different from each other and are each independently a direct bond; or a phenylene group; L3 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; Ar1 and Ar2 are the same as or different from each other and are each independently phenyl; unsubstituted or phenyl-substituted biphenyl; naphthyl; phenanthrenyl; dibenzofuranyl; dibenzothienyl; dimethylfluorenyl; spirobifluorenyl; unsubstituted or phenyl-substituted carbazolyl; -NR201R202 or spiro[fluorene-9,9'-xanthene]; a to c are integers from 0 to 4; m and n are integers from 0 to 3; When a to c, m and n are 2 or more, the substituents in the brackets are the same as or different from each other; R201, R202, R, R' and R" are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, Wherein, when X is S, N-het is represented by any one of Chemical Formula 1-1 and Chemical Formula 1-3 to Chemical Formula 1-5; and "Substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of: C1 to C60 straight or branched alkyl; C2 to C60 straight or branched alkenyl; C2 to C60 straight or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P(=O)RR'; and -NRR', or is unsubstituted, or is substituted by a substituent linked to two or more substituents selected from the above substituents, or is unsubstituted, and R, R' and R" are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

2. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 5: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] In Chemical Formula 2 to Chemical Formula 5, Each substituent has the same definition as in Chemical Formula 1.

3. The heterocyclic compound according to claim 1, wherein It is represented by any one of the following Chemical Formulas 1-1-1 to 1-1-5: [Chemical formula 1-1-1] [Chemical formula 1-1-2] [Chemical formula 1-1-3] [Chemical formula 1-1-4] [Chemical formula 1-1-5] In Chemical Formulas 1-1-1 to 1-1-5, Ar1, L3 and c have the same definitions as in Chemical Formula 1, and means the position of connection to Chemical Formula 1; Ar12 is phenyl; naphthyl; unsubstituted or phenyl-substituted biphenyl; phenanthrenyl or -NR201 R202; Y1 is O; S; or NRb; Y2 is O; or S; Ar21 and Ar22 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group, or two adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; R31 to R38 are the same as or different from each other and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl. R201 and R202 have the same meanings as in Chemical Formula 1; Rb is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; p, q and r are integers from 0 to 4; and "Substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of: C1 to C60 straight or branched alkyl; C2 to C60 straight or branched alkenyl; C2 to C60 straight or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P(=O)RR'; and -NRR', or is unsubstituted, or is substituted by a substituent linked to two or more substituents selected from the above substituents, or is unsubstituted, and R, R' and R" are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. The heterocyclic compound according to claim 1 , wherein R 1 and R 2 are hydrogen.

5. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds:

6. An organic light-emitting element, comprising: a first electrode; a second electrode, disposed opposite to the first electrode; as well as One or more organic material layers are disposed between the first electrode and the second electrode, One or more layers of the organic material layers contain one or more types of heterocyclic compounds according to any one of claims 1 to 5. 7 . The organic light emitting element according to claim 6 , wherein the organic material layer includes a light emitting layer, and the light emitting layer contains the heterocyclic compound. 8 . The organic light emitting element according to claim 6 , wherein the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer contains the heterocyclic compound. 9 . The organic light emitting element according to claim 6 , wherein the organic material layer comprises an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer contains the heterocyclic compound. 10 . The organic light emitting element according to claim 6 , wherein the organic material layer comprises a hole transport layer, and the hole transport layer contains the heterocyclic compound.

11. The organic light-emitting element according to claim 6, further comprising one, two 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.

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