Heterocyclic compounds and organic light emitting elements comprising the same

Abstract

This invention relates to a heterocyclic compound represented by chemical formula 1 and an organic light-emitting element comprising the same.

Description

Technical Field

[0001] This application claims priority based on Korean Patent Application No. 10-2023-0163820 dated November 22, 2023 and Korean Patent Application No. 10-2024-0143678 dated October 21, 2024, the entire contents of which are incorporated herein by reference.

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

[0003] Organic light-emitting elements (OLEDs), as a type of self-emissive display element, not only have the advantages of wide viewing angle and excellent contrast, but also fast response speed.

[0004] Organic light-emitting elements (OLEDs) have a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an OLED with such a structure, electrons and holes injected from the two electrodes combine and annihilate in the organic thin film, emitting light simultaneously. The organic thin film can be composed of a single layer or multiple layers as needed.

[0005] Organic thin film materials can possess light-emitting capabilities as needed. For example, as organic thin film materials, compounds that can independently form the light-emitting layer can be used, or compounds that can act as the host or dopant in a host-dopant type light-emitting layer can be used. In addition, as organic thin film materials, compounds capable of performing functions such as hole injection, hole transport, electron blocking, and electron transport can also be used.

[0006] To improve the performance, lifespan, or efficiency of organic light-emitting elements, it is necessary to continuously develop materials for organic thin films.

[0007] It is necessary to study organic light-emitting elements (OLEDs) that meet the requirements of substances available in OLEDs, such as appropriate energy levels, electrochemical stability, and thermal stability, and have chemical structures that can perform various functions required in OLEDs depending on the substituents.

[0008] [Existing Literature] [Patent Literature] U.S. Patent No. 4,356,429 Summary of the Invention The purpose of this invention is to provide a heterocyclic compound and an organic light-emitting element comprising the same.

[0009] To achieve the stated objective, the present invention provides a heterocyclic compound represented by the following chemical formula 1.

[0010] [Chemical Formula 1]

[0011] In the chemical formula 1, X is O; or S, R1 to R6 may be the same as or different from each other, and are each independently selected from hydrogen; deuterium; 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; -SiR101R102R103 ; -NR101R102; the following chemical formula 2; the following chemical formula 3; the following chemical formula 4; and the following chemical formula 5, wherein two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl. Any one of R1, R4, and R6 is any one of the following chemical formulas 2 to 5. Where 'a' is an integer from 0 to 3, and when 'a' is 2 or greater, R2 is either the same or different from each other. b is an integer from 0 to 3. When b is 2 or greater, R5 is either the same or different from each other. [Chemical Formula 2]

[0012] [Chemical Formula 3]

[0013] [Chemical Formula 4]

[0014] [Chemical Formula 5]

[0015] In the chemical formulas 2 to 5, R11 to R20 may be the same as or different from each other, and are each independently selected from hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 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. The groups -SiR201R202R203 and -NR201R202, or two or more adjacent groups, are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R201, R202, and R203 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl. The d is an integer from 0 to 6. When d is 2 or greater, R12 are either the same or different from each other. h is an integer from 0 to 4. When h is 2 or greater, R15 are either the same or different from each other. Where i is an integer from 0 to 2, when i is greater than 2, R16 are either the same or different from each other. j is an integer from 0 to 4. When i is greater than or equal to j, R17 are either the same or different from each other. The value of l is an integer from 0 to 3. When l is 2 or greater, R18 may be the same or different from each other. m is an integer from 0 to 2. When m is greater than 2, R19 are either the same or different from each other. The n is an integer from 0 to 4. When n is 2 or more, R20 is either the same or different from each other. The Ar1 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. The L1 to L4 may be the same as or different from each other, and each is independently directly bonded; substituted or unsubstituted C6 to C60 arylene groups; or substituted or unsubstituted C2 to C60 heteroarylene groups. c is an integer from 0 to 5. When c is greater than 2, L1 values ​​are either the same or different. The value of e is an integer from 0 to 5. When e is greater than 2, L2 values ​​are either the same or different from each other. k is an integer from 0 to 5. When k is 2 or greater, L3 are either the same or different from each other. The value of o is an integer from 0 to 5. When o is 2 or higher, L4 are either the same or different from each other.

[0016] In addition, the present invention provides an organic light-emitting element, the organic light-emitting element comprising: First electrode; The second electrode is disposed opposite to the first electrode; and One or more organic layers are disposed between the first electrode and the second electrode. One or more of the organic layers comprise heterocyclic compounds represented by the chemical formula 1.

[0017] The heterocyclic compounds of the present invention can be used as organic layer materials for organic light-emitting elements. In particular, they can be used as electron transport layers, charge generation layers, electron injection layers, electron blocking layers, or hole blocking layer materials to provide significant effects such as reducing the driving voltage of organic light-emitting elements, improving luminous efficiency, and improving lifetime characteristics. Attached Figure Description

[0018] Figures 1 to 4 These are schematic diagrams illustrating the stacked structure of an organic light-emitting element according to one embodiment of this application. Detailed Implementation

[0019] The present invention will now be described in more detail.

[0020] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The position of substitution is not limited as long as it is the position where the hydrogen atom is substituted, i.e., the position where the substituent can be substituted. When two or more substituents are substituted, the two or more substituents can be the same or different from each other.

[0021] In this specification, "substituted or unsubstituted" means selected from deuterium; halogen; cyano; C1 to C60 straight-chain or branched alkyl; C2 to C60 straight-chain or branched alkenyl; C2 to C60 straight-chain or branched alkynyl; C1 to C60 straight-chain, branched or cyclic alkoxy; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocyclic alkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R''; -P(=O)RR' The substituent is substituted or unsubstituted by one or more of the following groups: C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine, or is substituted or unsubstituted by substituents connected by two or more substituents selected from the exemplified substituents, wherein R, R', and R'' are the same or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl.

[0022] In this specification, halogen can be fluorine; chlorine; bromine; or iodine.

[0023] In this specification, alkyl groups may include straight or branched chains having 1 to 60 carbon atoms, further substituted by other substituents. The alkyl group may have 1 to 60 carbon atoms, specifically 1 to 40, and more specifically 1 to 20. Specific examples include methyl; ethyl; n-propyl; isopropyl; n-butyl; isobutyl; tert-butyl; sec-butyl; 1-methyl-butyl; 1-ethyl-butyl; n-pentyl; isopentyl; neopentyl; tert-pentyl; n-hexyl; 1-methylpentyl; 2-methylpentyl; 4-methyl-2-pentyl; 3,3-dimethylbutyl; 2-ethylbutyl; n-heptyl; 1-methylhexyl; cyclopentylmethyl; cyclohexylmethyl; n-octyl; tert-octyl; 1-methylheptyl; 2-ethylhexyl; 2-propylpentyl; n-nonyl; 2,2-dimethylheptyl; 1-ethyl-propyl; 1,1-dimethyl-propyl; isohexyl; 4-methylhexyl; 5-methylhexyl, etc., but are not limited to these.

[0024] In this specification, the alkenyl group may include a straight or branched chain having 2 to 60 carbon atoms, further substituted by other substituents. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40, and more specifically 2 to 20. Specific examples 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(biphenyl-1-yl)vinyl-1-yl; stilbene; styryl, etc., but are not limited thereto.

[0025] In this specification, the alkynyl group may include a straight or branched chain having 2 to 60 carbon atoms, which may be further substituted by other substituents. The alkynyl group may have 2 to 60 carbon atoms, specifically 2 to 40, and more specifically 2 to 20.

[0026] In this specification, the alkoxy group can be straight-chain, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20. Specifically, it includes, but is not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc.

[0027] In this specification, cycloalkyl groups can include monocyclic or polycyclic groups having 3 to 60 carbon atoms, further substituted by other substituents. Here, polycyclic means a group in which the cycloalkyl group is directly attached to or fused with other cyclic groups. These other cyclic groups can be cycloalkyl groups, but can also be other types of cyclic groups; for example, heterocycloalkyl groups; aryl groups; heteroaryl groups, etc. The cycloalkyl group can have 3 to 60 carbon atoms, specifically 3 to 40, more specifically 5 to 20. Specifically, it may have 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 is not limited thereto.

[0028] In this specification, heterocyclic alkyl groups may include O, S, Se, N, or Si as heteroatoms, and may be monocyclic or polycyclic with 2 to 60 carbon atoms, further substituted by other substituents. Here, polycyclic means a group in which a heterocyclic alkyl group is directly attached to or fused with other cyclic groups. These other cyclic groups may be heterocyclic alkyl groups, but may also be other types of cyclic groups; for example, cycloalkyl, aryl, heteroaryl, etc. The heterocyclic alkyl group may have 2 to 60 carbon atoms, specifically 2 to 40, and more specifically 3 to 20.

[0029] In this specification, aryl groups may include monocyclic or polycyclic groups having 6 to 60 carbon atoms, further substituted by other substituents. Here, polycyclic means a group in which the aryl group is directly attached to or fused with other cyclic groups. These other cyclic groups may be aryl, but may also be other types of cyclic groups; for example, cycloalkyl, heterocycloalkyl, heteroaryl, etc. The aryl group may include spirocyclic groups. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40, more specifically 6 to 20. Specific examples of the aryl group include phenyl; biphenyl; triphenyl; naphthyl; anthracene; phenyl; phenanthyl; perylene; fluoranthracene; phenoxide; phenatenyl; pyrene; tetraphenyl; pentaphenyl; fluorenyl; indene; acenaphthene; benzo[a]fluorenyl; spirodifluorenyl; 2,3-dihydro-1H-indene; their fused cyclic groups, etc., but are not limited thereto.

[0030] In this specification, the phosphine oxide group can be represented by -P(=O)R101R102, where R101 and R102 may be the same as or different from each other, and each is independently a substituent formed from at least one of hydrogen, deuterium, halogen group, alkyl, alkenyl, alkoxy, cycloalkyl, aryl, and heterocyclic groups. Specifically, it can be substituted with an aryl group, which may be applicable to the foregoing examples. For example, the phosphine oxide group has diphenylphosphine oxide, dinaphthylphosphine oxide, etc., but is not limited thereto.

[0031] In this specification, a silane may be a substituent comprising Si, wherein the Si atom is directly attached as a free radical, represented by -SiR101R102R103, wherein R101 to R103 may be the same as or different from each other, and each is independently a substituent formed from at least one of hydrogen, deuterium, halogen group, alkyl, alkenyl, alkoxy, cycloalkyl, aryl, and heterocyclic group. Specific examples of the silane include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc., but are not limited thereto.

[0032] In this specification, the fluorene group may be substituted, and adjacent substituents may bond to each other to form a ring.

[0033] When the fluorene group is substituted, it can form , , , , , And so on, but not limited to these.

[0034] In this specification, a spirocyclic group can be a group comprising a spirocyclic structure with 15 to 60 carbon atoms. For example, the spirocyclic group can include a 2,3-dihydro-1H-indenyl or a cyclohexyl spirocyclic structure bonded to a fluorenyl group. Specifically, the following spirocyclic groups can include any of the groups with the following structural formulas.

[0035]

[0036] In this specification, a heteroaryl group may include S, O, Se, N, or Si as a heteroatom, comprising a monocyclic or polycyclic ring having 2 to 60 carbon atoms, further substituted by other substituents. Here, "polycyclic" refers to a group in which a heteroaryl group is directly attached to or fused with other cyclic groups. These other cyclic groups may be heteroaryl groups, but may also be other types of cyclic groups, such as cycloalkyl, heterocycloalkyl, aryl, etc. 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 the aforementioned heteroaryl groups include pyridyl; pyrroloyl; pyrimidinyl; pyridazinyl; furanyl; thiopheneyl; imidazolyl; pyrazolyl; oxazolyl; isoxazolyl; thiazolyl; isothiazolyl; triazolyl; furazolyl; oxadiazolyl; thiazolyl; dithiazolyl; tetrazolyl; pyranyl; thiaranyl; diazinyl; oxazinyl; thiazolyl; dioxinyl; triazinyl; tetraazinyl; Quinolinyl; isoquinolinyl; quinazolinyl; isoquinazolinyl; quinoxalinyl; naphridinyl; acridineyl; phenanthridineyl; imidazopyridinyl; diazanaphthyl; triazaindenyl; 2-indolyl; indazinyl; benzothiazolyl; benzoxazolyl; benzoimidazolyl; benzothiophenyl; benzofuranyl; dibenzothiophenyl; dibenzofuranyl; carbazoleyl; benzocarbazoleyl; dibenzocarbazoleyl; Phenazinyl; dibenzothiopyryl; spirobiso(dibenzothiopyryl); dihydrophenazinyl; phenoxazinyl; phenanthidyl; thiopheninyl; indolo[2,3-a]carbazoleyl; indolo[2,3-b]carbazoleyl; indololinyl; 10,11-dihydro-dibenzo[b,f]azapyryl; 9,10-dihydroacridyl; phenanthazinyl; phenthiazinyl; phthalazinyl; naphridinyl; phenanthiopyryl Linoyl; benzo[c][1,2,5]thiadiazolyl; 5,10-dihydrodibenzo[b,e][1,4]azasilinyl; pyrazolo[1,5-c]quinazolinyl; pyrido[1,2-b]indazoleyl; pyrido[1,2-a]imidazo[1,2-e]indololinyl; 5,11-dihydroindodin[1,2-b]carbazoleyl, etc., but not limited to these.

[0037] In this specification, the amino group may be selected from the group consisting of monoalkylamino, monoarylamino, monoheteroarylamino, -NH2, dialkylamino, diarylamino, diheteroarylamino, alkylarylamino, alkylheteroarylamino, and arylheteroarylamino, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amino group include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, dibiphenylamino, anthraceneamino, 9-methyl-anthraylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenyltolylamino, triphenylamino, biphenylnaphthylamino, phenylbiphenylamino, biphenylfluorenylamino, phenyltriphenylamine, biphenyltriphenylamine, etc., but are not limited thereto.

[0038] In this specification, arylene means an aryl group having two bonding sites, i.e., a divalent group. The description of aryl groups as described above applies, except that they are both divalent groups. Similarly, heteroarylene means a heteroaryl group having two bonding sites, i.e., a divalent group. The description of heteroaryl groups as described above applies, except that they are both divalent groups.

[0039] In this specification, "adjacent" groups may mean a substituent that is directly bonded to the atom substituted by the corresponding substituent; a substituent that is stereoscopically closest to the corresponding substituent; or another substituent that is substituted on the atom substituted by the corresponding substituent. For example, two substituents in a benzene ring that are ortho-substituted, and two substituents in an aliphatic ring that are substituted on the same carbon atom, can be interpreted as "adjacent" groups.

[0040] In this invention, "in the case where no substituent is indicated in the chemical formula or compound structure" means the case where a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 H, Deuterium (D) is an isotope of hydrogen, so some hydrogen atoms can be deuterium.

[0041] In one embodiment of the present invention, "in the case where no substituent is indicated in the chemical formula or compound structure" can mean that all positions that can be occupied by substituents are hydrogen or deuterium. That is, deuterium is an isotope of hydrogen, and some of the hydrogen atoms can be deuterium as an isotope. In this case, the deuterium content can be 0% to 100%.

[0042] In one embodiment of the present invention, for cases where "the substituent is not indicated in the chemical formula or compound structure", when deuterium is not explicitly excluded in cases such as "the content of deuterium is 0%", "the content of hydrogen is 100%", or "all substituents are hydrogen", hydrogen and deuterium can be mixed and used in the compound.

[0043] In one embodiment of the invention, deuterium is an isotope of hydrogen, and is an element possessed by an atomic nucleus consisting of a deuteron formed by one proton and one neutron, which can be produced by hydrogen. -2 The element symbol can also be written as D or 2 H.

[0044] In one embodiment of the present invention, isotopes refer to atoms with the same atomic number (Z) but different mass numbers (A). Isotopes can also be interpreted as elements having the same number of protons but different numbers of neutrons.

[0045] In one embodiment of the present invention, when the total number of substituents that the base compound may have is defined as T1, and the number of specific substituents is defined as T2, the meaning of the content of specific substituents T% can be defined as T2 / T1×100=T.

[0046] That is, in one example, in the case of... The 20% deuterium content in the phenyl group can mean that the phenyl group can have a total of 5 substituents (T1 in the formula), of which 1 is deuterium (T2 in the formula). That is, the 20% deuterium content in the phenyl group can be represented by the following structural formula.

[0047]

[0048] In addition, in one embodiment of the present invention, "phenyl with a deuterium content of 0%" can mean phenyl that does not contain deuterium atoms, i.e., has five hydrogen atoms.

[0049] In this invention, C6 to C60 aromatic rings refer to compounds comprising aromatic rings formed by C6 to C60 carbons and hydrogens. Examples include phenyl, biphenyl, terphenyl, triphenylene, naphthyl, anthracene, finadeninyl, phenanthyl, fluorenyl, pyrene, thionyl, perylene, azulene, etc., but are not limited thereto. As long as the number of carbons is satisfied, it includes all aromatic ring compounds known in the art.

[0050] The present invention provides a heterocyclic compound represented by the following chemical formula 1.

[0051] [Chemical Formula 1]

[0052] In the chemical formula 1, X is O; or S, R1 to R6 may be the same as or different from each other, and are each independently selected from hydrogen; deuterium; 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; -SiR101R102R103 ; -NR101R102; the following chemical formula 2; the following chemical formula 3; the following chemical formula 4; and the following chemical formula 5, wherein two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl. Any one of R1, R4, and R6 is any one of the following chemical formulas 2 to 5. Where 'a' is an integer from 0 to 3, and when 'a' is 2 or greater, R2 is either the same or different from each other. b is an integer from 0 to 3. When b is 2 or greater, R5 is either the same or different from each other. [Chemical Formula 2]

[0053] [Chemical Formula 3]

[0054] [Chemical Formula 4]

[0055] [Chemical Formula 5]

[0056] In the chemical formulas 2 to 5, R11 to R20 may be the same as or different from each other, and are each independently selected from hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 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. The groups -SiR201R202R203 and -NR201R202, or two or more adjacent groups, are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R201, R202, and R203 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl. The d is an integer from 0 to 6. When d is 2 or greater, R12 are either the same or different from each other. h is an integer from 0 to 4. When h is 2 or greater, R15 are either the same or different from each other. Where i is an integer from 0 to 2, when i is greater than 2, R16 are either the same or different from each other. j is an integer from 0 to 4. When i is greater than or equal to j, R17 are either the same or different from each other. The value of l is an integer from 0 to 3. When l is 2 or greater, R18 may be the same or different from each other. m is an integer from 0 to 2. When m is greater than 2, R19 are either the same or different from each other. The n is an integer from 0 to 4. When n is 2 or more, R20 is either the same or different from each other. The Ar1 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. The L1 to L4 may be the same as or different from each other, and each is independently directly bonded; substituted or unsubstituted C6 to C60 arylene groups; or substituted or unsubstituted C2 to C60 heteroarylene groups. c is an integer from 0 to 5. When c is greater than 2, L1 values ​​are either the same or different. The value of e is an integer from 0 to 5. When e is greater than 2, L2 values ​​are either the same or different from each other. k is an integer from 0 to 5. When k is 2 or greater, L3 are either the same or different from each other. The value of o is an integer from 0 to 5. When o is 2 or higher, L4 are either the same or different from each other.

[0057] In one embodiment of the present invention, R1 to R6 may be the same as or different from each other, and each may independently be hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C2 to C30 alkenyl; substituted or unsubstituted C2 to C30 alkynyl; substituted or unsubstituted C1 to C30 alkoxy; substituted or unsubstituted C3 to C30 cycloalkyl; substituted or unsubstituted C2 to C30 heterocycloalkyl; substituted or unsubstituted C6 to C30 aryl; substituted or unsubstituted C2 to C30 heteroaryl; -Si R101R102R103; -NR101R102; Formula 2; Formula 3; Formula 4; or Formula 5, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic ring; or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C30 alkyl; a substituted or unsubstituted C6 to C30 aryl; or a substituted or unsubstituted C2 to C30 heteroaryl.

[0058] In another embodiment of the invention, R1 to R6 may be the same as or different from each other, each independently being hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C2 to C20 alkenyl; substituted or unsubstituted C2 to C20 alkynyl; substituted or unsubstituted C1 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 heterocycloalkyl; substituted or unsubstituted C6 to C20 aryl; substituted or unsubstituted C2 to C20 heteroaryl; -Si R101R102R103; -NR101R102; Formula 2; Formula 3; Formula 4; or Formula 5, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic ring; or a substituted or unsubstituted C2 to C20 heterocycle, wherein R101, R102 and R103 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C20 alkyl; a substituted or unsubstituted C6 to C20 aryl; or a substituted or unsubstituted C2 to C20 heteroaryl.

[0059] In another embodiment of the invention, R1 to R6 may be the same as or different from each other, and each independently represents hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C2 to C20 alkenyl; substituted or unsubstituted C2 to C20 alkynyl; substituted or unsubstituted C1 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 heterocycloalkyl; substituted or unsubstituted C6 Aryl groups up to C20; substituted or unsubstituted heteroaryl groups from C2 to C20; -SiR101R102R103; -NR101R102; Formula 2; Formula 3; Formula 4; or Formula 5, wherein R101, R102, and R103 are the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group from C1 to C20; substituted or unsubstituted aryl groups from C6 to C20; substituted or unsubstituted heteroaryl groups from C2 to C20.

[0060] In another embodiment of the present invention, R1, R4 and R6 may be the same as or different from each other, and each may be hydrogen; deuterium; the chemical formula 2; the chemical formula 3; the chemical formula 4; or the chemical formula 5, wherein any one of R1, R4 and R6 is any one of the chemical formulas 2 to 5, and the rest may be the same as or different from each other, and each may be hydrogen; or deuterium.

[0061] In another embodiment of the invention, R1 may be any one of chemical formulas 2 to 5, and R4 and R6 may be the same as or different from each other, each being hydrogen independently; or deuterium.

[0062] In another embodiment of the invention, R4 may be any one of chemical formulas 2 to 5, and R1 and R6 may be the same as or different from each other, each being hydrogen independently; or deuterium.

[0063] In another embodiment of the invention, R6 may be any one of chemical formulas 2 to 5, and R1 and R4 may be the same as or different from each other, each being hydrogen independently; or deuterium.

[0064] In another embodiment of the invention, R2, R3 and R5 may be the same as or different from each other, and each may be hydrogen or deuterium.

[0065] In one embodiment of the present invention, R11 to R20 may be the same as or different from each other, each independently the same as or different from each other, and each independently being hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C2 to C30 alkenyl; substituted or unsubstituted C2 to C30 alkynyl; substituted or unsubstituted C1 to C30 alkoxy; substituted or unsubstituted C3 to C30 cycloalkyl; substituted or unsubstituted C2 to C30 heterocycloalkyl; substituted or unsubstituted C6 to C30 aryl; or... Substituted or unsubstituted C2 to C30 heteroaryl groups; -SiR201R202R203; or -NR201R202, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic ring; or a substituted or unsubstituted C2 to C30 heterocycle, wherein R201, R202 and R203 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C30 alkyl group; substituted or unsubstituted C6 to C30 aryl group; substituted or unsubstituted C2 to C30 heteroaryl group.

[0066] In another embodiment of the invention, R11 to R20 may be the same as or different from each other, and each independently represents hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C2 to C20 alkenyl; substituted or unsubstituted C2 to C20 alkynyl; substituted or unsubstituted C1 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 heterocycloalkyl; substituted or unsubstituted C6 to C20 aryl; substituted or unsubstituted C2 to C20 heteroaryl groups; -SiR201R202R203; or -NR201R202, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic ring; or a substituted or unsubstituted C2 to C20 heterocycle, wherein R201, R202 and R203 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C6 to C20 aryl group; substituted or unsubstituted C2 to C20 heteroaryl group.

[0067] In another embodiment of the invention, R11 to R20 may be the same as or different from each other, and each independently represents hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C2 to C20 alkenyl; substituted or unsubstituted C2 to C20 alkynyl; substituted or unsubstituted C1 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; or substituted or unsubstituted C2 to C20 heterocycle. Alkyl; substituted or unsubstituted C6 to C20 aryl; substituted or unsubstituted C2 to C20 heteroaryl; -SiR201R202R203; or -NR201R202, wherein R201, R202, and R203 may be the same as or different from each other, and each is independently a substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl; substituted or unsubstituted C2 to C20 heteroaryl.

[0068] In another embodiment of the invention, R11 to R20 may be the same as or different from each other, and each may be independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0069] In another embodiment of the invention, R11 to R20 may be the same as or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0070] In another embodiment of the invention, R11 to R12 may be the same as or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

[0071] In another embodiment of the invention, R11 to R12 may be the same as or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

[0072] In another embodiment of the invention, R11 to R12 may be the same as or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0073] In another embodiment of the invention, R11 may be hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

[0074] In another embodiment of the invention, R11 may be hydrogen; deuterium; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

[0075] In another embodiment of the invention, R11 may be hydrogen; deuterium; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0076] In another embodiment of the invention, R11 may be hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted naphthyl; or substituted or unsubstituted pyridyl.

[0077] In another embodiment of the invention, R12 may be hydrogen; or deuterium.

[0078] In another embodiment of the invention, R13 and R14 may be the same as or different from each other, and each may be 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.

[0079] In another embodiment of the invention, R13 and R14 may be the same as or different from each other, and each may be independently a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0080] In another embodiment of the invention, R13 and R14 may be the same as or different from each other, and each may be independently a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0081] In another embodiment of the invention, R13 and R14 may be the same as or different from each other, and each may be independently a substituted or unsubstituted methyl; a substituted or unsubstituted ethyl; a substituted or unsubstituted isopropyl; a substituted or unsubstituted phenyl; or a substituted or unsubstituted pyridyl.

[0082] In another embodiment of the invention, R15 to R20 may be the same as or different from each other, each being hydrogen; or deuterium.

[0083] In one embodiment of the present invention, Ar1 may be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0084] In another embodiment of the invention, Ar1 may be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0085] In another embodiment of the invention, Ar1 may be a substituted or unsubstituted aryl group of C6 to C60.

[0086] In another embodiment of the invention, Ar1 may be a substituted or unsubstituted aryl group of C6 to C30.

[0087] In another embodiment of the invention, Ar1 may be a substituted or unsubstituted aryl group of C6 to C20.

[0088] In another embodiment of the invention, Ar1 may be a substituted or unsubstituted phenyl group.

[0089] In one embodiment of the invention, L1 to L4 may be the same as or different from each other, and each may be directly bonded; substituted or unsubstituted C6 to C30 arylene groups; or substituted or unsubstituted C2 to C30 heteroarylene groups.

[0090] In another embodiment of the invention, L1 to L4 may be the same as or different from each other, each being independently directly bonded; substituted or unsubstituted C6 to C20 arylene groups; or substituted or unsubstituted C2 to C20 heteroarylene groups.

[0091] In another embodiment of the invention, L1 and L2 may be the same as or different from each other, and each may be independently directly bonded; substituted or unsubstituted phenylene; substituted or unsubstituted naphthylene; substituted or unsubstituted pyridylene; substituted or unsubstituted quinoline; or substituted or unsubstituted isoquinoline.

[0092] In another embodiment of the invention, L3 and L4 may be the same as or different from each other, each being independently directly bonded; or substituted or unsubstituted C6 to C60 aryl groups.

[0093] In another embodiment of the invention, L3 and L4 may be the same as or different from each other, each being directly bonded independently; or substituted or unsubstituted C6 to C30 aryl groups.

[0094] In another embodiment of the invention, L3 and L4 may be the same as or different from each other, each being independently directly bonded; or substituted or unsubstituted C6 to C20 aryl groups.

[0095] In another embodiment of the invention, L3 and L4 may be the same as or different from each other, each being independently directly bonded; or substituted or unsubstituted phenylene.

[0096] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-12.

[0097] [Chemical Formula 1-1]

[0098] [Chemical Formula 1-2]

[0099] [Chemical Formulas 1-3]

[0100] [Chemical Formulas 1-4]

[0101] [Chemical Formulas 1-5]

[0102] [Chemical Formulas 1-6]

[0103] [Chemical Formulas 1-7]

[0104] [Chemical Formulas 1-8]

[0105] [Chemical Formulas 1-9]

[0106] [Chemical Formulas 1-10]

[0107] [Chemical Formula 1-11]

[0108] [Chemical Formula 1-12]

[0109] In the chemical formulas 1-1 to 1-12, X, R1 to R6, a, and b are defined in the same way as in chemical formula 1. The definitions of L1, R11, R12, c, and d are the same as those of chemical formula 2. The definitions of L2, R13, R14, and e are the same as those of chemical formula 3. The definitions of L3, R15 to R17, and h to k are the same as those of chemical formula 4. The L4, R18 to R20, and l to o are defined in the same way as in chemical formula 5.

[0110] In one embodiment of the present invention, R1 to R6, R11 to R20, Ar1 and L1 to L4 may include undeuterated hydrogen (H).

[0111] In another embodiment of the invention, at least one of R1 to R6, R11 to R20, Ar1 and L1 to L4 may include deuterium (D), and at least one of R1 to R6, R11 to R20, Ar1 and L1 to L4 may include undeuterated hydrogen.

[0112] In another embodiment of the present invention, R1 to R6, R11 to R20, Ar1 and L1 to L4 may all include deuterium.

[0113] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1 may not include deuterium as a substituent, or the deuterium content relative to the total number of hydrogen atoms and deuterium atoms may be, for example, more than 0%, more than 1%, more than 10%, more than 20%, more than 30%, more than 40%, or more than 50%, or less than 100%, less than 90%, less than 80%, less than 70%, or less than 60%.

[0114] In another embodiment of the invention, the heterocyclic compound represented by the chemical formula 1 may not include deuterium as a substituent, or the deuterium content relative to the total number of hydrogen atoms and deuterium atoms may be from 1% to 100%.

[0115] In another embodiment of the invention, the heterocyclic compound represented by the chemical formula 1 may not include deuterium as a substituent, or the deuterium content relative to the total number of hydrogen and deuterium atoms may be 20% to 90%.

[0116] In another embodiment of the invention, the heterocyclic compound represented by the chemical formula 1 may not include deuterium as a substituent, or the deuterium content relative to the total number of hydrogen and deuterium atoms may be 30% to 80%.

[0117] In another embodiment of the invention, the heterocyclic compound represented by the chemical formula 1 may not include deuterium as a substituent, or the deuterium content relative to the total number of hydrogen and deuterium atoms may be 50% to 70%.

[0118] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1 may be represented by any of the following compounds.

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155] Furthermore, compounds possessing the inherent properties of the introduced substituents can be synthesized by introducing various substituents into the structure of Formula 1. For example, substances satisfying the requirements of each organic layer can be synthesized by introducing substituents primarily used in the manufacture of hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, electron blocking layer materials, and charge generation layer materials into the core structure.

[0156] In addition, the energy band gap can be finely tuned by introducing various substituents into the structure of the chemical formula 1, which can improve the properties at the interface between organic compounds and diversify the uses of the substances.

[0157] On the other hand, the heterocyclic compound has a high glass transition temperature (Tg) and excellent thermal stability. This increased thermal stability is an important factor in providing driving stability for the device.

[0158] The heterocyclic compound according to one embodiment of the present invention can be manufactured by a multi-step chemical reaction. This can be achieved by first manufacturing a portion of an intermediate compound, from which the heterocyclic compound represented by Chemical Formula 1 is manufactured. More specifically, the heterocyclic compound according to one embodiment of the present invention can be manufactured based on the manufacturing examples described later.

[0159] Another embodiment of the present invention provides an organic light-emitting element comprising a heterocyclic compound represented by the aforementioned chemical formula 1. The term "organic light-emitting element" can be represented by terms such as "organic light-emitting diode," "OLED (Organic Light Emitting Diode)," "OLED element," or "organic electroluminescent element."

[0160] In addition, the present invention provides an organic light-emitting element, the organic light-emitting element comprising: First electrode; The second electrode is disposed opposite to the first electrode; and One or more organic layers are disposed between the first electrode and the second electrode. One or more of the organic layers comprise heterocyclic compounds represented by the chemical formula 1.

[0161] In one embodiment of the present invention, the first electrode may be an anode and the second electrode may be a cathode.

[0162] In yet another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0163] In one embodiment of the present invention, the organic light-emitting element may be a blue organic light-emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the blue organic light-emitting element. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in the electron transport layer or charge generation layer of the blue organic light-emitting element.

[0164] In another embodiment of this application, the organic light-emitting element may be a green organic light-emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the green organic light-emitting element. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in the electron transport layer or charge generation layer of the green organic light-emitting element.

[0165] In another embodiment of this application, the organic light-emitting element may be a red organic light-emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the red organic light-emitting element. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in the electron transport layer or charge generation layer of the red organic light-emitting element.

[0166] The specific details regarding the heterocyclic compounds represented by the aforementioned chemical formula 1 are the same as those described above.

[0167] The organic light-emitting element of the present invention can be manufactured using conventional organic light-emitting element manufacturing methods and materials, except that it utilizes a heterocyclic compound represented by the aforementioned chemical formula 1 to form one or more organic layers.

[0168] In manufacturing organic light-emitting elements, the heterocyclic compound can form an organic layer not only through vacuum deposition but also through solution coating. Here, solution coating refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, etc., but is not limited to these methods.

[0169] The organic layer of the organic light-emitting element of the present invention can be formed as a single-layer structure, or it can be formed as a multilayer structure with two or more organic layers stacked together. For example, the organic light-emitting element of the present invention can have a structure including a hole injection layer, an electron blocking layer, a hole transport layer, a light-emitting layer, an electron transport layer, a hole blocking layer, and an electron injection layer as organic layers. However, the structure of the organic light-emitting element is not limited to this, and may include fewer organic layers.

[0170] In the organic light-emitting element of the present invention, the organic layer may include a light-emitting layer, and the light-emitting layer may include the heterocyclic compound.

[0171] In the organic light-emitting element of the present invention, the organic layer may include an electron injection layer or an electron transport layer, and the electron injection layer or electron transport layer may include the heterocyclic compound.

[0172] In the organic light-emitting element of the present invention, the organic layer may include an electron transport layer, and the electron transport layer may include the heterocyclic compound.

[0173] In another organic light-emitting element, the organic layer may include an electron blocking layer or a hole blocking layer, wherein the electron blocking layer or hole blocking layer includes the heterocyclic compound.

[0174] In another organic light-emitting element, the organic layer may include an electron transport layer, a light-emitting layer, or a hole-blocking layer, wherein the electron transport layer, light-emitting layer, or hole-blocking layer includes the heterocyclic compound.

[0175] The organic light-emitting element 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 blocking layer, an electron injection layer, an electron transport layer, a hole auxiliary layer, and a hole blocking layer.

[0176] exist Figures 1 to 3The figures illustrate the stacking sequence of electrodes and organic layers of an organic light-emitting element according to an embodiment of this application. However, the scope of this application is not intended to be limited by these figures, and structures of organic light-emitting elements known in the art can also be applied to this application.

[0177] according to Figure 1 This illustrates an organic light-emitting element in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, it is not limited to this structure, such as... Figure 2 In that way, it is also possible to realize an organic light-emitting element by sequentially stacking a cathode, an organic layer, and a positive electrode on a substrate.

[0178] Figure 3 This example illustrates the case where organic matter has multiple layers. According to... 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 this application is not limited to this stacked structure, and the other layers besides the light-emitting layer can be omitted as needed, and other functional layers can be added as required.

[0179] In addition, in one embodiment of the present invention, the organic light-emitting element includes: anode; cathode; and Two or more stacked components are arranged between the anode and the cathode. Each of the two or more stacked components independently includes a light-emitting layer. A charge generation layer is included between the two or more stacked components. The charge-generating layer comprises a heterocyclic compound represented by the chemical formula 1.

[0180] In addition, in one embodiment of the present invention, the organic light-emitting element includes: First electrode; A first stacked component is disposed on the first electrode and includes a first light-emitting layer; A charge generation layer is disposed on the first stack; A second stacked component, disposed on the charge generation layer, and including a second light-emitting layer; and The second electrode is disposed on the second stack.

[0181] At this time, the charge generation layer may include a heterocyclic compound represented by the chemical formula 1. Additionally, the first stack and the second stack may each independently further include one or more of the aforementioned hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, etc.

[0182] The charge-generating layer may be an N-type charge-generating layer, which may include a heterocyclic compound represented by Formula 1. In addition to the heterocyclic compound represented by Formula 1, the N-type charge-generating layer may further include dopants known in the art.

[0183] As an organic light-emitting element according to one embodiment of the present invention, Figure 4 An outline of an organic light-emitting element with a 2-stacked tandem structure is shown.

[0184] The organic light-emitting element according to this specification, except that it includes a heterocyclic compound represented by the stated chemical formula 1 in one or more layers of organic material, can be manufactured using materials and methods known in the art.

[0185] The organic layer comprising the heterocyclic compound represented by the chemical formula 1 may further include other substances as needed.

[0186] The heterocyclic compound represented by the chemical formula 1 can be used as a material for the charge generation layer in organic light-emitting elements.

[0187] In addition, the present invention provides a composition for an organic layer comprising an organic light-emitting element comprising a heterocyclic compound represented by the aforementioned chemical formula 1.

[0188] The specific details regarding the heterocyclic compounds represented by the aforementioned chemical formula 1 are the same as those described above.

[0189] The composition for the organic layer of the organic light-emitting element can be used when forming the organic layer of the organic light-emitting element, and is more preferably used when forming an electron transport layer or a charge generation layer.

[0190] In one embodiment of the invention, the organic layer may include a heterocyclic compound represented by the chemical formula 1, used in conjunction with a phosphorescent dopant.

[0191] Materials known in the art can be used as the phosphorescent dopant material. For example, phosphorescent dopant materials represented by LL'MX', LL'L''M, LMX'X'', L2MX', and L3M can be used, but the scope of the invention is not limited to these examples.

[0192] The M can be iridium, platinum, osmium, etc.

[0193] It is possible that L is through sp 2Carbon and heteroatoms are coordinated to the anionic bidentate ligand of M, and X performs the function of trapping electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, phenylpyridine, benzothiophene pyridine, 3-methoxy-2-phenylpyridine, thiophene pyridine, tolylpyridine, etc. Non-limiting examples of X' and X'' include acetylacetone (acac), hexafluoroacetylacetone, salicylaldehyde condensate, pyridine carboxylate, 8-hydroxyquinoline, etc.

[0194] In one embodiment of the invention, the organic layer may include a heterocyclic compound represented by the chemical formula 1, used in conjunction with an iridium-based dopant.

[0195] In one embodiment of the present invention, the iridium dopant can be (piq)2(Ir)(acac) as a red phosphorescent dopant, FIrpic as a blue phosphorescent dopant, or Ir(ppy)3 as a green phosphorescent dopant.

[0196] In one embodiment of the present invention, the content of the dopant can be based on the total weight of the light-emitting layer, having a content of 1% to 15%, preferably 2% to 10%, and more preferably 3% to 7%.

[0197] This invention provides a method for manufacturing an organic light-emitting element, the method comprising: Steps for preparing the substrate; The step of forming a first electrode on the substrate; The step of forming one or more organic layers on the first electrode; and The step of forming a second electrode on the organic layer or more includes forming the organic layer or more using a composition of the organic layer of an organic light-emitting element according to an embodiment of the present invention.

[0198] In one embodiment of the present invention, the step of forming the organic layer can be performed by using a thermal vacuum evaporation method to form a heterocyclic compound represented by the chemical formula 1.

[0199] The organic layer comprising the heterocyclic compound represented by the chemical formula 1 may further include other substances as needed.

[0200] In an organic light-emitting element according to an embodiment of the present invention, materials other than heterocyclic compounds represented by the chemical formula 1 are exemplified below, but these are merely illustrative and not intended to limit the scope of this application, and materials known in the art may be substituted.

[0201] As an anode material, materials with a high work function can be used, such as transparent conductive oxides, metals, or conductive polymers. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; 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-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0202] As cathode materials, materials with low work functions can be used, such as metals, metal oxides, or conductive polymers. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer structures such as LiF / Al or LiO2 / Al, but are not limited to these.

[0203] As a hole injection layer material, known hole injection layer materials can also be used, but phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or star-shaped amine derivatives described in [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazole-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), and soluble conductive polymers such as polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic acid) can also be used. Poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrenesulfonate), etc.

[0204] As hole transport layer materials, pyrazoline derivatives, aromatic amine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc., can be used, as well as low molecular weight or high molecular weight materials.

[0205] As electron transport layer materials, metal complexes of oxadiazole derivatives, anthraquinone dimethyl ether and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethyl ether and its derivatives, fluorenone derivatives, diphenyl dicyanoethylene and its derivatives, dibenzoquinone derivatives, 8-hydroxyquinoline and its derivatives, etc. can be used. Not only low molecular weight substances, but also high molecular weight substances can be used.

[0206] As an electron injection layer material, LiF is a representative example used in the art, but this application is not limited thereto.

[0207] Red, green, or blue luminescent materials can be used as the luminescent layer material, and two or more luminescent materials can be mixed and used if necessary. In this case, the two or more luminescent materials can be used as individual supply sources for vapor deposition, or premixed and used as a single supply source for vapor deposition. Additionally, fluorescent materials can be used as the luminescent layer material, but phosphorescent materials can also be used. Materials that emit light by combining holes and electrons injected from the anode and cathode respectively can be used alone as the luminescent layer material, but materials in which both the host material and dopant material participate in luminescence can also be used.

[0208] When mixing and using the main body of the luminescent layer material, main bodies from the same series or different series can be mixed and used. For example, any two or more types of materials from type n or type p can be selected as the main body material of the luminescent layer.

[0209] Depending on the materials used, an organic light-emitting element according to an embodiment of the present invention can be a front-emitting type, a rear-emitting type, or a dual-emitting type.

[0210] According to one embodiment of the present invention, the heterocyclic compound can function in organic electronic components, including organic solar cells, organic photoreceptors, organic transistors, etc., in a principle similar to that applicable to organic light-emitting elements.

[0211] The following preferred embodiments are provided to aid in understanding the present invention; however, these embodiments are provided merely to facilitate a better understanding of the invention, and the invention is not limited thereto.

[0212] <Manufacturing Example> Manufacturing Example 1. Manufacturing of Compound 001

[0213] Manufacturing Example 1-1. Manufacturing of Compound 1-1 Under a nitrogen atmosphere, 7-chlorobenzo[b]thiophene (81.21 g, 0.481 mol, 1 eq) and 1200 mL of tetrahydrofuran (THF) were stirred in an ice bath below 0°C. An n-Butyllithium solution (37.02 g, 0.578 mol, 1.2 eq) was added dropwise, and after stirring for 3 minutes, trimethylborate (75.06 g, 0.722 mol, 1.5 eq) was added dropwise using a syringe. The mixture was stirred at room temperature for 1 hour, followed by the addition of saturated NH4Cl solution and stirring for another hour.

[0214] Subsequently, the organic layer was extracted and concentrated to obtain 82.87 g (yield 81%) of compound 1-1.

[0215] Manufacturing Example 1-2. Manufacturing of Compound 1-2 Compound 1-1 (82.87 g, 0.39 mol, 1 eq), 2-bromobenzaldehyde (60 g, 0.324 mol, 1 eq), Pd(OAc)2 (3.6 g, 0.016 mol, 0.05 eq), Na2CO3 (102.07 g, 0.963 mol, 3 eq), 1200 mL of acetone, and 1200 mL of distilled water (H2O) were added and stirred at room temperature for 4 hours.

[0216] Subsequently, water and dichloromethane were added, and the organic layer was concentrated after separation. Then, a silica pass was performed to obtain 39 g (45% yield) of compounds 1-2.

[0217] Manufacturing Examples 1-3. Manufacturing of Compounds 1-3 After adding dry ice to acetone to create conditions below 0°C, 600 mL of tetrahydrofuran (THF) and (methoxymethyl)tri-phenylphosphonium chloride were added for dissolution. Potassium tert-butoxide was then slowly added at below 0°C with the inlet plugged, and the mixture was stirred at room temperature for 30 minutes to prepare a mixed solution.

[0218] A solution of compound 1-2 dissolved in 400 mL of tetrahydrofuran was added to a dropping funnel. The mixture was stirred again in a bath below 0°C, and the solution of compound 1-2 was added dropwise. The mixture was stirred at room temperature for 3 hours to obtain 24.7 g (66% yield) of compound 1-3.

[0219] Manufacturing Examples 1-4. Manufacturing of Compounds 1-4 Compounds 1-3 (24.7 g, 0.092 mol, 1 eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1,3,2-dioxaborolane (22.69 g, 0.089 mol, 1.5 eq), KOAc (14.92 g, 0.152 mol, 2.5 eq), Pd2(dba)3 (2.7 g, 0.003 mol, 0.05 eq), and P(Cy)3 (1.69 g, 0.006 mol, 0.1 eq) were stirred at 120 °C for 3 hours. At the stated temperature, the substance dissolves into a transparent state, and the temperature is then lowered to room temperature.

[0220] After diatomite filtration, the solution is concentrated, dissolved in dichloromethane, and then propelled into the silica pass using a dichloromethane:hexane (1:1 volume ratio) as the developing solvent.

[0221] The mixture was then concentrated, redissolved in dichloromethane, and slowly added to 2L of methanol to precipitate the solid. The solid was then filtered to give 30.1g (82% yield) of compounds 1-4.

[0222] Manufacturing Examples 1-5. Manufacturing of Compound 1 Compounds 1-4 (10 g, 0.028 mol, 1 eq), 2-bromo-9-phenyl-1,10-phenanthroline (7.58 g, 0.029 mol, 1.05 eq), Pd(pph3)4 (1.6 g, 0.001 mol, 0.05 eq), and K3PO4 (11.51 g, 0.083 mol, 3 eq) were dissolved in 120 mL of 1,4-dioxane and 30 mL of water and stirred at 120 °C for 4 hours.

[0223] After the reaction was complete, the solid was filtered through a filter and then washed with 1,4-dioxane to remove the alkali. The mixture was then concentrated, dissolved in dichloromethane, and advanced into the silica pass using a dichloromethane:hexane (5:1 volume ratio) as the developing solvent.

[0224] After further concentration, the compound was purified with dichloromethane and acetone to obtain 8.34 g (yield 48%) of compound 1.

[0225] Except for using compound A from Table 1 below to replace 7-chlorobenzo[b]thiophene in Manufacturing Example 1, using compound B from Table 1 below to replace 2-bromobenzaldehyde, and using compound C from Table 1 below to replace 2-bromo-9-phenyl-1,10-phenanthroline, the target compounds in Table 1 below were manufactured and synthesized by the same method as in Manufacturing Example 1.

[0226] Table 1

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233] Manufacturing Example 2. Manufacturing of Compound 9

[0234] After adding benzo(B)naphtho(2,1-D)thiophene (25 g, 0.093 mol, 1 eq), N-bromosuccinimide (NBS) (18.21 g, 0.102 mol, 1.1 eq) and dimethylformamide (DMF) (375 mL), the mixture was stirred at 60 °C for 4 hours.

[0235] If the reaction is complete, a solid precipitates. Water is added to the reaction flask and stirred. The flask is then washed with water and filtered. The solid is washed with methanol and dried to obtain compound 9-1.

[0236] Subsequently, the same procedures as described in Manufacturing Examples 1-4 and 1-5 were followed to obtain Compound 9 (yield 55%).

[0237] Except for using compound D from Table 2 below to replace benzo(B)naphtho(2,1-D)thiophene in Manufacturing Example 2, and using compound E from Table 2 below to replace 2-bromo-9-phenyl-1,10-phenanthroline, the target compounds in Table 2 below were manufactured and synthesized by the same method as in Manufacturing Example 1.

[0238] Table 2

[0239]

[0240]

[0241]

[0242] Manufacturing Example 3. Manufacturing of Compound 566

[0243] Compound 005 (5 g, 12.12 mmol) was added to 50 mL of LC6D6 and purged with nitrogen for 2 hours. Trifluoromethanesulfonic acid (84.84 mmol, 7 eq) was added dropwise using a syringe, and the reaction mixture was refluxed and heated for 2 hours.

[0244] After cooling to room temperature, 50 mL of heavy water (D2O) was added for extraction. The organic layer was dried with anhydrous MgSO4 and then concentrated using a rotary evaporator.

[0245] Subsequently, 4.4 g (85% yield) of compound 566 was obtained by ethyl acetate (EA) slurry.

[0246] Except that the reaction temperature, reaction time, and equivalent amount of trifluoromethanesulfonic acid in Manufacturing Example 3 were performed according to the conditions in Table 3 below, the target compounds in Table 3 below were manufactured and synthesized by the same method as in Manufacturing Example 3.

[0247] Table 3

[0248]

[0249]

[0250] The synthesis results of manufacturing examples 1 to 3 and the compounds described in Tables 1 to 3, as well as the synthesis results of heterocyclic compounds represented by the chemical formula 1, are shown in Tables 4 and 5 below.

[0251] Table 4 below is 1 The measured values ​​of H NMR (DMSO, 200MHz) are shown in Table 5 below, which are the measured values ​​of FD-MS (Field desorption mass spectrometry).

[0252] Table 4

[0253]

[0254]

[0255] Table 5

[0256]

[0257] <Experimental Example> Experimental Example 1. Experiment Example 1-1. Fabrication of Organic Light-Emitting Element For the transparent electrode indium tin oxide (ITO) film obtained from OLED glass (manufactured by Samsung Corning), after ultrasonic cleaning for 5 minutes each with trichloroethylene, acetone, ethanol, and distilled water, it was placed in isopropanol for storage before use. Next, an ITO substrate was placed in the substrate holder of a vacuum evaporation equipment, and 4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was added to the unit in the vacuum evaporation equipment.

[0258]

[0259] Next, the vacuum level inside the chamber is reduced to 10. -6 After torsion, current is applied to the cells to evaporate 2-TNATA and deposit 600 on the ITO substrate. A hole-injection layer of thickness. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) is added to other units within the vacuum evaporation apparatus. Current is applied to the units to evaporate the N,N'-diphenyl-4,4'-diamine, depositing a 300-degree layer on top of the hole-injection layer. A hole transport layer of thickness.

[0260]

[0261] Thus, after forming the hole injection layer and the hole transport layer, a blue luminescent material with the structure shown below is deposited on top as the luminescent layer. Specifically, in one unit of the vacuum evaporation apparatus, at a temperature of 200... A blue luminescent host material, H1, is vacuum-deposited with a thickness of 5% relative to the host material, and a blue luminescent dopant material, D1, is vacuum-deposited on top of it.

[0262]

[0263] Next, with 300 A compound with the following structural formula E1 is deposited as an electron transport layer by thickness vapor deposition.

[0264]

[0265] With 10 Thickness of lithium fluoride (LiF) vapor-deposited as electron injection layer and with a thickness of 1,000 Al is deposited in a thick layer to form a cathode, thereby creating an organic light-emitting element.

[0266] On the other hand, all the organic compounds required for OLED device fabrication are processed according to the specific materials at 10... -8 10 -6 The material is purified by vacuum sublimation under torsion for use in the manufacture of OLEDs.

[0267] Comparative Example 1 uses E1 as the electron transport layer. The organic light-emitting element was fabricated in the same manner as Comparative Example 1, except that the compounds shown in Table 6 below were used instead of E1.

[0268] Experimental Example 1-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Element For the organic electroluminescent element fabricated as described above, the electroluminescence (EL) characteristics were measured using a McScience M7000. Based on these measurements, lifetime measurement was performed using a McScience M6000 lifetime measurement device at a reference luminance of 3,500 cd / m².2 The lifetime T is the time it takes for the brightness to reach 95% of its initial brightness. 95 .

[0269] The driving voltage, luminous efficiency, and lifetime (T) of the green organic light-emitting element manufactured by the aforementioned method were measured. 95 The results are shown in Table 6.

[0270] Table 6

[0271]

[0272] [Compare compounds]

[0273] As can be seen from the results in Table 6, compared with Comparative Examples 1 to 9, the organic light-emitting elements, namely Examples 1 to 63, which use the heterocyclic compound represented by the chemical formula 1 as the electron transport layer material of the blue organic light-emitting element of the present invention, exhibited low driving voltage, significantly improved luminous efficiency and lifetime.

[0274] The heterocyclic compound of the present invention, represented by Chemical Formula 1, has a core structure with suitable electron transport capability and possesses functional groups of Chemical Formula 2 (phenanthroline), Chemical Formula 3 (phosphine oxide), Chemical Formula 4 (terpyridine), or Chemical Formula 5 (terpyridine), thereby exhibiting rapid electron transport capability. In the case of these functional groups, it can also function as a metal-acceptor, thereby forming a stable bond with the metal used as the cathode. For this reason, electrons can be efficiently transported with relatively little decomposition or destruction of the compound. Therefore, the heterocyclic compound of the present invention, represented by Chemical Formula 1, can possess suitable electron transport capability for inducing luminescence, improving stability when stacking electron transport layers, thus resulting in low driving voltage, high luminescence efficiency, and excellent lifetime.

[0275] Experimental Example 2. Experiment Example 2-1. Fabrication of Organic Light-Emitting Element Glass substrates coated with ITO at a thickness of 1500 Å were ultrasonically cleaned with distilled water. After distilled water cleaning, they were ultrasonically cleaned with solvents such as acetone, methanol, and isopropanol, and then dried before undergoing a 5-minute UVO treatment in a UV cleaner. Following this, the substrates were transferred to a plasma cleaner (PT) for plasma treatment to achieve the ITO work function under vacuum and remove residual film, and then transferred to a thermal evaporation equipment for organic deposition.

[0276] An organic material is formed on the ITO transparent electrode (anode) in a 2-stack WOLED (White Organic Light-Emitting Device) structure. The first stack is formed by first stacking TAPC at 300... A hole transport layer is formed by thermal vacuum evaporation to a thickness of [thickness value missing]. After forming the hole transport layer, a light-emitting layer is formed on top of it by thermal vacuum evaporation in the following manner: The light-emitting layer is formed by evaporating 300 [units missing] filaments of 8% FIrpic as a blue phosphorescent dopant in the substrate, i.e., TCz1. The electron transport layer is formed using TmPyPB to create a 400... Subsequently, 20% Cs₂CO₃ was doped into the compounds listed in Table 7 below as a charge-generating layer to achieve a 100 Thickness formation.

[0277] The second stacking process involves first placing MoO3 at a 50°C solution. The hole injection layer is formed by thermal vacuum evaporation of a certain thickness. The common layer, i.e., the hole transport layer, is doped with 20% MoO3 in TAPC to achieve a thickness of 100... After the thickness is formed, the Tapc is applied at 300... The thickness is formed by vapor deposition, and the light-emitting layer is formed on top of it by doping the main body, TCz1, with 8% green phosphorescent dopant, Ir(ppy)3, at 300. After a thickness of evaporation, TmPyPB is used as the electron transport layer to achieve a thickness of 600. The thickness is formed. Finally, a layer with a thickness of 10 is formed on top of the electron transport layer. After forming an electron injection layer by thickly depositing lithium fluoride (LiF), a 1,200-degree latitude layer is then applied over the electron injection layer. Aluminum (Al) is vapor-deposited to a certain thickness to form a cathode, thereby manufacturing organic electroluminescent devices.

[0278] On the other hand, all the organic compounds required for OLED device fabrication are processed according to the specific materials at 10... -8 10 -6 The material is purified by vacuum sublimation under torsion for use in the manufacture of OLEDs.

[0279]

[0280] Experimental Example 2-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Element For the organic electroluminescent element fabricated as described above, the electroluminescence (EL) characteristics were measured using a McScience M7000. Based on these measurements, lifetime measurement was performed using a McScience M6000 lifetime measurement device at a reference luminance of 3,500 cd / m². 2 The lifetime T is the time it takes for the brightness to reach 95% of its initial brightness. 95 .

[0281] The driving voltage, luminous efficiency, and lifetime (T) of the green organic light-emitting element manufactured by the aforementioned method were measured. 95 The results are shown in Table 7.

[0282] Table 7

[0283]

[0284] [Compare compounds]

[0285] As can be seen from the results in Table 7, compared with Comparative Examples 10 to 18, the organic light-emitting elements, namely Examples 64 to 126, which use the heterocyclic compound represented by the chemical formula 1 as the charge generation layer material of the 2-stacked white organic electroluminescent element of the present invention, exhibited low driving voltage, significantly improved lifetime and luminous efficiency.

[0286] The heterocyclic compound represented by Formula 1 of the present invention has a core structure with suitable electron transport capability. It simultaneously possesses functional groups of Formula 2 (phenanthroline), Formula 3 (phosphine oxide), Formula 4 (terpyridine), or Formula 5 (terpyridine), thus exhibiting a suitable LUMO level. Furthermore, these functional groups are characterized by their ability to bind with metals such as Li and Yb used for N-type charge generation layers. Due to this structural feature, electrons formed in the N-type charge generation layer can be readily injected into the electron transport layer.

[0287] Therefore, it is believed that by doping the heterocyclic compound represented by the present invention with an alkali metal or alkaline earth metal to form interstitial states within the N-type charge generation layer, electrons generated from the P-type charge generation layer can be easily injected into the electron transport layer through the interstitial states formed within the N-type charge generation layer. For this reason, it is determined that the driving voltage of the organic light-emitting element is reduced and the efficiency and lifetime are improved. Therefore, based on the reasons shown above, it is understood that the heterocyclic compound represented by the present invention can improve electron transport characteristics and bonding stability with the metal in the N-type charge generation layer to achieve low driving voltage, improved luminous efficiency, and longer lifetime.

[0288] (Explanation of reference numerals in the attached image) 100: Substrate 200: Anode 300: Organic layer 301: Hole Injection Layer 302: Hole transport layer 303: Emissive layer 304: Cavity Blocking Layer 305: Electron Transport Layer 306: Electron Injection Layer 400: Cathode

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, X is O; or S, R1 to R6 may be the same as or different from each other, and are each independently selected from hydrogen; deuterium; 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; -SiR101R102R103 ; -NR101R102; the following chemical formula 2; the following chemical formula 3; the following chemical formula 4; and the following chemical formula 5, wherein two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl. Any one of R1, R4, and R6 is any one of the following chemical formulas 2 to 5. Where 'a' is an integer from 0 to 3, and when 'a' is 2 or greater, R2 is either the same or different from each other. b is an integer from 0 to 3. When b is 2 or greater, R5 is either the same or different from each other. [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] In the chemical formulas 2 to 5, R11 to R20 may be the same as or different from each other, and are each independently selected from hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 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. The groups -SiR201R202R203 and -NR201R202, or two or more adjacent groups, are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R201, R202, and R203 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl. The d is an integer from 0 to 6. When d is 2 or greater, R12 are either the same or different from each other. h is an integer from 0 to 4. When h is 2 or greater, R15 are either the same or different from each other. Where i is an integer from 0 to 2, when i is greater than 2, R16 are either the same or different from each other. j is an integer from 0 to 4. When i is greater than or equal to j, R17 are either the same or different from each other. The value of l is an integer from 0 to 3. When l is 2 or greater, R18 may be the same or different from each other. m is an integer from 0 to 2. When m is greater than 2, R19 are either the same or different from each other. The n is an integer from 0 to 4. When n is 2 or more, R20 is either the same or different from each other. The Ar1 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. The L1 to L4 may be the same as or different from each other, and each is independently directly bonded; substituted or unsubstituted C6 to C60 arylene groups; or substituted or unsubstituted C2 to C60 heteroarylene groups. c is an integer from 0 to 5. When c is greater than 2, L1 values ​​are either the same or different. The value of e is an integer from 0 to 5. When e is greater than 2, L2 values ​​are either the same or different from each other. k is an integer from 0 to 5. When k is 2 or greater, L3 are either the same or different from each other. The value of o is an integer from 0 to 5. When o is 2 or higher, L4 are either the same or different from each other.

2. The heterocyclic compound according to claim 1, wherein, R1, R4, and R6 may be the same as or different from each other, and each is independently hydrogen; deuterium; chemical formula 2; chemical formula 3; chemical formula 4; or chemical formula 5. Any one of R1, R4, and R6 is any one of the chemical formulas 2 to 5, and the others are the same as or different from each other, and are each independently hydrogen; or deuterium.

3. The heterocyclic compound according to claim 1, wherein, R2, R3, and R5 may be the same as or different from each other, and each may be hydrogen or deuterium.

4. The heterocyclic compound according to claim 1, wherein, R13 and R14 may be the same as or different from each other, and each is 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.

5. The heterocyclic compound according to claim 1, wherein, Heterocyclic compounds represented by Chemical Formula 1 are represented by any one of the following Chemical Formulas 1-1 to 1-12: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] [Chemical Formulas 1-5] [Chemical Formulas 1-6] [Chemical Formulas 1-7] [Chemical Formulas 1-8] [Chemical Formulas 1-9] [Chemical Formulas 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12] In the chemical formulas 1-1 to 1-12, X, R1 to R6, a, and b are defined in the same way as in chemical formula 1. The definitions of L1, R11, R12, c, and d are the same as those of chemical formula 2. The definitions of L2, R13, R14, and e are the same as those of chemical formula 3. The definitions of L3, R15 to R17, and h to k are the same as those of chemical formula 4. The L4, R18 to R20, and l to o are defined in the same way as in chemical formula 5.

6. The heterocyclic compound according to claim 1, wherein, The heterocyclic compound represented by the chemical formula 1 does not contain deuterium as a substituent, or the deuterium content relative to the total number of hydrogen and deuterium atoms is 1% to 100%.

7. The heterocyclic compound according to claim 1, wherein, The heterocyclic compound represented by the stated chemical formula 1 is represented by any one of the following compounds: 。 8. An organic light-emitting element, comprising: First electrode; The second electrode is disposed opposite to the first electrode; as well as One or more organic layers are disposed between the first electrode and the second electrode. One or more of the organic layers comprise any one of the heterocyclic compounds according to claims 1 to 7.

9. The organic light-emitting element according to claim 8, wherein, The organic layer includes an electron transport layer. The electron transport layer includes the heterocyclic compound.

10. The organic light-emitting element according to claim 8, wherein, The organic light-emitting element further includes one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole auxiliary layer, and a hole blocking layer.

11. The organic light-emitting element according to claim 8, wherein, The organic light-emitting element includes: First electrode; A first stacked component is disposed on the first electrode and includes a first light-emitting layer; A charge generation layer is disposed on the first stack; A second stacked component, disposed on the charge generation layer, and including a second light-emitting layer; and The second electrode is disposed on the second stack.

12. The organic light-emitting element according to claim 11, wherein, The charge-generating layer includes the heterocyclic compound.

13. The organic light-emitting element according to claim 11, wherein, The charge generation layer is an N-type charge generation layer. The N-type charge-generating layer includes the heterocyclic compound.

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