Heterocyclic compounds, organic light emitting element including the same, and composition of organic material layer of organic light emitting element

Abstract

Provided are: a heterocyclic compound capable of significantly improving the lifespan, efficiency, electrochemical stability, and thermal stability of an organic light emitting element; an organic light emitting element including the heterocyclic compound in an organic material layer; and a composition of an organic material layer.

Description

[0001] This application claims priority and benefits to Korean Patent Application No. 10-2020-0093407, filed on July 27, 2020, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0002] This specification relates to a heterocyclic compound, an organic light-emitting element including the same, and a composition of an organic material layer of the organic light-emitting element. Background Technology

[0003] Electroluminescent elements are self-emissive display elements with advantages such as wide viewing angle, high response speed, and excellent contrast.

[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 this structure, electrons and holes injected from the two electrodes combine and pair in the organic thin film, and emit light as they annihilate. The organic thin film can be formed as a single layer or multiple layers as needed.

[0005] Organic thin film materials can possess light-emitting properties as needed. For example, as materials for organic thin films, compounds capable of forming a light-emitting layer independently can be used, or compounds capable of functioning as the host or dopant of a light-emitting layer based on a host dopant can be used. In addition, compounds capable of functioning as hole injection, hole transport, electron blocking, and electron transport can also be used as materials for organic thin films.

[0006] To improve the performance, lifespan, or efficiency of organic light-emitting elements, there has always been a need to develop organic thin film materials.

[0007] <Previous Technical Documents>

[0008] U.S. Patent No. 4,356,429 Summary of the Invention

[0009] Technical issues

[0010] This disclosure relates to providing a heterocyclic compound and an organic light-emitting element comprising the same.

[0011] Technical solutions

[0012] One embodiment of this application provides a heterocyclic compound represented by the following chemical formula 1.

[0013] [Chemical Formula 1]

[0014]

[0015] In chemical formula 1,

[0016] X1 and X2 may be the same as or different from each other, and each can be O or S independently.

[0017] L1 and L2 may be the same or different from each other, and each is an independent direct bond; substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms, and m and n are each independently 0 or 1.

[0018] Ar1 and Ar2 may be the same as or different from each other, and are each independently selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 60 carbon atoms and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms, or two or more adjacent groups bonded to each other to form substituted or unsubstituted aliphatic or aromatic hydrocarbon rings or heterocycles.

[0019] R1 to R4 may be the same or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 6 to 60 carbon atoms, a to d are each an integer from 0 to 3, and when a to d are each 2 or greater than 2, the substituents in parentheses are the same as each other, and

[0020] N-Het is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 1 to 60 carbon atoms, and includes one or more N atoms.

[0021] Another embodiment of this application provides an organic light-emitting element, the organic light-emitting element including a first electrode, a second 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 a heterocyclic compound represented by chemical formula 1.

[0022] Another embodiment of this application provides a composition of an organic material layer for an organic light-emitting element, the composition comprising a heterocyclic compound represented by chemical formula 1 and a heterocyclic compound represented by chemical formula 13 or chemical formula 14.

[0023] Beneficial effects

[0024] According to one embodiment of this application, a heterocyclic compound can be used as a material for the organic material layer of an organic light-emitting element (OLED). The heterocyclic compound can be used as a material for hole injection layers, hole transport layers, light-emitting layers, electron transport layers, electron injection layers, charge generation layers, etc., in the OLED. Specifically, a heterocyclic compound represented by Chemical Formula 1 can be used as a material for the light-emitting layer of the OLED. Furthermore, using a heterocyclic compound represented by Chemical Formula 1 in an OLED can reduce the driving voltage of the element, improve light efficiency, and enhance the lifetime properties of the element through the thermal stability of the compound. Attached Figure Description

[0025] Figures 1 to 3 These are schematic diagrams illustrating the stacked structure of an organic light-emitting element according to one embodiment of this application.

[0026] Explanation of icon numbers

[0027] 100:Substrate

[0028] 200: Anode

[0029] 300: Organic material layer

[0030] 301: Hole Injection Layer

[0031] 302: Hole transport layer

[0032] 303: Emissive layer

[0033] 304: Cavity Blocking Layer

[0034] 305: Electron Transport Layer

[0035] 306: Electron Injection Layer

[0036] 400: Cathode Detailed Implementation

[0037] This application will be described in detail below.

[0038] One embodiment of this application provides a heterocyclic compound represented by the following chemical formula 1.

[0039] [Chemical Formula 1]

[0040]

[0041] In chemical formula 1,

[0042] X1 and X2 may be the same as or different from each other, and each can be O or S independently.

[0043] L1 and L2 may be the same or different from each other, and each is an independent direct bond; substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms, and m and n are each independently 0 or 1.

[0044] Ar1 and Ar2 may be the same as or different from each other, and are each independently selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 60 carbon atoms and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms, or two or more adjacent groups bonded to each other to form substituted or unsubstituted aliphatic or aromatic hydrocarbon rings or heterocycles.

[0045] R1 to R4 may be the same or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 6 to 60 carbon atoms, a to d are each an integer from 0 to 3, and when a to d are each 2 or greater than 2, the substituents in parentheses are the same as each other, and

[0046] N-Het is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 1 to 60 carbon atoms, and includes one or more N atoms.

[0047] The compound represented by chemical formula 1 is replaced by a carbazole or amine with a strong electron-donating ability, thereby having a high highest occupied molecular orbital (HOMO) level, and therefore, when used as a material (specifically a dopant material) for the light-emitting layer of an organic light-emitting element, it can help hole transfer.

[0048] Furthermore, the compound represented by Formula 1 has a structure in which the lowest unoccupied molecular orbital (LUMO) is extended, thereby enhancing electron mobility and stabilizing electrons. Therefore, when the compound represented by Formula 1 is used in organic light-emitting devices, the device efficiency and lifetime can be improved.

[0049] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and 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), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0050] In this specification, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; cyano; straight-chain or branched alkyl having 1 to 60 carbon atoms; straight-chain or branched alkenyl having 2 to 60 carbon atoms; straight-chain or branched alkynyl having 2 to 60 carbon atoms; monocyclic or polycyclic cycloalkyl having 3 to 60 carbon atoms; monocyclic or polycyclic heterocyclic alkyl having 2 to 60 carbon atoms; monocyclic or polycyclic aryl having 6 to 60 carbon atoms; monocyclic or polycyclic heteroaryl having 2 to 60 carbon atoms; -SiRR'R"; -P(=O) RR'; an alkylamine having 1 to 20 carbon atoms; a monocyclic or polycyclic arylamine having 6 to 60 carbon atoms; and a monocyclic or polycyclic heteroarylamine having 2 to 60 carbon atoms, either unsubstituted or substituted with a substituent connected to two or more substituents selected from the above substituents, or unsubstituted, and R, R' and R" may be the same as or different from each other, and each independently is a substituted or unsubstituted alkyl having 1 to 60 carbon atoms; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms.

[0051] In this specification, "where no substituent is specified in the chemical formula or compound structure" refers to the bond between hydrogen and carbon atoms. However, due to deuterium ( 2 H is an isotope of hydrogen, therefore some hydrogen atoms can be deuterium.

[0052] In one embodiment of this application, "where no substituent is specified in the 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 as an isotope, and in this document, the deuterium content may be 0% to 100%.

[0053] In one embodiment of this application, when "no substituents are specified in the chemical formula or compound structure", hydrogen and deuterium can be mixed in the compound when deuterium is not explicitly excluded (e.g., the deuterium content is 0%, the hydrogen content is 100%, or all substituents are hydrogen).

[0054] In one embodiment of this application, deuterium is an isotope of hydrogen, an element having a deuterium nucleus formed by one proton and one neutron, and can be represented as hydrogen-2, and its element symbol can also be written as D or 2 H.

[0055] In one embodiment of this application, an isotope refers to an atom having the same atomic number (Z) but different mass numbers (A), and can also be interpreted as an element having the same number of protons but different numbers of neutrons.

[0056] In one embodiment of this application, when the total number of substituents that a basic compound may have is defined as T1, and the number of a particular substituent is defined as T2, the meaning of the content T% of the particular substituent can be defined as T2 / T1×100=T.

[0057] In other words, in one instance, in the case of... The 20% deuterium content in a phenyl group indicates that the total number of substituents that the phenyl group may have is 5 (T1 in the formula), and the number of deuterium substituents is 1 (T2 in the formula). In other words, a 20% deuterium content in a phenyl group can be represented by the following structural formula.

[0058]

[0059] Furthermore, in one embodiment of this application, "the deuterium content of the phenyl is 0%" may refer to a phenyl that does not contain deuterium atoms, that is, a phenyl with 5 hydrogen atoms.

[0060] In this specification, halogen may be fluorine, chlorine, bromine or iodine.

[0061] In this specification, alkyl groups include straight-chain or branched alkyl groups having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in an alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tributyl, dibutyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tripentyl, 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, tri-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0062] In this specification, alkenyl groups include straight-chain or branched alkenyl groups having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in an alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples 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, stilbene, styrene, etc., but are not limited thereto.

[0063] In this 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.

[0064] In this specification, the alkoxy group may be a straight-chain, 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 may include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tributoxy, dibutoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc.

[0065] In this specification, cycloalkyl includes monocyclic or polycyclic cycloalkyl groups having 3 to 60 carbon atoms, and may be further substituted with other substituents. Polycyclic refers to a group in which the cycloalkyl group is directly attached to or fused with other cyclic groups. Other cyclic groups may be cycloalkyl, but may also be different types of cyclic groups, such as heterocycloalkyl, aryl, and heteroaryl. The number of carbon groups in a cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples 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.

[0066] In this specification, heterocyclic alkyl groups include O, S, Se, N, or Si as heteroatoms, and include monocyclic or polycyclic heterocyclic alkyl groups having 2 to 60 carbon atoms, and may be further substituted with other substituents. Polycyclic refers to a group in which the heterocyclic alkyl group is directly attached to or fused with other cyclic groups. Other cyclic groups may be heterocyclic alkyl groups, but may also be different types of cyclic groups, such as cycloalkyl, aryl, and heteroaryl. The number of carbon atoms in a heterocyclic alkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0067] In this specification, aryl groups include monocyclic or polycyclic aryl groups having 6 to 60 carbon atoms, and may be further substituted with other substituents. Polycyclic refers to a group in which the aryl group is directly attached to or fused with other cyclic groups. Other cyclic groups may be aryl, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl, and heteroaryl. Aryl groups include spirocyclic groups. The number of carbon atoms in an 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, terphenyl, naphthyl, anthracene, etc. The group includes, but is not limited to, phenanthrene, perylene, fluoranthracene, dithionylene, fenylene, pyrene, fused tetraphenyl, fused pentaphenyl, fluorenyl, indene, acenaphthene, benzofluorenyl, spirodifluorenyl, 2,3-dihydro-1H-indene, and its fused cyclic groups.

[0068] In this specification, the phosphine oxide group is represented by -P(=O)R101R102, and R101 and R102 may be the same as or different from each other, and may each be an independent substituent formed from at least one of hydrogen, deuterium, halogen, alkyl, alkenyl, alkoxy, cycloalkyl, aryl, and heterocyclic groups. Specific examples of phosphine oxide groups may include, but are not limited to, diphenylphosphine oxide, dinaphthylphosphine oxide, etc.

[0069] In this specification, silyl is a substituent containing Si, with a Si atom directly attached as a free radical, and is represented by -SiR104R105R106. R104 to R106 may be the same as or different from each other, and may each be an independent substituent formed from at least one of hydrogen; deuterium; halogen; alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and heterocyclic. Specific examples of silyl groups may include, but are not limited to, trimethylsilyl, triethylsilyl, tributyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc.

[0070] In this specification, the fluorene group may be substituted, and adjacent substituents may bond to each other to form a ring.

[0071] In this specification, a spirocyclic group is a group comprising a spirocyclic structure and may have 15 to 60 carbon atoms. For example, a spirocyclic group may include a structure in which a 2,3-dihydro-1H-indenyl or cyclohexyl spirocyclic bond is to a fluorenyl group. Specifically, a spirocyclic group may include any of the groups with the following structural formulas.

[0072]

[0073] In this specification, heteroaryl groups include S, O, Se, N, or Si as heteroatoms, and include monocyclic or polycyclic heteroaryl groups having 2 to 60 carbon atoms, and may be further substituted with other substituents. Herein, polycyclic means a group in which the heteroaryl group is directly attached to or fused with other cyclic groups. Herein, the other cyclic groups may be heteroaryl, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl, and aryl. The number of carbon atoms in a 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, pyrroloyl, pyrimidinyl, pyridazinyl, furanyl, thiopheneyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazolyl, oxadiazolyl, thiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiaranyl, diazinyl, oxazinyl, thiazolyl, dioxinylgroup, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, isoquinazolinyl, quinazolinyl, quinazolinyl (group), naphthidyl, acridineyl, phenanthridineyl, imidazopyridyl, diazanaphthyl, triazaindyl, indoleyl, benzothiazolyl, benzoxazolyl, benzoimidazolyl, benzothiophene, benzofuranyl, dibenzothiophene, dibenzofuranyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, phenazinyl, dibenzosilyl group), spirocyclic di(dibenzosilicyclopentadienyl), dihydrophenazinyl, phenoxazinyl, phenanthridine, imidazopyridyl, thiophene, indolo[2,3-a]carbazole, indolo[2,3-b]carbazole, indololinyl, 10,11-dihydro-dibenzo[b,f]-nitroheptenyl, 9,10-dihydroacridyl, phenolazinyl, phenoxazinyl, phthalazinyl, naphthalene Pyridyl, benzylinyl, benzo[c][1,2,5]thiadiazolyl, 5,10-dihydrobenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]inzolyl, pyrido[1,2-a]imidazo[1,2-e]dihydroindoleyl, 5,11-dihydroindodin[1,2-b]carbazolyl, etc., but not limited to these.

[0074] 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 although not particularly limited thereto, the number of carbon atoms is preferably from 1 to 30. Specific examples of the amino group may include, but are not limited to, methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, diphenylamino, anthraceneamino, 9-methyl-anthraylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenyltolylamino, triphenylamino, biphenylnaphthylamino, phenylbiphenylamino, biphenylfluorenylamino, phenylbitriphenylamino, biphenylbitriphenylamino, etc.

[0075] In this specification, aryl(II) means an aryl group having two bonding sites, i.e., a divalent group. Except that each of them is divalent, the above-described description of para-aryl(II) can be applied to them. Furthermore, heteroaryl(II) means a heteroaryl group having two bonding sites, i.e., a divalent group. Except that each of them is divalent, the above-described description of para-heteroaryl(II) can be applied to them.

[0076] In this specification, "adjacent" groups may mean a substituent that replaces an atom directly bonded to the atom replaced by the corresponding substituent, a substituent spatially closest to the corresponding substituent, or another substituent that replaces the atom replaced by the corresponding substituent. For example, two substituents that replace adjacent positions in a benzene ring, and two substituents that replace the same carbon atom in an aliphatic ring, can be understood as "adjacent" groups.

[0077] According to one embodiment of this application, the heterocyclic compound is represented by Chemical Formula 1. More specifically, through its core structure and structural properties having the substituents described above, the heterocyclic compound represented by Chemical Formula 1 can be used as a material for the organic material layer of an organic light-emitting element.

[0078] In one embodiment of this application, the heterocyclic compound represented by Formula 1 may have a deuterium content of 0% to 100%.

[0079] In one embodiment of this application, the heterocyclic compound represented by Formula 1 may have a deuterium content greater than 10% and less than or equal to 100%.

[0080] In one embodiment of this application, X1 and X2 of chemical formula 1 may be the same as or different from each other, and may each be O or S independently.

[0081] In another embodiment, X1 and X2 are 0.

[0082] In another embodiment, X1 and X2 are S.

[0083] In another embodiment, in chemical formula 1, X1 is O and X2 is S.

[0084] In another embodiment, in chemical formula 1, X1 is S and X2 is O.

[0085] In one embodiment of this application, L1 and L2 of Formula 1 may be the same as or different from each other and may each be a direct bond independently; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0086] In one embodiment of this application, L1 and L2 may be the same as or different from each other and may each be a direct bond; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0087] In one embodiment of this application, L1 and L2 may be the same or different from each other and may each be a direct bond; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0088] In one embodiment of this application, L1 may be a direct bond; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0089] In another embodiment, L1 is a direct bond.

[0090] In another embodiment, L1 is a phenylene oxide.

[0091] In one embodiment of this application, L2 may be a direct bond; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0092] In another embodiment, L2 is a direct bond.

[0093] In another embodiment, L2 is a phenylene oxide.

[0094] In one embodiment of this application, Ar1 and Ar2 of Formula 1 may be the same as or different from each other, and each is independently selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 60 carbon atoms and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms, or two or more adjacent groups may be bonded to each other to form substituted or unsubstituted aliphatic or aromatic hydrocarbon rings or heterocycles.

[0095] In one embodiment of this application, Ar1 and Ar2 may be the same as or different from each other, and each is independently selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 40 carbon atoms and substituted or unsubstituted heteroaryl groups having 2 to 40 carbon atoms, or two or more adjacent groups may be bonded to each other to form substituted or unsubstituted aliphatic or aromatic hydrocarbon rings or heterocycles.

[0096] In one embodiment of this application, Ar1 and Ar2 may be the same or different from each other, and each is independently selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 20 carbon atoms and substituted or unsubstituted heteroaryl groups having 2 to 20 carbon atoms, or two or more adjacent groups may be bonded to each other to form substituted or unsubstituted aliphatic or aromatic hydrocarbon rings or heterocycles.

[0097] In one embodiment of this application, R1 to R4 of Formula 1 may be the same or different from each other, and may each be hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 6 to 60 carbon atoms.

[0098] In another embodiment, R1 to R4 are hydrogen; or deuterium.

[0099] In another embodiment, R1 to R4 are hydrogen.

[0100] In another embodiment, R1 to R4 are deuterium.

[0101] In one embodiment of this application, a to d of chemical formula 1 are each integers from 0 to 3, and when a to d are each 2 or greater than 2, the substituents in parentheses may be the same to each other.

[0102] In another embodiment, a is 0.

[0103] In another embodiment, a is 1.

[0104] In another embodiment, a is 2.

[0105] In another embodiment, a is 3.

[0106] In one embodiment of this application, when a is 2 or greater than 2, the substituents in the parentheses are the same to each other.

[0107] In another embodiment, b is 0.

[0108] In another embodiment, b is 1.

[0109] In another embodiment, b is 2.

[0110] In another embodiment, b is 3.

[0111] In one embodiment of this application, when b is 2 or greater than 2, the substituents in the parentheses are the same to each other.

[0112] In another embodiment, c is 0.

[0113] In another embodiment, c is 1.

[0114] In another embodiment, c is 2.

[0115] In another embodiment, c is 3.

[0116] In one embodiment of this application, when c is 2 or greater than 2, the substituents in the parentheses are the same to each other.

[0117] In another embodiment, d is 0.

[0118] In another embodiment, d is 1.

[0119] In another embodiment, d is 2.

[0120] In another embodiment, d is 3.

[0121] In one embodiment of this application, when d is 2 or greater than 2, the substituents in parentheses are the same to each other.

[0122] In one embodiment of this application, chemical formula 1 may be represented by any of the following chemical formulas 1-1 to 1-4.

[0123] [Chemical Formula 1-1]

[0124]

[0125] [Chemical Formula 1-2]

[0126]

[0127] [Chemical Formulas 1-3]

[0128]

[0129] [Chemical Formulas 1-4]

[0130]

[0131] In chemical formulas 1-1 to 1-4

[0132] L11 and L21 may be the same as or different from each other, and each is an independent direct bond; substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms, and m1 and n1 are each independently 0 or 1.

[0133] Ar11 and Ar22 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0134] X3 and X4 are each independently O; S; CRaRb or NRc, Ra and Rb may be the same as or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and Rc is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0135] R5 to R12 and Rp may be the same or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, where p is an integer from 0 to 2, and when p is 2, the substituents in parentheses are the same as each other, and

[0136] X1, X2, R1 to R4, N-Het, and a to d have the same definitions as in Formula 1.

[0137] In one embodiment of this application, L11 and L21 may be the same as or different from each other, and may each be a direct bond independently; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0138] In one embodiment of this application, L11 and L21 may be the same as or different from each other, and may each be a direct bond independently; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0139] In one embodiment of this application, L11 and L21 may be the same as or different from each other, and may each be a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted naphthylene.

[0140] In one embodiment of this application, L11 and L21 may be the same as or different from each other, and may each be a direct bond; phenylene; biphenylene; or naphthylene.

[0141] In one embodiment of this application, L11 is a direct key.

[0142] In one embodiment of this application, L11 is phenylene.

[0143] In one embodiment of this application, L11 is a biphenylene oxide.

[0144] In one embodiment of this application, L11 is naphthylene.

[0145] In one embodiment of this application, L21 is a direct key.

[0146] In one embodiment of this application, L21 is phenylene.

[0147] In one embodiment of this application, L21 is a biphenylene oxide.

[0148] In one embodiment of this application, L21 is a naphthylene group.

[0149] In one embodiment of this application, Ar11 and Ar22 may be the same as or different from each other, and may each be independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0150] In one embodiment of this application, Ar11 and Ar22 may be the same as or different from each other, and may each be independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0151] In one embodiment of this application, Ar11 and Ar22 may be the same as or different from each other, and may each be independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0152] In one embodiment of this application, Ar11 and Ar22 may be the same as or different from each other, and may each be independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzothiophene; or a substituted or unsubstituted dibenzofuranyl.

[0153] In one embodiment of this application, Ar11 and Ar22 may be the same as or different from each other, and may each be independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; an unsubstituted or substituted fluorenyl group selected from one or more of the group consisting of phenyl and alkyl groups having 1 to 10 carbon atoms; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted dibenzofuran group.

[0154] In one embodiment of this application, Ar11 and Ar22 may be the same as or different from each other, and may each be independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; an unsubstituted or substituted fluorenyl group selected from one or more of the group consisting of phenyl and methyl; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted dibenzofuran group.

[0155] In one embodiment of this application, Ar11 and Ar22 may be the same as or different from each other, and may each be independently phenyl; biphenyl; naphthyl; unsubstituted or substituted fluorenyl selected from one or more of the group consisting of phenyl and methyl; substituted or unsubstituted dibenzothiophene; or substituted or unsubstituted dibenzofuranyl.

[0156] In one embodiment of this application, m1 and n1 can each be 0 or 1 independently.

[0157] In one embodiment of this application, R5 to R12 and Rp may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, p is an integer from 0 to 2, and when p is 2, the substituents in parentheses may be the same as each other.

[0158] In one embodiment of this application, R5 to R12 and Rp may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano group; aryl group having 6 to 20 carbon atoms that is unsubstituted or deuterated; or heteroaryl group having 2 to 20 carbon atoms that is unsubstituted or deuterated, p is an integer from 0 to 2, and when p is 2, the substituents in parentheses may be the same as each other.

[0159] In one embodiment of this application, R5 to R12 and Rp may be the same as or different from each other, and each is independently hydrogen; or deuterium, where p is an integer from 0 to 2, and when p is 2, the substituents in parentheses may be the same as each other.

[0160] In one embodiment of this application, R5 to R12 and Rp are hydrogen.

[0161] In one embodiment of this application, R5 to R12 and Rp are deuterium.

[0162] In one embodiment of this application, X3 and X4 are each independently O; S; CRaRb; or NRc, Ra and Rb may be the same as or different from each other, and may each be independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and Rc may be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0163] In one embodiment of this application, X3 and X4 are O; S; CRaRb; or NRc, and Rc may be phenyl.

[0164] In one embodiment of this application, X3 is O.

[0165] In one embodiment of this application, X3 is S.

[0166] In one embodiment of this application, X3 is CRaRb, and Ra and Rb may be the same as or different from each other, and may each be independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0167] In one embodiment of this application, Ra and Rb may be the same as or different from each other, and each is independently a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

[0168] In one embodiment of this application, X3 is NRc and Rc is phenyl.

[0169] In one embodiment of this application, X4 is O.

[0170] In one embodiment of this application, X4 is S.

[0171] In one embodiment of this application, X4 is CRaRb, and Ra and Rb may be the same as or different from each other, and may each be independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0172] In one embodiment of this application, Ra and Rb may be the same as or different from each other, and each is independently a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

[0173] In one embodiment of this application, X4 is NRc and Rc is phenyl.

[0174] In one embodiment of this application, N-Het is a substituted or unsubstituted monocyclic or polycyclic heterocycle having 1 to 60 carbon atoms and including one or more N atoms.

[0175] In another embodiment, N-Het is a monocyclic or polycyclic heterocycle having 1 to 60 carbon atoms, which is unsubstituted or substituted with one or more substituents selected from the group consisting of aryl and heteroaryl groups, and includes one or more N atoms.

[0176] In another embodiment, N-Het is a monocyclic or polycyclic heterocycle having 1 to 60 carbon atoms, which is unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, diphenylfluorenyl, pyridyl, spirodifluorenyl and dibenzothiophene, and includes one or more N atoms.

[0177] In another embodiment, N-Het is a monocyclic or polycyclic heterocycle that is unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, diphenylfluorenyl, pyridyl, spirodifluorenyl and dibenzothiopheneyl, and includes one or more and three or fewer N.

[0178] In one embodiment of this application, N-Het is a substituted or unsubstituted monocyclic heterocycle and includes one or more N atoms.

[0179] In one embodiment of this application, N-Het is a substituted or unsubstituted divalent or higher-valent heterocycle and includes one or more N.

[0180] In one embodiment of this application, N-Het is a substituted or unsubstituted monocyclic or polycyclic heterocycle and includes two or more N atoms.

[0181] In one embodiment of this application, N-Het is a divalent or higher-valent polycyclic heterocycle comprising two or more N atoms.

[0182] In one embodiment of this application, N-Het may be an unsubstituted or phenyl-substituted pyrimidinyl group; an unsubstituted or substituted triazine group substituted with one or more substituents selected from the group consisting of phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, diphenylfluorenyl, pyridyl, spirodifluorenyl and dibenzothiopheneyl; an unsubstituted or phenyl-substituted benzimidazolyl group; an unsubstituted or substituted quinazoline group substituted with one or more substituents selected from the group consisting of phenyl and biphenyl; or an unsubstituted or phenyl-substituted phenanthroline group.

[0183] In one embodiment of this application, N-Het may be an unsubstituted or phenyl-substituted pyrimidinyl group; an unsubstituted or substituted triazine group substituted with one or more substituents selected from the group consisting of phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, diphenylfluorenyl, pyridyl, spirodifluorenyl and dibenzothiopheneyl; an unsubstituted or phenyl-substituted benzimidazolyl group; an unsubstituted or substituted quinazolinyl group substituted with one or more substituents selected from the group consisting of phenyl and biphenyl; or an unsubstituted or phenyl-substituted phenanthrolineyl group.

[0184] In one embodiment of this application, N-Het may be a group represented by any of the following chemical formulas 2 to 4.

[0185] [Chemical Formula 2]

[0186]

[0187] [Chemical Formula 3]

[0188]

[0189] [Chemical Formula 4]

[0190]

[0191] In chemical formulas 2 to 4

[0192] Y1 is CR12 or N, Y2 is CR13 or N, Y3 is CR14 or N, Y4 is CR15 or N, Y5 is CR16 or N, and at least one of Y1 to Y5 is N.

[0193] R12 to R16 and R17 to R22 may be 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 alkyl groups having 1 to 60 carbon atoms; substituted or unsubstituted alkenyl groups having 2 to 60 carbon atoms; substituted or unsubstituted alkynyl groups having 2 to 60 carbon atoms; substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms; substituted or unsubstituted cycloalkyl groups having 3 to 60 carbon atoms; substituted or unsubstituted heterocycloalkyl groups having 2 to 60 carbon atoms; substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; substituted or unsubstituted phosphine oxide groups; and substituted or unsubstituted amino groups, or two or more adjacent groups bonded together to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or heterocycle, and It is the site that is attached to chemical formula 1.

[0194] In one embodiment of this application, chemical formula 2 may be represented by one of chemical formulas 5 and 6. In this document, It is the site that is attached to L in chemical formula 1.

[0195] [Chemical Formula 5]

[0196]

[0197] [Chemical Formula 6]

[0198]

[0199] [Chemical Formula 7]

[0200]

[0201] [Chemical Formula 8]

[0202]

[0203] In chemical formula 5, one or more of Y1, Y3, and Y5 are N, and the others have the same definitions as in chemical formulas 5 and 8.

[0204] In chemical formula 6, one or more of Y1, Y2, and Y5 are N, and the others have the same definitions as in chemical formula 5.

[0205] In chemical formula 7, one or more of Y1 to Y3 are N, and the others have the same definitions as in chemical formula 5.

[0206] In chemical formula 8, one or more of Y1, Y2, and Y5 are N, and the others have the same definitions as in chemical formula 5.

[0207] X5 is O; or S.

[0208] R12, R14, and R23 through R26 may be the same as or different from each other, and each is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms; substituted or unsubstituted alkenyl groups having 2 to 60 carbon atoms; substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms; substituted or unsubstituted cycloalkyl groups having 3 to 60 carbon atoms; substituted or unsubstituted heterocycloalkyl groups having 2 to 60 carbon atoms; substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; substituted or unsubstituted heteroaryl groups having 6 to 60 carbon atoms; substituted or unsubstituted phosphine oxide groups; and substituted or unsubstituted amino groups, or two or more adjacent groups bonded together to form substituted or unsubstituted aliphatic or aromatic hydrocarbon rings or heterocycles.

[0209] In one embodiment of this application, chemical formula 5 may be selected from the structural formula of group A below.

[0210] [Group A]

[0211]

[0212] The substituents in the structural formula of group A have the same definitions as in chemical formula 5.

[0213] In one embodiment of this application, chemical formula 6 may be represented by the following chemical formula 9.

[0214] [Chemical Formula 9]

[0215]

[0216] The substituents in Formula 9 have the same definition as those in Formula 6.

[0217] In one embodiment of this application, chemical formula 7 may be represented by chemical formula 10.

[0218] [Chemical Formula 10]

[0219]

[0220] The substituents in Formula 10 have the same definition as those in Formula 7.

[0221] In one embodiment of this application, chemical formula 6 may be represented by the following chemical formula 11.

[0222] [Chemical Formula 11]

[0223]

[0224] In chemical formula 11,

[0225] R27 are identical or different from each other and are selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms; substituted or unsubstituted alkenyl groups having 2 to 60 carbon atoms; substituted or unsubstituted alkynyl groups having 2 to 60 carbon atoms; substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms; substituted or unsubstituted cycloalkyl groups having 3 to 60 carbon atoms; and substituted or unsubstituted cycloalkyl groups having 2 to 60 carbon atoms. The substituted or unsubstituted heterocyclic alkyl group; the substituted or unsubstituted aryl group having 6 to 60 carbon atoms; the substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; the substituted or unsubstituted phosphine oxide group; and the substituted or unsubstituted amino group, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or heterocycle, where e is an integer from 0 to 7, and when e is 2 or greater than 2, R27 are the same or different from each other.

[0226] In one embodiment of this application, chemical formula 8 may be represented by chemical formula 12.

[0227] [Chemical Formula 12]

[0228]

[0229] The substituents in Formula 12 have the same definition as those in Formula 8.

[0230] According to one embodiment of this application, chemical formula 1 Bonded to N-Het of Formula 1 and Formula 1 The bond positions are shown in group B below.

[0231] [Group B]

[0232]

[0233] In group B, * is N-Het or The positions of the bonds, and X1, X2, and N-Het have the same definitions as in Formula 1.

[0234] According to one embodiment of this application, chemical formula 1 Bonded to chemical formula 1 and chemical formula 1 The bond positions are shown in group C below.

[0235] [Group C]

[0236]

[0237] In group C, * is... The location of the bond, and X1, X2 and It has the same definition as in chemical formula 1.

[0238] More specifically, when Position 3 was replaced by N-Het and Position 3 was When replaced, the mobility and stability of holes and electrons can be further enhanced, and therefore, when the above-mentioned bonding sites are present, the lifetime of organic light-emitting elements can be further enhanced.

[0239] In this specification, the position of substitution refers to the position indicated by the numbers in the following chemical formulas A and B.

[0240] [Chemical Formula A]

[0241]

[0242] [Chemical Formula B]

[0243]

[0244] In chemical formulas A and B, X1 and X2 have the same definitions as in chemical formula 1, and each number indicates the position where a substituent is substituted.

[0245] Therefore, in the following chemical formula C, it can be described that The 4th position is replaced by a triazine group, and The 4th position is replaced by a carbazoyl group.

[0246] [Chemical formula C]

[0247]

[0248] According to one embodiment of this application, chemical formula 1 may be represented by any of the following compounds, but is not limited thereto.

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305] In the compounds represented by Formula 1 of this application, including specific examples, orbital domain breakage occurs around the N atom of carbazole, and the HOMO orbitals are typically localized to the carbazole. Localization refers to the relative concentration of the electron cloud on the carbazole.

[0306] When the HOMO orbital domain is delocalized more extensively as described above, hole mobility and stability may increase.

[0307] Furthermore, including specific examples, the dibenzofuran or dibenzothiophene of the compounds represented by Formula 1 of this application correspond to groups that affect the LUMO orbitals of heterocyclic groups containing N.

[0308] Therefore, the LUMO level of the compound can be adjusted according to the substitution position of the heterocyclic groups, including N-substituted dibenzofuran or dibenzothiophene. This means that the compound represented by Chemical Formula 1 of this application can be used as a material for organic light-emitting elements, specifically as a material for the light-emitting layer, and more specifically as a host material by appropriately adjusting the LUMO level according to the dopant and electron transfer layer (ETL) material in the organic light-emitting element. In other words, this means that when the dopant and electron transfer layer materials are changed, the host material needs to be changed according to the charge balance.

[0309] Specifically, when a compound with a low LUMO level is used as the material of the light-emitting layer, electrons can be easily injected into the dopant from the host, and when a compound with a high LUMO level is used as the material of the light-emitting layer, electrons can be easily injected into the host from the electron transport layer (ETL).

[0310] Furthermore, in the compounds represented by Formula 1 of this application, including specific examples, the dibenzofuran or dibenzothiophene substituted with amine or carbazole may be affected by the LUMO orbitals widely distributed in heterocyclic groups including N, thereby affecting the enhancement of electron mobility and stability.

[0311] Furthermore, when the compounds represented by Formula 1 of this application, including specific examples, have a broken structure based on the substitution positions of the amine or carbazole, the HOMO domains of the carbazole or amine are affected, and the HOMO level can be adjusted. This means that the compounds represented by Formula 1 of this application can be used as materials for organic light-emitting elements, specifically as materials for the light-emitting layer, and more specifically as host materials by appropriately adjusting the HOMO level based on the dopant and electron transport layer (ETL) materials. In other words, this means that when the dopant and electron transport layer materials are changed, the host material needs to be changed according to the charge balance.

[0312] Furthermore, by introducing various substituents into the structure of Formula 1, compounds possessing the 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 elements into the core structure, materials that meet the requirements of each organic material layer can be synthesized.

[0313] Furthermore, by introducing various substituents into the structure of Formula 1, the band gap can be precisely controlled, while simultaneously enhancing the properties at the interface between organic materials, and the application of the materials can be diversified.

[0314] Meanwhile, the heterocyclic compound possesses a high glass transition temperature (Tg) and excellent thermal stability. This increase in thermal stability becomes an important factor in providing driving stability for the device.

[0315] The heterocyclic compound according to one embodiment of this application can be prepared using a multi-step chemical reaction. First, some intermediate compounds are prepared, and the heterocyclic compound of Formula 1 can be prepared from said intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of this application can be prepared based on the preparation examples described later.

[0316] Another embodiment of this application provides an organic light-emitting element comprising a heterocyclic compound represented by chemical formula 1. The term "organic light-emitting element" can be used, for example, as "organic light-emitting diode," "OLED," "OLED element," and "organic electroluminescent element."

[0317] When manufacturing organic light-emitting elements, solution coating and vacuum deposition methods can be used to form heterocyclic compounds into organic material layers. In this article, solution coating methods refer to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but are not limited to these.

[0318] Specifically, an organic light-emitting element according to one embodiment of this application includes a first electrode, a second 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 a heterocyclic compound represented by Chemical Formula 1. When the organic material layers contain a heterocyclic compound represented by Chemical Formula 1, the organic light-emitting element exhibits excellent luminous efficiency and lifetime.

[0319] In one embodiment of this application, the first electrode may be an anode and the second electrode may be a cathode.

[0320] In another embodiment, the first electrode may be a cathode, and the second electrode may be an anode.

[0321] In one embodiment of this application, the organic light-emitting element may be a blue organic light-emitting element, and the heterocyclic compound according to Formula 1 may be used as a material for the blue organic light-emitting element.

[0322] In one embodiment of this application, the organic light-emitting element may be a green organic light-emitting element, and the heterocyclic compound according to Formula 1 may be used as a material for the green organic light-emitting element.

[0323] In one embodiment of this application, the organic light-emitting element may be a white organic light-emitting element, and the heterocyclic compound according to Formula 1 may be used as a material for the white organic light-emitting element.

[0324] In one embodiment of this application, the organic light-emitting element may be a red organic light-emitting element, and the heterocyclic compound according to Formula 1 may be used as a material for the red organic light-emitting element.

[0325] Furthermore, the organic material layer includes one or more light-emitting layers, and the light-emitting layers contain heterocyclic compounds represented by Formula 1. When the light-emitting layers in the organic material layer contain heterocyclic compounds represented by Formula 1, the organic light-emitting element exhibits superior luminous efficiency and lifetime.

[0326] Furthermore, in the organic light-emitting element of this application, the organic material layer contains a heterocyclic compound represented by chemical formula 1 as a first compound, and may also contain a heterocyclic compound represented by chemical formula 13 or chemical formula 14 as a second compound.

[0327] [Chemical Formula 13]

[0328]

[0329] [Chemical Formula 14]

[0330]

[0331] In chemical formulas 13 and 14

[0332] L3 is a direct bond; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms;

[0333] R28 to R31, Rd, and Re may be the same as or different from each other, and each is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms; substituted or unsubstituted alkenyl groups having 2 to 60 carbon atoms; substituted or unsubstituted alkynyl groups having 2 to 60 carbon atoms; substituted or unsubstituted alkoxy groups having 2 to 60 carbon atoms; substituted or unsubstituted cycloalkyl groups having 3 to 60 carbon atoms; substituted or unsubstituted heterocycloalkyl groups having 2 to 60 carbon atoms; substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; substituted or unsubstituted phosphino groups. ; and substituted or unsubstituted amino groups, or two or more adjacent groups bonded together to form a substituted or unsubstituted aromatic ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms, where r and s are integers from 0 to 7, and when r is 2 or greater than 2, Rd are the same or different from each other; when s is 2 or greater than 2, Re are the same or different from each other; e is an integer from 0 to 4; g and h are each an integer from 0 to 7; f is an integer from 0 to 2, and when e is 2 or greater than 2, R28 are the same or different from each other; when f is an integer of 2, R29 are the same or different from each other; when g is 2 or greater than 2, R30 are the same or different from each other; and when h is 2 or greater than 2, R31 are the same or different from each other.

[0334] Ar3 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0335] Ar4 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0336] R32 and R33 may be the same as or different from each other, and each may be independently a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0337] In one embodiment of this application, the heterocyclic compound represented by chemical formula 13 may have a deuterium content of 0% to 100%.

[0338] In one embodiment of this application, the heterocyclic compound represented by chemical formula 13 may have a deuterium content greater than 10% and less than or equal to 100%.

[0339] In one embodiment of this application, the heterocyclic compound represented by chemical formula 14 may have a deuterium content of 0% to 100%.

[0340] In one embodiment of this application, the heterocyclic compound represented by chemical formula 14 may have a deuterium content greater than 10% and less than or equal to 100%.

[0341] In one embodiment of this application, L3 may be a direct bond; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0342] In one embodiment of this application, L3 may be a direct bond; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0343] In another embodiment, L3 is a direct bond; or a substituted or unsubstituted phenylene oxide.

[0344] In one embodiment of this application, R28 to R31 are hydrogen.

[0345] In one embodiment of this application, R28 to R31 are deuterium.

[0346] In one embodiment of this application, Ar3 may be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0347] In one embodiment of this application, Ar3 may be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0348] In one embodiment of this application, Ar3 may be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0349] In another embodiment, Ar3 may be a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiopheneyl.

[0350] In another embodiment, Ar3 may be phenyl; biphenyl; fluorenyl substituted with one or more groups selected from the group consisting of alkyl groups having 1 to 10 carbon atoms; dibenzofuranyl; or dibenzothiophenyl.

[0351] In one embodiment of this application, Ar4 may be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0352] In one embodiment of this application, Ar4 may be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0353] In one embodiment of this application, Ar4 may be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0354] In another embodiment, Ar4 is a substituted or unsubstituted phenyl group.

[0355] In another embodiment, Ar4 is a phenyl group.

[0356] According to one embodiment of this application, chemical formula 13 may be represented by any of the following compounds, but is not limited thereto.

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363] In one embodiment of this application, Rd and Re may be the same as or different from each other, and may each be hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0364] In one embodiment of this application, Rd and Re may be the same as or different from each other, and may each be hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

[0365] In one embodiment of this application, Rd and Re may be the same as or different from each other, and may each be hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0366] In one embodiment of this application, Rd and Re may be the same as or different from each other, and may each be hydrogen; deuterium; substituted or unsubstituted phenyl; or substituted or unsubstituted biphenyl.

[0367] In one embodiment of this application, Rd and Re may be the same as or different from each other, and may each be hydrogen, deuterium, phenyl, or biphenyl independently.

[0368] In one embodiment of this application, Rd and Re may be the same as or different from each other, and may each be hydrogen or deuterium independently.

[0369] In one embodiment of this application, Rd and Re are hydrogen.

[0370] In one embodiment of this application, Rd and Re are deuterium.

[0371] In another embodiment, r is an integer from 0 to 7, and when r is 2 or greater than 2, Rd are the same or different from each other, and two or more adjacent Rd may bond to each other to form substituted or unsubstituted aliphatic or aromatic hydrocarbon rings or heterocycles.

[0372] In one embodiment of this application, R32 and R33 may be the same as or different from each other, and each is independently a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0373] In one embodiment of this application, R32 and R33 may be the same as or different from each other, and each is independently a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0374] In one embodiment of this application, R32 and R33 may be the same as or different from each other, and may each be independently a substituted or unsubstituted silyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted dibenzofuran group.

[0375] According to one embodiment of this application, chemical formula 14 may be represented by any of the following compounds, but is not limited thereto.

[0376]

[0377]

[0378]

[0379]

[0380]

[0381] Furthermore, the organic material layer includes one or more light-emitting layers, and the light-emitting layer contains a heterocyclic compound represented by Chemical Formula 1 as a first compound, and also contains a heterocyclic compound represented by Chemical Formula 13 or Chemical Formula 14 as a second compound. When the light-emitting layer in the organic material layer contains a heterocyclic compound represented by Chemical Formula 1, the organic light-emitting element has superior luminous efficiency and lifetime.

[0382] Furthermore, by introducing various substituents into structures of Formula 13 or Formula 14, compounds possessing the 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 elements into the core structure, materials that meet the requirements of each organic material layer can be synthesized.

[0383] Furthermore, by introducing various substituents into the structure of Formula 13 or Formula 14, the band gap can be precisely controlled, while simultaneously enhancing the properties at the interface between organic materials, and the application of the materials can be diversified.

[0384] Meanwhile, the heterocyclic compound possesses a high glass transition temperature (Tg) and excellent thermal stability. This increase in thermal stability becomes an important factor in providing driving stability for the device.

[0385] The heterocyclic compound according to one embodiment of this application can be prepared using a multi-step chemical reaction. First, some intermediate compounds are prepared, and the heterocyclic compound of formula 13 or formula 14 can be prepared from said intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of this application can be prepared based on the preparation examples described later.

[0386] Furthermore, the organic material layer includes one or more light-emitting layers, and the light-emitting layer further comprises one of a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 13. When the light-emitting layer in the organic material layer comprises one of a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 13, the organic light-emitting element exhibits superior luminous efficiency and lifetime due to the exciplex phenomenon.

[0387] Furthermore, the organic material layer includes one or more light-emitting layers, and the light-emitting layer further comprises one of a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 14. When the light-emitting layer in the organic material layer comprises one of a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 14, the organic light-emitting element exhibits superior luminous efficiency and lifetime due to the excitation of the miscible compound phenomenon.

[0388] In the organic light-emitting element of this application, the organic material layer includes a light-emitting layer, and the light-emitting layer may contain a heterocyclic compound as the host material of the light-emitting material.

[0389] In the organic light-emitting element of this application, the light-emitting layer may contain two or more host materials, and at least one of the host materials may contain a heterocyclic compound as the host material of the light-emitting material.

[0390] In the organic light-emitting element of this application, two or more host materials may be premixed and used as the light-emitting layer, and at least one of the two or more host materials may contain a heterocyclic compound as the host material of the light-emitting material.

[0391] Premixing refers to placing and mixing two or more host materials of the light-emitting layer in a supply source before depositing them onto the organic material layer.

[0392] In the organic light-emitting element of this application, the light-emitting layer may comprise two or more host materials, and each of the two or more host materials may include one or more p-type host materials and n-type host materials, and at least one of the host materials may comprise a heterocyclic compound as the host material for the light-emitting material. In this case, the organic light-emitting element can have excellent driving performance, efficiency, and lifetime.

[0393] The organic light-emitting element disclosed herein may further include one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole auxiliary layer, and a hole blocking layer.

[0394] In addition to using the aforementioned heterocyclic compounds to form the organic material layer, an organic light-emitting element according to an embodiment of this application can be manufactured using commonly used organic light-emitting element manufacturing methods and materials.

[0395] Furthermore, another embodiment of this application provides a composition of an organic material layer for an organic light-emitting element, the composition comprising a heterocyclic compound represented by chemical formula 1 and a heterocyclic compound represented by chemical formula 13 or chemical formula 14.

[0396] In another embodiment of this application, the heterocyclic compound represented by chemical formula 1 and the heterocyclic compound represented by chemical formula 13 or chemical formula 14 may have a weight ratio of 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1 or 1:2 to 2:1 in the composition; however, the weight ratio is not limited to these.

[0397] The specific descriptions of heterocyclic compounds represented by chemical formula 1 and compounds represented by chemical formula 13 or chemical formula 14 are the same as those provided above.

[0398] Figures 1 to 3The diagram illustrates the stacking sequence of electrodes and organic material layers in an organic light-emitting element according to one embodiment of this application. However, the scope of this application is not limited to these figures, and structures of organic light-emitting elements known in this art can also be used in this application.

[0399] Figure 1 This illustrates an organic light-emitting element in which an anode 200, an organic material layer 300, and a cathode 400 are continuously stacked on a substrate 100. However, the structure is not limited to this one, and other structures are also possible. Figure 2 As shown, an organic light-emitting element in which the cathode, organic material layer and anode are continuously stacked on the substrate can also be obtained.

[0400] Figure 3 This illustrates the case where the organic material layers are multiple. 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 layers other than the light-emitting layer may be excluded as needed, and other required functional layers may be added further.

[0401] In an organic light-emitting element according to one embodiment of this application, materials other than heterocyclic compounds of Formula 1 are shown below. However, these are for illustrative purposes only and are not intended to limit the scope of this application, and may be replaced by materials known in the art.

[0402] As anode materials, materials with relatively large work functions 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] (PEDT), polypyrrole, and polyaniline, etc., but not limited to these.

[0403] Materials with relatively small work functions can be used as cathode materials, 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; multilayer structure materials, such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0404] As hole injection materials, known hole injection materials can be used, and for example, phthalocyanine compounds, such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429; or star-shaped catalytic amine derivatives, 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) as conductive polymers with solubility, such as polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / poly(4-styrene sulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrene-sulfonate), etc.

[0405] As hole transport materials, 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.

[0406] As an electron transport material, 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, as well as polymeric and low-molecular-weight materials.

[0407] LiF is commonly used as an example of an electron-injection material in this technology; however, this application is not limited to this.

[0408] Red, green, or blue luminescent materials can be used, and two or more luminescent materials can be mixed and used as needed. Furthermore, fluorescent materials can also be used as luminescent materials; however, phosphorescent materials can also be used. As luminescent materials, materials that emit light by combining electrons and holes injected from the anode and cathode respectively can be used alone; however, materials having a host material and a dopant material that participate in luminescence together can also be used.

[0409] Depending on the materials used, an organic light-emitting element according to an embodiment of this application may be a top-emission type, a bottom-emission type, or a dual-emission type.

[0410] The heterocyclic compound according to one embodiment of this application can also be used in organic electronic components, including organic solar cells, organic photoconductors, organic transistors, etc., based on similar principles used in organic light-emitting elements.

[0411] The present specification will be described in more detail below with reference to examples; however, these are for illustrative purposes only, and the scope of this application is not limited thereto.

[0412] <Preparation Example>

[0413] <Preparation Example 1> Preparation of target compound 1-86

[0414]

[0415] 1) Preparation of compound 1-86-4

[0416] 3-Bromo-7-chlorodibenzo[b,d]furan (B) (16.8 g, 59.8 mmol / L (mM)), B(Pin)2 (22.8 g, 89.7 mM), Pd(dppf)Cl3 (2.2 g, 3.0 mM) and KOAc (17.6 g, 179.4 mM) were dissolved in 1,4-dioxane (300 mL) and refluxed for 12 hours. After the reaction was complete, the results were extracted by introducing distilled water and dichloromethane (DCM) at room temperature, and the solvent was removed using a rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:2) to obtain compound 1-86-4 (35.8 g, 82%). Hex refers to hexane.

[0417] 2) Preparation of compound 1-86-3

[0418] Compound 1-86-4 (35.8 g, 49.0 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (A) (15.7 g, 58.8 mM), Pd(PPh3)4 (2.8 g, 2.4 mM), and K2CO3 (13.5 g, 98.0 mM) were dissolved in 1,4-dioxane / H2O (600 mL / 120 mL) and refluxed for 12 hours. After the reaction was complete, the result was extracted by introducing distilled water and dichloromethane (DCM) at room temperature, and the solvent was removed using a rotary evaporator after drying the organic layer with MgSO4. The reaction material was recrystallized from methanol to obtain compound 1-86-3 (18.2 g, 86%).

[0419] 3) Preparation of compound 1-86-2

[0420] Compounds 1-86-3 (18.2 g, 41.9 mM), B(Pin)2 (16.0 g, 62.8 mM), Pd2(dba)3 (1.9 g, 2.1 mM), XPhos (2.0 g, 4.2 mM), and KOAc (12.3 g, 125.7 mM) were dissolved in 1,4-dioxane (300 mL) and refluxed for 12 hours. After the reaction was complete, the results were extracted by introducing distilled water and dichloromethane (DCM) at room temperature, and the solvent was removed using a rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:2) to obtain compound 1-86-2 (17.8 g, 81%).

[0421] 4) Preparation of compound 1-86-1

[0422] Compound 1-86-2 (17.8 g, 33.9 mM), 3-bromo-7-chlorodibenzo[b,d]furan(C) (11.4 g, 40.7 mM), Pd(PPh3)4 (2.0 g, 1.7 mM), and K2CO3 (9.3 g, 67.8 mM) were dissolved in 1,4-dioxane / H2O (300 mL / 60 mL) and refluxed for 12 hours. After the reaction was complete, the result was extracted by introducing distilled water and dichloromethane (DCM) at room temperature, and the solvent was removed using a rotary evaporator after drying the organic layer with MgSO4. The reaction material was recrystallized from methanol to obtain compound 1-86-1 (17.7 g, 87%).

[0423] 5) Preparation of target compound 1-86

[0424] Compound 1-86-1 (17.7 g, 29.5 mM), 9H-carbazole (D) (5.9 g, 35.4 mM), Pd2(dba)3 (1.4 g, 1.5 mM), XPhos (1.4 g, 3.0 mM), and NaOt-Bu (5.7 g, 59.0 mM) were dissolved in 1,4-dioxane (300 mL) and refluxed for 12 hours. After the reaction was complete, the results were extracted by introducing distilled water and dichloromethane (DCM) at room temperature, and the solvent was removed using a rotary evaporator after drying the organic layer with MgSO4. The reaction material was recrystallized from methanol to obtain the target compound 1-86 (19.2 g, 89%).

[0425] Except that intermediate A from Table 1 was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in Preparation Examples 1-2), intermediate B was used instead of 3-bromo-7-chlorodibenzo[b,d]furan in Preparation Example 1-1), intermediate C was used instead of 3-bromo-7-chlorodibenzo[b,d]furan in Preparation Examples 1-4), and intermediate D was used instead of 9H-carbazole in Preparation Examples 1-5, the target compounds in Table 1 were synthesized in the same manner as in Preparation Example 1.

[0426] [Table 1]

[0427]

[0428]

[0429]

[0430]

[0431]

[0432] <Preparation Example 2> Preparation of target compound 5-2

[0433]

[0434] 1) Preparation of compound 5-2-2

[0435] 2-Bromodibenzo[b,d]thiophene (4.2 g, 15.8 mM), 9-phenyl-9H,9'H-3,3'-biscarbazole (6.5 g, 15.8 mM), CuI (3.0 g, 15.8 mM), trans-1,2-diaminocyclohexane (1.9 mL, 15.8 mM), and K3PO4 (3.3 g, 31.6 mM) were dissolved in 1,4-dioxane (100 mL) and refluxed for 24 hours. After the reaction was complete, the results were extracted by introducing distilled water and dichloromethane (DCM) at room temperature, and the solvent was removed using a rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to obtain compound 5-2-2 (7.9 g, 85%).

[0436] 2) Preparation of compound 5-2-1

[0437] 2.5 mol / L (M) n-butyllithium (n-BuLi) (7.4 mL, 18.6 mmol) was added dropwise to a mixture of compound 5-2-1 (8.4 g, 14.3 mmol) and tetrahydrofuran (THF) (100 mL) at -78 °C, and the mixture was stirred at room temperature for 1 h. Trimethyl borate (4.8 mL, 42.9 mmol) was added dropwise to the reaction mixture, and the mixture was stirred at room temperature for 2 h. After the reaction was complete, the mixture was extracted by introducing distilled water and dichloromethane (DCM) at room temperature, and the solvent was removed using a rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:MeOH = 100:3) and recrystallized from dichloromethane (DCM) to obtain compound 5-2-1 (3.9 g, 70%). MeOH refers to methanol.

[0438] 3) Preparation of target compound 5-2

[0439] Compound 5-2-1 (6.7 g, 10.5 mM), iodobenzene (2.1 g, 10.5 mM), Pd(PPh3)4 (606 mg, 0.52 mM) and K2CO3 (2.9 g, 21.0 mM) were dissolved in toluene / ethanol / water (toluene / EtOH / H2O) (100 mL / 20 mL / 20 mL) and refluxed for 12 hours. After the reaction was complete, the results were extracted by introducing distilled water and DCM at room temperature, and the solvent was removed by rotary evaporation after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to obtain the target compound 5-2 (4.9 g, 70%).

[0440] <Preparation Example 3> Preparation of target compound 5-3

[0441] Except that 4-iodo-1,1'-biphenyl was used instead of iodobenzene, target compound 5-3 (83%) was obtained in the same manner as compound 5-2 of Preparation Example 2.

[0442] <Preparation Example 4> Preparation of target compound 5-12

[0443] Except that 4-iododibenzo[b,d]furan was used instead of iodobenzene, the target compound 5-12 (80%) was obtained in the same manner as the preparation of compound 5-2 in Preparation Example 2.

[0444] <Preparation Example 5> Preparation of target compound 6-3

[0445]

[0446] 1) Preparation of target compound 6-3

[0447] 3-Bromo-1,1'-biphenyl (A) (3.7 g, 15.8 mM), 9-phenyl-9H,9'H-3,3'-biscarbazole (B) (6.5 g, 15.8 mM), CuI (3.0 g, 15.8 mM), trans-1,2-diaminocyclohexane (1.9 mL, 15.8 mM), and K3PO4 (3.3 g, 31.6 mM) were dissolved in 1,4-dioxane (100 mL) and refluxed for 24 hours. After the reaction was complete, the results were extracted by introducing distilled water and dichloromethane (DCM) at room temperature, and the solvent was removed using a rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol (MeOH) to obtain the target compound 6-3 (7.5 g, 85%).

[0448] The target compound was synthesized in the same manner as in Preparation Example 5, except that intermediate A from Table 2 was used instead of 3-bromo-1,1'-biphenyl and intermediate B from Table 2 was used instead of 9-phenyl-9H,9'H-3,3'-biscarbazole.

[0449] [Table 2]

[0450]

[0451] <Preparation Example 6> Preparation of target compound 1-273

[0452]

[0453] 1) Preparation of target compound 1-273

[0454] Compound 1-86 (7.7 g, 10.5 mM) was dissolved in trifluoromethanesulfonic acid (23 mL, 262.5 mM) and benzene-d6 (70 mL) and refluxed at 50 °C. After the reaction was complete, the result was extracted by introducing distilled water and DCM at room temperature, and the solvent was removed using a rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to obtain the target compound 1-273 (6.2 g, 78%).

[0455] <Preparation Example 7> Preparation of target compound 5-105

[0456]

[0457] 1) Preparation of target compound 5-105

[0458] Except that compound 5-2 was used instead of compound 1-86, target compound 5-105 (80%) was obtained in the same manner as compound 1-273 of Preparation Example 6.

[0459] <Preparation Example 8> Preparation of target compound 6-99

[0460]

[0461] 1) Preparation of target compound 6-99

[0462] Except that compound 6-42 was used instead of compound 1-86, target compound 6-99 (79%) was obtained in the same manner as compound 1-273 of Preparation Example 6.

[0463] Compounds other than those described in Preparation Examples 1 to 8 and in Tables 1 and 2 were also prepared in the same manner as those described in the above preparation examples.

[0464] The synthetic identification results of the prepared compounds are shown in Tables 3 and 4 below. Table 3 shows... 1 The measurements were obtained by H NMR (CDCl3, 200 MHz), and Table 4 below shows the measurements by FD-MS (field desorption mass spectrometry).

[0465] [Table 3]

[0466]

[0467]

[0468] [Table 4]

[0469]

[0470] <Experimental Example 1>

[0471] (1) Manufacturing organic light-emitting elements

[0472] The glass substrate with an indium tin oxide (ITO) film coated to a thickness of 1,500 angstroms was cleaned using distilled water ultrasonic cleaning. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropanol, then dried, and treated with ultraviolet ozone (UVO) for 5 minutes using an ultraviolet (UV) cleaner. The substrate was then transferred to a plasma cleaner (PT) and subjected to plasma treatment under vacuum to achieve the required ITO work function and remove residual film. Finally, the substrate was transferred to a thermal deposition apparatus for organic deposition.

[0473] 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) are formed as a common layer.

[0474] A light-emitting layer was thermally vacuum-deposited on it as follows. As the light-emitting layer, a compound represented by chemical formula 1 as described in Table 5 was deposited to a thickness of 400 Å as the host, and a green phosphorescent dopant [Ir(ppy)3] was deposited at 7 wt% of the deposited thickness of the light-emitting layer. Subsequently, bathocuproine (BCP) was deposited to a thickness of 60 Å as a hole-blocking layer, and Alq3 was deposited thereon to a thickness of 200 Å as an electron transport layer.

[0475] 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 an aluminum (Al) 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 fabricated (Examples 1 to 29 and Comparative Examples 1 to 8).

[0476] Meanwhile, for each material to be used in the manufacture of organic light-emitting elements, all the organic compounds required to manufacture the organic light-emitting elements are within 10 -8 Up to 10 -6 Vacuum sublimation purification was carried out under a support.

[0477] (2) Driving voltage and luminous efficiency of organic light-emitting elements

[0478] For each of the organic light-emitting elements manufactured as described above in Examples 1 to 29 and Comparative Examples 1 to 8, the electroluminescent (EL) properties were measured using an M7000 manufactured by McScience Inc., and using the measurement results, the lifetime measurement time (T) was measured using a lifetime measurement system (M6000) manufactured by McScience Inc. at a standard luminance of 6,000 candela / m². 90 In this article, T 90 The lifetime (in hours, time) that takes for the initial brightness to reach 90% of its original value.

[0479] The measurement results of the driving voltage, luminous efficiency, color (EL color), and lifetime of the organic light-emitting element manufactured according to this disclosure are shown in Table 5 below.

[0480] [Table 5]

[0481]

[0482] Furthermore, the comparative compounds Ref.1 to Ref.8 used in Comparative Examples 1 to 8 are as follows.

[0483]

[0484] As can be seen from the results in Table 5, compared with Comparative Examples 1 to 8 which used comparative compounds, the organic light-emitting elements of Examples 1 to 29 which used compounds represented by Chemical Formula 1 of this disclosure as the light-emitting layer material of the organic light-emitting element have lower driving voltage, enhanced luminous efficiency and significantly improved lifetime.

[0485] In this regard, the HOMO and LUMO orbitals of the compounds represented by chemical formula 1 (compound 1-1) and the comparative compounds Ref. 1 to Ref. 4 disclosed herein are shown in Table 6 below.

[0486] [Table 6]

[0487]

[0488] As can be seen from Table 6, the HOMO domains of compounds Ref.1, Ref.2, Ref.3, and Ref.4 are delocalized to phenylene and dibenzofuran (DBF), and the HOMO level is approximately -5.7. However, it can be seen that compound 1-1 (represented by chemical formula 1 of this disclosure) is substituted with carbazole, which has a strong electron-donating ability, and the HOMO level is measured to be -5.40. In other words, the compound represented by chemical formula 1 of this disclosure has a higher HOMO level, and when the compound represented by chemical formula 1 of this disclosure is used in the light-emitting layer of an organic light-emitting element, the lifetime and efficiency of the electroluminescent element can be improved by promoting the host injection of holes into the dopant.

[0489] Furthermore, the HOMO and LUMO orbitals of the compounds represented by chemical formula 1 (compounds 1-86) and the comparative compounds Ref.5 to Ref.8 disclosed herein are shown in Table 7 below.

[0490] [Table 7]

[0491]

[0492] As shown in Table 7, the LUMO orbitals of compounds Ref. 5, Ref. 6, Ref. 7, and Ref. 8 are compared, showing that the LUMO orbitals of compounds 1-86 (i.e., compounds represented by Chemical Formula 1 of this disclosure) are delocalized from triazine to two heterocycles. Due to this extension of the LUMO orbitals, the efficiency and lifetime of organic light-emitting devices can be enhanced when compounds represented by Chemical Formula 1 of this disclosure are used in the emissive layer of organic light-emitting devices by enhancing electron mobility and stabilizing electrons.

[0493] Furthermore, the HOMO and LUMO orbitals of compounds 1-1, 2-11, 1-86, and 2-87 (which are compounds represented by chemical formula 1 disclosed herein) are shown in Table 8 below.

[0494] [Table 8]

[0495]

[0496] Generally speaking, the main body of the light-emitting layer is a layer in which both holes and electrons are injected, and the efficiency and lifetime vary depending on the stability and mobility of holes and electrons.

[0497] The compound represented by chemical formula 1 disclosed herein is a compound formed by an electron-pulling triazine, an electron-driving carbazole, and two heterocycles connecting the donor and acceptor.

[0498] Compounds represented by chemical formula 1 can alter the mobility and stability of holes and electrons by changing the binding positions of the donor and acceptor on the heterocycle.

[0499] Specifically, carbazoles or amines substituted at the ends of compounds represented by Formula 1 have orbital breaks around N, and therefore, HOMO orbitals are typically localized to carbazoles or amines. In this paper, HOMO orbitals can be extensively delocalized by altering the binding site, which contributes to increased hole mobility and stability.

[0500] Furthermore, in compounds represented by Formula 1, the N-containing heterocyclic group (e.g., triazine) is substituted with dibenzofuran or dibenzothiophene, which can affect the LUMO orbital domain of the N-containing heterocyclic group.

[0501] Therefore, the LUMO level of a compound can be adjusted based on the substitution position of the N-containing heterocyclic group substituted by dibenzofuran or dibenzothiophene. In other words, this means that the LUMO level can be adjusted based on the position of the N-containing heterocyclic group (e.g., triazine) substituted by dibenzofuran or dibenzothiophene.

[0502] This means that, by appropriately adjusting the LUMO level according to the dopant and electron transport layer (ETL) material, the compound represented by chemical formula 1 of this application can be used as a material for organic light-emitting elements, specifically as a material for the light-emitting layer, and more specifically as a host material. In other words, when changing the dopant and electron transport layer materials, the host material needs to be changed according to the charge balance.

[0503] Specifically, when a compound with a low LUMO level is used as the material of the light-emitting layer, electrons can be easily injected into the dopant from the host, and when a compound with a high LUMO level is used as the material of the light-emitting layer, electrons can be easily injected into the host from the electron transport layer (ETL).

[0504] Specifically, in compounds 1-86, the triazine is bonded to position 3 of the dibenzofuran ring, and the carbazole is also bonded to position 3 of the dibenzofuran ring. Furthermore, the LUMO and HOMO orbitals are relatively extensively delocalized into the heterocycle. This is identifiable as improving the mobility and stability of holes and electrons, thereby increasing the lifetime.

[0505] When the electron mobility from the electrode to the light-emitting layer in an electroluminescent element is fast, the above results can lead to favorable outcomes. However, the results for the bulk of the light-emitting layer can vary depending on the balance between holes and electrons in the element.

[0506] Generally, the charge balance between holes and electrons in the emissive layer varies depending on the phosphorescent dopant, and the mobilities of holes and electrons can be adjusted accordingly by using a hole transfer auxiliary layer (G'HTL), a hole blocking layer (HBL), or an electron blocking layer (EBL), or by doping to a hole transfer layer (HTL) or an electron transfer layer (ETL). In this paper, excessive accumulation of holes and electrons in the emissive layer may shorten the device lifetime.

[0507] When a compound having a structure containing a heterocyclic group containing N and a carbazole or amine is used as a material for the light-emitting layer, the mobility of holes and electrons can be reduced, thereby reducing the amount of holes and electrons accumulated in the light-emitting layer and thus improving the device lifetime.

[0508] Furthermore, in the compounds of this application, the dibenzofuran or dibenzothiophene substituted with amine or carbazole affects the LUMO orbitals that are widely distributed in the N-containing heterocyclic groups, which may affect the enhancement of electron mobility and stability.

[0509] <Experimental Example 2>

[0510] (1) Manufacturing organic light-emitting elements

[0511] The glass substrate with an indium tin oxide (ITO) film coated to a thickness of 1,500 angstroms was cleaned using distilled water ultrasonic cleaning. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropanol, then dried, and treated with ultraviolet ozone (UVO) for 5 minutes using an ultraviolet (UV) cleaner. The substrate was then transferred to a plasma cleaner (PT) and subjected to plasma treatment under vacuum to achieve the ITO work function and remove residual film. Finally, the substrate was transferred to a thermal deposition apparatus for organic deposition.

[0512] 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) are formed as a common layer.

[0513] A light-emitting layer was thermally vacuum deposited on it as follows. As the light-emitting layer, a compound of a type represented by Chemical Formula 1 of this disclosure (N-type) and a compound of a type represented by Chemical Formula 13 or 14 of this disclosure (P-type), or a compound of a type represented by Chemical Formula 1 of this disclosure (N-type) and a comparative compound of a type (P-type), were premixed and deposited to a thickness of 400 Å in a supply source as the host, and a green phosphorescent dopant [Ir(ppy)3] was deposited at a thickness of 7 wt% of the deposited light-emitting layer. Subsequently, copper bath (BCP) was deposited to a thickness of 60 Å as a hole-blocking layer, and Alq3 was deposited thereon to a thickness of 200 Å as an electron transport layer.

[0514] 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 an aluminum (Al) 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 fabricated (Examples 30 to 54 and Comparative Examples 9 to 20).

[0515] At the same time, for each material that will be used in OLED manufacturing, all the organic compounds required to manufacture OLED elements are within 10 -8Up to 10 -6 Vacuum sublimation purification was carried out under a support.

[0516] (2) Driving voltage and luminous efficiency of organic light-emitting elements

[0517] For each of the organic light-emitting elements manufactured as described above in Examples 30 to 54 and Comparative Examples 9 to 20, the electroluminescence (EL) properties were measured using an M7000 manufactured by Maxey Systems, and using the measurement results, the lifetime measurement time (T) was measured using a lifetime measurement system (M6000) manufactured by Maxey Systems at a standard luminance of 6,000 candela / m². 90 In this article, T 90 The lifetime (in hours, time) that takes for the initial brightness to reach 90% of its original value.

[0518] The measurement results of the driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the organic light-emitting element manufactured according to this disclosure are shown in Table 9 below.

[0519] [Table 9]

[0520]

[0521]

[0522] Furthermore, the comparative compounds Ref.9 to Ref.12 used in Comparative Examples 9 to 20 are as follows.

[0523]

[0524] As shown in Table 9, superior efficiency and lifetime were achieved when both the compound represented by Chemical Formula 1 (N-type) and the compound represented by Chemical Formula 13 or 14 (P-type) of this disclosure were included. This result suggests that an excited miscible phenomenon will occur when both compounds are included.

[0525] Excited misalignment is a phenomenon in which energy of HOMO level (donor-host) and LUMO level (acceptor-host) magnitudes is released due to electron exchange between two molecules. When excited misalignment occurs between two molecules, reverse intersystem crossing (RISC) takes place, and thus, the internal quantum efficiency of fluorescence can be increased to up to 100%. When a donor (p-host) with good hole transport capability and an acceptor (n-host) with good electron transport capability are used as the host of the emitting layer, holes are injected into the p-host and electrons are injected into the n-host, and therefore, the driving voltage can be reduced, which helps to improve lifetime.

[0526] In this disclosure, it was identified that when compounds representing the donor function (represented by chemical formula 13 or chemical formula 14) and compounds representing the acceptor function (represented by chemical formula 1) are used as the host of the luminescent layer, excellent element properties are obtained.

[0527] In this regard, the HOMO and LUMO orbitals of the compounds represented by chemical formula 13 disclosed herein (compounds 5-2), the compounds represented by chemical formula 13 disclosed herein (compounds 6-31), and the comparative compounds Ref. 9 to Ref. 12 are shown in Table 10 below.

[0528] [Table 10]

[0529]

[0530] As seen in Table 10, the HOMO domain of compound Ref. 9 is localized to the two terminal carbazoles, resulting in a low HOMO level and hole mobility. This leads to an imbalance between holes and electrons in the device, resulting in a shortened lifetime.

[0531] The HOMO domain of compound Ref.10 was delocalized to carbazole and triphenylene, resulting in a higher HOMO level and enhanced hole mobility compared to Ref.9; however, the imbalance in the device still exists.

[0532] When there is no aryl substituent at position 4 of the dibenzothiophene (DBT) core, as in comparative compound Ref. 11, the molecular stability decreases because there is no protective substituent at position 4 of the highly reactive dibenzothiophene (DBT) core, and compared to compound 5-2, the LUMO orbital is localized to the dibenzothiophene (DBT) core, and therefore, the lifetime is shortened due to the inability to effectively stabilize electrons.

[0533] Using an amine as the p-type in the comparative compound Ref. 12 can lead to imbalances in the device due to excessively high HOMO levels and rapid hole mobility, and can also result in a shortened lifetime.

[0534] The HOMO levels of compounds 5-2 (represented by chemical formula 13) and 6-31 (represented by chemical formula 14) disclosed herein are extensively delocalized to the two carbazoles. When compounds represented by chemical formula 1 are used simultaneously with compounds represented by chemical formula 13 or chemical formula 14 disclosed herein in organic light-emitting devices (OLEDs), the HOMO level, hole mobility, and stability increase compared to the basic carbazole, and the lifetime of the OLED is improved. Specifically, the structure of compound 5-2 effectively stabilizes electrons and improves the lifetime of the OLED by introducing a dibenzothiophene (DBT) core and an aryl group, taking into account electronic stability.

Claims

1. A heterocyclic compound represented by the following chemical formulas 1-2: [Chemical Formula 1-2] in, In chemical formulas 1-2, X1 and X2 are either the same as or different from each other, and each is independently O; or S; R1 to R4 may be the same or different from each other, and each is hydrogen; or deuterium, a to d are each an integer from 0 to 3, and when a to d are each 2 or greater than 2, the substituents in parentheses are the same. R5 to R12 may be the same as or different from each other, and each is independently hydrogen; or deuterium; N-Het is a group represented by the following chemical formula 2: [Chemical Formula 2] In chemical formula 2, Y1 is CR12' or N, Y2 is CR13' or N, Y3 is CR14' or N, Y4 is CR15' or N, Y5 is CR16' or N, and at least one of Y1 to Y5 is N; R12' to R16' may be the same as or different from each other, and each is independently phenyl, biphenyl, naphthyl, dimethylfluorenyl, dibenzofuranyl, or dibenzothiopheneyl; and It is the site attached to the heterocyclic compound represented by chemical formulas 1-2; Wherein, when the heterocyclic compound is represented by chemical formula 1-2, Position 3 is replaced by the N-Het; The substitution position refers to the position indicated by the number in the following chemical formula A; [Chemical Formula A] 。 2. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by chemical formulas 1-2 has a deuterium content of 0% to 100%.

3. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by chemical formulas 1-2 is represented by any of the following compounds: 。 4. An organic light-emitting element, comprising: First electrode; Second 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 layer contain a heterocyclic compound as described in any one of claims 1 to 3.

5. The organic light-emitting element according to claim 4, wherein the organic material layer comprises one or more light-emitting layers, and the light-emitting layer contains the heterocyclic compound.

6. The organic light-emitting element according to claim 5, wherein the light-emitting layer comprises two or more host materials, and at least one of the host materials comprises the heterocyclic compound as the host material of the light-emitting material.

7. The organic light-emitting element according to claim 5, wherein, In addition to the light-emitting layer comprising the heterocyclic compound included in the organic material layer, the organic light-emitting element further includes one, two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole auxiliary layer and a hole blocking layer.

8. The organic light-emitting element according to claim 4, wherein the organic material layer comprises a heterocyclic compound as described in any one of claims 1 to 3 as a first compound, and further comprises a heterocyclic compound represented by chemical formula 13 or chemical formula 14 as a second compound: [Chemical Formula 13] [Chemical Formula 14] In chemical formulas 13 and 14, L3 is a direct bond; or a substituted or unsubstituted phenylene; R28 to R31, Rd and Re are the same or different from each other, and each is independently hydrogen; or deuterium, r and s are integers from 0 to 7, and when r is 2 or greater than 2, Rd are the same or different from each other, when s is 2 or greater than 2, Re are the same or different from each other, e is an integer from 0 to 4, g and h are each integers from 0 to 7, f is an integer from 0 to 2, and when e is 2 or greater than 2, R28 are the same or different from each other, when f is an integer of 2, R29 are the same or different from each other, when g is 2 or greater than 2, R30 are the same or different from each other, and when h is 2 or greater than 2, R31 are the same or different from each other; Ar3 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted dibenzofuranyl group; Ar4 is a substituted or unsubstituted phenyl group; and R32 and R33 may be the same as or different from each other, and each may independently be a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; or a substituted or unsubstituted terphenyl. in, The substitution mentioned refers to substitution with deuterium or cyano groups.

9. The organic light-emitting element according to claim 8, wherein the heterocyclic compound represented by chemical formula 13 has a deuterium content of 0% to 100%.

10. The organic light-emitting element according to claim 8, wherein the heterocyclic compound represented by chemical formula 14 has 0% to 100% deuterium.

11. The organic light-emitting element according to claim 8, wherein chemical formula 13 is represented by any of the following compounds: 。 12. The organic light-emitting element according to claim 8, wherein chemical formula 14 is represented by any of the following compounds: 。 13. A composition of an organic material layer for an organic light-emitting element, said composition comprising: The heterocyclic compound represented by chemical formulas 1-2 as described in claim 1; and Heterocyclic compounds represented by the following chemical formulas 13 or 14: [Chemical Formula 13] [Chemical Formula 14] In chemical formulas 13 and 14, L3 is a direct bond; or a substituted or unsubstituted phenylene; R28 to R31, Rd and Re are the same or different from each other, and each is independently hydrogen; or deuterium, r and s are integers from 0 to 7, and when r is 2 or greater than 2, Rd are the same or different from each other, when s is 2 or greater than 2, Re are the same or different from each other, e is an integer from 0 to 4, g and h are each integers from 0 to 7, f is an integer from 0 to 2, and when e is 2 or greater than 2, R28 are the same or different from each other, when f is an integer of 2, R29 are the same or different from each other, when g is 2 or greater than 2, R30 are the same or different from each other, and when h is 2 or greater than 2, R31 are the same or different from each other; Ar3 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted dibenzofuranyl group; Ar4 is a substituted or unsubstituted phenyl group; and R32 and R33 may be the same as or different from each other, and each may independently be a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; or a substituted or unsubstituted terphenyl. in, The substitution mentioned refers to substitution with deuterium or cyano groups.

14. The composition of the organic material layer of the organic light-emitting element according to claim 13, wherein, In the composition, the heterocyclic compounds represented by chemical formulas 1-2 and 13 or 14 have a weight ratio of 1:10 to 10:1.

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