Heterocyclic compounds and organic light emitting elements comprising the same

Abstract

The present application provides a heterocyclic compound and an organic light emitting device comprising the heterocyclic compound in an organic layer.

Description

[0001] This application claims priority and benefits from Korean Patent Application No. 10-2020-0103402, filed on August 18, 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 and an organic light-emitting element comprising the same. 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] U.S. Patent No. 4,356,429 Summary of the Invention

[0008] Technical issues

[0009] This disclosure relates to providing a heterocyclic compound and an organic light-emitting element comprising the same.

[0010] Technical solutions

[0011] One embodiment of this application provides a heterocyclic compound represented by the following chemical formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In chemical formula 1,

[0015] L1 to L5 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.

[0016] a, b, c, d, and e are each integers from 0 to 3, and when a, b, c, d, and e are each 2 or greater than 2, the substituents in parentheses are either the same or different from each other.

[0017] Ar1 to Ar5 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.

[0018] At least one of Ar1 to Ar5 is a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted, and containing one or more N atoms; or an aryl group having 6 to 60 carbon atoms, substituted with one or more cyano groups.

[0019] Rp is hydrogen; deuterium; halogen group; or substituted or unsubstituted alkyl group having 6 to 60 carbon atoms, p is an integer from 0 to 4, and when p is 2 or greater than 2, the substituents in parentheses are the same or different from each other.

[0020] In addition, 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 the one or more organic material layers contain a heterocyclic compound represented by chemical formula 1.

[0021] Beneficial effects

[0022] 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

[0023] Figures 1 to 4 The diagrams illustrate, for each illustrative purposes, the stacked structure of an organic light-emitting element according to one embodiment of the present application.

[0024] Explanation of icon numbers

[0025] 100:Substrate

[0026] 200: Anode

[0027] 300: Organic material layer

[0028] 301: Hole Injection Layer

[0029] 302: Hole transport layer

[0030] 303: Emissive layer

[0031] 304: Cavity Blocking Layer

[0032] 305: Electron Transport Layer

[0033] 306: Electron Injection Layer

[0034] 400: Cathode Detailed Implementation

[0035] This application will be described in detail below.

[0036] One embodiment of this application provides a heterocyclic compound represented by the following chemical formula 1.

[0037] [Chemical Formula 1]

[0038]

[0039] In chemical formula 1,

[0040] L1 to L5 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.

[0041] a, b, c, d, and e are each integers from 0 to 3, and when a, b, c, d, and e are each 2 or greater than 2, the substituents in parentheses are either the same or different from each other.

[0042] Ar1 to Ar5 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.

[0043] At least one of Ar1 to Ar5 is a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted, and containing one or more N atoms; or an aryl group having 6 to 60 carbon atoms, substituted with one or more cyano groups.

[0044] Rp is hydrogen; deuterium; halogen group; or substituted or unsubstituted alkyl group having 6 to 60 carbon atoms, p is an integer from 0 to 4, and when p is 2 or greater than 2, the substituents in parentheses are the same or different from each other.

[0045] By having a monocyclic or polycyclic heterocyclic group containing one or more N or an aryl group substituted with a cyano group as a substituent in the dibenzofuran structure, Formula 1 has improved electron transport capability, and by improving current, the effect of reducing driving voltage is achieved when a compound represented by Formula 1 is used in a device.

[0046] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of the compound is replaced by another substituent, and the substitution position 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.

[0047] In this specification, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; cyano; halogen; 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 R, R', and R'" are alkylamines having 1 to 20 carbon atoms; monocyclic or polycyclic arylamines having 6 to 60 carbon atoms; and monocyclic or polycyclic heteroarylamines 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'" are the same as or different from each other, and each is independently 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.

[0048] 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.

[0049] 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%.

[0050] 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).

[0051] 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.

[0052] 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.

[0053] 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.

[0054] 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.

[0055]

[0056] 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.

[0057] In this specification, halogen may be fluorine, chlorine, bromine or iodine.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] 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.

[0063] 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.

[0064] 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.

[0065] 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 the following: hydrogen; deuterium; halogen; alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and heterocyclic groups. Specific examples of the phosphine oxide group may include, but are not limited to, diphenylphosphine oxide, dinaphthylphosphine oxide, etc.

[0066] In this specification, silyl is a substituent containing Si, with Si atoms 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 the following: hydrogen; deuterium; halogen; alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and heterocyclic groups. Specific examples of silyl groups may include, but are not limited to, trimethylsilyl, triethylsilyl, tributyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc.

[0067] In this specification, the fluorene group may be substituted, and adjacent substituents may bond to each other to form a ring.

[0068] 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 group having the following structural formula.

[0069]

[0070] 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, thiopheneyl, indolo[2,3-a]carbazoleyl, indolo[2,3-b]carbazoleyl, indololinyl, 10,11-dihydro-dibenzo[b,f]-nitroheptenyl, 9,10-dihydroacridyl, phenolazinyl, phenoxazinyl, phthalazinyl, naphthidine The group includes, but is not limited to, 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]carbazoleyl, etc.

[0071] 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 methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, diphenylamino, anthraceneamino, 9-methyl-anthraylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenyltolylamino, triphenylamino, biphenylnaphthylamino, phenylbiphenylamino, biphenylfluorenylamino, phenylbitriphenylamino, biphenylbitriphenylamino, etc., but are not limited thereto.

[0072] In this specification, arylene refers to an aryl group having two binding sites, i.e., a divalent group. The above description of aryl groups, except that each is a divalent group, applies here. Furthermore, heteroarylene refers to a heteroaryl group having two binding sites, i.e., a divalent group. The above description of heteroaryl groups, except that each is a divalent group, applies here.

[0073] In this specification, "adjacent" groups may refer to a substituent that substitutes for an atom directly attached to an atom substituted by the corresponding substituent, a substituent that is spatially closest to the corresponding substituent, or another substituent that substitutes for an atom substituted by the corresponding substituent. For example, two substituents that substitute for an ortho position on a benzene ring, and two substituents that substitute for the same carbon atom in an aliphatic ring, may be interpreted as "adjacent" groups.

[0074] 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.

[0075] In one embodiment of this application, L1 to L5 of Formula 1 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 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0076] In one embodiment of this application, L1 to L5 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.

[0077] In one embodiment of this application, L1 to L5 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 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0078] In another embodiment, L1 is a direct bond.

[0079] In another embodiment, L1 is phenylene.

[0080] In another embodiment, L1 is a naphthylene group.

[0081] In another embodiment, L2 is a direct bond.

[0082] In another embodiment, L2 is phenylene.

[0083] In another embodiment, L2 is a naphthylene group.

[0084] In another embodiment, L3 is a direct bond.

[0085] In another embodiment, L3 is phenylene.

[0086] In another embodiment, L3 is a naphthylene group.

[0087] In another embodiment, L4 is a direct bond.

[0088] In another embodiment, L4 is phenylene.

[0089] In another embodiment, L4 is a naphthylene group.

[0090] In another embodiment, L5 is a direct bond.

[0091] In another embodiment, L5 is phenylene.

[0092] In another embodiment, L5 is a naphthylene group.

[0093] In one embodiment of this application, a, b, c, d and e of chemical formula 1 are each integers from 0 to 3, and when a, b, c, d and e are each 2 or greater than 2, the substituents in parentheses may be the same or different from each other.

[0094] In one embodiment of this application, Ar1 to Ar5 of Formula 1 may be the same as or different from each other, and each independently is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and at least one of Ar1 to Ar5 may be a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N atoms; or an aryl group having 6 to 60 carbon atoms substituted with one or more cyano groups.

[0095] In one embodiment of this application, Ar1 to Ar5 may be the same as or different from each other, and each is 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, and at least one of Ar1 to Ar5 may be a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 40 carbon atoms and containing one or more N atoms; or an aryl group having 6 to 40 carbon atoms substituted with one or more cyano groups.

[0096] In one embodiment of this application, Ar1 to Ar5 may be the same as or different from each other, and each is 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, and at least one of Ar1 to Ar5 may be a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms and containing one or more N; or an aryl group having 6 to 20 carbon atoms substituted with one or more cyano groups.

[0097] In one embodiment of this application, Ar1 to Ar5 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl having 2 to 60 carbon atoms and containing one or more N; or an aryl having 6 to 60 carbon atoms substituted with one or more cyano groups, and at least one of Ar1 to Ar5 may be a substituted or unsubstituted monocyclic or polycyclic heteroaryl having 2 to 60 carbon atoms and containing one or more N; or an aryl having 6 to 60 carbon atoms substituted with one or more cyano groups.

[0098] In one embodiment of this application, a monocyclic or polycyclic heteroaryl group containing one or more N atoms and having 2 to 60 carbon atoms may be a group represented by the following chemical formula 3.

[0099] [Chemical Formula 3]

[0100]

[0101] In chemical formula 3,

[0102] X1 is CR1 or N, X2 is CR2 or N, X3 is CR3 or N, X4 is CR4 or N, X5 is CR5 or N, and at least one of X1 to X5 is N, and

[0103] R1 to R5 may be identical 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 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 cycloalkyl groups having 6 to 60 carbon atoms. The following groups are used: substituted aryl groups; substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; -P(=O)R10R12; and NR13R14, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or heterocycle, wherein R10 and R12 to R14 are the same or different from each other and are each independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms; substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; or substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms. It is the site that is attached to chemical formula 1.

[0104] In one embodiment of this application, chemical formula 3 may be represented by one of the following chemical formulas 3-1 to 3-4.

[0105] In this article, It is the site that is attached to chemical formula 1.

[0106] [Chemical Formula 3-1]

[0107]

[0108] [Chemical Formula 3-2]

[0109]

[0110] [Chemical Formula 3-3]

[0111]

[0112] [Chemical Formula 3-4]

[0113]

[0114] In chemical formula 3-1, at least one of X1, X3, and X5 is N, and the others have the same definition as in chemical formula 3.

[0115] In chemical formula 3-2, at least one of X1, X2, and X5 is N, and the others have the same definition as in chemical formula 3.

[0116] In chemical formula 3-3, at least one of X1 to X3 is N, and the others have the same definition as in chemical formula 3.

[0117] In chemical formulas 3-4, at least one of X1, X2, and X5 is N, and the others have the same definition as in chemical formula 3.

[0118] Z1 is O; or S, and

[0119] R2, R4, and R6 through R9 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 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 cycloalkyl groups having 6 to 60 carbon atoms. Unsubstituted aryl; substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms; -P(=O)R10R12; and NR13R14, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or heterocycle, and R10 and R12 to R14 being the same or different from each other and each being hydrogen independently; deuterium; halogen group; substituted or unsubstituted alkyl having 1 to 60 carbon atoms; substituted or unsubstituted aryl having 6 to 60 carbon atoms; or substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms.

[0120] In one embodiment of this application, chemical formula 3 may be represented by any of the following group 1.

[0121] [Group 1]

[0122]

[0123] In group 1, R1 to R5 and It has the same definition as in chemical formula 3.

[0124] In another embodiment, Rp of Formula 1 is hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group having 6 to 60 carbon atoms, p is an integer from 0 to 4, and when p is 2 or greater than 2, the substituents in parentheses may be the same or different from each other.

[0125] In another embodiment, Rp may be hydrogen; or deuterium.

[0126] In another embodiment, Rp is hydrogen.

[0127] In one embodiment of this application, chemical formula 1 may be represented by chemical formula 1-1 or chemical formula 1-2.

[0128] [Chemical Formula 1-1]

[0129]

[0130] [Chemical Formula 1-2]

[0131]

[0132] In Formula 1-1, Ar1 and Ar4 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, wherein at least one of Ar1 and Ar4 is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N atoms; or an aryl group having 6 to 60 carbon atoms substituted with one or more cyano groups, and the others have the same definitions as in Formula 1.

[0133] In Formulas 1-2, Ar2 and Ar4 may be the same as or different from each other, and each independently 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, at least one of Ar2 and Ar4 being a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N atoms; or an aryl group having 6 to 60 carbon atoms substituted with one or more cyano groups, and the others having the same definition as in Formula 1.

[0134] Heterocyclic compounds represented by Formula 1-1 have linear and planar shapes, and therefore, the overlap between compounds increases the acceleration of electron transport. Thus, when heterocyclic compounds represented by Formula 1-1 are used in a device, the device can exhibit superior efficiency.

[0135] Furthermore, the heterocyclic compounds represented by Formulas 1-2 possess structures that are highly effective in separating the electron distributions of HOMO and LUMO, allowing the compounds to have suitable band gaps. Therefore, when heterocyclic compounds represented by Formulas 1-2 are used in components, the components can exhibit superior driving performance.

[0136] In one embodiment of this application, chemical formula 1 may be represented by any of the following chemical formulas 1-3 to 1-5.

[0137] [Chemical Formulas 1-3]

[0138]

[0139] [Chemical Formulas 1-4]

[0140]

[0141] [Chemical Formulas 1-5]

[0142]

[0143] In chemical formulas 1-3, Ar1 and Ar5 may be the same as or different from each other, and each independently 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, wherein at least one of Ar1 and Ar5 is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N atoms; or an aryl group having 6 to 60 carbon atoms substituted with one or more cyano groups, and the others have the same definitions as in chemical formula 1.

[0144] In chemical formulas 1-4, Ar2 and Ar5 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, wherein at least one of Ar2 and Ar5 is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N atoms; or an aryl group having 6 to 60 carbon atoms substituted with one or more cyano groups, and the others have the same definition as in chemical formula 1, and

[0145] In chemical formulas 1-5, Ar3 and Ar5 may be the same as or different from each other, and each independently 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, at least one of Ar3 and Ar5 being a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N atoms; or an aryl group having 6 to 60 carbon atoms substituted with one or more cyano groups, and the others having the same definition as in chemical formula 1.

[0146] Heterocyclic compounds represented by chemical formulas 1-3 have linear and planar shapes, and therefore, the overlap between compounds increases the acceleration of electron transport. Thus, when heterocyclic compounds represented by chemical formulas 1-3 are used in a device, the device can exhibit superior efficiency.

[0147] Heterocyclic compounds represented by chemical formulas 1-4 have relatively thermally stable structures due to less structural interference from surrounding functional groups and lower deposition temperatures due to moderate linearity and planarity. Therefore, when heterocyclic compounds represented by chemical formulas 1-4 are used in devices, the devices can exhibit superior lifetime.

[0148] Furthermore, the heterocyclic compounds represented by chemical formulas 1-5 possess structures that are highly effective in separating the electron distributions of HOMO and LUMO, allowing the compounds to have suitable band gaps. Therefore, when heterocyclic compounds represented by chemical formulas 1-5 are used in components, the components can exhibit superior driving performance.

[0149] According to one embodiment of this application, chemical formula 1 may be represented by any of the following compounds, but is not limited thereto.

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159] 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.

[0160] 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.

[0161] Meanwhile, heterocyclic compounds possess high glass transition temperatures (Tg) and excellent thermal stability. This increase in thermal stability becomes an important factor in providing driving stability to the device.

[0162] 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 from said intermediate compounds, a compound of Formula 1 can be prepared. More specifically, the heterocyclic compound according to one embodiment of this application can be prepared based on preparation examples described later.

[0163] Another embodiment of this application provides an organic light-emitting element comprising a heterocyclic compound represented by 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."

[0164] When manufacturing organic light-emitting elements, the heterocyclic compound can be formed into an organic material layer using solution coating and vacuum deposition methods. In this document, solution coating methods refer to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but are not limited to these.

[0165] 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.

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

[0167] In another embodiment, the first electrode may be a cathode, and the second electrode may be an anode.

[0168] 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.

[0169] In one embodiment of this application, a heterocyclic compound according to Formula 1 can be used as an N-type host.

[0170] Furthermore, the organic material layer includes one or more light-emitting layers, and the light-emitting layers contain heterocyclic compounds represented by Chemical Formula 1. When the light-emitting layers in the organic material layer contain heterocyclic compounds represented by Chemical Formula 1, the organic light-emitting element exhibits superior luminous efficiency and lifetime.

[0171] Furthermore, in the organic light-emitting element of this application, the organic material layer may also contain any one or more compounds from Groups A to C below.

[0172] [Group A]

[0173]

[0174] [Group B]

[0175]

[0176] [Group C]

[0177]

[0178]

[0179] Furthermore, the organic material layer includes one or more light-emitting layers, and the light-emitting layer contains a heterocyclic compound represented by Formula 1 as a first compound, and may also contain one of the compounds from Group A to Group C as a second compound. When the light-emitting layer in the organic material layer contains a heterocyclic compound represented by Formula 1 and compounds from Group A to Group C, the organic light-emitting element has superior luminous efficiency and lifetime.

[0180] In one embodiment of this application, heterocyclic compounds according to groups A to C can be used as P-type bodies.

[0181] Furthermore, the organic material layer includes one or more light-emitting layers, and the light-emitting layers contain heterocyclic compounds represented by Formula 1, and also contain one of the compounds from Group A to Group C. When the light-emitting layers in the organic material layer simultaneously contain a heterocyclic compound represented by Formula 1 and one of the compounds from Group A to Group C, the organic light-emitting element exhibits superior luminous efficiency and lifetime due to the excitation of miscible compounds.

[0182] 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.

[0183] 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.

[0184] 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.

[0185] 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.

[0186] 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 comprise one or more p-type host materials and n-type host materials, and at least one of the host materials may comprise the heterocyclic compound as the host material of the light-emitting material. In this case, the organic light-emitting element can have excellent driving force, efficiency, and lifetime.

[0187] 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.

[0188] In addition to using the aforementioned heterocyclic compounds to form an organic material layer, an organic light-emitting element according to an embodiment of this application can be manufactured using common organic light-emitting element manufacturing methods and materials.

[0189] 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 one of compounds from group A to group C.

[0190] In another embodiment of this application, the heterocyclic compound represented by Formula 1 in the composition: one of the compounds in Group A to Group C 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, however, the weight ratio is not limited to these.

[0191] The specific descriptions of the heterocyclic compounds represented by chemical formula 1 and the compounds of groups A to C contained in the composition of the organic material layer are the same as those provided above.

[0192] 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.

[0193] 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.

[0194] 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 layered structure, and layers other than the light-emitting layer may be excluded as needed, and other required functional layers may be added.

[0195] Furthermore, an organic light-emitting element according to an embodiment of this application includes: a first electrode; a first stack disposed on the first electrode and including a first light-emitting layer; a charge-generating layer disposed on the first stack; a second stack disposed on the charge-generating layer and including a second light-emitting layer; and a second electrode disposed on the second stack.

[0196] Here, the charge generation layer may contain a heterocyclic compound represented by Formula 1. When the heterocyclic compound is used in the charge generation layer, the driving, efficiency, and lifetime of the organic light-emitting element can be excellent.

[0197] In addition, the first stack and the second stack may each independently include one or more types of the aforementioned hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer, etc.

[0198] As an embodiment of the organic light-emitting element according to this application Figure 4 The diagram schematically illustrates an organic light-emitting element with a 2-stacked tandem structure.

[0199] In this article, some cases may be excluded. Figure 4 The first electron blocking layer, the first hole blocking layer, the second hole blocking layer, etc., are described in the text.

[0200] 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.

[0201] 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] (PEDOT), polypyrrole, and polyaniline, etc., but are not limited to these.

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

[0203] 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.

[0204] 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.

[0205] 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.

[0206] As an example of an electron-injection material, LiF is commonly used in this technology; however, this application is not limited to this.

[0207] 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.

[0208] According to one embodiment of this application, the organic light-emitting element may be top-emitting, bottom-emitting, or dual-emitting, depending on the material used.

[0209] Heterocyclic compounds 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.

[0210] 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.

[0211] <Preparation Example 1> Preparation of Target Compound 1

[0212] (1) Preparation of compound F1

[0213]

[0214] 1) Preparation of compound D

[0215] Compound A (20 g, 89.68 mmol), compound B (15.6 g, 89.68 mmol), Pd(PPh3)4 (5.1 g, 4.48 mmol), and sodium hydroxide (7.2 g, 179.36 mmol) were dissolved in 1,4-dioxane / H2O (200 mL / 50 mL) and stirred at 100 °C for 8 hours. The resulting mixture was dissolved in methylene chloride (MC) and extracted with water. The organic layer was dried over anhydrous MgSO4 and then filtered through silica gel. The solvent in the filtrate was removed using a rotary evaporator to give compound D (11.7 g) as a yellow oil in 48% yield.

[0216] 2) Preparation of compound E

[0217] Compound D (11.7 g, 44.05 mmol) was dissolved in CHCl3 (150 mL), and Br2 (1.2 mL, 44.05 mmol) was added dropwise at 0 °C. The mixture was then stirred at room temperature for 2 hours. Methanol (MeOH) was introduced into the resulting solution, and the mixture was stirred for 30 minutes and then filtered to give compound E (14.3 g) as a white solid in 93% yield.

[0218] 3) Preparation of compound F1

[0219] Compound E (14.3 g, 40.89 mmol) was dissolved in dimethylacetamide (DMA) (150 mL), and after introducing Cs₂CO₃ (26.5 g, 81.79 mmol), the mixture was stirred at 160 °C for 3 hours. The resulting solution was filtered, and the solvent was removed from the filtrate using a rotary evaporator, yielding a white solid compound F₁ (11.5 g) in 85% yield.

[0220] (2) Preparation of target compound 1

[0221]

[0222] 1) Preparation of compound G

[0223] Compound F1 (20 g, 60.31 mmol), bis(pinacolyl)diboron (30.6 g, 120.63 mmol), PdCl2dppf (2.2 g, 3.02 mmol), and KOAc (18 g, 180.93 mmol) were dissolved in 1,4-dioxane (250 mL) and stirred at 100 °C for 4 h. The resulting mixture was concentrated, dissolved in MC, and extracted with water. The organic layer was dried over anhydrous MgSO4 and then filtered through silica gel. The solvent in the filtrate was removed using a rotary evaporator, yielding compound G (20 g) as a crude, brown solid, not prepared separately.

[0224] 2) Preparation of compound I

[0225] Compound G (20 g, 52.83 mmol), compound H (14 g, 52.83 mmol), Pd(PPh3)4 (3 g, 2.64 mmol), and K2CO3 (14.5 g, 105.66 mmol) were dissolved in 1,4-dioxane / H2O (250 mL / 50 mL) and stirred at 100 °C for 6 hours. After the reaction was complete, the precipitated solid was filtered and washed with water (H2O), methanol (MeOH), and acetone to give compound I (13.8 g) as a white solid in 54% yield.

[0226] 3) Preparation of compound J

[0227] Compound I (13.8 g, 28.53 mmol), bis(pinacolyl)diboron (14.5 g, 57.06 mmol), Pd(dba)2 (1.6 g, 2.85 mmol), XPhos (2.7 g, 5.71 mmol), and KOAc (8.4 g, 85.59 mmol) were dissolved in 1,4-dioxane (150 mL) and stirred at 100 °C for 14 h. The resulting mixture was concentrated, dissolved in dichloromethane (MC), and extracted with water. The organic layer was dried over anhydrous MgSO4 and then filtered through silica gel. The solvent in the filtrate was removed using a rotary evaporator, yielding compound J (14 g) as a crude, brown solid, not prepared separately.

[0228] 4) Preparation of target compound 1

[0229] Compound J (14 g, 24.35 mmol), compound K (6.9 g, 24.35 mmol), Pd(PPh3)4 (1.4 g, 1.22 mmol), and K2CO3 (6.7 g, 48.69 mmol) were dissolved in 1,4-dioxane / H2O (200 mL / 40 mL) and stirred at 100 °C for 5 hours. After the reaction was complete, the precipitated solid was filtered and washed with H2O, MeOH, and acetone to give a white solid, target compound 1(K) (11.7 g), in 74% yield.

[0230] Except that intermediates A and B in Table 1 are used to replace compounds A and B respectively, compound F1 is prepared in the same manner as compound F1.

[0231] [Table 1]

[0232]

[0233] In addition, except that intermediates F1, H and K in Table 2 are used to replace compounds F1, H and K respectively, the target compounds in Table 2 are prepared in the same manner as the target compound 1.

[0234] [Table 2]

[0235]

[0236]

[0237]

[0238] <Preparation Example 2> Preparation of target compound 43

[0239] (1) Preparation of compound F2

[0240]

[0241] Compound C (10 g, 39.57 mmol) was dissolved in CHCl3 (100 mL), and Br2 (2.04 mL, 39.57 mmol) was added dropwise at 0 °C. The mixture was then stirred at room temperature for 2 hours. Methanol (MeOH) was introduced into the resulting solution, and the mixture was stirred for 30 minutes and then filtered to give a white solid compound F2 (11.8 g) in 90% yield.

[0242] Except that intermediate C in Table 3 is used instead of compound C, compound F2 is prepared in the same manner as compound F2.

[0243] [Table 3]

[0244]

[0245]

[0246] (2) Preparation of target compound 43

[0247] Except that compound F2 was used instead of compound F1, target compound 43 (13.7 g) was obtained in the same manner as the preparation of target compound 1 in Preparation Example 1, with a yield of 59%.

[0248] In addition, except that intermediates F2, H and K in Table 4 are used to replace compounds F2, H and K respectively, the target compounds in Table 4 are prepared in the same manner as the target compound 43.

[0249] [Table 4]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255] All compounds other than those in the preparation examples were synthesized in the same manner as in Preparation Examples 1 and 2, and the synthesis identification results are shown in Tables 5 and 6 below. Table 5 shows the measurements by FD-MS (field desorption mass spectrometry), and Table 6 shows... 1 Measurements by H NMR (CDCl3, 200 MHz).

[0256] [Table 5]

[0257]

[0258]

[0259]

[0260]

[0261] [Table 6]

[0262]

[0263]

[0264] <Experimental Example 1> 1) Fabrication of Organic Light-Emitting Element - Red Single Subject

[0265] 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 any residual film. Finally, the substrate was transferred to a thermal deposition apparatus for organic deposition.

[0266] On a transparent ITO electrode (anode), a hole injection layer 4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA) and a hole transport layer 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC) are formed as a common layer.

[0267] A light-emitting layer was thermally vacuum deposited on it as follows. The light-emitting layer was deposited to 500 Å using the compounds described in Table 5 below as the red host, and a red phosphorescent dopant (piq)₂(Ir)(acac) was doped into the host at 3% by weight, based on the total weight of the light-emitting layer. Subsequently, copper bath (hereinafter, BCP) was deposited to 60 Å as a hole-blocking layer, and Alq₃ was deposited thereon to 200 Å as an electron transport layer. Finally, an electron injection layer was formed on the electron transport layer by depositing lithium fluoride (LiF) to a thickness of 10 Å, and then a cathode was formed on the electron injection layer by depositing an aluminum (Al) cathode to a thickness of 1,200 Å. Thus, organic light-emitting elements of Comparative Examples 1 to 10 and Examples 1 to 16 were fabricated.

[0268] At the same time, for each material that will be used in OLED manufacturing, the total organic compounds required to manufacture OLEDs are within 10 -8 Up to 10 -6 Vacuum sublimation purification was carried out under a support.

[0269] The compounds A to J used in Comparative Examples 1 to 10 are as follows.

[0270]

[0271] 2) Driving voltage and luminous efficiency of organic light-emitting elements

[0272] For each of the organic light-emitting elements manufactured as described above in Comparative Examples 1 to 4 and Examples 1 to 16, the electroluminescence (EL) properties were measured using an M7000 manufactured by McScience Inc., and using the measurement results, the Tt at a standard luminance of 6,000 candela / m² was measured using a lifetime measurement system (M6000) manufactured by McScience Inc. 90 T 90 It refers to lifespan (unit: h, time), which is the time required for the brightness to reach 90% relative to the initial brightness.

[0273] The measurement properties of organic light-emitting elements are shown in Table 7 below.

[0274] [Table 7]

[0275]

[0276]

[0277] As shown in Table 7, compared to Comparative Examples 1 to 4, which used comparative compounds A to D, which did not correspond to the chemical formula 1 of this application, as the single host of the light-emitting layer of the organic light-emitting element, the use of compounds corresponding to the chemical formula 1 of this application as the single host of the light-emitting layer of the organic light-emitting element in Examples 1 to 16 resulted in enhanced results in terms of element driving and efficiency.

[0278] This is believed to be because when a monopolar N-type compound similar to Comparative Compounds A to J is used as a single host in the light-emitting layer of an organic light-emitting element, high driving voltage and poor overall lifetime and efficiency properties are obtained due to the almost non-existent hole injection capability through the presence of dibenzofuran linkers.

[0279] On the other hand, it is believed that by introducing a naphthobenzofuran with extended π-conjugation into the dibenzofuran linker, the compound corresponding to Formula 1 of this application has a T1 value and band gap suitable for a red host, which helps to improve the efficiency and driving voltage of the device. Here, the T1 value refers to the energy level value in the triplet state.

[0280] Furthermore, it is believed that by substituting specific positions of the naphthobenzofuran linker with substituents, a more thermally stable structure with enhanced electron mobility can be obtained, which helps to improve the efficiency and driving voltage of the device.

[0281] Furthermore, compared to comparative compounds with simple dibenzofuran linkages or substituents formed in one direction, the compound corresponding to Chemical Formula 1 of this application, having substituents extending in two directions, has the following advantages: compared to comparative compounds, when used in components, it has a faster electron transport capability due to greater conjugation and is more thermally stable.

[0282] In compounds with substituents at the same positions as comparative compound B, intermolecular interactions are suppressed due to strong steric hindrance and oxygen atom masking. When compounds similar to comparative compound B are used in components, this is one cause of packing structure defects in the compound, which can lead to reduced component efficiency and lifetime.

[0283] Furthermore, when the substituent is located at the same position as in comparative compounds A and C to J, the HOMO / LUMO electron distribution clouds largely overlap compared to the compounds corresponding to chemical formula 1 of this application. This increases the band gap difference between S1 and T1, and it may not be desirable to achieve the effect of improving efficiency through intersystem crossing (ISC) of excitons.

[0284] <Experimental Example 2>

[0285] 1) Manufacturing organic light-emitting elements - red N+P hybrid substrate

[0286] In addition to serving as the red host when forming the light-emitting layer, the organic light-emitting elements of Comparative Examples 11 and 12, as well as Examples 17 to 32, were manufactured in the same manner as in Experimental Example 1, except that the compound corresponding to Chemical Formula 1 of this disclosure was mixed with a P-type host or a bipolar aromatic amine compound having strong hole transfer (HT) properties, as described in Table 8 below.

[0287] N+P hybridization refers to mixing an N-type substrate with a P-type substrate.

[0288] 2) Driving voltage and luminous efficiency of organic light-emitting elements

[0289] For each of the organic light-emitting elements in Comparative Examples 11 and 12 and Examples 17 to 32, the electroluminescence (EL) properties were measured using an M7000 manufactured by McScience Inc., and using the measurement results, the lifetime of the element at a standard luminance of 6,000 candela / m² (cd / m²) was measured using a lifetime measurement system (M6000) manufactured by McScience Inc. 2 T at time 90 .

[0290] The measurement properties of organic light-emitting elements are shown in Table 8 below.

[0291] [Table 8]

[0292]

[0293] The P-type host or bipolar aromatic amine compounds in Table 8 are selected from the compounds in groups A through C below.

[0294] [Group A]

[0295]

[0296] [Group B]

[0297]

[0298] [Group C]

[0299]

[0300]

[0301] As shown in Table 8, it was identified that when a monopolar N-type compound having a naphthobenzofuran linker corresponding to the chemical formula of this application is used as a single host, a mixture of a monopolar N-type compound having a naphthobenzofuran linker corresponding to the chemical formula of this application and a monopolar P-type compound or a bipolar aromatic amine compound corresponding to Group A to Group C is used as the host of the light-emitting layer of the organic light-emitting element as described in Examples 17 to 32, superior performance is achieved in terms of properties such as efficiency and lifetime.

[0302] This is believed to be due to the occurrence of excited miscible phenomena when a monopolar N-type compound corresponding to Chemical Formula 1 of this application is mixed with a monopolar P-type compound or a bipolar aromatic amine compound, due to the strong hole transport (HT) properties of aromatic amines. Furthermore, due to the low hole injection barrier, it is also believed that an excellent driving voltage is obtained.

[0303] Excited misalignment is a phenomenon in which the exchange of electrons between two molecules releases energy at the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host). When excited misalignment occurs between two molecules, reverse intersystem crossing (RISC) takes place, and as a result, the internal quantum efficiency of fluorescence can be increased to 100%.

[0304] Generally, aromatic amine bipolar compounds possess both strong hole transport (HT) and electron transport (ET) properties due to their low hole and electron injection barriers, resulting in narrow band gaps and low T1 energies. Consequently, they exhibit excellent efficiency as a single host in phosphorescent red devices. However, due to their rapid hole mobility, their lifetime tends to decrease to some extent as the device degrades.

[0305] However, this can be resolved by mixing with a monopolar N-type compound having a naphthobenzofuran linker, as in Formula 1 of this application. This means that a suitable charge rate balance is achieved by mixing the two compounds in the luminescent layer, which reduces degradation and expands the recombination region. Therefore, the advantage of the aromatic amine bipolar compound is that it achieves an increased lifetime without reducing excellent efficiency.

Claims

1. A heterocyclic compound represented by any one of the following chemical formulas 1-1 to 1-5: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] [Chemical Formulas 1-5] in, In chemical formulas 1-1 to 1-5, L1 to L5 are each a direct key independently; a, b, c, d, and e are each integers from 0 to 3, and when a, b, c, d, and e are each 2 or greater than 2, the substituents in parentheses are the same or different from each other; In chemical formula 1-1, one of Ar1 and Ar4 is a group represented by any of the following chemical formulas 3-1 to 3-4; and the other of Ar1 and Ar4 is a substituted or unsubstituted phenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl. In chemical formulas 1-2, one of Ar2 and Ar4 is a group represented by any of the following chemical formulas 3-1 to 3-4; and the other of Ar2 and Ar4 is a substituted or unsubstituted phenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl. In chemical formulas 1-3, one of Ar1 and Ar5 is a group represented by any of the following chemical formulas 3-1 to 3-4; and the other of Ar1 and Ar5 is a substituted or unsubstituted phenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl. In chemical formulas 1-4, one of Ar2 and Ar5 is a group represented by any of the following chemical formulas 3-1 to 3-4; and the other of Ar2 and Ar5 is a substituted or unsubstituted phenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl. In chemical formulas 1-5, one of Ar3 and Ar5 is a group represented by any of the following chemical formulas 3-1 to 3-4; and the other of Ar3 and Ar5 is a substituted or unsubstituted phenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl. [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] In chemical formula 3-1, X1 is CR1 or N, X3 is CR3 or N, X5 is CR5 or N, and at least one of X1, X3, and X5 is N. In chemical formula 3-2, X1 is CR1 or N, X2 is CR2 or N, X5 is CR5 or N, and at least one of X1, X2, and X5 is N. In chemical formula 3-3, X1 is CR1 or N, X2 is CR2 or N, X3 is CR3 or N, and at least one of X1 to X3 is N. In chemical formulas 3-4, X1 is CR1 or N, X2 is CR2 or N, and X5 is CR5 or N, with at least one of X1, X2, and X5 being N. Z1 is O; or S, R1 to R9 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted biphenyl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothiopheneyl. Rp is hydrogen; or deuterium; p is an integer from 0 to 4, and when p is 2 or greater than 2, the substituents in parentheses are the same or different from each other. The substituted or unsubstituted meaning refers to substitution with one or more substituents selected from the group consisting of: deuterium; halogen; phenyl; naphthyl; biphenyl; terphenyl; or unsubstituted. It is a site that connects to any of the chemical formulas 1-1 to 1-5.

2. The heterocyclic compound according to claim 1, wherein the heterocyclic compound of formulas 1-1 to 1-5 is represented by any one of the following compounds: 。 3. 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 or 2.

4. The organic light-emitting element according to claim 3, wherein the organic material layer comprises one or more light-emitting layers, and the light-emitting layer contains the heterocyclic compound.

5. The organic light-emitting element according to claim 4, 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.

6. The organic light-emitting element according to claim 3 further comprises one, two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole auxiliary layer and a hole blocking layer.

7. The organic light-emitting element according to claim 3, comprising the heterocyclic compounds according to chemical formulas 1-1 to 1-5 as a first compound, and further comprising one of the compounds from groups A to C as a second compound: [Group A] [Group B] [Group C] 。

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