Heterocyclic compounds and organic light emitting elements comprising the same

Abstract

The present application provides a heterocyclic compound represented by formula 1 and an organic light emitting element including the same.

Description

[0001] This application claims priority based on Korean Patent Application No. 10-2020-0179956, filed on December 21, 2020, the entire contents of which are incorporated herein by reference. Technical Field

[0002] The present invention relates to a heterocyclic compound, an organic light-emitting element comprising the heterocyclic compound, and an organic layer composition of an organic light-emitting element. Background Technology

[0003] Due to the increasing demand for flat panel display components, organic light-emitting diodes (OLEDs) have recently received much attention. OLEDs are devices that convert electrical energy into light, and their performance is greatly influenced by the organic materials positioned between the electrodes.

[0004] An organic light-emitting element (OLED) has 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 recombine in the organic thin film to form pairs, and then emit light as they disappear. The organic thin film can be composed of a single layer, or, if necessary, multiple layers.

[0005] If necessary, organic thin film materials can possess light-emitting capabilities. For example, as organic thin film materials, compounds capable of forming a light-emitting layer by themselves can be used, or compounds capable of serving as a host or dopant in a host-dopant-based light-emitting layer can be used. Additionally, as organic thin film materials, compounds capable of functioning as hole injection layers, hole transport layers, electron blocking layers, electron transport layers, electron injection layers, electron generation layers, and the like can be used.

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

[0007] Previous technical references

[0008] Patent documents

[0009] Korean Patent Application Publication No. 10-2018-0035116 Summary of the Invention

[0010] Technical challenges

[0011] One object of the present invention is to provide a heterocyclic compound that can impart low driving voltage, excellent luminous efficiency and excellent lifetime properties to organic light-emitting elements.

[0012] Another object of the present invention is to provide an organic light-emitting element comprising the heterocyclic compound.

[0013] Another object of the present invention is to provide an organic layer composition comprising the heterocyclic compound.

[0014] Technical solutions

[0015] The present invention provides a heterocyclic compound, which is represented by the following formula 1.

[0016] A heterocyclic compound represented by Formula 1:

[0017] [Formula 1]

[0018]

[0019] in,

[0020] X is O or S;

[0021] Ar1, Ar2 and Ar3 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C60 aryl or a substituted or unsubstituted C2 to C60 heteroaryl;

[0022] R1 to R8 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or Unsubstituted C2 to C60 heteroaryl; or -NR21R22, wherein R21 and R22 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C10 alkyl, a substituted or unsubstituted C6 to C60 aryl, or a substituted or unsubstituted C2 to C60 heteroaryl; and the above R21 and R22 can be combined with each other to form a substituted or unsubstituted C6 to C60 aromatic ring or a substituted or unsubstituted C2 to C60 heterocycle;

[0023] L1 to L4 may be the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted C6 to C60 arylene, or a substituted or unsubstituted C2 to C60 heteroarylene.

[0024] m is an integer from 1 to 3, provided that when m is 2 or greater than 2, each Ar1 is either the same or different from the others.

[0025] n, o, p, and q are either the same or different from each other, and each is an integer from 0 to 3 independently, provided that each of n, o, p, and q is 2 or greater than 2, and each of L1, L2, L3, and L4 is either the same or different from each other.

[0026] In addition, the present invention provides an organic light-emitting element, the organic light-emitting element comprising:

[0027] First electrode;

[0028] The second electrode is positioned to face the first electrode; and

[0029] One or more organic layers are disposed between the first electrode and the second electrode.

[0030] The organic layer therein comprises the heterocyclic compound represented by Formula 1.

[0031] In addition, the present invention provides an organic layer composition for an organic light-emitting element, the organic layer composition comprising the heterocyclic compound represented by Formula 1.

[0032] Invention Effects

[0033] The heterocyclic compounds of the present invention and the organic layer compositions comprising the heterocyclic compounds can be usefully used as materials for the organic layers of organic light-emitting elements (OLEDs). Specifically, these materials are used as hole transport layer materials and / or electron blocking layer materials, thereby providing significant effects in reducing the driving voltage of OLEDs, improving the luminous efficiency of OLEDs, and improving the lifetime properties of OLEDs. Furthermore, the heterocyclic compounds of the present invention provide excellent thermal stability.

[0034] The organic light-emitting element of the present invention includes the heterocyclic compound, thereby providing excellent driving voltage, luminous efficiency and lifetime properties. Attached Figure Description

[0035] Figures 1 to 3 These are schematic diagrams illustrating the stacked structure of an organic light-emitting element according to an embodiment of the present invention.

[0036] [Symbol Explanation]

[0037] 100:Substrate

[0038] 200: Anode

[0039] 300: Organic layer

[0040] 301: Hole Injection Layer

[0041] 302: Hole Transport Layer

[0042] 303: Emissive layer

[0043] 304: Cavity Blocking Layer

[0044] 305: Electron transport layer

[0045] 306: Electron Injection Layer

[0046] 400: Cathode Detailed Implementation

[0047] The invention will be described in detail below.

[0048] In this invention, the term "substituted" means that a hydrogen atom bonded to a carbon atom in a compound is replaced by another substituent, and the position to be substituted is not limited, as long as it is the position where the hydrogen atom is substituted (i.e., the position where it can be substituted by a substituent). When substituted by two or more substituents, the two or more substituents may be the same as or different from each other.

[0049] In this invention, the term "substituted or unsubstituted" means that it is not substituted or substituted by one or more substituents selected from the group consisting of C1 to C60 straight-chain or branched alkyl; C2 to C60 straight-chain or branched alkenyl; C2 to C60 straight-chain or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocyclic alkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R", -P(=O)RR'; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine, or it is not substituted or substituted by two or more substituents selected from the substituents exemplified above that are linked together.

[0050] In this invention, the alkyl group comprises a straight or branched chain having 1 to 60 carbon atoms and may be further substituted with another substituent. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tributyl, dibutyl, 1-methyl-butyl, 1-ethyl-butyl, 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, trioctyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

[0051] In this invention, the alkenyl group comprises a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted with another substituent. The number of carbon atoms in the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples include, but are not limited to, 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, and the like.

[0052] In this invention, the alkynyl group comprises a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The number of carbon atoms in the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0053] In this invention, cycloalkyl groups comprise monocyclic or polycyclic compounds having 3 to 60 carbon atoms, and may be further substituted with another substituent. In this case, polycyclic refers to a group in which the cycloalkyl group is directly attached to or condensed with another cyclic group. In this case, the other cyclic group may be a cycloalkyl group, but may be a different type of cyclic group such as a heterocycloalkyl, aryl, heteroaryl, or the like. The number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, more specifically 5 to 20. Specifically, it includes, but is not limited to, 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, and the like.

[0054] In this invention, the heterocyclic alkyl group includes O, S, Se, N, or Si as heteroatoms, comprising a monocyclic or polycyclic structure having 2 to 60 carbon atoms, and may be further substituted with another substituent. In this case, the polycyclic group refers to a group in which the heterocyclic alkyl group is directly attached to or condensed with another cyclic group. In this case, the other cyclic group may be a heterocyclic alkyl group, but may be a different type of cyclic group such as cycloalkyl, aryl, heteroaryl, or the like. The number of carbon atoms in the heterocyclic alkyl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 20.

[0055] In this invention, the aryl group comprises a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted with other substituents. In this case, polycyclic refers to a group in which the aryl group is directly attached to or condensed with another cyclic group. In this case, the other cyclic group may be an aryl group, but may be a different type of cyclic group such as cycloalkyl, heterocycloalkyl, heteroaryl, or the like. The aryl group includes spirocyclic groups. The number of carbon atoms in the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of aryl groups include, but are not limited to, phenyl, biphenyl, triphenyl, naphthyl, anthracene, etc. Benzyl, phenanthrene, perylene, fluoranthracene, dithionyl, fenyl, pyrene, condensed tetraphenyl, condensed pentaphenyl, fluorenyl, indene, acenaphthene, benzofluorenyl, spirodifluorenyl, 2,3-dihydro-1H-indene, their condensed cyclic groups and analogues.

[0056] In this invention, the fluorene group can be substituted, and adjacent substituents can bond to each other to form a ring.

[0057] When the fluorene group is substituted, it can be, but is not limited to, the following: Or similar items.

[0058] In this invention, the heteroaryl group includes S, O, Se, N, or Si as heteroatoms, comprising a monocyclic or polycyclic structure having 2 to 60 carbon atoms, and may be further substituted with other substituents. In this case, the polycyclic group refers to a group in which the heteroaryl group is directly connected to or condensed with another cyclic group. In this art, the other cyclic group may be a heteroaryl group, but may be a different type of cyclic group such as cycloalkyl, heterocycloalkyl, aryl, or the like. The number of carbon atoms in the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of heteroaryl groups include, but are not limited to, pyridyl, pyrroloyl, pyrimidinyl, pyridazinyl, furanyl, thiophene, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazolyl, oxadiazolyl, thiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiaranyl, diazinyl, oxazinyl, thiazolyl, dioxinyl group, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, isoquinazolinyl, quinozolylyl (group), naphthidyl, acridineyl, phenanthridineyl, imidazopyridyl, diazanaphthyl, triazaindyl, indoleyl, indoleazinyl, benzothiazolyl, benzoxazolyl, benzoimidazolyl, benzothiopheneyl, benzofuranyl, dibenzothiopheneyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenanthridineyl, indole[2,3-a]carbazolyl, indole[2,3-b]carbazolyl Azolyl, indololinyl, 10,11-dihydro-dibenzo[b,f]azolinyl, 9,10-dihydroacridyl, phenazinyl, phenanthrazinyl, phthalazinyl, naphridinyl, phenolinyl, benzo[c][1,2,5]thiadiazolyl, 5,10-dihydrodibenzo[b,e][1,4]azasilolinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]inzolyl, pyrido[1,2-a]imidazo[1,2-e]indololinyl, 5,11-dihydroindo[1,2-b]carbazoleyl and analogues.

[0059] In this invention, the amino group may be selected from the group consisting of monoalkylamino, monoarylamino, monoheteroarylamino, -NH2, dialkylamino, diarylamino, diheteroarylamino, alkylarylamino, alkylheteroarylamino, and arylheteroarylamino, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amino groups include, but are not limited to, methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, diphenylamino, anthraceneamino, 9-methyl-anthraylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenylxylylamino, triphenylamino, biphenylnaphthylamino, phenylbiphenylamino, biphenylfluorenylamino, phenylbitriphenylamino, biphenylbitriphenylamino, and the like.

[0060] In this invention, arylene refers to a group having two bonding positions on an aryl group, i.e., a divalent group. The above description of aryl groups applies, except that each of them is a divalent group. Conversely, heteroarylene refers to a group having two bonding positions on a heteroaryl group, i.e., a divalent group. The above description of heteroaryl groups applies, except that each of them is a divalent group.

[0061] In this invention, "adjacent" groups can refer to a substituent substituted on an atom directly connected to the atom on which the related substituent is substituted, a substituent spatially closest to the substituent, or another substituent substituted on the atom on which the related substituent is substituted. For example, two substituents substituted at an ortho position on a benzene ring and two substituents substituted at the same carbon atom on an aliphatic ring can be interpreted as groups "adjacent" to each other.

[0062] In this invention, "when no substituent is indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium (2H) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0063] In one embodiment of the invention, "when no substituent is indicated in the chemical formula or compound structure" may mean that hydrogen or deuterium is present at all positions that can be substituted by substituents. That is, deuterium is an isotope of hydrogen, and therefore some hydrogen atoms may be deuterium as an isotope, and in this case, the deuterium content may be 0% to 100%.

[0064] In one embodiment of the invention, in the case where "no substituent is indicated in the chemical formula or compound structure", hydrogen and deuterium can be used interchangeably in the compound unless deuterium is explicitly excluded (e.g., "0% deuterium content", "100% hydrogen content", and "all substituents are hydrogen").

[0065] In one embodiment of the present invention, deuterium is an isotope of hydrogen and is an element having a deuterium nucleus consisting of a proton and a neutron, and can be expressed as hydrogen-2, and its element symbol can also be written as D or 2H.

[0066] In one embodiment of the present invention, isotopes refer to atoms having the same number of atoms (Z) but different mass numbers (A), and can also be interpreted as elements having the same number of protons but different numbers of neutrons.

[0067] In one embodiment of the present invention, the meaning of the T% content of a specific substituent can be defined by the equation: T2 / T1×100=T%, where T1 is defined as the total number of substituents that the basic compound may have, and T2 is defined as the number of specific substituents that are substituted therein.

[0068] That is, in one instance, by The indicated 20% deuterium content in a phenyl group may mean that the total number of substituents the phenyl group can have is 5 (T1 in the equation), and the number of deuterium substituents is 1 (T2 in the equation). That is, the 20% deuterium content in a phenyl group can be represented by the following structural formula:

[0069]

[0070] Additionally, in one embodiment of the present invention, the case of "phenyl having a deuterium content of 0%" may mean that it does not contain deuterium atoms, that is, phenyl having 5 hydrogen atoms.

[0071] In this invention, the deuterium content in the heterocyclic compound represented by Formula 1 can be from 0% to 100%.

[0072] This invention provides a heterocyclic compound, which is represented by the following formula 1:

[0073] [Formula 1]

[0074]

[0075] in,

[0076] X is O or S;

[0077] Ar1, Ar2, and Ar3 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0078] R1 to R8 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or Unsubstituted C2 to C60 heteroaryl; or -NR21R22, wherein R21 and R22 may be the same as or different from each other, and each is independently a substituted or unsubstituted C1 to C10 alkyl, a substituted or unsubstituted C6 to C60 aryl, or a substituted or unsubstituted C2 to C60 heteroaryl; and the above R21 and R22 may combine with each other to form a substituted or unsubstituted C6 to C60 aromatic ring or a substituted or unsubstituted C2 to C60 heterocycle.

[0079] L1 to L4 may be the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted C6 to C60 arylene, or a substituted or unsubstituted C2 to C60 heteroarylene.

[0080] m is an integer from 1 to 3, provided that when m is 2 or greater than 2, each Ar1 is either the same as or different from the others.

[0081] n, o, p, and q are either the same or different from each other, and each is an integer from 0 to 3 independently, provided that each of n, o, p, and q is 2 or greater than 2, and each of L1, L2, L3, and L4 is either the same or different from each other.

[0082] In one embodiment of the present invention, the heteroatom in the heteroatom-containing substituent may be one or more selected from O, S, Se, N and Si.

[0083] In another embodiment of the invention, the heteroatom in the heteroatom-containing substituent may be one or more selected from O, S and N.

[0084] In one embodiment of the invention, X may be O, and in another embodiment, X may be S.

[0085] In one embodiment of the present invention, Ar1, Ar2 and R3 may be the same as or different from each other, and may each be independently a substituted or unsubstituted C6 to C30 aryl or a substituted or unsubstituted C2 to C30 heteroaryl.

[0086] In another embodiment of the invention, Ar1, Ar2 and R3 may be the same as or different from each other, and may each be independently a substituted or unsubstituted C6 to C20 aryl or a substituted or unsubstituted C2 to C20 heteroaryl.

[0087] In another embodiment of the invention, Ar1, Ar2 and Ar3 may be the same as or different from each other, and may each be independently substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, anthracene, phenanthrene, pyrene, ditriphenylene, carbazolyl, dibenzofuranyl, dibenzothiophene, 9,9'-dimethylfluorenyl, 9,9'-dibenzofluorenyl or 9,9'-spirodifluorenyl.

[0088] In one embodiment of the present invention, R1 to R8 may be the same as or different from each other, and each may independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C60 aryl, substituted or unsubstituted C2 to C60 heteroaryl, or -NR21R22, wherein R21 and R22 may be the same as or different from each other, and each may independently be substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C60 aryl, or substituted or unsubstituted C2 to C60 heteroaryl; and R21 and R22 may be combined with each other to form a substituted or unsubstituted C6 to C30 aromatic ring or a substituted or unsubstituted C2 to C30 heterocycle, and

[0089] In another embodiment of the invention, R1 to R8 may be the same as or different from each other, and may each be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl, or -NR21R22, wherein R21 and R22 may be the same as or different from each other, and may each be independently substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heteroaryl; and R21 and R22 may be combined with each other to form a substituted or unsubstituted C6 to C30 aromatic ring or a substituted or unsubstituted C2 to C30 heterocycle.

[0090] In another embodiment of the present invention, R1 to R8 may be the same as or different from each other, and may each be independently hydrogen, deuterium, substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted C2 to C20 heteroaryl, or -NR21R22, wherein R21 and R22 may be the same as or different from each other, and may each be independently substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, anthracene, phenanthrene, pyrene, bitriphenylene, carbazolyl, dibenzofuranyl, dibenzothiophene, 9,9'-dimethylfluorenyl, 9,9'-dibenzofluorenyl, or 9,9'-spirodifluorenyl.

[0091] In another embodiment of the present invention, R1 to R8 may be the same as or different from each other, and may each be independently hydrogen, deuterium, substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, anthracene, phenanthrene, pyrene, bitriphenylene, carbazolyl, dibenzofuranyl, dibenzothiophene, 9,9'-dimethylfluorenyl, 9,9'-dibenzofluorenyl or 9,9'-spirodifluorenyl.

[0092] In another embodiment of the present invention, R1 to R8 may be the same as or different from each other, and may be hydrogen or deuterium.

[0093] In one embodiment of the present invention, L1 to L4 may be the same as or different from each other, and may each be independently a substituted or unsubstituted C6 to C30 aryl or a substituted or unsubstituted C2 to C30 heteroaryl.

[0094] In another embodiment of the invention, L1 to L4 may be the same as or different from each other, and may each be independently a substituted or unsubstituted C6 to C20 aryl or a substituted or unsubstituted C2 to C20 heteroaryl.

[0095] In another embodiment of the present invention, L can be a substituted or unsubstituted phenylene, naphthyl, anthraceneyl, phenanthryl, pyridyl or pyrimidinyl group.

[0096] In one embodiment of the invention, the "substitution" in the definitions of Ar1, Ar2, and Ar3; R1 to R8; and L1 to L4 may each be independently achieved by one or more substituents selected from the group consisting of C1 to C10 straight-chain or branched alkyl; C2 to C10 straight-chain or branched alkenyl; C2 to C10 straight-chain or branched alkynyl; C3 to C15 cycloalkyl; C2 to C20 heterocycloalkyl; C6 to C30 aryl; C2 to C30 heteroaryl; C1 to C10 alkylamine; C6 to C30 arylamine; and C2 to C30 heteroarylamine.

[0097] In another embodiment of the invention, the “substitution” in the definitions of Ar1, Ar2 and Ar3; R1 to R8; and L1 to L4 may each be independently carried out using one or more substituents selected from the group consisting of C1 to C10 straight-chain or branched alkyl; C2 to C10 straight-chain or branched alkenyl; C2 to C10 straight-chain or branched alkynyl; C6 to C30 aryl; C2 to C30 heteroaryl; C6 to C30 arylamine; and C2 to C30 heteroarylamine.

[0098] In another embodiment of the invention, the “substitution” in the definitions of Ar1, Ar2 and Ar3; R1 to R8; and L1 to L4 may each be independently carried out using one or more substituents selected from the group consisting of C6 to C30 aryl; C2 to C30 heteroaryl; C6 to C30 arylamine; and C2 to C30 heteroarylamine.

[0099] In another embodiment of the invention, the “substitution” in the definitions of Ar1, Ar2 and Ar3; R1 to R8; and L1 to L4 may each be independently carried out using one or more substituents selected from the group consisting of phenyl, naphthyl, pyridyl, anthracene, carbazole, biphenyl, dibenzothiophene, dibenzofuran and phenanthrene.

[0100] In one embodiment of the invention, m can be an integer from 1 to 2, provided that when m is 2, each Ar1 can be selected independently.

[0101] In another embodiment of the invention, m may be 1.

[0102] In one embodiment of the invention, n, o, p and q may be the same as or different from each other, and each may be an integer from 0 to 2 independently, provided that when each of n, o, p and q is 2, each of L1, L2, L3 and L4 is the same as or different from each other.

[0103] In another embodiment of the invention, n, o, p and q may be the same as or different from each other, and each may be 0 or 1 independently.

[0104] In one embodiment of the invention, the heterocyclic compound represented by Formula 1 may be a compound represented by any of the following Formulas 2 to 5:

[0105] [Equation 2]

[0106]

[0107] [Formula 3]

[0108]

[0109] [Formula 4]

[0110]

[0111] [Formula 5]

[0112]

[0113] in,

[0114] X, Ar1, Ar2, Ar3, R1 to R8, L1 to L4, n, o, p and q are as defined in Equation 1.

[0115] In one embodiment of the invention, the heterocyclic compound represented by Formula 1 may be a compound represented by any of the following compounds:

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149] By introducing various substituents into the corresponding structures, compounds of Formula 1 above can be synthesized into compounds possessing the inherent properties of the introduced substituents. For example, by introducing substituents, primarily used in the manufacture of hole injection layer materials, hole transport layer materials, electron blocking layer materials, light-emitting layer materials, hole blocking layer materials, electron transport layer materials, electron injection layer materials, and electron generation layer materials, into the core structure, materials that meet the requirements of each organic layer can be synthesized.

[0150] Furthermore, by introducing various substituents into the structure of Formula 1, the energy band gap can be precisely controlled, while improving the properties at the interface between organic materials and diversifying the applications of the materials.

[0151] Heterocyclic compounds can be used as one or more of the following applications in organic layers for organic light-emitting elements: hole injection layer material, hole transport layer material, electron blocking layer material, light-emitting layer material, hole blocking layer material, electron transport layer material, and electron injection layer material, and more particularly, they can be used as electron transport layer material and / or hole blocking layer material.

[0152] By enhancing the hole characteristics in the dibenzofuran skeleton, the heterocyclic compounds of the present invention can exhibit excellent performance in hole transport layers and / or electron blocking layers by controlling the band gap and T1 value. Specifically, by widening the band gap and increasing the T1 value, excellent performance can be exhibited in hole transport layers and / or electron blocking layers.

[0153] In addition, the present invention relates to an organic light-emitting element, the organic light-emitting element comprising: a first electrode; a second electrode disposed facing the first electrode; and one or more organic layers disposed between the first electrode and the second electrode, wherein the organic layers comprise a heterocyclic compound represented by Formula 1 above.

[0154] In one embodiment of the present invention, the first electrode may be an anode and the second electrode may be a cathode.

[0155] In another embodiment, the first electrode may be a cathode, and the second electrode may be an anode.

[0156] An organic light-emitting element according to an embodiment of the present invention may include one or two layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer on an organic layer, and may have a stacked structure in the order of anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode, but is not limited to.

[0157] In one embodiment of the present invention, the organic light-emitting element may be a blue organic light-emitting element, and the heterocyclic compound represented by Formula 1 may be used as a material for the blue organic light-emitting element.

[0158] In one embodiment of the present invention, the organic light-emitting element may be a red organic light-emitting element, and the heterocyclic compound represented by Formula 1 may be used as a material for the red organic light-emitting element.

[0159] In one embodiment of the present invention, the organic light-emitting element may be a green organic light-emitting element, and the heterocyclic compound represented by Formula 1 may be used as a material for the green organic light-emitting element.

[0160] The specific details of the heterocyclic compounds represented by Formula 1 are as described above.

[0161] In addition to using the aforementioned heterocyclic compounds to form one or more organic layers, the organic light-emitting elements of the present invention can be manufactured using conventional methods and materials for manufacturing organic light-emitting elements.

[0162] In one embodiment of the present invention, in the blue organic light-emitting element, the red organic light-emitting element and the green organic light-emitting element, the heterocyclic compound represented by Formula 1 above can be used for one or more uses selected from hole injection layer material, hole transport layer material, electron blocking layer material, light-emitting layer material, hole blocking layer material, electron transport layer material and electron injection layer material, and specifically, can be used as hole transport layer material and / or electron blocking layer material.

[0163] The following is attached Figures 1 to 3 The diagram illustrates the stacking order of electrodes and organic layers in an organic light-emitting element according to an embodiment of the present invention. However, the scope of the invention is not intended to be limited by these figures, and structures of organic light-emitting elements known in this art can also be applied to the present invention.

[0164] according to Figure 1 This illustrates an organic light-emitting element in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, it is not limited to this structure and can be configured as follows: Figure 2The embodiment shown is an organic light-emitting element in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate.

[0165] Figure 3 This illustrates a scenario where the organic layers are composed of multiple layers. According to... Figure 3 The organic light-emitting element includes a hole injection layer 301, a hole transport layer 302, a light-emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present invention is not limited to this stacked structure, and if necessary, the remaining layers other than the light-emitting layer can be omitted, and other necessary functional layers, such as an electron blocking layer, can be further added.

[0166] When manufacturing organic light-emitting elements, heterocyclic compounds can be formed into organic layers using solution coating and vacuum deposition methods. In this context, solution coating methods refer to, but are not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and similar methods.

[0167] The organic layer of the organic light-emitting element of the present invention may have a single-layer structure, or it may have a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure comprising one or more of the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron generating layer, and the like as organic layers. However, the structure of the organic light-emitting element is not limited thereto, and may include a smaller or larger number of organic layers.

[0168] In an organic light-emitting element according to an embodiment of the present invention, materials other than the heterocyclic compounds represented by Formula 1 above are listed below, but these are for illustrative purposes only and are not intended to limit the scope of the invention, and can be replaced by materials known in this art.

[0169] As anode materials, materials with relatively large work functions can be used, and transparent conductive oxides, metals, conductive polymers, or the like can be used. Specific examples of anode materials include, but are not limited to: metals, such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and the like.

[0170] Materials with relatively low work functions can be used as cathode materials, and metals, metal oxides, conductive polymers, or the like can be used. Specific examples of cathode materials include, but are not limited to: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; multilayer structures such as LiF / Al or LiO2 / Al; and the like.

[0171] As a hole injection layer material, known hole injection layer materials can be used, such as phthalocyanine compounds, such as copper phthalocyanine and the like disclosed in U.S. Patent No. 4,356,429; or starburst-type amine derivatives disclosed in document [Advanced Material, 6, page 677 (1994)]. Derivatives, such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4',4”-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB); soluble conductive polymers, polyaniline / dodecylbenzenesulfonic acid; or poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid, or polyaniline / poly(4-styrene-sulfonate) and the like.

[0172] As a hole transport layer material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives or similar materials can be used, and low molecular weight or high molecular weight materials can be used.

[0173] As an electron transport layer 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 and its derivatives, diphenyl dicyanoethylene and its derivatives, biphenylquinone derivatives, 8-hydroxyquinoline and its derivatives and similar compounds can be used, and both high molecular weight and low molecular weight materials can be used.

[0174] As an electron injection layer material, LiF is commonly used in this technology, for example, but the invention is not limited thereto.

[0175] Red, green, or blue luminescent materials can be used as the luminescent layer material, and mixtures of two or more luminescent materials can be used if necessary. In this case, the two or more luminescent materials can be used as separate sources by deposition, or they can be premixed and used as a single source by deposition. Additionally, fluorescent materials and phosphorescent materials can be used as the luminescent layer material. Materials that emit light by combining holes and electrons injected from the anode and cathode, respectively, can be used as the luminescent layer material, and materials in which the host material and dopant material participate in luminescence together can also be used.

[0176] When using a substrate of mixed luminescent layer materials, it can be used by mixing the same type of substrate or by mixing different types of substrates. For example, it can be used by selecting any two or more types of n-type or p-type substrate materials as the substrate material of the luminescent layer.

[0177] In the phosphorescent materials described herein, phosphorescent materials known in this art can be used as phosphorescent dopant materials. For example, phosphorescent dopant materials represented by LL'MX', LL'L”M, LMX'X”, L2MX', and L3M can be used, but the scope of the invention is not limited to these examples.

[0178] M can be iridium, platinum, osmium, or the like.

[0179] L is an anionic bidentate ligand coordinated to M via sp2 carbon and heteroatoms, and X can trap electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (7,8-benzoquinoline), (thienopyridine), phenylpyridine, benzothienopyridine, 3-methoxy-2-phenylpyridine, thienopyrazine, tolylpyridine, and the like. Non-limiting examples of X' and X” include acetylacetonate (acac), hexafluoroacetylacetonate, salinomycete, pyridine carboxylate, 8-hydroxyquinoline ester, and the like.

[0180] Specific examples of phosphorescent dopants are shown below, but are not limited to these examples:

[0181]

[0182] In one embodiment of the invention, the light-emitting layer comprises a heterocyclic compound represented by Formula 1, and the heterocyclic compound can be used in conjunction with an iridium dopant.

[0183] In one embodiment of the present invention, red phosphorescent dopant (piq)2(Ir)(acac), green phosphorescent dopant Ir(ppy)3, and the like can be used as iridium dopants.

[0184] In one embodiment of the present invention, the dopant content, based on the entire light-emitting layer, may be 1% to 15%, more preferably 3% to 10%, and even more preferably 5% to 10%.

[0185] As an electron blocking layer material, materials selected from, but not limited to, tri(phenylylprazole)iridium, 9,9-bis[4-(N,N-bis-biphenyl-4-ylamino)phenyl]-9H-fluorene (BPAPF), bis[4-(p,p-xylamino)phenyl]diphenylsilane, and 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (BPAF) can be used. One or more of the following compounds: [hyl)-N-phenylamino]biphenyl (NPD), N,N'-dicarbazolyl-3,5-benzene (N,N'-dicarbazolyl-3,5-benzene (mCP), and bis[4-(N,N-diethylamino)-2-methylphenyl](4-methylphenyl)methane (MPMP).

[0186] In addition, the electron blocking layer material may contain inorganic compounds. For example, it may contain, but is not limited to, at least one of the following: halide compounds, such as LiF, NaF, KF, RbF, CsF, FrF, MgF2, CaF2, SrF2, BaF2, LiCl, NaCl, KCl, RbCl, CsCl, and FrCl; and oxides, such as Li2O, Li2O2, Na2O, K2O, Rb2O, Rb2O2, Cs2O, Cs2O2, LiAlO2, LiBO2, LiTaO3, LiNbO3, LiWO4, Li2CO, NaWO4, KAlO2, K2SiO3, B2O5, Al2O3, and SiO2; or combinations thereof.

[0187] As a hole-blocking layer material, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), aluminum complexes and the like can be used without restriction.

[0188] In the organic light-emitting element of the present invention, materials known in this art can be used without limitation as materials not described above.

[0189] Depending on the material to be used, the organic light-emitting element according to one embodiment of the present invention may be a top-emitting, bottom-emitting, or dual-emitting type.

[0190] In addition, the present invention relates to an organic layer composition of an organic light-emitting element, the organic layer composition comprising a heterocyclic compound represented by Formula 1.

[0191] The specific details of the heterocyclic compounds represented by Formula 1 are as described above.

[0192] The organic layer composition can be used as a hole injection layer material, a hole transport layer material, an electron blocking layer material, a light-emitting layer material, a hole blocking layer material, an electron transport layer material, and an electron injection layer material, and more specifically, it can be preferably used as a hole transport layer material and / or an electron blocking layer material.

[0193] The organic layer composition may further include materials commonly used in organic layer compositions in this art, as well as heterocyclic compounds represented by Formula 1. For example, it may further include materials and the like included for the preparation of heterocyclic compounds to be used in the deposition process.

[0194] In addition, the present invention relates to a method for manufacturing an organic light-emitting element, the method comprising the following steps: preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layers, wherein the step of forming the organic layers includes forming one or more organic layers using a heterocyclic compound represented by Formula 1 of the present invention or the composition of the organic layers.

[0195] In one embodiment of the invention, the step of forming the organic layer can be achieved by depositing a heterocyclic compound represented by Formula 1 or the organic layer composition using a thermal vacuum deposition method.

[0196] If necessary, the organic layer comprising the organic layer composition may further include other materials commonly used in this technology.

[0197] Methods of implementing the present invention

[0198] According to an embodiment of the present invention, the heterocyclic compound represented by Formula 1 can function in organic electronic components, including organic solar cells, organic photoacceptors, organic transistors and the like, in a manner similar to that applied to said organic light-emitting elements.

[0199] In the following sections, preferred examples will be presented to aid in understanding the invention, but these examples are provided not to limit the invention, but to promote an understanding of the invention.

[0200] [Preparation Example 1] Preparation of Compound 1

[0201]

[0202] 1) Preparation of compound 1-1

[0203] Compound 10-bromophenanthrene-9-ol (50 g, 0.183 mol, 1 equivalent), (6-bromo-3-chloro-2-fluorophenyl)boronic acid (A) (50.9 g, 0.201 mol, 1.1 equivalent), K3PO4 (77.7 g, 0.366 mol, 2 equivalent), and Pd(PPh3)4 (10.6 g, 0.0092 mol, 0.05 equivalent) were placed in 1,4-dioxane (600 mL) and water (150 mL) and stirred at 100 °C for 6 h. Upon completion of the reaction, it was cooled to room temperature and the reaction was stopped by adding water. Extraction was then performed using methylene chloride (MC) and water. The water was subsequently removed with MgSO4. Separation was performed using a silica gel column to obtain 51.4 g of compound 1-1, in 70% yield.

[0204] 2) Preparation of compounds 1-2

[0205] Compound 1-1 (50 g, 0.124 mol, 1 equivalent) was placed in dimethylacetamide (DMA) (500 mL) and stirred at 140 °C. Upon completion of the reaction, it was cooled to room temperature and then filtered to remove Cs₂CO₃ (80.2 g, 0.246 mol, 2 equivalents). The filtered solid was washed with water and MeOH and then dried to obtain 42.6 g of compound 1-2, in 90% yield.

[0206] 3) Preparation of compounds 1-3

[0207] Compounds 1-2 (40 g, 0.105 mol, 1 equivalent), phenylboronic acid (14.1 g, 0.116 mol, 1.1 equivalent), K3PO4 (44.6 g, 0.210 mol, 2 equivalent), and Pd(PPh3)4 (6.1 g, 0.0053 mol, 0.05 equivalent) were placed in 1,4-dioxane (480 mL) and water (120 mL) and stirred at 100 °C for 6 h. Upon completion of the reaction, it was cooled to room temperature and the reaction was stopped by adding water. Extraction was then performed using MC and water. The water was subsequently removed with MgSO4. Separation was performed using a silica gel column to obtain 33.8 g of compounds 1-3, in 85% yield.

[0208] 4) Preparation of Compound 1

[0209] 9,9-Dimethyl-N-phenyl-9H-fluorene-2-amine (B) (10 g, 0.035 mol, 1 equivalent), compounds 1-3 (14 g, 0.037 mol, 1.05 equivalent), NaOt-Bu (6.7 g, 0.070 mol, 2 equivalent), Pd2(dba)3 (1.6 g, 0.0018 mol, 0.05 equivalent), and P(t-Bu)3 (0.7 g, 0.0035 mol, 0.1 equivalent) were placed in toluene (100 mL) and stirred at 100 °C for 3 h. After stopping the reaction by adding water, extraction was performed using MC and water. Water was then removed with MgSO4. Separation was performed by silica gel column chromatography to obtain 15.4 g of compound 1, in 76% yield.

[0210] The compound was synthesized in the same manner as in Preparation Example 1 above, except that intermediate A from Table 1 was used instead of (6-bromo-3-chloro-2-fluorophenyl)boronic acid (A) and intermediate B from Table 1 was used instead of 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine (B).

[0211] [Preparation Example 2] Preparation of Compound 49

[0212]

[0213] 1) Preparation of compound 2-1

[0214] 5-Bromo-2-chlorobenzylthiol (A) (30 g, 0.134 mol, 1.0 equivalent), 9,10-dibromophenanthrene (54.1 g, 0.161 mol, 1.2 equivalent), and NaOH (10.7 g, 0.268 mol, 2.5 equivalent) were placed in EtOH (300 mL) and stirred under reflux for 4 hours. Upon completion of the reaction, it was cooled to room temperature, and the reaction was stopped by adding water. Extraction was then performed using MC and water. Subsequently, the water was removed with MgSO4. Separation was performed using a silica gel column to obtain 51.3 g of compound 2-1 in 80% yield.

[0215] 2) Preparation of compound 2-2

[0216] Compound 2-3 (50 g, 0.104 mol, 1 equivalent) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (47.2 g, 0.208 mol, 2 equivalents) were placed in dichloromethane (MC) (500 mL) and stirred at room temperature for 24 hours. At the completion of the reaction, the reaction was stopped by adding water, and extraction was then performed using MC and water. The water was subsequently removed with MgSO4. Separation was performed using a silica gel column to obtain 35.1 g of compound 2-2, in 80% yield.

[0217] 3) Preparation of compounds 2-3

[0218] Compounds 2-3 were obtained in the same manner as those used in Preparation Example 1 above for the synthesis of compounds 1-3.

[0219] 4) Preparation of compound 49

[0220] Compound 49 was obtained in the same manner as the synthesis of compound 1 in Preparation Example 1 above.

[0221] The compound was synthesized in the same manner as in Preparation Example 2 above, except that intermediate A from Table 1 was used instead of 5-bromo-2-chlorobenzylthiol (A) and intermediate B from Table 1 was used instead of 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine (B).

[0222] [Table 1]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228] The compound was prepared in the same manner as in the preparation example above, and the results of the synthesis confirmation are shown in Tables 2 and 3. Table 2 shows the 1H nuclear magnetic resonance (NMR) measurements (CDCl3, 300 MHz), and Table 3 shows the field desorption mass spectrometry (FD-MS) measurements.

[0229] [Table 2]

[0230]

[0231]

[0232] [Table 3]

[0233]

[0234] [Experimental Example]

[0235] <Experimental Example 1>

[0236] 1) Manufacturing of organic light-emitting elements

[0237] The transparent electrode ITO film, obtained from OLED glass (manufactured by Samsung-Corning), was ultrasonically washed every 5 minutes using trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropanol before use. Next, the ITO substrate was mounted in the substrate holder of the vacuum deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum deposition apparatus:

[0238]

[0239] Next, after evacuating the chamber to a vacuum level of 10⁻⁶ Torr, a current is applied to the cell to evaporate 2-TNATA, thereby depositing a 600 Å thick hole injection layer on the ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) is placed in another cell of the vacuum deposition apparatus and evaporated by applying a current to the cell, thereby depositing a 300 Å thick hole transport layer on the hole injection layer.

[0240]

[0241] After forming the hole injection layer and hole transport layer in this manner, a blue luminescent material with the following structure is deposited on them as the luminescent layer. Specifically, a blue luminescent host material H1 with a thickness of 200 angstroms is vacuum deposited in a cell of a vacuum deposition apparatus, and a blue luminescent dopant material D1 is vacuum deposited on it at an amount of 5% by weight relative to the host material.

[0242]

[0243] Next, an electron transport layer with a thickness of 300 angstroms is deposited using a compound with the following structural formula E1:

[0244]

[0245] OLED devices were fabricated by depositing an electron injection layer with a thickness of 10 angstroms using lithium fluoride (LiF) and an Al cathode with a thickness of 1,000 angstroms. On the other hand, all organic compounds required for the fabrication of OLED devices were vacuum sublimated and purified at 10⁻⁶ Torr to 10⁻⁸ Torr for each material before being used in OLED fabrication.

[0246] Organic light-emitting elements of the examples and comparative examples of the present invention were manufactured in the same manner as described above, except that the compounds of the present invention shown in Table 4 below and compounds A to G shown above were used instead of the NPB used in forming the hole transport layer. For the organic light-emitting elements manufactured as described above, the electroluminescence (EL) properties were measured using an M7000 from McScience, and based on the measurement results, the lifetime measurement was performed using a lifetime measurement element (M6000) manufactured by McScience at a reference luminance of 700 candela / m² (cd / m²). 2The driving voltage, luminous efficiency, color coordinates (International Commission on Illumination, CIE), and lifetime of the blue organic light-emitting elements manufactured above are shown in Table 4 below.

[0247] [Table 4]

[0248]

[0249] Based on the results in Table 4, it can be confirmed that compared to the blue organic light-emitting elements of Comparative Examples 1 to 8 which used NPB and compounds A to G as hole transport layer materials, the blue organic light-emitting elements using the heterocyclic compounds of the present invention as hole transport layer materials provide significantly improved driving voltage, luminous efficiency, and lifetime properties.

[0250] The NPB used in the organic light-emitting element of Comparative Example 1 is similar to the heterocyclic compound of the present invention in that it has an arylamine group, but does not include a disubstituted dibenzofuran structure different from the heterocyclic compound of the present invention. Therefore, due to this structural difference, the organic light-emitting element of the present invention exhibits significantly superior performance in all aspects of driving voltage, luminous efficiency, and lifetime properties compared to the organic light-emitting element of Comparative Example 1.

[0251] The structural difference between compounds A to G of Comparative Examples 2 to 8 and the heterocyclic compounds of the present invention comprising a disubstituted dibenzofuran structure is that they comprise a monosubstituted dibenzofuran structure having one substituent. In the case of monosubstituted dibenzofurans, π-π stacking of aromatic rings occurs, which increases the driving voltage and can degrade the device properties. On the other hand, in the case of disubstituted dibenzofurans, π-π stacking of aromatic rings is suppressed, thereby exhibiting the effect of suppressing the degradation of device properties due to the increase in the driving voltage of the organic light-emitting element. Therefore, compared with the compounds of Comparative Examples 2 to 8 comprising a monosubstituted dibenzofuran structure, the heterocyclic compounds of the present invention comprising such a disubstituted dibenzofuran structure provide significantly improved hole transport properties or stability. In addition, due to these effects, compared with the organic light-emitting elements of Comparative Examples 2 to 8, the organic light-emitting element of the present invention comprising a hole transport layer formed using the heterocyclic compounds of the present invention provides very superior driving voltage, luminous efficiency, and lifetime properties.

[0252] <Experimental Example 2>

[0253] 1) Manufacturing of organic light-emitting elements

[0254] The transparent electrode ITO film obtained from glass used in OLEDs (manufactured by Samsung Corning) was ultrasonically washed every 5 minutes using trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropanol before use. Next, the ITO substrate was mounted in the substrate holder of the vacuum deposition apparatus, and the following 4,4',4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in the cell of the vacuum deposition apparatus:

[0255]

[0256] Next, after evacuating the chamber to a vacuum level of 10⁻⁶ Torr, a current is applied to the cell to evaporate 2-TNATA, thereby depositing a 600 Å thick hole injection layer on the ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) is placed in another cell of the vacuum deposition apparatus and evaporated by applying a current to the cell, thereby depositing a 300 Å thick hole transport layer on the hole injection layer.

[0257]

[0258] After forming the hole injection layer and hole transport layer in this manner, a blue luminescent material with the following structure is deposited on them as the luminescent layer. Specifically, a blue luminescent host material H1 with a thickness of 200 angstroms is vacuum deposited in a cell of a vacuum deposition apparatus, and a blue luminescent dopant material D1 is vacuum deposited on it at an amount of 5% by weight relative to the host material.

[0259]

[0260] Next, an electron transport layer with a thickness of 300 angstroms is deposited using a compound with the following structural formula E1:

[0261]

[0262] OLED devices were fabricated by depositing an electron injection layer with a thickness of 10 angstroms using lithium fluoride (LiF) and an Al cathode with a thickness of 1,000 angstroms. On the other hand, all organic compounds required for the fabrication of OLED devices were vacuum sublimated and purified at 10⁻⁶ Torr to 10⁻⁸ Torr for each material before being used in OLED fabrication.

[0263] Except for forming a hole transport layer NPB with a thickness of 250 angstroms, and then forming an electron blocking layer with a thickness of 50 angstroms by depositing the heterocyclic compounds of the present invention shown in Table 5 and compounds A to G shown above on the hole transport layer, the organic light-emitting elements of the examples and comparative examples of the present invention were manufactured in the same manner as described above. The driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the blue organic light-emitting elements manufactured above are shown in Table 5 below.

[0264] [Table 5]

[0265]

[0266] Based on the results in Table 5, it can be confirmed that compared with the blue organic light-emitting elements of Comparative Examples 9 and 10 to 16 which used NPB and compounds A to G as electron blocking layer materials, the blue organic light-emitting elements using the heterocyclic compounds of the present invention as electron blocking layer materials show significant improvements in all aspects of driving voltage, luminous efficiency, and lifetime properties.

[0267] In organic light-emitting devices (OLEDs), the efficiency and lifetime of the OLED device decrease when electrons reach the anode through the hole transport layer instead of recombinating in the emissive layer. To prevent this, compounds with high lowest unoccupied molecular orbitals (LUMO) are used as electron blocking layers. In this case, electrons reaching the anode through the emissive layer are blocked by the energy barrier of the electron blocking layer. Therefore, the probability of holes and electrons forming excitons increases, and their likelihood of being emitted as light in the emissive layer also increases.

[0268] As demonstrated in Experimental Example 2 above, when used as an electron blocking layer material, the heterocyclic compound of the present invention exhibits excellent electron blocking performance compared to NPB and compounds A to G. Furthermore, compared to the organic light-emitting elements of Comparative Examples 9 to 16, the organic light-emitting element of the present invention, including an electron blocking layer formed from such a heterocyclic compound, provides significantly superior driving voltage, luminous efficiency, and lifetime properties.

Claims

1. A heterocyclic compound, represented by formula 1: [Formula 1] in, X is O or S. Ar1 is a substituted or unsubstituted C6 to C30 aryl group. Ar2 and Ar3 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group. R1 to R8 may be the same as or different from each other, and each is independently hydrogen; or deuterium. L1 to L4 may be the same as or different from each other, and each is independently a direct bond or an unsubstituted C6 to C30 aryl group. m is an integer from 1 to 3, provided that when m is 2 or greater than 2, each Ar1 is either the same as or different from the others. n, o, p, and q are either the same or different from each other, and each is an independent integer from 0 to 3, provided that each of n, o, p, and q is 2 or greater than 2, and each of L1, L2, L3, and L4 is either the same or different from each other. The "substitution" in the definitions of Ar1, Ar2 and Ar3 can be carried out independently using one or more substituents selected from the group consisting of C1 to C10 alkyl and C6 to C30 aryl groups.

2. The heterocyclic compound according to claim 1, characterized in that... The heterocyclic compound represented by Formula 1 above is a compound represented by any one of Formulas 2 to 5: [Equation 2] [Formula 3] [Formula 4] [Formula 5] in, X, Ar1, Ar2, Ar3, R1 to R8, L1 to L4, n, o, p and q as defined in claim 1.

3. The heterocyclic compound according to claim 1, characterized in that... The heterocyclic compound represented by Formula 1 above is a compound represented by any of the following compounds: 。 4. An organic light-emitting element, comprising: First electrode; The second electrode is positioned to face the first electrode; as well as One or more organic layers are disposed between the first electrode and the second electrode. The organic layer thereof comprises a heterocyclic compound as described in any one of claims 1 to 3.

5. The organic light-emitting element according to claim 4, characterized in that... The organic layer includes a light-emitting layer, and further includes one or more layers selected from an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, and a hole injection layer.

6. The organic light-emitting element according to claim 5, characterized in that... The organic layer includes the electron blocking layer and the hole transport layer, and any one or more of the electron blocking layer and the hole transport layer contains the heterocyclic compound.

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