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

Abstract

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

Description

Technical Field

[0001] The present invention relates to a heterocyclic compound, an organic light-emitting element including the heterocyclic compound, and a composition for an organic material layer of an organic light-emitting element.

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0101857, filed in the Korean Intellectual Property Office on August 13, 2020, the entire contents of which are incorporated herein by reference. Background Art

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

[0004] An organic light-emitting element has an organic thin film disposed between two electrodes. When voltage is applied to an organic light-emitting element having this structure, electrons and holes injected from the two electrodes combine and pair up in the organic thin film, emitting light when the electrons and holes annihilate. The organic thin film can be formed as a single layer or multiple layers, as desired.

[0005] If desired, the material of the organic thin film may have a light-emitting function. For example, a compound capable of forming a light-emitting layer on its own may be used as the material of the organic thin film, or a compound capable of acting as a host or dopant in a host-dopant type light-emitting layer may be used as the material of the organic thin film. Furthermore, compounds capable of performing hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and similar functions may also be used as the material of the organic thin film.

[0006] The development of organic thin film materials continues to require enhancement of the performance, lifespan or efficiency of organic light emitting devices.

[0007] [Patent Document]

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

[0009] Technical issues

[0010] The present disclosure provides a heterocyclic compound, an organic light-emitting element containing the same, and a composition of an organic material layer for an organic light-emitting element.

[0011] Technical Solutions

[0012] One embodiment of the present application provides a heterocyclic compound represented by the following Chemical Formula 1.

[0013] [Chemical Formula 1]

[0014]

[0015] In Chemical Formula 1,

[0016] X is O; or S,

[0017] L1and L2are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

[0018] R1to R6are the same as or different from each other, and each independently hydrogen, deuterium, 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,

[0019] Ar1and Ar2are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 60 carbon atoms including one or more =N- bonds, or a substituted or unsubstituted amine group, and

[0020] m and n are each an integer of 0 to 3, and when m and n are each 2 or more, the substituents in the parentheses are the same as or different from each other.

[0021] In addition, another embodiment of the present application provides an organic light emitting element including a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layers include a heterocyclic compound represented by Chemical Formula 1.

[0022] Another embodiment of the present application provides a composition for an organic material layer of an organic light emitting element, the composition including a heterocyclic compound represented by Chemical Formula 1 and one of heterocyclic compounds represented by Chemical Formula 4 to Chemical Formula 6.

[0023] Advantageous Effects

[0024] The heterocyclic compound according to one embodiment of the present application can be used as a material for an organic material layer of an organic light emitting element. The heterocyclic compound can be used as a material for a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a charge generation layer, and the like in an organic light emitting element. In particular, the heterocyclic compound represented by Chemical Formula 1 can be used as a material for a light emitting layer of an organic light emitting element. In addition, the use of the heterocyclic compound represented by Chemical Formula 1 in an organic light emitting element can reduce the driving voltage of the element, enhance the light emitting efficiency, and enhance the lifespan characteristics of the element through the thermal stability of the compound. BRIEF DESCRIPTION OF DRAWINGS

[0025] Figures 1 to 3 FIGS. 1 to 3 are diagrams each schematically showing a laminate structure of an organic light emitting element according to an embodiment of the present application.

[0026] Figure 4 FIG. 4 is a diagram showing photoluminescence (PL) changes when a compound of the present application is used as a single host according to an example.

[0027] Figure 5 FIG. 5 is a diagram showing photoluminescence (PL) changes when a compound of the present application is used as a mixed host according to an example.

[0028] BRIEF DESCRIPTION OF DRAWINGS

[0029] 100: substrate

[0030] 200: anode

[0031] 300: organic material layer

[0032] 301: hole injection layer

[0033] 302: hole transport layer

[0034] 303: light emitting layer

[0035] 304: hole blocking layer

[0036] 305: electron transport layer

[0037] 306: electron injection layer

[0038] 400: cathode DETAILED DESCRIPTION

[0039] Hereinafter, the present application will be described in detail.

[0040] One embodiment of the present application provides a heterocyclic compound represented by the following Chemical Formula 1.

[0041] [Chemical Formula 1]

[0042]

[0043] In Chemical Formula 1,

[0044] X is O; or S,

[0045] L1and L2are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

[0046] R1to R6are the same as or different from each other, and each independently hydrogen, deuterium, 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,

[0047] Ar1and Ar2are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 60 carbon atoms including one or more =N- bonds, or a substituted or unsubstituted amine group, and

[0048] m and n are each an integer of 0 to 3, and when m and n are each 2 or more than 2, the substituents in the parentheses are the same as or different from each other.

[0049] By having an amine group and a monocyclic or polycyclic heterocyclic group having 2 to 60 carbon atoms including one or more =N- bonds as substituents in a dibenzofuran or dibenzothiophene structure, the electron of Chemical Formula 1 is more sufficient, and by increasing the current, the effect of reducing the driving voltage is obtained when using the compound represented by Chemical Formula 1 in an element. In addition, by having an amine group having a hole property as a substituent, Chemical Formula 1 has an excellent hole transport ability, and when using the compound represented by Chemical Formula 1 in an element, the effect of reducing the driving voltage is obtained.

[0050] In the present specification, the term "substituent" means that a hydrogen atom bonded to a carbon atom of a compound will be changed to another substituent, and the substitution site is not limited as long as the substitution site is a position where a hydrogen atom is substituted, i.e., a position where a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents can be the same as or different from each other.

[0051] In the present specification, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium, cyano, a halogen, a straight chain or branched alkyl group having 1 to 60 carbon atoms, a straight chain or branched alkenyl group having 2 to 60 carbon atoms, a straight chain or branched alkynyl group having 2 to 60 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 60 carbon atoms, a monocyclic or polycyclic heterocycloalkyl group having 2 to 60 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 60 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms, -SiRR'R", -P(=O)RR', an alkylamine having 1 to 20 carbon atoms, a monocyclic or polycyclic arylamine having 6 to 60 carbon atoms, and a monocyclic or polycyclic heteroarylamine having 2 to 60 carbon atoms, or unsubstituted; or substituted with a substituent that links two or more substituents selected from the substituents shown above, or unsubstituted; and R, R', and R" are the same or different from each other and each independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, 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.

[0052] In the present specification, "a case where a substituent is not specified in a chemical formula or a 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 can be deuterium.

[0053] In one embodiment of the present application, "a case where a substituent is not specified in a chemical formula or a compound structure" can mean that the position where a substituent can occur can be all hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms can be deuterium as an isotope, and herein, the content of deuterium can be 0% to 100%.

[0054] In one embodiment of the present application, in "a case where a substituent is not specified in a chemical formula or a compound structure", when deuterium is not explicitly excluded, such as when the deuterium content is not determined to be 0%, the hydrogen content is 100%, or the substituent is all hydrogen, hydrogen and deuterium can be mixed in the compound.

[0055] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, is an element having a deuteron formed of one proton and one neutron as a nucleus, and can be represented as hydrogen-2, and the element symbol can also be written as D or 2 H.

[0056] In one embodiment of the present application, an isotope means an atom having the same atomic number (Z) but a different mass number (A), and can also be interpreted as an element having the same number of protons but a different number of neutrons.

[0057] In one embodiment of the present application, the meaning of the content T% of a specific substituent can be defined as T2 / T1 x 100 = T%, wherein the total number of substituents that the basic compound can have is defined as T1, and the number of the specific substituent among these substituents is defined as T2.

[0058] In other words, in one example, having a deuterium content of 20% in a phenyl group represented by In other words, having a deuterium content of 20% in a phenyl group can be represented by the following structural formula.

[0059]

[0060] In addition, in one embodiment of the present application, "a phenyl group having a deuterium content of 0%" can mean a phenyl group not containing a deuterium atom, i.e., a phenyl group having 5 hydrogen atoms.

[0061] In the present specification, halogen can be fluorine, chlorine, bromine, or iodine.

[0062] In the present specification, an alkyl group includes a straight chain or branched chain having 1 to 60 carbon atoms, and can be further substituted with other substituents. The number of carbon atoms of the alkyl group can be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples thereof can include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tertiary butyl, secondary butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tertiary octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

[0063] In the present specification, an alkenyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and can be further substituted with other substituent groups. The number of carbon atoms of the alkenyl group can be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples thereof can include ethenyl, 1- propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-buten- dienyl, allyl, 1-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2- diphenylethen-1-yl, 2-phenyl-2-(naphth-1-yl)ethen-1-yl, 2,2- bis(diphenyl-1-yl)ethen-1-yl, stilbenyl, styryl, and the like, but are not limited thereto.

[0064] In the present specification, an alkynyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and can be further substituted with other substituent groups. The number of carbon atoms of the alkynyl group can be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0065] In the present specification, an alkoxy group can be straight chain, branched chain, or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specific examples thereof can include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tertiary butoxy, secondary butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3,3-dimethylbutoxy, 2- ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p- methylbenzyloxy, and the like, but are not limited thereto.

[0066] In the present specification, a cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and can be further substituted with other substituent groups. In the present context, polycyclic means a group in which the cycloalkyl group is directly bonded to or fused with other cyclic groups. In the present context, the other cyclic groups can be cycloalkyl groups, but can also be different types of cyclic groups, such as heterocycloalkyl, aryl, and heteroaryl. The number of carbons of the cycloalkyl group can be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples thereof can 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, and the like, but are not limited thereto.

[0067] In the present specification, a heterocycloalkyl group contains O, S, Se, N or Si as a heteroatom, contains a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and can be further substituted with other substituents. In the present context, polycyclic means a group in which the heterocycloalkyl group is directly bonded to or fused with other cyclic groups. In the present context, the other cyclic groups can be heterocycloalkyl groups, but can also be different types of cyclic groups such as cycloalkyl, aryl and heteroaryl groups. The number of carbon atoms of the heterocycloalkyl group can be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0068] In the present specification, an aryl group contains a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and can be further substituted with other substituents. In the present context, polycyclic means a group in which the aryl group is directly bonded to or fused with other cyclic groups. In the present context, the other cyclic groups can be aryl groups, but can also be different types of cyclic groups such as cycloalkyl, heterocycloalkyl and heteroaryl groups. The aryl group contains spirocyclic groups. The number of carbon atoms of the aryl group can be 6 to 60, specifically 6 to 40 and more specifically 6 to 25. Specific examples of the aryl group can include phenyl, biphenyl, terphenyl, naphthyl, anthryl, perylenyl, phenanthryl, chrysenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl, indenyl, acenaphthyl, benzofluorenyl, spirobifluorenyl, 2,3-dihydro-lH-indenyl, fused ring groups thereof, and the like, but are not limited thereto.

[0069] In the present specification, a phosphine oxide group is represented by -P(=O)R101R102, and R101and R102are the same as or different from each other and can each independently be a substituent formed from at least one of hydrogen, deuterium, a halogen, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. Specific examples of the phosphine oxide group can include diphenylphosphine oxide, dinaphthylphosphine oxide, and the like, but are not limited thereto.

[0070] In the present specification, a silicon group is a substituent containing Si, having a Si atom directly bonded as a free radical, and is represented by SiR104R105R106. R104to R106are the same as or different from each other, and can each independently be a substituent formed from at least one of hydrogen, deuterium, a halogen, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. Specific examples of the silicon group can include trimethylsilyl, triethylsilyl, tertiary butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like, but are not limited thereto.

[0071] In the present specification, a fluorenyl group can be substituted, and adjacent substituents can be bonded to each other to form a ring.

[0072] In this specification, a spirocyclic group is a group including a spirocyclic structure, and can have 15 to 60 carbon atoms. For example, the spirocyclic group can include a structure in which a 2,3-dihydro-lH-indenyl group or a cyclohexyl group is spiro-bonded to a fluorenyl group. Specifically, the spirocyclic group can include any one of the group of the following structural formulas.

[0073]

[0074] In this specification, a heteroaryl group includes S, O, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and can be further substituted with other substituents. Herein, polycyclic means a group in which a heteroaryl group is directly linked to or fused with other cyclic groups. Herein, the other cyclic groups can be heteroaryl groups, but can also be different types of cyclic groups such as cycloalkyl, heterocycloalkyl, and aryl. The number of carbon atoms of the heteroaryl group can be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heteroaryl group can include pyridyl, pyrrolyl, pyrimidinyl, pyrazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinylyl, oxazinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, isoquinazolinyl, quinoxazolinyl, naphthridinyl, acridinyl, phenazinyl, imidazopyridinyl, naphthylidinyl, indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, spirobis(benzothiophene), dihydrophenoxazine, phenoxazine, phenanthridinyl, imidazopyridinyl, indol[2,3-a]carbazolyl, indol[2,3-b]carbazolyl, indolinyl, 10,11-dihydrobenzo[b,f]azepinyl, 9,10-dihydroacridinyl, phenanthroxinyl, phenothiazinyl, phenoxazinyl, naphthindolyl, phenanthrolinyl, benzo[c][l,2,5]thiadiazolyl, 5,10-dihydrobenzo[b,e][l,4]azasilinyl, pyrazolo[l,5-c]quinazolinyl, pyrido[l,2-b]indazolyl, pyrido[l,2-a]imidazo[l,2-e]indolinyl, 5,11-dihydroindenol[l,2-b]carbazolyl, and the like, but are not limited thereto.

[0075] In the present specification, an amine group can be selected from the group consisting of a monoalkyl amine group, a monoaryl amine group, a monoheteroaryl amine group, -NH2, a dialkyl amine group, a diaryl amine group, a diheteroaryl amine group, an alkylaryl amine group, an alkylheteroaryl amine group, and an arylheteroaryl amine group, and although the number of carbon atoms is not particularly limited, it is preferably 1 to 30. Specific examples of the amine group can include a methyl amine group, a dimethyl amine group, an ethyl amine group, a diethyl amine group, an aniline group, a naphthylamine group, a benzidine group, a dianisidine group, an anthracene amine group, a 9-methyl-anthracene amine group, a diphenyl amine group, a phenylnaphthylamine group, a dimethylphenyl amine group, a phenyltolyl amine group, a triphenyl amine group, a biphenylnaphthyl amine group, a phenylbiphenyl amine group, a biphenylfluorene amine group, a phenylbenzidine amine group, a biphenylbiphenyl amine group, and the like, but is not limited thereto.

[0076] In the present specification, an arylene group means an aryl group having two bonding sites, that is, a divalent group. The above description provided for the aryl group can be applied to this except that these groups are each a divalent group. In addition, a heteroarylene group means a heteroaryl group having two bonding sites, that is, a divalent group. The above description provided for the heteroaryl group can be applied to this except that these groups are each a divalent group.

[0077] In the present specification, an "adjacent" group can mean a substituent that is directly bonded to an atom of a substituted atom by a corresponding substituent, a substituent that is spatially closest to a corresponding substituent, or another substituent that substitutes an atom substituted by a corresponding substituent. For example, substituents of ortho positions in two substituted benzene rings and substituents of the same carbon in two substituted aliphatic rings can be interpreted as groups that are "adjacent" to each other.

[0078] The heterocyclic compound according to one embodiment of the present application is represented by Chemical Formula 1. More specifically, since the above-described substituent has a core structure and structural properties, the heterocyclic compound represented by Chemical Formula 1 can be used as a material for an organic material layer of an organic light emitting element.

[0079] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 can have a deuterium content of 0% to 100%.

[0080] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 can have a deuterium content of greater than or equal to 10% and less than or equal to 100%.

[0081] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 can have a deuterium content of greater than or equal to 20% and less than or equal to 100%.

[0082] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 can have a deuterium content of greater than or equal to 30% and less than or equal to 100%.

[0083] In an embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 can have a deuterium content greater than or equal to 40% and less than or equal to 100%.

[0084] In an embodiment of the present application, L1 and L2 of Chemical Formula 1 are the same as or different from each other, and can each independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0085] In an embodiment of the present application, L1 and L2 are the same as or different from each other, and can each independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

[0086] In an embodiment of the present application, L1 and L2 are the same as or different from each other, and can each independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0087] In an embodiment of the present application, L1 can be a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0088] In another embodiment, L1 is a direct bond.

[0089] In another embodiment, L1 is an arylene group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

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

[0091] In an embodiment of the present application, L2 can be a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

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

[0093] In another embodiment, L2 is an arylene group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0094] In another embodiment, L2 is a phenylene group.

[0095] In an embodiment of the present application, X of Chemical Formula 1 can be O or S.

[0096] In another embodiment, X of Formula 1 is O.

[0097] In another embodiment, X of Formula 1 is S.

[0098] In one embodiment of the present application, R1to R6of Formula 1 are the same or different from each other, and can each independently be hydrogen, deuterium, 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.

[0099] In one embodiment of the present application, R1to R6are the same or different from each other, and can each independently be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0100] In one embodiment of the present application, R1to R6are the same or different from each other, and can each independently be hydrogen or deuterium.

[0101] In another embodiment, R1to R6are hydrogen.

[0102] In another embodiment, R1to R6are deuterium.

[0103] In one embodiment of the present application, Ar1and Ar2of Formula 1 are the same or different from each other, and can each independently be a substituted or unsubstituted a monocyclic or polycyclic heterocyclic group having 2 to 60 carbon atoms including one or more =N- bonds, or a substituted or unsubstituted amine group.

[0104] In one embodiment of the present application, at least one of Ar1and Ar2is a substituted or unsubstituted amine group.

[0105] In one embodiment of the present application, Ar1may be a substituted or unsubstituted amine group, and Ar2may be a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 60 carbon atoms including one or more =N- bonds.

[0106] In one embodiment of the present application, Ar1may be an unsubstituted or one or more substituted amine group selected from a group consisting of an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 2 to 60 carbon atoms, and Ar2may be a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 60 carbon atoms including one or more =N- bonds.

[0107] In one embodiment of the application, Ar1may be unsubstituted or one or more substituted aminyl groups selected from the group consisting of aryl groups having 6 to 40 carbon atoms and heteroaryl groups having 2 to 40 carbon atoms, and Ar2may be substituted or unsubstituted monocyclic or polycyclic heterocyclyl groups having 2 to 60 carbon atoms comprising one or more =N- bonds.

[0108] In one embodiment of the application, Ar1may be unsubstituted or one or more substituted aminyl groups selected from the group consisting of aryl groups having 6 to 20 carbon atoms and heteroaryl groups having 2 to 20 carbon atoms, and Ar2may be substituted or unsubstituted monocyclic or polycyclic heterocyclyl groups having 2 to 60 carbon atoms comprising one or more =N- bonds.

[0109] In one embodiment of the application, Ar1may be unsubstituted or one or more substituted aminyl groups selected from the group consisting of substituted or unsubstituted phenyl groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted dibenzofuranyl groups, and substituted or unsubstituted dibenzothiophenyl groups, and Ar2may be substituted or unsubstituted monocyclic or polycyclic heterocyclyl groups having 2 to 60 carbon atoms comprising one or more =N- bonds.

[0110] In one embodiment of the application, Ar1may be unsubstituted or one or more substituted aminyl groups selected from the group consisting of substituted or unsubstituted phenyl groups, substituted or unsubstituted biphenyl groups, one or more substituted fluorenyl groups consisting of alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted dibenzofuranyl groups, and substituted or unsubstituted dibenzothiophenyl groups, and Ar2may be substituted or unsubstituted monocyclic or polycyclic heterocyclyl groups having 2 to 60 carbon atoms comprising one or more =N- bonds.

[0111] In one embodiment of the application, Ar2may be unsubstituted or one or more substituted aminyl groups selected from the group consisting of aryl groups having 6 to 60 carbon atoms and heteroaryl groups having 2 to 60 carbon atoms, and Ar1may be substituted or unsubstituted monocyclic or polycyclic heterocyclyl groups having 2 to 60 carbon atoms comprising one or more =N- bonds.

[0112] In one embodiment of the application, Ar2may be unsubstituted or one or more substituted aminyl groups selected from the group consisting of aryl groups having 6 to 40 carbon atoms and heteroaryl groups having 2 to 40 carbon atoms, and Ar1may be substituted or unsubstituted monocyclic or polycyclic heterocyclyl groups having 2 to 60 carbon atoms comprising one or more =N- bonds.

[0113] In one embodiment of the present application, Ar2may be an unsubstituted or one or more substituted amine group selected from the group consisting of an aryl group having 6 to 20 carbon atoms and a heteroaryl group having 2 to 20 carbon atoms, and Ar1may be a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 60 carbon atoms including one or more =N- bonds.

[0114] In one embodiment of the present application, Ar2may be an unsubstituted or one or more substituted amine group selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group, and Ar1may be a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 60 carbon atoms including one or more =N- bonds.

[0115] In one embodiment of the present application, Ar2may be an unsubstituted or one or more substituted amine group selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group, and Ar1may be a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 60 carbon atoms including one or more =N- bonds.

[0116] In one embodiment of the present application, Chemical Formula 1 can be represented by the following Chemical Formula 2 or Chemical Formula 3.

[0117] [Chemical Formula 2]

[0118]

[0119] [Chemical Formula 3]

[0120]

[0121] In Chemical Formula 2 and Chemical Formula 3,

[0122] R8and R9are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0123] N-Het is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 60 carbon atoms including one or more =N- bonds, and

[0124] X, L1, L2, R1to R6, Ar1, Ar2, m, and n have the same definitions as in Chemical Formula 1.

[0125] As in Chemical Formula 2 and Chemical Formula 3, when the 1st and 4th positions of dibenzofuran are substituted with an amine group and a monocyclic or polycyclic heterocyclic group having 2 to 60 carbon atoms and including one or more =N- bonds, it is more stable in structure, and the use of the heterocyclic compound represented by Chemical Formula 2 and Chemical Formula 3 in an organic light emitting element is effective in further increasing the lifespan of the element and in further reducing the driving voltage of the element due to the reduction in the band gap.

[0126] In the present specification, N-Het of Chemical Formula 2 and Chemical Formula 3 means that Ar1and Ar2may be changed to a monocyclic or polycyclic heterocyclic group having 2 to 60 carbon atoms, which is substituted or unsubstituted and includes one or more =N- bonds.

[0127] In the present specification, "including one or more =N- bonds" means including one or more double bonds including N.

[0128] In one embodiment of the present application, R8and R9are the same as or different from each other, and can each independently be hydrogen, deuterium, 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.

[0129] In one embodiment of the present application, R8and R9are the same as or different from each other, and can each independently be hydrogen, deuterium, 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.

[0130] In one embodiment of the present application, R8and R9are the same as or different from each other, and can each independently be hydrogen, deuterium, 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.

[0131] In one embodiment of the present application, R8and R9are the same as or different from each other, and can each independently be hydrogen, deuterium, a substituted or unsubstituted heteroaryl group.

[0132] In one embodiment of the present application, R8and R9are the same as or different from each other, and can each independently be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0133] In one embodiment of the application, R8and R9are the same or different from each other, and can each independently be hydrogen, deuterium, phenyl, biphenyl, naphthyl, one or more substituted fluorenyl groups selected from the group consisting of alkyl groups having 1 to 10 carbon atoms, dibenzofuranyl, or dibenzothiophenyl.

[0134] In one embodiment of the application, N-Het can be a group represented by any one of the following Chemical Formula A-1 to Chemical Formula A-3.

[0135] [Chemical Formula A-1]

[0136]

[0137] [Chemical Formula A-2]

[0138]

[0139] [Chemical Formula A-3]

[0140]

[0141] In Chemical Formula A-1 to Chemical Formula A-3,

[0142] X1is CR11or N, X2is CR12or N, X3is CR13or N, X4is CR14or N, X5is CR15or N, and at least one of X1to X5is N, and

[0143] R11to R15and R17to R22are the same or different from each other, and each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 60 carbon atoms, substituted or unsubstituted alkenyl having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl having 2 to 60 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms, substituted or unsubstituted heterocycloalkyl having 2 to 60 carbon atoms, substituted or unsubstituted aryl having 6 to 60 carbon atoms, substituted or unsubstituted heteroaryl having 2 or 60 carbon atoms, substituted or unsubstituted phosphine, and substituted or unsubstituted amine, or two or more of the groups adjacent to each other are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or heterocyclic ring, and is a site bonded to Chemical Formula 1.

[0144] also means a site bonded to Chemical Formula 2 or Chemical Formula 3.

[0145] Since the chemical formula 1 has an aromatic amine, the aromatic amine has a more excellent hole-transporting ability as a donor, i.e., has a higher donating strength as a substituent, and the balance with an acceptor becomes greater compared to that of carbazole (a donor having a weaker donating strength) as a substituent, thereby resulting in an increase in the HOMO level. In other words, the use of the compound represented by the chemical formula 1 in an element is effective in further reducing the driving voltage and further prolonging the service life compared to the use of a compound having carbazole as a substituent.

[0146] In one embodiment of the present application, the chemical formula A-1 can be represented by the following group A.

[0147] [Group A]

[0148]

[0149] In the group A, R11to R15and have the same definitions as in the chemical formula A-1.

[0150] In one embodiment of the present application, m and n of the chemical formula 1 are each independently an integer of 0 to 3, and when m and n are each 2 or more than 2, the substituents in the parentheses can be the same as or different from each other.

[0151] In another embodiment, m is 0.

[0152] In another embodiment, m is 1.

[0153] In another embodiment, m is 2.

[0154] In another embodiment, m is 3.

[0155] In one embodiment of the present application, when m is 2 or more than 2, the substituents in the parentheses can be the same as or different from each other.

[0156] In another embodiment, n is 0.

[0157] In another embodiment, n is 1.

[0158] In another embodiment, n is 2.

[0159] In another embodiment, n is 3.

[0160] In one embodiment of the present application, when n is 2 or more than 2, the substituents in the parentheses can be the same as or different from each other.

[0161] According to one embodiment of the present application, the chemical formula 1 can be represented by any one of the following compounds, but is not limited thereto.

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170] In addition, by introducing various substituents to the structure of Chemical Formula 1, compounds having unique properties of the introduced substituents can be synthesized. For example, by introducing substituents commonly used as a hole injection layer material, a hole transport layer material, a light emitting layer material, an electron transport layer material, and a charge generation layer material for manufacturing an organic light emitting element to a core structure, materials satisfying the required conditions for each organic material layer can be synthesized.

[0171] In addition, by introducing various substituents to the structure of Chemical Formula 1, the band gap can be finely controlled, and at the same time, the properties at the interface between organic materials can be enhanced, and the material application can become diversified.

[0172] Meanwhile, the heterocyclic compound has a high glass transition temperature (Tg), and has excellent thermal stability. This improvement in thermal stability becomes an important factor in providing driving stability to an element.

[0173] The heterocyclic compound according to one embodiment of the present application can be prepared using a multi-step chemical reaction. Some intermediate compounds are first prepared, and the compound of Chemical Formula 1 can be prepared from the intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of the present application can be prepared based on the preparation examples described later.

[0174] Another embodiment of the present application provides an organic light emitting element including the heterocyclic compound represented by Chemical Formula 1. The "organic light emitting element" can be expressed by terms such as "organic light emitting diode", "OLED", "OLED element", and "organic electroluminescent element".

[0175] When manufacturing an organic light emitting element, the heterocyclic compound can form an organic material layer using a coating method as well as a vacuum deposition method. Herein, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating method, and the like, but is not limited thereto.

[0176] Specifically, an organic light emitting element according to one embodiment of the present application includes a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode, and one or more layers of the organic material layers include a heterocyclic compound represented by Chemical Formula 1. When the heterocyclic compound represented by Chemical Formula 1 is included in the organic material layer, the organic light emitting element has excellent luminous efficiency and lifespan.

[0177] In one embodiment of the present application, the first electrode can be an anode, and the second electrode can be a cathode.

[0178] In another embodiment, the first electrode can be a cathode, and the second electrode can be an anode.

[0179] In one embodiment of the present application, the organic light emitting element can be a red organic light emitting element, and the heterocyclic compound according to Chemical Formula 1 can be used as a material for the red organic light emitting element. The heterocyclic compound according to Chemical Formula 1 has a high HOMO level, and is considered to be more suitable as a red host for an organic light emitting element.

[0180] In one embodiment of the present application, the organic light emitting element can be a green organic light emitting element, and the heterocyclic compound according to Chemical Formula 1 can be used as a material for the green organic light emitting element.

[0181] In one embodiment of the present application, the organic light emitting element can be a blue organic light emitting element, and the heterocyclic compound according to Chemical Formula 1 can be used as a material for the blue organic light emitting element.

[0182] Further, the organic material layer includes one or more light emitting layers, and the light emitting layer includes the heterocyclic compound represented by Chemical Formula 1. When the heterocyclic compound represented by Chemical Formula 1 is included in the light emitting layer among the organic material layers, the organic light emitting element has more excellent luminous efficiency and lifespan.

[0183] Further, in the organic light emitting element of the present application, the organic material layer includes the heterocyclic compound represented by Chemical Formula 1 as a first compound, and can further include one of the heterocyclic compounds represented by Chemical Formulae 4 to 6 as a second compound.

[0184] [Chemical Formula 4]

[0185]

[0186] [Chemical Formula 5]

[0187]

[0188] [Chemical Formula 6]

[0189]

[0190] In Chemical Formula 4 to Chemical Formula 6,

[0191] L3to L5are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

[0192] R23to R27are the same as or different from each other, and each independently hydrogen, deuterium, 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,

[0193] Y3is O; or S,

[0194] Ar3to Ar8are the same as or different from each other, and each 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,

[0195] one of Y1and Y2is N, the other is CRk, and Rkis 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,

[0196] Z1to Z3are each independently CH or N, and at least one of Z1to Z3is N,

[0197] p, q, and r are each an integer of 0 to 3, and when p, q, and r are each 2 or more than 2, the substituents in the parentheses are the same as or different from each other, and

[0198] a is an integer of 0 to 4, and when a is 2 or more than 2, the substituents in the parentheses are the same as or different from each other.

[0199] According to one embodiment of the present application, Chemical Formula 4 to Chemical Formula 6 can be represented by any one of the following compounds, but are not limited thereto.

[0200]

[0201]

[0202] Further, the organic material layer includes one or more light-emitting layers, and the light-emitting layer includes the heterocyclic compound represented by Chemical Formula 1 as a first compound, and further includes one of the heterocyclic compounds represented by Chemical Formula 4 to Chemical Formula 6 as a second compound. When the heterocyclic compound represented by Chemical Formula 1 is included in the light-emitting layer among the organic material layers, the organic light-emitting element has more excellent light-emitting efficiency and lifespan.

[0203] In addition, by introducing various substituents to the structures of Chemical Formula 4 to Chemical Formula 6, compounds having unique properties of the introduced substituents can be synthesized. For example, by introducing substituents commonly used as a hole injection layer material, a hole transport layer material, a light emitting layer material, an electron transport layer material, and a charge generation layer material for manufacturing an organic light emitting element to a core structure, materials satisfying the required conditions for each organic material layer can be synthesized.

[0204] In addition, by introducing various substituents to the structures of Chemical Formula 4 to Chemical Formula 6, the band gap can be finely controlled, and at the same time, the properties at the interface between organic materials can be enhanced, and the material application can become diversified.

[0205] Meanwhile, the heterocyclic compound has a high glass transition temperature (Tg), and has excellent thermal stability. This improvement in thermal stability is an important factor in providing driving stability to the element.

[0206] The heterocyclic compound according to one embodiment of the present application can be prepared using a multi-step chemical reaction. Some intermediate compounds are first prepared, and the compounds of Chemical Formula 4 to Chemical Formula 6 can be prepared from the intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of the present application can be prepared based on the preparation examples described later.

[0207] In addition, the organic material layer includes one or more light emitting layers, and the light emitting layer further includes one of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compounds represented by Chemical Formula 4 and Chemical Formula 5. When one of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compounds represented by Chemical Formula 4 and Chemical Formula 5 is included in the light emitting layer among the organic material layers, the organic light emitting element has more excellent light emitting efficiency and lifespan due to the exciplex phenomenon.

[0208] In the organic light emitting element of the present application, the organic material layer includes a light emitting layer, and the light emitting layer can include the heterocyclic compound as a host material of a light emitting material.

[0209] In the organic light emitting element of the present application, the light emitting layer can include two or more host materials, and at least one of the host materials can include the heterocyclic compound as a host material of a light emitting material.

[0210] In the organic light emitting element of the present application, two or more host materials can be premixed and used as a light emitting layer, and at least one of the two or more host materials can include the heterocyclic compound as a host material of a light emitting material.

[0211] Premixing means that two or more host materials of a light emitting layer are placed and mixed in one supply source before deposition on the organic material layer.

[0212] In the organic light emitting element of the present application, the light emitting layer can include two or more host materials, and the two or more host materials can each include one or more p-type host materials and n-type host materials, and at least one of the host materials can include a heterocyclic compound as a host material for the light emitting material. In this case, the organic light emitting element can have excellent driving, efficiency, and lifespan.

[0213] The organic light emitting element of the present disclosure can further include one, two, or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole auxiliary layer, and a hole blocking layer.

[0214] In addition to forming the organic material layer using the above-described heterocyclic compound, the organic light emitting element according to one embodiment of the present application can be manufactured using common organic light emitting element manufacturing methods and materials.

[0215] In addition, another embodiment of the present application provides a composition for an organic material layer of an organic light emitting element, which simultaneously includes a heterocyclic compound represented by Chemical Formula 1 and one of the heterocyclic compounds represented by Chemical Formula 4 to Chemical Formula 6.

[0216] In another embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1: the heterocyclic compound represented by any one of Chemical Formula 4 to Chemical Formula 6 can have a weight ratio of 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1, or 1:2 to 2:1 in the composition, however, the weight ratio is not limited thereto.

[0217] The specific description of the heterocyclic compound represented by Chemical Formula 1 and the compounds represented by Chemical Formula 4 to Chemical Formula 6 is the same as that provided above.

[0218] Figures 1 to 3 The lamination order of the electrode and the organic material layer of the organic light emitting element according to one embodiment of the present application is shown. However, the scope of the present application is not limited to such drawings, and the structure of the organic light emitting element known in the art can also be used in the present application.

[0219] Figure 1 An organic light emitting element is shown in which the anode 200, the organic material layer 300, and the cathode 400 are sequentially laminated on the substrate 100. However, the structure is not limited to such a structure, and as shown in Figure 2 An organic light emitting element in which the cathode, the organic material layer, and the anode are sequentially laminated on the substrate can also be obtained, as shown in

[0220] Figure 3 A case in which the organic material layer is a multi-layer is shown. According to Figure 3The organic light emitting element includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited to this layer structure, and, as necessary, layers other than the light emitting layer can not be included, and other desired functional layers can be further added.

[0221] In the organic light emitting element according to one embodiment of the present application, materials other than the heterocyclic compound of Chemical Formula 1 are shown below, however, such materials are for illustrative purposes only and are not used to limit the scope of the present application, and can be replaced by materials known in the art.

[0222] Materials having a relatively large work function can be used as the anode material, and transparent conductive oxides, metals, conductive polymers, or the like can be used as the anode material. Specific examples of the anode material 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); compositions of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, and the like, but are not limited thereto.

[0223] Materials having a relatively small work function can be used as the cathode material, and metals, metal oxides, conductive polymers, or the like can be used as the cathode material. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, and the like, but are not limited thereto.

[0224] As the hole injection material, a known hole injection material can be used, and for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a starburst-type amine derivative such as tris(4-hydrazinocarboxy-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-methylphenylamino)]triphenylamine (m-MTDATA), or 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB) described in document [Advanced Material, 6, p. 677 (1994)], a conductive polymer having solubility, polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonic acid), polyaniline / camphorsulfonic acid, or polyaniline / poly(4-styrene-sulfonate), and the like can be used.

[0225] As the hole transport material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyl diamine derivative, and the like can be used, and a low molecular or high molecular material can also be used as the hole transport material.

[0226] As the electron transport material, a metal complex of an oxadiazole derivative, an anthracenequinone dimethane and a derivative thereof, a benzoquinone and a derivative thereof, a naphthoquinone and a derivative thereof, an anthraquinone and a derivative thereof, a tetracyanoanthraquinone dimethane and a derivative thereof, a fluorenone derivative, a diphenyldicyanoethylene and a derivative thereof, a diphenoquinone derivative, 8-hydroxyquinoline and a derivative thereof, and the like can be used, and a high molecular material and a low molecular material can also be used as the electron transport material.

[0227] As an example of the electron injection material, LiF is generally used in the art, however, the present application is not limited thereto.

[0228] As the light emitting material, a red, green, or blue light emitting material can be used, and two or more light emitting materials can be mixed and used as necessary. In addition, a fluorescent material can also be used as the light emitting material, however, a phosphorescent material can also be used. A material that emits light by bonding of electrons and holes respectively injected from the anode and the cathode alone can be used as the light emitting material, however, a material having a host material and a dopant material that emit light together can also be used as the light emitting material.

[0229] Depending on the material used, the organic light emitting element according to one embodiment of the present application can be a top emission type, a bottom emission type, or a dual emission type.

[0230] The heterocyclic compound according to one embodiment of the present application can also be used in an organic electronic element including an organic solar cell, an organic photoconductor, an organic transistor, and the like according to a similar principle used in an organic light emitting element.

[0231] Hereinafter, the present specification will be described in more detail with reference to examples, however, such examples are for illustrative purposes only, and the scope of the present application is not limited thereto.

[0232] <Preparation Example 1> Preparation of target compound 1

[0233]

[0234] 1) Preparation of compound 1-2

[0235] Dissolve 1-bromo-4-chlorodibenzo[b,d]furan (6.0 g, 21.31 mmol), bis([1,1'-biphenyl]-4-yl)amine (A) (6.8 g, 21.31 mmol), Pd(OAc)2(0.24 g, 1.06 mmol), Xantphos (1.23 g, 2.13 mmol), and NaOtBu (4.1 g, 42.62 mmol) in toluene (60 mL) and reflux for 24 hours. After completion of the reaction, extract the resultant by introducing distilled water and dichloromethane (DCM) thereto at room temperature, and after drying the organic layer with MgSO4, remove the solvent using a rotary evaporator. Purify the solvent-removed reaction material on a silica gel, and purify the reaction material again by column chromatography (DCM:Hex=1:5) to obtain compound 1-2 (5.0 g, 50.35%). Hex means hexane.

[0236] 2) Preparation of compound 1-1

[0237] Dissolve compound 1-2 (5.0 g, 9.58 mmol), bis(pinacolato)diboron (3.16 g, 12.45 mmol), Pd2(dba)3(0.44 g, 1.07 mmol), Sphos (0.4 g, 0.958 mmol), and KOAc (1.9 g, 19.16 mmol) in 1,4-dioxane (50 mL) and reflux for 5 hours. After completion of the reaction, extract the resultant by introducing distilled water and dichloromethane (DCM) thereto at room temperature, and after drying the organic layer with MgSO4, remove the solvent using a rotary evaporator. Purify the solvent-removed reaction material on a silica gel, and then recrystallize by methanol to obtain compound 1-1 (3.27 g, 56%).

[0238] 3) Preparation of target compound 1

[0239] Compound 1-1 (3.27 g, 5.33 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (B) (1.43 g, 5.33 mmol), Pd(PPh3)4(0.31 g, 0.27 mmol) and K2CO3(1.47 g, 10.66 mmol) were dissolved in 1,4-dioxane / H2O (25 mL / 5 mL) and refluxed for 3 hours. After completion of the reaction, the resulting solid was filtered, washed with distilled water and dried. The dried solid was dissolved in chloroform for silica gel purification and the solvent was removed using a rotary evaporator. The resulting product was recrystallized by acetone to obtain the target compound 1 (3.5 g, 91%).

[0240] 4) Preparation of additional target compounds

[0241] The target compounds of Table 1 below were additionally synthesized in the same manner as in Preparation Example 1 except that A and B of Table 1 below were used as intermediates instead of using di([1,1'-biphenyl]-4-yl)amine (A) and 2-chloro-4,6-diphenyl-1,3,5-triazine (B) as Intermediate A and Intermediate B.

[0242] [Table 1]

[0243]

[0244]

[0245]

[0246]

[0247] Preparation Example 2> Preparation of target compound 20

[0248]

[0249] 1) Preparation of compound 20-2

[0250] Dichloromethane (DCM) (30 mL) was added to compound 20-1 (3.27 g, 5.33 mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine (D) (1.43 g, 5.33 mmol), Pd(PPh3)4(0.31 g, 0.27 mmol) and K2CO3(1.47 g, 10.66 mmol) at room temperature. The reaction mixture was refluxed for 3 h. After completion of the reaction, the solid formed was filtered, washed with distilled water and dried. The dried solid was dissolved in chloroform for silica gel purification and the solvent was removed using a rotary evaporator. The product was recrystallized from acetone to obtain the target compound 20 (3.5 g, 91 %).

[0251] 2) Preparation of compound 20-1

[0252] Compound 20-2 (5.0 g, 9.58 mmol), bis(pinacolato)diboron (3.16 g, 12.45 mmol), Pd2(dba)3(0.44 g, 1.07 mmol), Sphos (0.4 g, 0.958 mmol) and KOAc (1.9 g, 19.16 mmol) were dissolved in 1,4-dioxane (50 mL) and refluxed for 5 h. After completion of the reaction, the product was extracted by introducing distilled water and dichloromethane (DCM) into it at room temperature and the organic layer was dried over MgSO4. The solvent was removed using a rotary evaporator. The solvent removed reaction material was purified on silica gel and then recrystallized from methanol to obtain compound 20-1 (3.27 g, 56 %).

[0253] 3) Preparation of target compound 20

[0254] Compound 20-1 (3.27 g, 5.33 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (D) (1.43 g, 5.33 mmol), Pd(PPh3)4(0.31 g, 0.27 mmol) and K2CO3(1.47 g, 10.66 mmol) were dissolved in 1,4-dioxane / H2O (25 mL / 5 mL) and refluxed for 3 h. After completion of the reaction, the solid formed was filtered, washed with distilled water and dried. The dried solid was dissolved in chloroform for silica gel purification and the solvent was removed using a rotary evaporator. The product was recrystallized from acetone to obtain the target compound 20 (3.5 g, 91 %).

[0255] 4) Preparation of additional target compounds

[0256] The target compounds of Table 2 below were additionally synthesized in the same manner as in Preparation Example 2, except that C and D of Table 2 below were used as intermediates instead of using N-phenyl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-[1,1'-biphenyl]-4-amine (C) and 2-chloro-4,6-diphenyl-1,3,5-triazine (D) as Intermediate C and Intermediate D.

[0257] [Table 2]

[0258]

[0259]

[0260]

[0261] Preparation of target compound 54

[0262] 1) Preparation of compound 54-2

[0263] Dissolve 1-bromo-4-chlorodibenzo[b,d]furan (10.0 g, 35.5 mmol), bis(pinacolato)diboron (9.92 g, 39.05 mmol), Pd(dppf)Cl2(1.29 g, 1.77 mmol), and KoAc (6.97 g, 71 mmol) in 1,4-dioxane (100 mL) and reflux for 2 hours. After completion of the reaction, extract the resulting product by introducing distilled water and dichloromethane (DCM) thereto at room temperature, and after drying the organic layer with MgSO4, remove the solvent using a rotary evaporator. Purify the solvent-removed reaction material on a silica gel to obtain compound 54-2 (10.05 g, 86%).

[0264] 2) Preparation of compound 54-1

[0265] Dissolve compound 54-2 (10.05 g, 30.58 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (E) (8.19 g, 30.58 mmol), Pd(PPh3)4(1.77 g, 1.53 mmol), and K2CO3(8.45 g, 61.16 mmol) in 1,4-dioxane / H2O (100 mL / 20 mL) and reflux for 4 hours. After completion of the reaction, filter the resulting solid, wash with distilled water, and dry. Purify the dried reaction material on a silica gel, and then recrystallize by methanol to obtain compound 54-1 (11.51 g, 87%).

[0266] 3) Preparation of target compound 54

[0267] Compound 54-1 (4.69 g, 11.43 mmol), N-phenyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (F) (6.58 g, 12.57 mmol), Pd2(dba)3 (0.52 g, 0.57 mmol), Xphos (0.545 g, 1.143 mmol), and K2CO3 (3.16 g, 22.86 mmol) were dissolved in 1,4-dioxane / H2O (50 mL / 10 mL) and refluxed for 4 h. After completion of the reaction, the resulting solid was filtered, washed with distilled water and dried. The dried solid was dissolved in chloroform for silica gel purification and the solvent was removed using a rotary evaporator. The solvent removed reaction material was purified by silica gel and the reaction material was purified again by column chromatography (DCM:Hex = 1:5) to obtain the target compound 54 (4.84 g, 53.30 %). Hex means hexane.

[0268] 4) Preparation of additional target compounds

[0269] The target compounds of Table 3 below were additionally synthesized in the same manner as in Preparation Example 3, except that E and F of Table 3 below were used as intermediates instead of using 2-chloro-4,6-diphenyl-1,3,5-triazine (E) and N-phenyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (F) as Intermediate E and Intermediate F.

[0270] [Table 3]

[0271]

[0272]

[0273]

[0274] <Preparation Example 4> Preparation of target compound 51

[0275]

[0276] 1) Preparation of compound 51-2

[0277] Dissolve 1-bromo-4-chlorodibenzo[b,d]furan (10.0 g, 35.5 mmol), bis(pinacolato)diboron (9.92 g, 39.0 mmol), Pd(dppf)Cl2(1.29 g, 1.77 mmol), and KoAc (6.97 g, 71 mmol) in 1,4-dioxane (100 mL) and reflux for 2 hours. After the reaction is complete, extract the resulting product by introducing distilled water and dichloromethane (DCM) thereto at room temperature, and after drying the organic layer with MgSO4, remove the solvent using a rotary evaporator. Purify the solvent-removed reaction material on a silica gel to obtain compound 51-2 (10.05 g, 86%).

[0278] 2) Preparation of compound 51-1

[0279] Dissolve compound 51-2 (10.05 g, 30.58 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (G) (8.19 g, 30.58 mmol), Pd(PPh3)4(1.77 g, 1.53 mmol), and K2CO3(8.45 g, 61.16 mmol) in 1,4-dioxane / H2O (100 mL / 20 mL) and reflux for 4 hours. After the reaction is complete, filter the resulting solid, wash with distilled water, and dry. Purify the reaction material on a silica gel, and then recrystallize by methanol to obtain compound 51-1 (11.51 g, 87%).

[0280] 3) Preparation of target compound 51

[0281] Dissolve compound 51-1 (4.8 g, 11.06 mmol), di([1,1'-biphenyl]-4-yl)amine (H) (4.27 g, 13.27 mmol), Pd2dba3(0.5 g, 0.55 mmol), P(t-Bu)3(0.45 g, 1.1 mmol), and NaOtBu (2.13 g, 22.1 mmol) in toluene (50 mL) and reflux for 2 hours. After the reaction is complete, purify the resulting product on a silica gel, and purify the reaction material by column chromatography (THF:Hex = 1:8) to obtain target compound 51 (3.86 g, 48%). THF means tetrahydrofuran, and Hex means hexane.

[0282] 4) Preparation of additional target compounds

[0283] The target compounds of Table 4 below are additionally synthesized in the same manner as in Preparation Example 4, except that G and H of Table 4 below are used as intermediates instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (G) and di([1,1'-biphenyl]-4-yl)amine (H) as intermediate G and intermediate H.

[0284] [Table 4]

[0285]

[0286]

[0287]

[0288]

[0289] In addition, compounds not described in Preparation Examples 1 to 4 among the heterocyclic compounds represented by Chemical Formula 1 according to the present application were also prepared in the same manner as in the Preparation Examples.

[0290] In addition, the synthetic identification results are shown in the following Tables 5 and 6. 1 The measured values ​​of H NMR (CDCl 3 , 300 Mz) and the measured values ​​of FD-mass spectrometry (FD-MS: field desorption mass spectrometry) are shown in Table 6 below.

[0291] [Table 5]

[0292]

[0293]

[0294] [Table 6]

[0295]

[0296]

[0297] <Preparation Example 5> Preparation of target compound 1-1

[0298]

[0299] 1) Preparation of compound 1-1-2

[0300] Dissolve 1-bromo-3-chloronaphtho[2,3-b]benzofuran (6.0 g, 18.09 mmol), phenylboronic acid (C) (2.65 g, 21.71 mmol), Pd(PPh3)4(1.23 g, 1.07 mmol) and K2CO3(5.89 g, 42.62 mmol) in 1,4-dioxane / H2O (30 mL / 6 mL) and reflux for 24 hours. After completion of the reaction, extract the resulting product by introducing distilled water and dichloromethane (DCM) thereto at room temperature, and after drying the organic layer with MgSO4, remove the solvent using a rotary evaporator. Purify the solvent-removed reaction material on a silica gel, and purify the reaction material again by column chromatography (DCM:Hex=1:5) to obtain compound 1-1-2 (5 g, 45%). Hex means hexane.

[0301] 2) Preparation of compound 1-1-1

[0302] Dissolve compound 1-1-2 (5.0 g, 15.21 mmol), bis(pinacolato)diboron (4.3 g, 16.73 mmol), Pd2(dba)3(0.44 g, 1.07 mmol), Sphos (0.4 g, 0.958 mmol) and KOAc (1.9 g, 19.16 mmol) in 1,4-dioxane (50 mL) and reflux for 5 hours. After completion of the reaction, extract the resulting product by introducing distilled water and dichloromethane (DCM) thereto at room temperature, and after drying the organic layer with MgSO4, remove the solvent using a rotary evaporator. Purify the solvent-removed reaction material on a silica gel, and then recrystallize by methanol to obtain compound 1-1-1 (3.27 g, 56%).

[0303] 3) Preparation of target compound 1-1

[0304] Dissolve compound 1-1-1 (3.27 g, 7.8 mmol), 2-chloro-4-phenylquinazoline (D) (1.9 g, 7.8 mmol), Pd(PPh3)4(0.31 g, 0.27 mmol) and K2CO3(1.47 g, 10.66 mmol) in 1,4-dioxane / H2O (25 mL / 5 mL) and reflux for 3 hours. After completion of the reaction, filter the resulting solid, wash with distilled water and dry. Dissolve the dried solid in chloroform for silica gel purification, and remove the solvent using a rotary evaporator. Recrystallize the resulting product by acetone to obtain target compound 1-1 (3.1 g, 80%).

[0305] 4) Preparation of additional target compounds

[0306] The target compounds of Table 7 below were additionally synthesized in the same manner as in Preparation Example 5, except that C and D of Table 7 below were used as intermediates instead of phenylboronic acid (C) and 2-chloro-4-phenylquinazoline (D) as Intermediate C and Intermediate D.

[0307] [Table 7]

[0308]

[0309]

[0310] In addition, the compounds of the heterocyclic compounds represented by Chemical Formula 4 to Chemical Formula 6, which are not described in Preparation Example 5, according to the present application are also prepared in the same manner as in Preparation Example.

[0311] In addition, the synthesis of the resulting products is shown in Tables 8 and 9 below. Table 8 below shows 1 The measurement values of H NMR (CDC13, 300 Mz) and the measurement values of FD-mass spectrometry (FD-MS: field desorption mass spectrometry) are shown in Table 9 below.

[0312] [Table 8]

[0313]

[0314] [Table 9]

[0315] Compound FD-MS Compound FD-MS 1-1 m / z = 498.17 (C 36 H 22 N2O = 498.59)]]> 1-5 <![CDATA[m / z=680.19(C 48 H 28 N2OS=680.83)]]> 1-6 m / z = 644.16 (C 44 H 24 N2O2S = 644.75)]]> 1-7 m / z = 680.19 (C 48 H 28 N2OS = 680.83)]]> 1-8 m / z = 651.23 (C 47 H 29 N3O = 651.77)]]> 1-9 m / z = 574.20 (C 42 H 26 N2O = 574.68)]]> 1-10 m / z = 534.21 (C 40 H 26 N2= 534.66)]]> 1-13 m / z = 670.17 (C 46 H 26 N2O2S = 670.79)]]> 1-18 m / z = 601.22 (C 43 H 27 N3O = 601.71)]]> 1-19 m / z = 611.24 (C 45 H 29 N3= 611.75)]]>

[0316] [Experimental Example 1]

[0317] (1) Manufacture of Organic Light Emitting Element (Red Host)

[0318] A glass substrate on which indium tin oxide (ITO) was coated in a thin film to a thickness of 1,500 angstroms was ultrasonically cleaned with distilled water. After the cleaning with distilled water was completed, the substrate was ultrasonically washed with solvents such as acetone, methanol, and isopropanol, and then dried, and UVO treatment was performed for 5 minutes using UV in a UV cleaner. Thereafter, the substrate was transferred to a plasma cleaner (PT), and plasma treatment was performed under vacuum for ITO work function and residual film removal, and the substrate was transferred to a thermal deposition apparatus for organic deposition.

[0319] On a transparent ITO electrode (anode), a hole injection layer 2-TNATA (4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) were formed as common layers.

[0320] Thereafter, bathocuproine (BCP) (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) was deposited to a thickness of 60 angstroms as a hole blocking layer, and Alq3 was deposited thereon to a thickness of 200 angstroms as an electron transport layer.

[0321] Thereafter, bathocuproine (BCP) (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) was deposited to a thickness of 60 angstroms as a hole blocking layer, and Alq3 was deposited thereon to a thickness of 200 angstroms as an electron transport layer.

[0322] Finally, an electron injection layer was formed on the electron transport layer by depositing lithium fluoride (LiF) to a thickness of 10 angstroms, and then a cathode was formed on the electron injection layer by depositing aluminum (Al) cathode to a thickness of 1,200 angstroms, and thus, the organic electroluminescent device (Comparative Examples 1 to 9 and Examples 1 to 43) was manufactured.

[0323] Meanwhile, all of the organic compounds required for manufacturing the OLED were used in a vacuum state at a pressure of 10 -8 tons to 10 -6 tons to 10

[0324] Herein, Table 10 below corresponds to a case where a single host material is used, and Table 11 corresponds to a case where a compound of Chemical Formula 1 according to the present application having an advantageous hole transport ability is used as a first host and a compound of any one of Chemical Formulas 4 to 6 according to the present application having an advantageous electron transport ability is used as a second host, and the two host compounds are deposited as one supply source.

[0325] Herein, Comparative Compounds A to I used in Comparative Examples 1 to 9 are as follows.

[0326]

[0327] (2) Driving voltage and luminous efficiency of the organic electroluminescent device

[0328] For each of the organic electroluminescent devices manufactured as above, electroluminescence (EL) characteristics were measured using M7000 manufactured by McScience Inc., and according to the measurement results, T90 was measured at a standard luminance of 6,000 candela / meter2via a lifespan measurement system (M6000) manufactured by McScience Inc. Herein, T90 means a lifespan (unit: hour, time) that becomes a time taken to become 90% relative to an initial luminance.

[0329] The properties of the organic light-emitting element of the present disclosure obtained according to the measurement are shown in Tables 10 and 11 below.

[0330] [Table 10]

[0331]

[0332]

[0333] [Table 11]

[0334]

[0335] In addition, the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO), and the band gap of each of the heterocyclic compounds of the present disclosure and the comparative example compounds are shown in Table 12 below.

[0336] [Table 12]

[0337]

[0338] As seen from Table 12, the heterocyclic compounds of the present disclosure were identified to have a high HOMO level due to an increase in the balance effect with acceptors because of the presence of an aromatic amine having a better hole-transporting ability (as a donor) as a substituent, i.e., having a higher donor strength.

[0339] Therefore, as seen from Table 10, the element using the heterocyclic compound of the present disclosure in the organic material layer has a lower driving voltage and a longer service life compared to the element using Comparative Compound A and Comparative Compound B having carbazole (a donor having a weak donor strength) as a substituent in the organic material layer, and the heterocyclic compound of the present disclosure is suitable as a red host for an organic light-emitting element.

[0340] In addition, when compared to the compounds of the present application, the compounds C and D of the comparative example do not have an acceptor having a good electron-transporting ability, and thus, electron injection does not occur, and as seen from Table 10, the efficiency and service life of the element using Comparative Compound C and Comparative Compound D in the organic material layer are both decreased.

[0341] Further, although the compounds E to I of the comparative example have a reduced driving voltage as seen from Table 10, both the efficiency and the lifespan are low even though substitution is made with an aromatic amine having strong donor properties. This is because, depending on the position of the substituent of the heterocyclic compound core, the T1 level is high, making it difficult for energy to be transferred to the red dopant, and a large band gap causes high resistance, adversely affecting the lifespan due to reduced stability.

[0342] Accordingly, it was identified that the compounds of the present application have a lower band gap and a smaller T1 level, which significantly improves the lifespan and efficiency.

[0343] Further, as seen from Table 11, it was identified that the simultaneous inclusion of the heterocyclic compound of Chemical Formula 1 in the organic material layer of the organic light emitting element with the heterocyclic compound corresponding to any one of Chemical Formula 4 to Chemical Formula 6 will improve the driving voltage, efficiency, and lifespan.

[0344] Such a result can predict that the exciplex phenomenon occurs when two compounds are simultaneously included. The exciplex phenomenon is a phenomenon in which energy having the size of the donor (p-host) HOMO level and the size of the acceptor (n-host) LUMO level is released due to electron exchange between a molecule having strong donor properties and a molecule having strong acceptor properties. When a donor (p-host) having good hole transport ability and an acceptor (n-host) having good electron transport ability are used as the host of the light emitting layer, holes are injected to the p-host and electrons are injected to the n-host, and thus, the driving voltage can be reduced, ultimately contributing to the enhancement of the lifespan.

[0345] In particular, it was identified that the heterocyclic compound corresponding to any one of Chemical Formula 4 to Chemical Formula 6 is more effective in improving the lifespan when a triazine or a benzothienopyrimidine, which is an n-host and a strong acceptor, is present than when a quinazoline is present.

[0346] When the exciplex phenomenon occurs between the above two molecules, reverse intersystem crossing (RISC) occurs, and thus, the internal quantum efficiency can increase up to 100%.

[0347] In particular, the heterocyclic compound of Chemical Formula 1 is a bipolar compound and does not have strong acceptor ability, however, by injecting an acceptor (n-host) having good electron transport ability corresponding to any one of Chemical Formula 4 to Chemical Formula 6, as shown in Figure 4 and Figure 5 as shown in the above, photoluminescence (PL) produces a red shift change, and thus, an exciplex contributing to the enhancement of the light emitting property is formed. Figure 4 (a) of the above and Figure 4(b) is a drawing showing photoluminescence (PL) changes when using the heterocyclic compound of Chemical Formula 1 as a single host of an organic light emitting element and when using a heterocyclic compound corresponding to any one of Chemical Formula 4 to Chemical Formula 6 as a single host of an organic light emitting element, and Figure 5 (b) is a drawing showing photoluminescence (PL) changes when using the heterocyclic compound of Chemical Formula 1 as a single host of an organic light emitting element and when using a heterocyclic compound corresponding to any one of Chemical Formula 4 to Chemical Formula 6 as a single host of an organic light emitting element, and

[0348] In addition, it was identified that by injecting an acceptor (n-host) having good electron transport ability of a heterocyclic compound corresponding to any one of Chemical Formula 4 to Chemical Formula 6, the service life was significantly improved due to proper movement of the light emitting region in the light emitting layer.

[0349] <Experimental Example 2> Thermal stability of an organic electroluminescent element

[0350] For each of the above manufactured organic electroluminescent elements, the temperature measurement points (Ts) and the evaluation time were set as described in Table 13 below, and based on the temperature measurement points, the purity at 50℃, 70℃, and 90℃ was measured using M7000 of Mac Science Co. to evaluate the thermal stability of the organic light emitting element.

[0351] In addition, based on the temperature measurement points, the electroluminescence (EL) properties at 50℃, 70℃, and 90℃ were measured using M7000 of Mac Science Co., and according to the measurement results, when the standard luminance was 6,000 candela / square meter, T90 was measured by a service life measurement system (M6000) manufactured by Mac Science Co. to measure the driving voltage, efficiency, and service life (T90) of the element.

[0352] As a result, it is shown in Table 13 and Table 14 below.

[0353] [Table 13]

[0354]

[0355] [Table 14]

[0356]

[0357] As seen from Table 13 and Table 14, the compounds of the present disclosure have excellent thermal stability due to their structural stability. In particular, compared to Compound 11 and Compound 12 according to the present application having a dimethylfluorenyl group in the arylamine functional group which is easily affected by heat, the thermal stability is more excellent when having a phenyl or heterocyclic compound. In addition, it was identified that when the arylamine functional group is not directly bonded and is embedded in an intermediate phenyl linking group, the molecular weight is increased and the structural flatness is improved, and thus, a compound having more excellent thermal stability can be obtained.

Claims

1. A heterocyclic compound represented by the following Chemical Formula 2 or Chemical Formula 3: [Chemical Formula 2] [Chemical Formula 3] in, In Chemical Formula 2 and Chemical Formula 3, X is O; or S; L1 and L2 are the same as or different from each other and are each independently a direct bond, a phenylene group or a naphthylene group; R1 to R6 are the same as or different from each other and are each independently hydrogen or deuterium; R8 and R9 are the same as or different from each other and are each independently hydrogen, deuterium, 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; N-Het is a group represented by any one of the following Chemical Formulas A-1 to A-3: [Chemical Formula A-1] [Chemical Formula A-2] [Chemical Formula A-3] In Chemical Formulas A-1 to A-3, X1 is CR11 or N, X2 is CR12 or N, X3 is CR13 or N, X4 is CR14 or N, X5 is CR15 or N, and at least one of X1 to X5 is N; and R11 to R15 and R17 to R22 are the same as or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted thiophene having 5 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 or 25 carbon atoms, a substituted or unsubstituted phosphine oxide group, and a substituted or unsubstituted amino group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or heterocycle, and is a site bonded to Chemical Formula 2 or Chemical Formula 3, m and n are each an integer from 0 to 3, and when m and n are each 2 or greater, the substituents in the parentheses are the same as or different from each other, Wherein the substituted or unsubstituted group means substituted with one or more substituents selected from the group consisting of deuterium, cyano, halogen, straight-chain or branched alkyl having 1 to 20 carbon atoms, straight-chain or branched alkenyl having 2 to 20 carbon atoms, straight-chain or branched alkynyl having 2 to 20 carbon atoms, monocyclic or polycyclic cycloalkyl having 5 to 20 carbon atoms, monocyclic or polycyclic heterocycloalkyl having 3 to 20 carbon atoms, monocyclic or polycyclic aryl having 6 to 25 carbon atoms, monocyclic or polycyclic heteroaryl having 3 to 25 carbon atoms, -SiRR'R", -P(= O) RR', an alkylamine having 1 to 20 carbon atoms, a monocyclic or polycyclic aromatic amine having 6 to 60 carbon atoms, and a monocyclic or polycyclic heteroaromatic amine having 2 to 60 carbon atoms, or is unsubstituted; or is substituted by two or more substituents selected from the substituents shown above, or is unsubstituted; and R, R' and R" are the same as or different from each other and are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 25 carbon atoms.

2. The heterocyclic compound according to claim 1, wherein Chemical Formula 2 or Chemical Formula 3 is represented by any one of the following compounds:

3. An organic light-emitting element, comprising: a first electrode; a second electrode; as well as one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer comprises the heterocyclic compound according to any one of claims 1 to 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 layers comprise 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 a host material of the light-emitting material.

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

7. The organic light-emitting element according to claim 3, wherein the organic material layer comprises the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3 as a first compound, and further comprises one of the heterocyclic compounds represented by the following Chemical Formulas 4 to 6 as a second compound: [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] In Chemical Formulas 4 to 6, L3 to L5 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; R23 to R27 are the same as or different from each other, and are each independently hydrogen, deuterium, 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; Y3 is O; or S; Ar3 to Ar8 are the same as or different from each other, and are each 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; One of Y1 and Y2 is N, the other is CRk, and Rk 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; Z1 to Z3 are each independently CH or N, and at least one of Z1 to Z3 is N; p, q, and r are each an integer from 0 to 3, and when p, q, and r are each 2 or greater, the substituents in the parentheses are the same as or different from each other; and a is an integer of 0 to 4, and when a is 2 or greater, the substituents in the parentheses are the same as or different from each other.

8. The organic light emitting element according to claim 7, wherein Chemical Formula 4 to Chemical Formula 6 are represented by any one of the following compounds:

9. A composition for an organic material layer of an organic light-emitting element, the composition comprising: The heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3 according to claim 1; as well as One of the heterocyclic compounds represented by the following Chemical Formulas 4 to 6: [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] Among them, in Chemical Formula 4 to Chemical Formula 6, L3 to L5 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; R23 to R27 are the same as or different from each other, and are each independently hydrogen, deuterium, 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; Y3 is O; or S; Ar3 to Ar8 are the same as or different from each other, and are each 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; One of Y1 and Y2 is N, the other is CRk, and Rk 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; Z1 to Z3 are each independently CH or N, and at least one of Z1 to Z3 is N; p, q and r are each an integer from 0 to 3, and when p, q and r are each 2 or greater, the substituents in the parentheses are the same as or different from each other; as well as a is an integer of 0 to 4, and when a is 2 or greater, the substituents in the parentheses are the same as or different from each other.

10. The composition for an organic material layer of an organic light-emitting element according to claim 9, wherein: In the composition, the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3: the heterocyclic compound represented by any one of Chemical Formulas 4 to 6 has a weight ratio of 1:10 to 10:1.

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