Heterocyclic compound, organic light-emitting component including the same, and composition of organic material layer for organic light-emitting component

Abstract

The present application provides a heterocyclic compound, an organic light-emitting device containing the heterocyclic compound in an organic material layer, and a composition of an organic material layer for an organic light-emitting device.

Description

Technical Field

[0001] This specification claims priority to and the benefit of Korean Patent Application No. 10-2019-0175166 filed in the Korean Intellectual Property Office on December 26, 2019, the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to a heterocyclic compound, an organic light-emitting component containing the heterocyclic compound, and a composition of an organic material layer for an organic light-emitting component. Background Art

[0003] Electroluminescent components are a type of self-luminous display components and have the following advantages: wide viewing angle, fast response speed and excellent contrast.

[0004] The organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light-emitting device having this structure, electrons and holes injected from the two electrodes are combined and paired in the organic thin film, and light is emitted when the electrons and holes are annihilated. The organic thin film may be formed in a single layer or a multilayer as necessary.

[0005] If necessary, the material of the organic film may have a light-emitting function. For example, a compound capable of forming the light-emitting layer itself may be used alone as the material of the organic film, or a compound capable of playing the role of a host or a dopant of a host-dopant type light-emitting layer may be used as the material of the organic film. In addition, a compound capable of playing the role of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and the like may also be used as the material of the organic film.

[0006] The development of organic thin film materials has been continuously required to enhance the performance, lifespan or efficiency of organic light emitting devices.

[0007] (Patent Document 1) U.S. Patent No. 4,356,429 Summary of the invention

[0008] Technical issues

[0009] The present invention relates to providing a heterocyclic compound, an organic light-emitting component containing the heterocyclic compound, and a composition of an organic material layer used in an organic light-emitting component.

[0010] Technical Solutions

[0011] One embodiment of the present application provides a heterocyclic compound represented by the following Chemical Formula 1.

[0012] [Chemical formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] L 1 With L 2 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,

[0016] X is O; S; or NRa,

[0017] Y 1 To Y 5 are the same or different from each other and are each independently N or CRb, Y 1 To Y 5 At least one or more of is N, and when there are two or more CRb, Rb are the same or different from each other,

[0018] R 1 Represented by the following chemical formula A,

[0019] R 2 To R 9 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms,

[0020] Ra is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms,

[0021] Rb is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms,

[0022] m and n are each independently an integer from 0 to 3, and when m and n are each 2 or greater, the substituents in the brackets are the same as or different from each other, and

[0023] p is 0 or 1,

[0024] [Chemical formula A]

[0025]

[0026] In chemical formula A,

[0027] L 11 With L 12 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 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms,

[0028] Ar 11 with Ar 12 are the same as or different from each other and are each independently selected from the group consisting of: a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or Ar 11 with Ar 12 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms,

[0029] a and b are each 0 or 1, and

[0030] It means that the L bonded to the chemical formula 1 1 location.

[0031] In addition, one embodiment of the present application provides an organic light-emitting component, including a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers includes a heterocyclic compound represented by Chemical Formula 1.

[0032] Finally, one embodiment of the present application provides a composition for an organic material layer of an organic light-emitting device, the composition comprising a heterocyclic compound represented by Chemical Formula 1 and any one of the following heterocyclic compounds 1-1 to 1-14.

[0033]

[0034] Beneficial effects

[0035] The heterocyclic compounds described in this specification can be used as materials for the organic material layer of an organic light-emitting component. In the organic light-emitting component, the heterocyclic compounds can function as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials or the like.

[0036] Particularly, when the heterocyclic compound represented by Chemical Formula 1 is used in an organic material layer of an organic light-emitting device, the driving voltage of the device may be reduced, the light efficiency may be enhanced, and the lifespan characteristics of the device may be enhanced. BRIEF DESCRIPTION OF THE DRAWINGS

[0037] Figures 1 to 3 The drawings are diagrams each showing a laminated structure of an organic light emitting component according to one embodiment of the present application.

[0038]

Explanation of symbols

[0039] 100: Base

[0040] 200: Anode

[0041] 300: organic material layer

[0042] 301: hole injection layer

[0043] 302: hole transport layer

[0044] 303: Luminous layer

[0045] 304: Hole blocking layer

[0046] 305: electron transport layer

[0047] 306: electron injection layer

[0048] 400: cathode DETAILED DESCRIPTION

[0049] Hereinafter, the present specification will be described in more detail.

[0050] In the present specification, a part “including” certain components means that it can further include other components, and does not exclude other components unless otherwise specifically stated to the contrary.

[0051] In the present specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the substitution position is not limited as long as it is a position where a hydrogen atom is substituted (that is, a position where a substituent can replace), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0052] In the present specification, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of a straight chain or branched chain alkyl group having 1 to 60 carbon atoms; a straight chain or branched chain alkenyl group having 2 to 60 carbon atoms; a straight chain or branched chain 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; a silicon group; a phosphine oxide group; and an amine group, or is unsubstituted, or is substituted by a substituent connecting two or more substituents selected from the substituents shown above, or is unsubstituted.

[0053] More specifically, "substituted or unsubstituted" in the present specification means substituted with one or more substituents selected from the group consisting of: a monocyclic or polycyclic aromatic group having 6 to 60 carbon atoms; or a monocyclic or polycyclic heteroaromatic group having 2 to 60 carbon atoms.

[0054] In the present specification, halogen may be fluorine, chlorine, bromine or iodine.

[0055] In the present specification, the alkyl group includes a straight chain or branched chain having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples of the alkyl group may 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.

[0056] In the present specification, alkenyl includes a straight chain or branched chain with 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of alkenyl may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples of alkenyl may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl and similar groups, but are not limited thereto.

[0057] In the present specification, the alkynyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0058] In the present specification, the alkoxy group may 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 of the alkoxy group may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tertiary butoxy, secondary butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like, but are not limited thereto.

[0059] In this specification, cycloalkyl includes monocyclic or polycyclic rings with 3 to 60 carbon atoms, and may be further substituted with other substituents. In this article, polycyclic means a group in which the cycloalkyl is directly connected to other cyclic groups or fused with other cyclic groups. In this article, other cyclic groups may be cycloalkyl, but may also be different types of cyclic groups, such as heterocycloalkyl, aryl and heteroaryl. The carbon group number of the cycloalkyl may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples of cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tertiary butylcyclohexyl, cycloheptyl, cyclooctyl and similar groups, but are not limited thereto.

[0060] In this specification, heterocycloalkyl includes O, S, Se, N or Si as heteroatoms, includes monocyclic or polycyclic rings with 2 to 60 carbon atoms, and may be further substituted with other substituents. In this article, polycyclic means a group in which heterocycloalkyl is directly connected to other cyclic groups or fused with other cyclic groups. In this article, other cyclic groups may be heterocycloalkyl, but may also be different types of cyclic groups, such as cycloalkyl, aryl and heteroaryl. The number of carbon atoms of heterocycloalkyl may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0061] In this specification, aryl includes monocyclic or polycyclic rings with 6 to 60 carbon atoms, and may be further substituted with other substituents. In this article, polycyclic means a group in which the aryl is directly connected to other cyclic groups or fused with other cyclic groups. In this article, other cyclic groups may be aryl, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl and heteroaryl. Aryl includes spirocyclic groups. The number of carbon atoms of the aryl may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group may include phenyl, biphenyl, terphenyl, naphthyl, anthryl, chrysenyl, phenanthrenyl, perylenyl, fluoranthenyl, triphenylenyl, phenalenyl, pyrenyl, tetraphenyl, pentaphenyl, fluorenyl, indenyl, acenaphthylenyl, benzofluorenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, fused rings thereof, and the like, but are not limited thereto.

[0062] In the present specification, the phosphine oxide group is represented by -P(=O)R101R102, and R101 and R102 are the same as or different from each other and may each independently be a substituent formed by at least one of the following: hydrogen; deuterium; a halogen group; 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 may include a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but are not limited thereto.

[0063] In the present specification, a silicon group is a substituent group including Si, in which Si atoms are directly connected as a free radical, and is represented by -SiR104R105R106. R104 to R106 are the same or different from each other, and may each independently be a substituent group formed by at least one of the following: hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specific examples of silicon groups may include trimethylsilyl, triethylsilyl, tertiary butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like, but are not limited thereto.

[0064] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0065] In this specification, a spirocyclic group is a group comprising a spirocyclic structure and may have 15 to 60 carbon atoms. For example, a spirocyclic group may include a structure in which a 2,3-dihydro-1H-indenyl or a cyclohexane spirocyclic ring is bonded to a fluorenyl group. Specifically, the following spirocyclic group may include any one of the groups of the following structural formulas.

[0066]

[0067] In this specification, heteroaryl includes S, O, Se, N or Si as heteroatoms, includes monocyclic or polycyclic rings with 2 to 60 carbon atoms, and may be further substituted with other substituents. In this article, polycyclic means a group in which heteroaryl is directly connected to other cyclic groups or fused with other cyclic groups. In this article, other cyclic groups may be heteroaryl, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl and aryl. The number of carbon atoms of heteroaryl may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heteroaryl group may include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furanyl, thiophene group, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxynyl, group), triazine group, tetrazine group, quinolyl group, isoquinolyl group, quinazolyl group, isoquinazolyl group, quinazolinyl group, quinolizinyl group, naphthyridinyl group, acridinyl group, phenanthridinyl group, imidazopyridinyl group, diazonaphthyl group, triazindenyl group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothienyl group, benzofuranyl group, dibenzothienyl group, dibenzofuranyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilyl group, spirobi(dibenzosilole), dihydrophenazinyl group, phenoxazinyl group, phenanthridinyl group, imidazopyridinyl group, thienyl group The invention also includes but is not limited to 1,2-dihydro-1,2-dibenzo[b,f]-1,2-dihydro-1,2-dibenzo[c,1,2-dihydro-1,2-dibenzo[b,f]-1,2-dihydro-1,2-dibenzo[b,f]-1,2-dihydro-1,2-dibenzo[c,1,2-dihydro-1,2-dibenzo[b,e,1,4]- ...1,5-c]-1,2-dihydro-1,2-dibenzo[b,e,1,4]-1,2-dihydro-1,2-dibenzo[1,5-c]-1,2-dihydro-1,2-dibenzo[b,e,1,4]-1,2-dihydro-1,2-dibenzo[1,5-c]-1,2-dihydro-1,2-dibenzo[1,5-c]-1,2-dihydro-1,2-dibenzo[1,5-c]-1,2-dihydro-1,2-dibenzo[1,5-b,e]-1,2-dihydro-1,2-dibenzo[1,5-c]-1,2-dihydro-1,2-dibenzo[1,5-c]-1,2-dihydro-1,2-dibenzo[1,5-b,e]-1,2-dihydro-1,2-dibenzo[1,5-c]-1,2-dihydro-1,2-dibenzo[

[0068] In the present specification, the amino group can be selected from the group consisting of the following: monoalkylamino group, monoarylamino group, monoheteroarylamino group, -NH 2The amino group may be a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, an aniline group, a naphthylamino group, a benzidine group, a dibenzidine group, an anthracene group, a 9-methyl-anthracene group, a diphenylamine group, a phenylnaphthylamine group, a ditoluidine group, a phenyltoluidine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbenzidine group, a biphenylfluorenylamine group, a phenyltriphenylamine group, a biphenyltriphenylamine group and the like, but are not limited thereto.

[0069] In this specification, arylene means an aryl group having two bonding sites, i.e., a divalent group. Except for those groups each being a divalent group, the description of aryl provided above can be applied here. In addition, heteroarylene means a heteroaryl group having two bonding sites, i.e., a divalent group. Except for those groups each being a divalent group, the description of heteroaryl provided above can be applied here.

[0070] In the present invention, an "adjacent" group may mean a substituent that replaces an atom directly connected to the atom replaced by the corresponding substituent, a substituent that is closest in space to the corresponding substituent, or another substituent that replaces the atom replaced by the corresponding substituent. For example, two substituents that replace the ortho position in a benzene ring and two substituents that replace the same carbon in an aliphatic ring can be interpreted as groups that are "adjacent" to each other.

[0071] In the present specification, "a case where no substituent is indicated in a chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, due to the presence of deuterium ( 2 H) is an isotope of hydrogen, so some of the hydrogen atoms may be deuterium.

[0072] In one embodiment of the present application, "the situation where no substituent is indicated in the chemical formula or compound structure" may mean that the positions where the substituent may appear may all be hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms may be deuterium as an isotope, and herein, the content of deuterium may be 0% to 100%.

[0073] In one embodiment of the present application, in the case where “no substituent is indicated in the chemical formula or compound structure”, when deuterium is not explicitly excluded, such as when the deuterium content is 0%, the hydrogen content is 100%, or all substituents are hydrogen, hydrogen and deuterium may be mixed in the compound.

[0074] 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 an atomic nucleus, and can be represented as hydrogen-2, and the element symbol can also be written as D or 2H.

[0075] In one embodiment of the present application, isotopes refer to atoms having the same atomic number (Z) but different mass numbers (A), and can also be interpreted as elements having the same proton number but different neutron numbers.

[0076] In one embodiment of the present application, when the total number of substituents that a basic compound may have is defined as T1 and the number of specific substituents among these substituents is defined as T2, the content T% of the specific substituent may be defined as T2 / T1×100=T%.

[0077] In other words, in one example, The phenyl group represented by has a deuterium content of 20% means that the total number of substituents that the phenyl group may have is 5 (T1 in the formula), and the number of deuterium in these substituents is 1 (T2 in the formula). In other words, the phenyl group having a deuterium content of 20% can be represented by the following structural formula.

[0078]

[0079] Furthermore, in one embodiment of the present application, “a phenyl group having a deuterium content of 0%” may mean a phenyl group that does not include a deuterium atom, that is, a phenyl group having 5 hydrogen atoms.

[0080] One embodiment of the present application provides a heterocyclic compound represented by the following Chemical Formula 1.

[0081] [Chemical formula 1]

[0082]

[0083] In Chemical Formula 1,

[0084] L 1 With L 2 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,

[0085] X is O; S; or NRa,

[0086] Y 1 To Y 5 are the same or different from each other and are each independently N or CRb, Y 1 To Y 5 At least one or more of is N, and when there are two or more CRb, Rb are the same or different from each other,

[0087] R 1 Represented by the following chemical formula A,

[0088] R 2To R 9 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms,

[0089] Ra is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms,

[0090] Rb is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms,

[0091] m and n are each independently an integer from 0 to 3, and when m and n are each 2 or greater, the substituents in the brackets are the same as or different from each other, and

[0092] p is 0 or 1,

[0093] [Chemical formula A]

[0094]

[0095] In chemical formula A,

[0096] L 11 With L 12 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 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms,

[0097] Ar 11 with Ar 12 are the same as or different from each other and are each independently selected from the group consisting of: a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or Ar 11 with Ar 12 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms,

[0098] a and b are each 0 or 1, and

[0099] It means that the L bonded to the chemical formula 1 1 location.

[0100] The compound represented by Chemical Formula 1 has both a donor having good hole transporting ability and an acceptor having good electron transporting ability in one molecule and a substituent fixed at the 11th position of naphthobenzofuran, and spatially separates HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital), thereby allowing strong charge transport. Therefore, high efficiency can be expected when used as an organic material in an organic light-emitting device.

[0101] In one embodiment of the present application, L of Chemical Formula 1 1 To L 2 are the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

[0102] In another embodiment, L 1 With L 2 are the same as or different from each other, and may 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.

[0103] In another embodiment, L 1 With L 2 are the same as or different from each other, and may 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.

[0104] In another embodiment, L 1 To L 2 are the same as or different from each other, and may 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.

[0105] In another embodiment, L 1 With L 2 are the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0106] In another embodiment, L 1 With L 2 are the same as or different from each other, and may each independently be a direct bond; a phenylene group; or a biphenylene group.

[0107] In one embodiment of the present application, L 1 With L 2 Can be different from each other.

[0108] In one embodiment of the present application, L 1 With L 2 Can be the same as each other.

[0109] In one embodiment of the present application, L 1 Can be a direct key, and L 2 It may be 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.

[0110] In one embodiment of the present application, L 1 Can be a direct key, and L 2 It may be 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.

[0111] In one embodiment of the present application, L 1 Can be a direct key, and L 2 It may be 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.

[0112] In another embodiment, L 1 It may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0113] In another embodiment, L 1 It may be a direct bond; a phenylene group; or a biphenylene group.

[0114] In another embodiment, L 1 For direct keys.

[0115] In another embodiment, L 1 It is phenylene.

[0116] In another embodiment, L 1 It is a biphenylene group.

[0117] In one embodiment of the present application, L 2 Can be a direct key, and L 1 It may be 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.

[0118] In one embodiment of the present application, L 2 Can be a direct key, and L 1It may be 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.

[0119] In one embodiment of the present application, L 2 Can be a direct key, and L 1 It may be 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.

[0120] In one embodiment of the present application, L 2 It may 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.

[0121] In another embodiment, L 2 It may 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.

[0122] In another embodiment, L 2 It may 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.

[0123] In another embodiment, L 2 It may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0124] In another embodiment, L 2 It may be a direct bond; a phenylene group; a biphenylene group; or a naphthylene group.

[0125] In another embodiment, L 2 For direct keys.

[0126] In another embodiment, L 2 It is phenylene.

[0127] In another embodiment, L 2 It is a biphenylene group.

[0128] In one embodiment of the present application, m and n of Chemical Formula 1 are each independently an integer of 0 to 3, and when m and n are 2 or greater, the substituents in the brackets are the same as or different from each other.

[0129] In one embodiment of the present application, m is 3.

[0130] In one embodiment of the present application, m is 2.

[0131] In one embodiment of the present application, m is 1.

[0132] In one embodiment of the present application, m is 0.

[0133] In one embodiment of the present application, when m is 2 or greater, the substituents in brackets are the same as or different from each other.

[0134] In one embodiment of the present application, n is 3.

[0135] In one embodiment of the present application, n is 2.

[0136] In one embodiment of the present application, n is 1.

[0137] In one embodiment of the present application, n is 0.

[0138] In one embodiment of the present application, when n is 2 or greater, the substituents in brackets are the same as or different from each other.

[0139] In one embodiment of the present application, X in Chemical Formula 1 may be O; S or NRa.

[0140] In one embodiment of the present application, X is O; or NRa.

[0141] In one embodiment of the present application, X is O.

[0142] In one embodiment of the present application, X may be NRa.

[0143] In one embodiment of the present application, Y of Chemical Formula 1 1 To Y 5 are the same or different and are each independently N or CRb, Y 1 To Y 5 At least one or more of CRb is N, and when there are two or more CRb, CRb may be the same as or different from each other.

[0144] In one embodiment of the present application, in Y 1 To Y 5 There are one or more and three or less than three N, and the rest are CRb, and when there are two or more than two CRb, Rb may be the same as or different from each other.

[0145] In one embodiment of the present application, Ra may be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

[0146] In one embodiment of the present application, Ra may be a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

[0147] In one embodiment of the present application, Ra may be a substituted or unsubstituted phenyl group.

[0148] In one embodiment of the present application, Ra may be a phenyl group.

[0149] In one embodiment of the present application, Rb is selected from the group consisting of: hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or two or more adjacent groups can be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms.

[0150] In one embodiment of the present application, Rb is selected from the group consisting of: hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms.

[0151] In one embodiment of the present application, Rb may be selected from the group consisting of: hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0152] In one embodiment of the present application, Rb may be selected from the group consisting of: hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0153] In one embodiment of the present application, Rb may be selected from the group consisting of: hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0154] In one embodiment of the present application, Rb may be hydrogen; or deuterium.

[0155] In one embodiment of the present application, Rb is hydrogen.

[0156] In one embodiment of the present application, Rb is deuterium.

[0157] In one embodiment of the present application, Rb may be selected from the group consisting of: a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0158] In one embodiment of the present application, Rb can be selected from the group consisting of: a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0159] In one embodiment of the present application, Rb can be selected from the group consisting of: a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0160] In one embodiment of the present application, Rb can be selected from the group consisting of: hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted dibenzothienyl; and substituted or unsubstituted dibenzofuranyl.

[0161] In one embodiment of the present application, Rb can be selected from the group consisting of: hydrogen; deuterium; phenyl which is unsubstituted or substituted with phenyl or naphthyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; fluorenyl which is unsubstituted or substituted with an alkyl group having 2 to 10 carbon atoms; substituted or unsubstituted dibenzothienyl; and substituted or unsubstituted dibenzofuranyl.

[0162] In one embodiment of the present application, Rb can be selected from the group consisting of: hydrogen; deuterium; unsubstituted or phenyl or naphthyl substituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; unsubstituted or methyl substituted fluorenyl; substituted or unsubstituted dibenzothienyl; and substituted or unsubstituted dibenzofuranyl.

[0163] In one embodiment of the present application, Chemical Formula 1 may be represented by the following Chemical Formula 1-1.

[0164] [Chemical formula 1-1]

[0165]

[0166] In Chemical Formula 1-1,

[0167] Each substituent has the same definition as in Chemical Formula 1.

[0168] In one embodiment of the present application, Chemical Formula 1 may be represented by the following Chemical Formula 2 or Chemical Formula 3.

[0169] [Chemical formula 2]

[0170]

[0171] [Chemical formula 3]

[0172]

[0173] In Chemical Formula 2 and Chemical Formula 3,

[0174] Each substituent has the same definition as in Chemical Formula 1.

[0175] In one embodiment of the present application, Chemical Formula 2 may be represented by any one of the following Chemical Formulas 2-1 to 2-6.

[0176] [Chemical formula 2-1]

[0177]

[0178] [Chemical formula 2-2]

[0179]

[0180] [Chemical formula 2-3]

[0181]

[0182] [Chemical formula 2-4]

[0183]

[0184] [Chemical formula 2-5]

[0185]

[0186] [Chemical formula 2-6]

[0187]

[0188] In Chemical Formula 2-1 to Chemical Formula 2-6,

[0189] L 1 , L 2 ,X,R 1 , m and n have the same definitions as in Chemical Formula 1, and

[0190] Y 11 To Y 15 is CRb, and Rb has the same definition as in Chemical Formula 1.

[0191] In one embodiment of the present application, Chemical Formula 3 may be represented by any one of the following Chemical Formulas 3-1 to 3-6.

[0192] [Chemical formula 3-1]

[0193]

[0194] [Chemical formula 3-2]

[0195]

[0196] [Chemical formula 3-3]

[0197]

[0198] [Chemical formula 3-4]

[0199]

[0200] [Chemical formula 3-5]

[0201]

[0202] [Chemical formula 3-6]

[0203]

[0204] In Chemical Formula 3-1 to Chemical Formula 3-6,

[0205] L 1 , L 2 ,X,R 1 , m and n have the same definitions as in Chemical Formula 1, and

[0206] Y 11 To Y 15 is CRb, and Rb has the same definition as in Chemical Formula 1.

[0207] In one embodiment of the present application, R 1 It can be represented by the following chemical formula A.

[0208] [Chemical formula A]

[0209]

[0210] In chemical formula A,

[0211] L 11 With L 12 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 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms,

[0212] Ar 11 with Ar 12 are the same as or different from each other and are each independently selected from the group consisting of: a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or Ar 11 with Ar 12 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms,

[0213] a and b are 0 or 1, and

[0214] It means that the L bonded to the chemical formula 1 1 location.

[0215] In one embodiment of the present application, Chemical Formula A may be represented by any one of the following Chemical Formulas A-1 to A-5.

[0216] [Chemical formula A-1]

[0217]

[0218] [Chemical formula A-2]

[0219]

[0220] [Chemical formula A-3]

[0221]

[0222] [Chemical formula A-4]

[0223]

[0224] [Chemical formula A-5]

[0225]

[0226] In Chemical Formula A-1 to Chemical Formula A-5,

[0227] L 13 With L 14 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 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms,

[0228] Ar 13 with Ar 14are the same as or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms,

[0229] R 20 To R 26 are each independently hydrogen; deuterium; a halogen group; a cyano group; 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,

[0230] X 11 is O; S; or CRcRd, and Rc and Rd are the same as or different from each other and are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,

[0231] c and d are each 0 or 1, and

[0232] It means that the L bonded to the chemical formula 1 1 location.

[0233] In one embodiment of the present application, L of Chemical Formula A-1 13 With L 14 are the same as or different from each other, and may 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.

[0234] In one embodiment of the present application, L of Chemical Formula A-1 13 With L 14 are the same as or different from each other, and may 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.

[0235] In one embodiment of the present application, L 13 With L 14 are the same as or different from each other and may each independently be a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0236] In one embodiment of the present application, L 13 With L 14 are the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0237] In one embodiment of the present application, L 13 With L 14are the same as or different from each other and are each independently a direct bond; a phenylene group; a biphenylene group; or a naphthylene group.

[0238] In one embodiment of the present application, L 13 For direct keys.

[0239] In one embodiment of the present application, L 13 It is phenylene.

[0240] In one embodiment of the present application, L 13 It is a biphenylene group.

[0241] In one embodiment of the present application, L 13 It is naphthylene.

[0242] In one embodiment of the present application, L 14 For direct keys.

[0243] In one embodiment of the present application, L 14 It is phenylene.

[0244] In one embodiment of the present application, L 14 It is a biphenylene group.

[0245] In one embodiment of the present application, L 14 It is naphthylene.

[0246] In one embodiment of the present application, Ar of Formula A-1 13 with Ar 14 are the same as or different from each other and may each independently be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0247] In one embodiment of the present application, Ar13 and Ar14 of Chemical Formula A-1 are the same as or different from each other, and may each independently be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0248] In one embodiment of the present application, Ar 13 with Ar 14 are the same as or different from each other and may each independently be 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 dibenzothienyl group; or a substituted or unsubstituted dibenzofuranyl group.

[0249] In one embodiment of the present application, Ar 13 with Ar 14The same as or different from each other and may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a fluorenyl group which is unsubstituted or substituted by one or more selected from the group consisting of a phenyl group and an alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted dibenzothienyl group; or a substituted or unsubstituted dibenzofuranyl group.

[0250] In one embodiment of the present application, Ar 13 with Ar 14 The same as or different from each other and may be each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a fluorenyl group which is unsubstituted or substituted by one or more selected from the group consisting of a phenyl group and a methyl group; a substituted or unsubstituted dibenzothienyl group; or a substituted or unsubstituted dibenzofuranyl group.

[0251] In one embodiment of the present application, Ar 13 with Ar 14 The same as or different from each other and may be each independently phenyl; biphenyl; naphthyl; fluorenyl which is unsubstituted or substituted by one or more selected from the group consisting of phenyl and methyl; substituted or unsubstituted dibenzothienyl; or substituted or unsubstituted dibenzofuranyl.

[0252] In one embodiment of the present application, c and d in Chemical Formula A-1 may be 0 or 1, respectively.

[0253] In one embodiment of the present application, c is 0.

[0254] In one embodiment of the present application, c is 1.

[0255] In one embodiment of the present application, d is 0.

[0256] In one embodiment of the present application, d is 1.

[0257] In one embodiment of the present application, R of Chemical Formula A-1 to Chemical Formula A-5 20 To R 26 Each may independently be hydrogen; deuterium; a halogen group; a cyano group; 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.

[0258] In one embodiment of the present application, R 20 To R 26 and R and R are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0259] In one embodiment of the present application, R 20 To R 26 and may each independently be hydrogen; deuterium; or substituted or unsubstituted phenyl.

[0260] In one embodiment of the present application, R 20 To R 26 may each independently be hydrogen; or phenyl.

[0261] In one embodiment of the present application, R 20 It may be hydrogen; or phenyl.

[0262] In one embodiment of the present application, R 20 For hydrogen.

[0263] In one embodiment of the present application, R 20 It is phenyl.

[0264] In one embodiment of the present application, R 21 For hydrogen.

[0265] In one embodiment of the present application, R 22 For hydrogen.

[0266] In one embodiment of the present application, R 23 For hydrogen.

[0267] In one embodiment of the present application, R 24 For hydrogen.

[0268] In one embodiment of the present application, R 25 For hydrogen.

[0269] In one embodiment of the present application, R 26 For hydrogen.

[0270] In one embodiment of the present application, X of chemical formula A-5 11 is O; S; or CRcRd, and Rc and Rd are the same as or different from each other and may each independently be a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0271] In one embodiment of the present application, X 11 is O; S; or CRcRd, and Rc and Rd may all be methyl groups.

[0272] In one embodiment of the present application, X 11 is O.

[0273] In one embodiment of the present application, X 11 For S.

[0274] In one embodiment of the present application, X 11 is CRcRd, and both Rc and Rd are methyl groups.

[0275] In the chemical formula 1, when R 1 When the heterocyclic compound of Chemical Formula A-1 is used as an organic material in an organic light-emitting device, the organic light-emitting device has a lower driving voltage and can thereby have a higher efficiency. This is believed to be due to the fact that R 1 The heterocyclic compound of Chemical Formula A-1 has faster hole mobility.

[0276] In the heterocyclic compound provided in one embodiment of the present application, Chemical Formula 1 is represented by any one of the following compounds.

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285] In addition, by introducing various substituents into the structure of Chemical Formula 1, a compound having unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents commonly used as hole injection layer materials, hole transport layer materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials for manufacturing organic light emitting components into the core structure, a material that meets the conditions required for each organic material layer can be synthesized.

[0286] Furthermore, by introducing various substituents into the structure of Chemical Formula 1, the energy band gap may be finely controlled, and at the same time, characteristics at the interface between organic materials are enhanced, and material applications may become diversified.

[0287] At the same time, the heterocyclic compound has a high glass transition temperature (Tg), and thereby has excellent thermal stability. Such an increase in thermal stability becomes an important factor in providing driving stability to the device.

[0288] A 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, a heterocyclic compound according to one embodiment of the present application can be prepared based on a preparation example described later.

[0289] Another embodiment of the present application provides an organic light-emitting device including a heterocyclic compound represented by Chemical Formula 1. The "organic light-emitting device" may be expressed by terms such as "organic light-emitting diode", "OLED", "OLED device" and "organic electroluminescent device".

[0290] One embodiment of the present application provides an organic light-emitting component, including a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers includes a heterocyclic compound represented by Chemical Formula 1.

[0291] In one embodiment of the present application, the first electrode may be an anode, and the second electrode may be a cathode.

[0292] In another embodiment of the present application, the first electrode may be a cathode, and the second electrode may be an anode.

[0293] In one embodiment of the present application, the organic light emitting component may be a blue organic light emitting component, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the blue organic light emitting component.

[0294] In another embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the green organic light-emitting device.

[0295] In another embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the red organic light emitting device.

[0296] The specific description about the heterocyclic compound represented by Chemical Formula 1 is the same as the description provided above.

[0297] In addition to using the heterocyclic compound described above to form one or more of the organic material layers, the organic light-emitting device of the present application may be manufactured using commonly used organic light-emitting device manufacturing methods and materials.

[0298] When manufacturing an organic light-emitting device, the heterocyclic compound can be formed into an organic material layer via solution coating and vacuum deposition. Herein, solution coating means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

[0299] The organic material layer of the organic light-emitting component of the present application may be formed in a single-layer structure, but may be formed in a multi-layer structure in which two or more organic material layers are laminated. For example, the organic light-emitting component of the present disclosure may have a structure including a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like as organic material layers. However, the structure of the organic light-emitting component is not limited thereto, and may include a small amount of organic material layers.

[0300] In the organic light-emitting device of the present application, the organic material layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound. The use of a heterocyclic compound in the light-emitting layer spatially separates HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital), thereby allowing strong charge transport, and thus, excellent driving, efficiency and service life can be obtained in the organic light-emitting device.

[0301] The organic light-emitting device of the present disclosure may 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, an electron blocking layer, a hole auxiliary layer and a hole blocking layer.

[0302] Figures 1 to 3 The lamination sequence of the electrodes and organic material layers of the organic light emitting device according to one embodiment of the present application is shown. However, the scope of the present application is not limited to these figures, and the structure of the organic light emitting device known in the art can also be used in the present application.

[0303] Figure 1 1 shows an organic light emitting component in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially laminated on a substrate 100. However, the structure is not limited to such a structure, and as Figure 2 As shown in , an organic light emitting device can also be obtained in which a cathode, an organic material layer and an anode are sequentially laminated on a substrate.

[0304] Figure 3 The case where the organic material layer is multi-layered is shown. Figure 3 The organic light-emitting component 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 such a laminated structure, and if necessary, the layer other than the light-emitting layer may not be included, and other desired functional layers may be further added.

[0305] The organic material layer including the compound represented by Chemical Formula 1 may further include other materials as necessary.

[0306] In an organic light-emitting device according to one embodiment of the present application, materials other than the compound of Chemical Formula 1 are shown below, however, these materials are only for illustrative purposes and are not intended to limit the scope of the present application, and may be replaced by materials known in the art.

[0307] A material having a relatively large work function may be used as the anode material, and a transparent conductive oxide, metal, conductive polymer or the like may 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); combinations of metals and oxides such as ZnO:Al or SnO; 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, and similar materials, but not limited thereto.

[0308] A material having a relatively small work function can be used as the cathode material, and a metal, a metal oxide, a conductive polymer 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 LiO 2 / Al, and the like, but not limited thereto.

[0309] Known hole injection materials can be used as the hole injection material, and for example, the following can be used: phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429; or starburst-type amine derivatives such as tris(4-hydrazinocarbonyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA) or 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB) described in the document [Advanced Material, 6, p. 677 (1994)]; polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid or polyaniline / poly(4-styrenesulfonate) as conductive polymers having solubility; and similar materials.

[0310] As the hole transport material, pyrazoline derivatives, aromatic amine derivatives, stilbene derivatives, triphenyldiamine derivatives and the like can be used, and low molecular weight or high molecular weight materials can also be used as the hole transport material.

[0311] As electron transport materials, metal complexes of oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenylethylene dicyanide and its derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and its derivatives, and the like can be used, and polymer materials and low molecular weight materials can also be used as electron transport materials.

[0312] As an example of the electron injection material, LiF is generally used in the art, however, the present application is not limited thereto.

[0313] As the luminescent material, a material emitting red, green or blue light can be used, and if necessary, two or more luminescent materials can be mixed and used. Herein, two or more luminescent materials can be used by depositing as individual supply sources or by premixing and depositing as one supply source. In addition, a fluorescent material can also be used as a luminescent material, however, a phosphorescent material can also be used. A material that emits light by combining electrons and holes injected from an anode and a cathode, respectively, can be used alone as a luminescent material, however, a material having a host material and a doping material that participate in luminescence can also be used as a luminescent material.

[0314] When mixing the light emitting material host, the same series of hosts may be mixed, or different series of hosts may be mixed. For example, any two or more types of materials in n-type host materials or p-type host materials may be selected and used as host materials of the light emitting layer.

[0315] In the organic light-emitting device of the present application, the organic material layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound as a host material of the light-emitting material.

[0316] In the organic light-emitting device of the present application, the light-emitting layer may include two or more host materials, and at least one of the host materials may include a heterocyclic compound as a host material of the light-emitting material.

[0317] In the organic light-emitting device of the present application, the light-emitting layer may use two or more host materials after premixing, and at least one of the two or more host materials may include a heterocyclic compound as a host material of the light-emitting material.

[0318] Premixing means that two or more host materials of the light emitting layer are mixed in advance in one supply source before being deposited on the organic material layer.

[0319] In the organic light-emitting device of the present application, the light-emitting layer may include two or more host materials, each of which includes one or more p-type host materials and n-type host materials, and at least one of the host materials may include a heterocyclic compound as the host material of the light-emitting material. In this case, the organic light-emitting device may have excellent driving, efficiency and service life.

[0320] In the organic light-emitting device of the present application, the light-emitting layer may include a heterocyclic compound and any one of the following heterocyclic compounds 1-1 to 1-14.

[0321]

[0322] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 and any one of the heterocyclic compounds 1-1 to 1-14 may be used as a host material.

[0323] One embodiment of the present application provides a composition for an organic material layer of an organic light-emitting device, the composition comprising a heterocyclic compound represented by Chemical Formula 1 and any one of the following heterocyclic compounds 1-1 to 1-14.

[0324]

[0325] In the composition, the heterocyclic compound represented by Chemical Formula 1: any one of heterocyclic compounds 1-1 to 1-14 may have a weight ratio of 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1, or 1:2 to 2:1, however, the weight ratio is not limited thereto.

[0326] Depending on the materials used, the organic light-emitting device according to one embodiment of the present application may be a top emission type, a bottom emission type, or a double-sided emission type.

[0327] The heterocyclic compound according to one embodiment of the present application can also be used in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like based on similar principles to those used in organic light-emitting devices.

[0328] Methods of implementing this application

[0329] Hereinafter, the present specification will be described in more detail with reference to examples, however, these are only for illustrative purposes, and the scope of the present application is not limited thereto.

[0330] <Preparation Example>

[0331] <Preparation Example 1> Preparation of Compound 1

[0332]

[0333] 1) Preparation of Compound C-2

[0334] In the presence of 1-bromonaphthalene-2-ol (100 g, 448.29 mmol), (2-chloro-6-fluorophenyl)boronic acid (85.98 g, 493.12 mmol), Pd(PPh) 4 (25.9 g, 22.41 mmol) and Na 2 CO 3 (95.03 g, 896.58 mmol) dissolved in toluene / ethanol / H 2 O (1 L / 200 mL / 200 mL), the mixture was refluxed for 4 hours. After the reaction was completed, the resultant was extracted by introducing distilled water and dichloromethane (DCM) thereinto at room temperature, and then MgSO 4 After drying the organic layer, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex=1:1) to obtain the target compound C-1 (48.9 g, 40%).

[0335] 2) Preparation of Compound C-1

[0336] After compound C-2 (49 g, 179.68 mmol) and Cs 2 CO 3 (146.36 g, 449.21 mol) was dissolved in dimethylacetamide (DMA) (400 ml), and the mixture was refluxed for 2 hours. After the reaction was completed, the salt was filtered at room temperature, and the solvent was removed using a rotary evaporator. The reaction material was purified using DCM / MeOH to obtain the target compound C-1 (27.24 g, 60%).

[0337] 3) Preparation of Compound C

[0338] Compound C-1 (27 g, 106.84 mmol) was dissolved in chloroform (CHCl 3 ) (300 ml), Br was added dropwise 2 , and the resultant was reacted. After completing the reaction, the resultant was recrystallized with methanol to obtain the target compound C (26.93 g, 76%).

[0339]

[0340] 4) Preparation of compound 1-2

[0341] In the presence of compound 1-3 (compound C) (10.0 g, 30.15 mmol), diphenylamine (5.1 g, 30.15 mmol), Pd 2 (dba) 3 (1.38 g, 1.51 mmol), P(t-Bu) 3 After dissolving NaOtBu (1.22 g, 3.02 mmol) and NaOtBu (5.67 g, 60.32 mmol) in toluene (100 ml), the mixture was refluxed for 2 hours. After completing the reaction, the resultant was extracted by introducing distilled water and DCM therein at room temperature, and then MgSO 4 After drying the organic layer, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex=1:3) to obtain the target compound 1-2 (7.59 g, 60%).

[0342] 5) Preparation of compound 1-1

[0343] In the reaction mixture of compound 1-2 (7.59 g, 18.08 mmol), bis(pinacolyl)diboron (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis-1,3,2-dioxaborolane) (5.97 g, 23.5 mmol), Pd 2 (dba) 3 After (0.83 g, 0.903 mmol), Xphos (0.86 g, 1.81 mmol) and KOAc (3.55 g, 36.15 mmol) were dissolved in 1,4-dioxane (80 ml), the mixture was refluxed for 12 hours. After the reaction was completed, the resultant was extracted by introducing distilled water and DCM therein at room temperature, and then the mixture was washed with MgSO 4 After drying the organic layer, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex=1:2) to obtain the target compound 1-1 (4.81 g, 52%).

[0344] 6) Preparation of Compound 1

[0345] In the presence of compound 1-1 (4.81 g, 9.41 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.52 g, 9.41 mmol), Pd (pph 3 ) 4 (0.54 g, 0.47 mmol) and K 2 CO3 (2.6 g, 18.81 mmol) dissolved in 1,4-dioxane / H 2 O (50 ml / 10 ml), the mixture was refluxed for 3 hours. After the reaction was completed, the solid produced was filtered, washed with distilled water and dried. The dried solid was boiled and dissolved in DCB, purified by silica, and the solvent was removed using a rotary evaporator. The resulting product was recrystallized with acetone to obtain the target compound 1 (3.25 g, 56%).

[0346] The target compound was synthesized in the same manner as in Preparation Example 1, except that Intermediate A-1 in the following Table 1 was used instead of diphenylamine and Intermediate B-1 in the following Table 1 was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0347] [Table 1]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355] <Preparation Example 2> Preparation of Compound 13

[0356]

[0357] 1) Preparation of compound 13-3

[0358] Compound C (10.0 g, 30.15 mmol), bis(pinacolato)diboron (9.2 g, 36.2 mmol), Pd(dppf)Cl 2 After (1.1 g, 1.51 mmol) and KOAc (5.68 g, 60.32 mmol) were dissolved in 1,4-dioxane (100 mL), the mixture was refluxed for 2 hours. After the reaction was completed, the resultant was extracted by introducing distilled water and DCM therein at room temperature, and then MgSO 4 After drying the organic layer, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex=1:2) to obtain the target compound 13-3 (6.97 g, 61%).

[0359] 2) Preparation of compound 13-2

[0360] In the presence of compound 13-3 (6.97 g, 18.41 mmol), 4-bromo-N,N-diphenylaniline (5.97 g, 18.41 mmol), Pd (pph 3 ) 4 (1.06 g, 9.2 mmol) and K 2 CO 3 (5.09 g, 36.81 mmol) dissolved in 1,4-dioxane / H 2 O (80 ml / 12 ml), the mixture was refluxed for 3 hours. After the reaction was completed, the resultant was extracted by introducing distilled water and DCM therein at room temperature, and then MgSO 4 After drying the organic layer, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex=1:3) to obtain the target compound 13-2 (4.75 g, 52%).

[0361] 3) Preparation of compound 13-1

[0362] In the reaction mixture of compound 13-2 (4.75 g, 9.58 mmol), bis(pinacolyl)diboron (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis-1,3,2-dioxaborolane) (3.16 g, 12.45 mmol), Pd 2 (dba) 3 After (0.44 g, 0.48 mmol), Xphos (0.46 g, 0.96 mmol) and KOAc (1.88 g, 19.15 mmol) were dissolved in 1,4-dioxane (50 ml), the mixture was refluxed for 12 hours. After the reaction was completed, the resultant was extracted by introducing distilled water and DCM therein at room temperature, and then the mixture was washed with MgSO 4 After drying the organic layer, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex=1:2) to obtain the target compound 13-1 (4.28 g, 76%).

[0363] 4) Preparation of compound 13

[0364] In the presence of compound 13-1 (4.28 g, 7.28 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.95 g, 7.28 mmol), Pd (pph 3 ) 4 (0.42 g, 0.36 mmol) and K 2 CO 3(2.01 g, 14.57 mmol) dissolved in 1,4-dioxane / H 2 O (50 ml / 10 ml), the mixture was refluxed for 3 hours. After completing the reaction, the resulting solid was filtered, washed with distilled water and dried. The dried solid was boiled and dissolved in DCB, purified by silica, and the solvent was removed using a rotary evaporator. The resulting product was recrystallized with acetone to obtain the target compound 13 (2.93 g, 58%).

[0365] The target compound was synthesized in the same manner as in Preparation Example 2, except that Intermediate A-2 in the following Table 2 was used instead of 4-bromo-N,N-diphenylaniline and Intermediate B-2 in the following Table 2 was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0366] [Table 2]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373] <Preparation Example 3> Preparation of Compound 145

[0374]

[0375] 1) Preparation of compound 145-3

[0376] Compound C-1 (10 g, 39.57 mmol), bis(pinacolyl)diboron (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis-1,3,2-dioxaborolane) (12.06 g, 47.49 mmol), Pd 2 (dba) 3 After (1.81 g, 1.98 mmol), Xphos (1.89 g, 3.96 mmol) and KOAc (7.77 g, 79.15 mmol) were dissolved in 1,4-dioxane (100 ml), the mixture was refluxed for 12 hours. After the reaction was completed, the resultant was extracted by introducing distilled water and DCM therein at room temperature, and then the mixture was dried over MgSO 4After the organic layer was dried, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex=1:2) to obtain the target compound 145-3 (8.58 g, 63%).

[0377] 2) Preparation of compound 145-2

[0378] In the presence of compound 145-3 (8.58 g, 24.93 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.34 g, 27.42 mmol), Pd (pph 3 ) 4 (1.44 g, 1.25 mmol) and K 2 CO 3 (6.89 g, 49.85 mmol) dissolved in 1,4-dioxane / H 2 O (100 ml / 20 ml), the mixture was refluxed for 3 hours. After the reaction was completed, the resulting solid was filtered, washed with distilled water and dried. The dried solid was boiled and dissolved in DCB, purified by silica, and the solvent was removed using a rotary evaporator. The resulting product was recrystallized with acetone to obtain the target compound 145-2 (9.19 g, 82%).

[0379] 3) Preparation of compound 145-1

[0380] After dissolving compound 145-2 (9.19 g, 20.44 mmol) in THF (120 mL) under nitrogen substitution, the temperature was lowered to -78°C. After 2.5M n-BuLi (8.59 mL, 21.47 mmol) was added dropwise thereto, the temperature was raised to room temperature, and the resultant was reacted for 1 hour. The temperature was lowered to -78°C again, and B(OMe) was added dropwise thereto. 3 (2.74 ml, 24.53 mmol, d: 0.932 g / ml), the temperature was raised to room temperature, and the resultant was reacted for 1 hour. After the reaction was completed, MeOH was used to terminate the reaction, and after the resultant was purified by silica, the solvent was removed using a rotary evaporator. The resultant was recrystallized with EA and Hex to obtain the target compound 145-1 (5.24 g, 52%).

[0381] 4) Preparation of Compound 145

[0382] In the presence of compound 145-1 (5.24 g, 10.62 mmol), 4-bromo-N,N-diphenylaniline (3.79 g, 11.68 mmol), Pd (pph 3 ) 4 (0.61 g, 0.53 mmol) and K 2 CO3 (2.94 g, 21.24 mmol) dissolved in 1,4-dioxane / H 2 O (50 ml / 10 ml), the mixture was refluxed for 3 hours. After completing the reaction, the resulting solid was filtered, washed with distilled water and dried. The dried solid was boiled and dissolved in DCB, purified by silica, and the solvent was removed using a rotary evaporator. The resulting product was recrystallized with acetone to obtain the target compound 145 (2.58 g, 35%).

[0383] The target compound was synthesized in the same manner as in Preparation Example 3, except that Intermediate A-3 in the following Table 3 was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and Intermediate B-3 in the following Table 3 was used instead of 4-bromo-N,N-diphenylaniline.

[0384] [Table 3]

[0385]

[0386]

[0387]

[0388]

[0389] The compounds described in this specification were prepared in the same manner as in the Preparation Examples, and the synthetic identification results of the prepared compounds are shown in the following Tables 4 and 5. The following Table 4 shows 1 H NMR (CDCl 3 , 200Mz), and the following Table 5 shows the measured values ​​of FD-mass spectrometry (FD-MS: field desorption mass spectrometry).

[0390] [Table 4]

[0391]

[0392]

[0393]

[0394] [Table 5]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400] [Experimental Example]

[0401] <Experimental Example 1>

[0402] 1) Manufacturing of organic light-emitting components (red body)

[0403] A glass substrate on which indium tin oxide (ITO) is coated in a thin film form to a thickness of 1,500 angstroms is ultrasonically cleaned with distilled water. After the cleaning with distilled water is completed, the substrate is ultrasonically cleaned with a solvent such as acetone, methanol, and isopropyl alcohol, then dried, and UVO treated using UV in a UV cleaner for 5 minutes. Thereafter, the substrate is transferred to a plasma cleaner (PT), and after plasma treatment under vacuum for ITO work function and residual film removal, the substrate is transferred to a thermal deposition device for organic deposition.

[0404] On the transparent ITO electrode (anode), a hole injection layer 2-TNATA (4,4'4"-tri[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.

[0405] The light emitting layer was thermally vacuum deposited thereon as follows. The following compound A was used as the host and (piq) 2 (Ir)(acac) as a red phosphorescent dopant by doping the host with 3 wt% (piq) 2 (Ir)(acac) was used to deposit the light-emitting layer to 500 angstroms. Thereafter, BCP was deposited to 60 angstroms as a hole blocking layer, and Alq 3 Deposited to 200 angstroms as an electron transport layer.

[0406] 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 an aluminum (Al) cathode to a thickness of 1,200 angstroms, and thus, an organic light emitting device was manufactured (Comparative Example 1).

[0407] At the same time, in 10 -8 Support up to 10 -6 Under the support, all organic compounds required for the manufacture of OLEDs are purified by vacuum sublimation for each material to be used in the manufacture of OLEDs.

[0408] The organic light-emitting components of Comparative Examples 2 to 4 and Examples 1 to 65 were further manufactured in the same manner as the process for manufacturing the organic light-emitting component of Experimental Example 1, except that the compounds listed in the following Table 6 were used instead of Compound A used as the host of the light-emitting layer.

[0409] Specifically, the compounds used as the host of the light emitting layer in Examples 1 to 65 and Comparative Examples 1 to 4 are as shown in Table 6 below.

[0410] Herein, Compound A to Compound D of Comparative Examples 1 to 4 in the following Table 6 are as follows.

[0411]

[0412] 2) Driving voltage and luminous efficiency of organic light-emitting components

[0413] For each of the organic light-emitting components of Examples 1 to 65 and Comparative Examples 1 to 4 manufactured as above, electroluminescence (EL) characteristics were measured using M7000 manufactured by McScience Inc., and through the measurement results, T was measured by a service life measurement system (M6000) manufactured by McScience Inc. when the standard brightness was 6,000 cd / m2. 90 .

[0414] The measured properties of the organic light emitting device of the present disclosure are shown in Table 6 below.

[0415] [Table 6]

[0416]

[0417]

[0418]

[0419] According to Experimental Example 1, it was identified that when the heterocyclic compound of Chemical Formula 1 is used as a host of an organic material layer (especially a light-emitting layer) of an organic light-emitting device, the driving voltage and efficiency are improved. Specifically, it was identified that, compared to Comparative Examples 1 to Comparative Examples 4, when the benzene ring is extended in the central structure, Examples 1 to 65 using the heterocyclic compound of Chemical Formula 1 have an increased resonance effect, and are thereby suitable for use as a red host. In addition, by having both a donor with good hole transport capability and an acceptor with good electron transport capability in one molecule and fixing the substituent at the 11th position of naphthobenzofuran, Examples 1 to 65 have a spatial placement, and spatially separate HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital), thereby allowing strong charge transport, and high efficiency is expected when used as an organic material in an organic light-emitting device.

[0420] In addition, when comparing Examples 1 to 57 and Examples 58 to 65, it was identified that, in Chemical Formula 1, 1 Compared with the case where the hole unit is a carbazole group, the 1 A relatively low driving voltage is obtained when the hole unit is an amine group. The reason is believed to be due to the fact that 1 Compared with the case where the hole unit is a carbazole group, the 1 When the hole unit of is an amine group, the hole mobility is relatively fast, which enables light emission at a low voltage.

[0421] <Experimental Example 2>

[0422] 1) Manufacturing of organic light-emitting components (red body)

[0423] A glass substrate on which indium tin oxide (ITO) is coated in a thin film form to a thickness of 1,500 angstroms is ultrasonically cleaned with distilled water. After the cleaning with distilled water is completed, the substrate is ultrasonically cleaned with a solvent such as acetone, methanol, and isopropyl alcohol, then dried, and UVO treated using UV in a UV cleaner for 5 minutes. Thereafter, the substrate is transferred to a plasma cleaner (PT), and after plasma treatment under vacuum for ITO work function and residual film removal, the substrate is transferred to a thermal deposition device for organic deposition.

[0424] On the transparent ITO electrode (anode), a hole injection layer 2-TNATA (4,4'4"-tri[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.

[0425] The light-emitting layer was thermally vacuum deposited thereon as follows. Using a method in which the heterocyclic compound 5 of the present disclosure is deposited as the first host and the compound 1-1 is deposited as the second host in one supply source and using (piq) 2 (Ir)(acac) as a red phosphorescent dopant by doping the host with 3 wt% (piq) 2 (Ir)(acac) was deposited to 500 angstroms as a light-emitting layer. Thereafter, BCP was deposited to 60 angstroms as a hole blocking layer, and Alq 3 Deposited to 200 angstroms as an electron transport layer.

[0426] 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 an aluminum (Al) cathode to a thickness of 1,200 angstroms, and thus, an organic light-emitting component was manufactured (Example 66).

[0427] At the same time, in 10 -8 Support up to 10 -6 Under the support, all organic compounds required for the manufacture of OLEDs are purified by vacuum sublimation for each material to be used in the manufacture of OLEDs.

[0428] The organic light-emitting components of Examples 66 to 113 were further manufactured in the same manner as in the process for manufacturing the organic light-emitting component of Experimental Example 2, except that the compounds listed in the following Table 7 were used instead of Compound 1-1 used as the second host of the light-emitting layer.

[0429] Specifically, the compounds used as the first host and the second host of the light-emitting layer in Examples 66 to 113 are as shown in Table 7 below.

[0430] 2) Driving voltage and luminous efficiency of organic light-emitting components

[0431] For each of the organic light-emitting components of Examples 66 to 113 manufactured as above, the electroluminescent (EL) characteristics were measured using M7000 manufactured by MicroScience, and through the measurement results, when the standard brightness was 6,000 candelas / square meter, T was measured by a service life measurement system (M6000) manufactured by MicroScience. 95 .

[0432] The measured properties of the organic light emitting device of the present disclosure are shown in Table 7 below.

[0433] Herein, in the following Table 7, Compound 1-1 to Compound 1-14 are as follows. The following Compound 1-1 to Compound 1-14 are p-host (p-type host) compounds having excellent hole transporting ability.

[0434]

[0435] [Table 7]

[0436]

[0437]

[0438] According to Experimental Example 2, it was identified that when the heterocyclic compound of the present disclosure is used as the first host of the organic material layer (especially the light-emitting layer) of the organic light-emitting device and a specific compound having excellent hole transporting ability is used as the second host, the driving voltage and efficiency can be improved. In particular, it was identified that when Compounds 1-1 to 1-14 having the heterocyclic compound of the present disclosure having hole transporting ability are used, the phenomenon of performance degradation caused by the accumulation of electrons generated from the heterocyclic compound of the present disclosure is reduced, which improves the service life problem.

[0439] <Experimental Example 3>

[0440] 1) Manufacturing of organic light-emitting components (red body)

[0441] A glass substrate on which indium tin oxide (ITO) is coated in a thin film form to a thickness of 1,500 angstroms is ultrasonically cleaned with distilled water. After the cleaning with distilled water is completed, the substrate is ultrasonically cleaned with a solvent such as acetone, methanol, and isopropyl alcohol, then dried, and UVO treated using UV in a UV cleaner for 5 minutes. Thereafter, the substrate is transferred to a plasma cleaner (PT), and after plasma treatment under vacuum for ITO work function and residual film removal, the substrate is transferred to a thermal deposition device for organic deposition.

[0442] On the transparent ITO electrode (anode), a hole injection layer 2-TNATA (4,4'4"-tri[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.

[0443] A light-emitting layer was thermally vacuum deposited thereon as follows. Using a method in which the heterocyclic compound 14 of the present disclosure is deposited as a first host and the compound 2-1 is deposited as a second host in one supply source and using (piq) 2 (Ir)(acac) as a red phosphorescent dopant by doping the host with 3 wt% (piq) 2 (Ir)(acac) was deposited to 500 angstroms as a light-emitting layer. Thereafter, BCP was deposited to 60 angstroms as a hole blocking layer, and Alq 3Deposited to 200 angstroms as an electron transport layer.

[0444] 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 an aluminum (Al) cathode to a thickness of 1,200 angstroms, and thus, an organic light-emitting device was manufactured (Example 114).

[0445] At the same time, in 10 -8 Support up to 10 -6 Under the support, all organic compounds required for the manufacture of OLEDs are purified by vacuum sublimation for each material to be used in the manufacture of OLEDs.

[0446] The organic light-emitting components of Examples 114 to 153 were further manufactured in the same manner as in the process for manufacturing the organic light-emitting component of Experimental Example 3, except that the compounds listed in the following Table 8 were used instead of Compound 14 and Compound 2-1 used as the first host of the light-emitting layer.

[0447] Specifically, the compounds used as the first host and the second host of the light-emitting layer in Examples 114 to 153 are as shown in Table 8 below.

[0448] 2) Driving voltage and luminous efficiency of organic light-emitting components

[0449] For each of the organic light-emitting components of Examples 114 to 153 manufactured as above, electroluminescence (EL) characteristics were measured using M7000 manufactured by MicroScience, and through the measurement results, T was measured by a service life measurement system (M6000) manufactured by MicroScience when the standard brightness was 6,000 cd / m2. 95 .

[0450] The measured properties of the organic light emitting device of the present disclosure are shown in Table 8 below.

[0451] Herein, in the following Table 8, Compound 2-1 to Compound 2-4 are as follows. The following Compound 2-1 to Compound 2-4 are n-host (n-type host) compounds having excellent electron transporting ability.

[0452]

[0453] [Table 8]

[0454]

[0455] According to Experimental Example 3, it was identified that when the heterocyclic compound of the present disclosure is used as the first host of the organic material layer (especially the light-emitting layer) of the organic light-emitting component and a specific compound with excellent electron transport ability is used as the second host, the component service life can be improved. In particular, it was identified that when Compounds 2-1 to 2-4 of the heterocyclic compound of the present disclosure having electron transport ability are used, the charge balance in the light-emitting layer is maximized, thereby enhancing the light-emitting characteristics.

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical formula 1] Wherein in Chemical Formula 1, L 1 With L 2 are the same as or different from each other and are each independently a direct bond; a phenylene group; or a biphenylene group; X is O; Y 1 To Y 5 are the same or different from each other and are each independently N or CRb, Y 1 To Y 5 At least one or more of is N, and when there are two or more CRb, Rb are the same as or different from each other; R 1 Represented by any one of the following Chemical Formulas A-1 to A-5; R 2 To R 9 is hydrogen; or deuterium; Rb is hydrogen; deuterium; phenyl which is unsubstituted or substituted by phenyl or naphthyl; biphenyl; naphthyl; fluorenyl which is unsubstituted or substituted by methyl; dibenzothienyl; and dibenzofuranyl; m and n are each independently 0 or 1; p is 0 or 1, [Chemical formula A-1] [Chemical formula A-2] [Chemical formula A-3] [Chemical formula A-4] [Chemical formula A-5] In Chemical Formula A-1 to Chemical Formula A-5, L 13 With L 14 are the same as or different from each other and are each independently a direct bond; phenylene; biphenylene; or naphthylene; Ar 13 with Ar 14 are the same as or different from each other and are each independently phenyl; biphenyl; naphthyl; fluorenyl which is unsubstituted or substituted with one or more selected from the group consisting of phenyl and methyl; dibenzothienyl; or dibenzofuranyl; R 20 To R 26 are each independently hydrogen; or phenyl; X 11 is O; or S; c and d are each 0 or 1; and It means that it is bonded to L of the chemical formula 1 1 location.

2. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 2 or Chemical Formula 3: [Chemical formula 2] [Chemical formula 3] In Chemical Formula 2 and Chemical Formula 3, Each substituent has the same definition as in Chemical Formula 1.

3. The heterocyclic compound according to claim 2, wherein Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1 to 2-6: [Chemical formula 2-1] [Chemical formula 2-2] [Chemical formula 2-3] [Chemical formula 2-4] [Chemical formula 2-5] [Chemical formula 2-6] In Chemical Formula 2-1 to Chemical Formula 2-6, L 1 , L 2 ,X,R 1 , m and n have the same definitions as in Chemical Formula 1; and Y 11 To Y 15 is CRb, and Rb has the same definition as in Chemical Formula 1.

4. The heterocyclic compound according to claim 2, wherein Chemical Formula 3 is represented by any one of the following Chemical Formulas 3-1 to 3-6: [Chemical formula 3-1] [Chemical formula 3-2] [Chemical formula 3-3] [Chemical formula 3-4] [Chemical formula 3-5] [Chemical formula 3-6] In Chemical Formula 3-1 to Chemical Formula 3-6, L 1 , L 2 ,X,R 1 , m and n have the same definitions as in Chemical Formula 1, Y 11 To Y 15 is CRb, and Rb has the same definition as in Chemical Formula 1.

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

6. An organic light-emitting component, include: a first electrode; a second electrode; as well as One or more organic material layers are disposed between the first electrode and the second electrode, One or more layers of the organic material layers comprise the heterocyclic compound as claimed in any one of claims 1 to 5. 7 . The organic light-emitting device according to claim 6 , wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer comprises the heterocyclic compound. 8 . The organic light-emitting device according to claim 6 , wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer comprises the heterocyclic compound as a host material of a light-emitting material. 9 . The organic light-emitting device according to claim 8 , wherein the light-emitting layer comprises two or more host materials, and at least one of the two or more host materials is the heterocyclic compound.

10. The organic light-emitting device according to claim 6, 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, an electron blocking layer, a hole assisting layer and a hole blocking layer.

11. A composition for an organic material layer of an organic light-emitting component, wherein Composition include: The heterocyclic compound represented by Chemical Formula 1 as claimed in claim 1; as well as Any one of the following heterocyclic compounds 1-1 to 1-14:

12. The composition for an organic material layer of an organic light-emitting component according to claim 11, in, In the composition, a weight ratio of the heterocyclic compound represented by Chemical Formula 1 to any one of the heterocyclic compounds 1-1 to 1-14 is 1:10 to 10:1.

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