Heterocyclic compound and organic light-emitting component comprising the same

Abstract

The present specification relates to a heterocyclic compound represented by Chemical Formula 1 and an organic light-emitting component including the same. In Chemical Formula 1, the definition of each substituent is the same as that in the specification. The present application can reduce the driving voltage of the component, enhance the light efficiency, and enhance the service life characteristics of the component. [Chemical Formula 1]

Description

[0001] This specification claims priority to and the benefit of Korean Patent Application No. 10-2019-0158383, filed in the Korean Intellectual Property Office on December 2, 2019, the entire contents of which are incorporated herein by reference. Technical Field

[0002] This specification relates to heterocyclic compounds and organic light-emitting devices comprising the same. Background Art

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

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

[0005] The material of the organic thin film may optionally 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 thin film, or a compound capable of acting as a host or dopant in a host-dopant-based light-emitting layer may be used as the material of the organic thin film. Furthermore, compounds capable of performing hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and similar functions may also be used as the material of the organic thin film.

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

[0007] Technical issues

[0008] This specification provides a heterocyclic compound and an organic light-emitting component comprising the same.

[0009] Technical Solutions

[0010] One embodiment of the present specification provides a heterocyclic compound represented by the following Chemical Formula 1.

[0011] [Chemical Formula 1]

[0012]

[0013] In Chemical Formula 1,

[0014] R1 to R5 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0015] L is a direct bond; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and

[0016] Z is a substituted or unsubstituted aryl group having 10 to 60 carbon atoms; or a substituted or unsubstituted phosphine oxide group, or is represented by the following Chemical Formula 2,

[0017] [Chemical Formula 2]

[0018]

[0019] In Chemical Formula 2,

[0020] X1 to X3 are each CR or N, and at least one of them is N,

[0021] R, R21 and R22 are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0022] Adjacent groups among X1 to X3, R21 and R22 may be bonded to each other to form a substituted or unsubstituted ring,

[0023] r is an integer from 0 to 3,

[0024] a and b are each an integer from 1 to 5, and

[0025] When r, a, and b are each 2 or greater, the substituents in the brackets are the same as or different from each other.

[0026] Another embodiment of the present application provides an organic light-emitting component, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer comprises one or more types of heterocyclic compounds represented by Chemical Formula 1.

[0027] Beneficial effects

[0028] The heterocyclic compounds described herein can be used as materials for the organic material layer of an organic light-emitting device. Heterocyclic compounds can function as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, or similar materials in an organic light-emitting device. Specifically, heterocyclic compounds can be used as materials for the electron transport layer, hole blocking layer, or charge generation layer of an organic light-emitting device.

[0029] Chemical Formula 1 comprises a pyrazolo[5,1-a]isoquinoline core structure with a benzene ring substituted with substituents, including pyridine, pyrimidine, triazine, phenanthroline, or anthracene, and a substituent on the pyridine or pyrazole ring. The excellent electron-withdrawing properties of the azine functional group, which improve electron flow, enhance the electron transport capability of the electron transport layer. Furthermore, the presence of substituents that enhance hole-reinforcing properties and the bonded azine moieties enhance the thermal stability of the compound by increasing the planarity and glass transition temperature of the azine derivative. Electron transport and hole-blocking capabilities can be enhanced by adjusting the band gap and energy level in the triplet state.

[0030] In addition, when the heterocyclic compound of Chemical Formula 1 is used as a material for an electron transport layer or a hole blocking layer of an organic light-emitting device, the driving voltage of the device can be reduced, the light efficiency can be enhanced, and the service life characteristics of the device can be enhanced. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] Figures 1 to 5 1 and 2 are diagrams each illustrating a laminated structure of an organic light emitting assembly according to one embodiment of the present specification.

[0032] 100:Substrate

[0033] 200: Anode

[0034] 300: organic material layer

[0035] 301: hole injection layer

[0036] 302: hole transport layer

[0037] 303: Luminous layer

[0038] 304: hole blocking layer

[0039] 305: electron transport layer

[0040] 306: electron injection layer

[0041] 400: cathode DETAILED DESCRIPTION

[0042] Hereinafter, this specification will be described in more detail.

[0043] 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.

[0044] The term "substituted" 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. When two or more substituents replace, the two or more substituents may be the same as or different from each other.

[0045] In this manual, It means the replaced position.

[0046] In the present specification, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; a C1 to C60 straight or branched alkyl group; a C2 to C60 straight or branched alkenyl group; a C2 to C60 straight or branched alkynyl group; a C3 to C60 monocyclic or polycyclic cycloalkyl group; a C2 to C60 monocyclic or polycyclic heterocycloalkyl group; a C6 to C60 monocyclic or polycyclic aryl group; a C2 to C60 monocyclic or polycyclic heteroaryl group; a silicon group; a phosphine oxide group; and an amino group, or substituted with a substituent connecting two or more substituents selected from the substituents listed above, or unsubstituted.

[0047] In this 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, since deuterium ( 2 H) is an isotope of hydrogen, so some of the hydrogen atoms may be deuterium.

[0048] In one embodiment of the present application, "a situation in which no substituents are indicated in a chemical formula or compound structure" may mean that all positions where substituents may appear may be hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms may be deuterium, which is an isotope. In this context, the deuterium content may be 0% to 100%.

[0049] In one embodiment of the present application, in the case where no substituents are 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.

[0050] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, an element having a deuterium nucleus formed by one proton and one neutron, and can be represented as hydrogen-2, and the element symbol can also be written as D or 2 H.

[0051] 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 number of protons but different numbers of neutrons.

[0052] In one embodiment of the present application, when the total number of substituents that a base 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%.

[0053] In other words, in one instance, The phenyl group represented by 20% deuterium content 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.

[0054]

[0055] In addition, 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.

[0056] In the present specification, halogen may be fluorine, chlorine, bromine or iodine.

[0057] In the present specification, an 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.

[0058] In this specification, alkenyl 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 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, stilbenyl group, styryl and the like, but are not limited thereto.

[0059] 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 in the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0060] In this specification, cycloalkyl includes monocyclic or polycyclic rings having 3 to 60 carbon atoms, and may be further substituted with other substituents. In this article, polycyclic means a group in which a 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 number of carbon groups 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 the like, but are not limited thereto.

[0061] In this specification, heterocycloalkyl includes O, S, Se, N or Si as heteroatoms, including monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be further substituted with other substituents. In this article, polycyclic means a group in which the heterocycloalkyl is directly connected to other cyclic groups or fused to other cyclic groups. In this article, the 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 in the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0062] In this specification, aryl groups include monocyclic or polycyclic rings having 6 to 60 carbon atoms, and may be further substituted with other substituents. In this article, polycyclic means a group in which the aryl group is directly connected to another cyclic group or is fused to another cyclic group. In this article, the other cyclic groups may be aryl groups, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl, and heteroaryl groups. Aryl groups include spirocyclic groups. The number of carbon atoms in the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group may include a phenyl group, a biphenyl group, a triphenyl group (terphenyl), a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a biphenyl group, a phenalenyl group, a pyrenyl group, a fused tetraphenyl group, a fused pentaphenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorene, a spirobifluorene, a 2,3-dihydro-1H-indenyl group, fused rings thereof, and the like, but are not limited thereto.

[0063] In this specification, the terphenyl group can be selected from the following structural formulas.

[0064]

[0065] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0066] When the fluorenyl group is substituted, it may include and similar groups, however, the structure is not limited thereto.

[0067] In this specification, heteroaryl includes O, S, SO2, Se, N or Si as heteroatoms, including monocyclic or polycyclic rings with 2 to 60 carbon atoms, and can be further substituted with other substituents. In this article, polycyclic means a group in which the heteroaryl is directly connected to other cyclic groups or fused with other cyclic groups. In this article, the other cyclic group can be a heteroaryl, but can also be a different type of cyclic group, such as a cycloalkyl, a heterocycloalkyl and an aryl. The number of carbon atoms in the heteroaryl group can be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of heteroaryl can include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl (furazanyl) group), oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxoalkynyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinazolinyl, isoquinazolinyl, quinolizinyl, naphthyridinyl, acridinyl, phenanthridinyl, imidazopyridinyl, diazonaphthyl, triazindenyl, indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothiophenyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenazinyl group), dibenzothioyl, spirobi(dibenzothiole), dihydrophenazinyl, phenoxazinyl, phenanthridyl, imidazopyridyl, thienyl, indole[2,3-a]carbazolyl, indole[2,3-b]carbazolyl, dihydroindole, 10,11-dihydro-dibenzo[b,f]azepine, 9,10-dihydroacridinyl, phenanthrazinyl group, phenathiazinyl, phenazinyl, naphthylidinyl group, phenanthrolinyl group), benzo[c][1,2,5]thiadiazolyl, 5,10-dihydrobenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]dihydroindole, benzofuro[2,3-d]pyrimidinyl, benzothieno[2,3-d]pyrimidinyl, benzofuro[2,3-a]carbazolyl, benzothieno[2,3 -a]carbazolyl, 1,3-dihydroindole[2,3-a]carbazolyl, benzofurano[3,2-a]carbazolyl, benzothieno[3,2-a]carbazolyl, 1,3-dihydroindole[3,2-a]carbazolyl, benzofurano[2,3-b]carbazolyl, benzothieno[2,3-b]carbazolyl, 1,3-dihydroindole[2,3-b]carbazolyl, benzofurano[3,2-b]carbazolyl, benzothieno[3,2-b]carbazolyl, 1,3-dihydroindole[3,2-b]carbazolyl, benzofurano[2,3-c]carbazolyl, benzothieno[2,3-c]carbazolyl, 1,3-dihydroindole[2,3-c]carbazolyl, benzofurano[3,2-c]carbazolyl, benzothieno[3,2-c]carbazolyl, 1,3-dihydroindole[3,2-c]carbazolyl, 1,3-dihydro Indeno[2,1-b]carbazolyl, 5,11-dihydroindeno[1,2-b]carbazolyl, 5,12-dihydroindeno[1,2-c]carbazolyl, 5,8-dihydroindeno[2,1-c]carbazolyl, 7,12-dihydroindeno[1,2-a]carbazolyl, 11,12-dihydroindeno[2,1-a]carbazolyl and similar groups, but not limited thereto.

[0068] In the present specification, substitution with a carbazolyl group includes both carbon of carbazole and N of carbazole bonded to the substitution position.

[0069] In this specification, a silicon group is a substituent including Si, with the Si atom directly attached as a free radical, and is represented by -Si(R101)(R102)(R103). R101 to R103 are the same as or different from each other, and may each independently be a substituent formed from 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 heteroaryl group. Specific examples of the silicon group may include trimethylsilyl, triethylsilyl, tertiary butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like, but are not limited thereto.

[0070] In this specification, a phosphine oxide group is represented by -P(=O)(R104)(R105), and R104 and R105 are the same or different and may each independently be a substituent consisting of 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 heteroaryl group. Specifically, the phosphine oxide group may be substituted with an aryl group, and the examples described above are applicable as the aryl group. Examples of the phosphine oxide group may include, but are not limited to, a dimethylphosphinooxide group, a diphenylphosphinooxide group, a dinaphthylphosphinooxide group, and the like.

[0071] In the present specification, an amino group is represented by -N(R106)(R107), and R106 and R107 are the same or different and may each independently be a substituent consisting of 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 heteroaryl group. The amino group may be selected from the group consisting of -NH2; a monoalkylamino group; a monoarylamino group; a monoheteroarylamino group; a dialkylamino group; a diarylamino group; a diheteroarylamino group; an alkylarylamino group; an alkylheteroarylamino group; and an arylheteroarylamino group. Although not particularly limited thereto, the number of carbon atoms in the amino group is preferably 1 to 30. Specific examples of the amino group may include methylamino, dimethylamino, ethylamino, diethylamino, aniline, naphthylamino, benzidine, dibenzidine, anthracenylamino, 9-methyl-anthridine, diphenylamino, phenylnaphthylamino, dimethylamino, phenyltoluidine, triphenylamino, diphenylnaphthylamino, phenylbenzidine, diphenylfluorenylamino, phenyltriphenylamino, diphenyltriphenylamino, and the like, but are not limited thereto.

[0072] In the present specification, except that the arylene group is a divalent group, the examples of the aryl group described above can be applied to the arylene group.

[0073] In the present specification, except that the heteroaryl group is a divalent group, the examples of the heteroaryl group described above may be applied to the heteroaryl group.

[0074] In the present specification, an "adjacent" group may mean a substituent that replaces an atom directly connected to the atom substituted by the corresponding substituent, a substituent that is spatially closest to the corresponding substituent, or another substituent that replaces the atom substituted by the corresponding substituent. For example, two substituents that replace ortho positions 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.

[0075] As the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle or aromatic heterocycle which adjacent groups may form, structures shown as the cycloalkyl group, aryl group, cycloheteroalkyl group and heteroaryl group described above can be used except those groups which are not monovalent groups.

[0076] One embodiment of the present specification provides a heterocyclic compound represented by Chemical Formula 1.

[0077] In one embodiment of the present specification, L is a direct bond; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0078] In one embodiment of the present specification, L is a direct bond; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0079] In one embodiment of the present specification, L may be a direct bond; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0080] In one embodiment of the present specification, L is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted anthracene group; an unsubstituted or aryl-substituted divalent pyridyl group; an unsubstituted or aryl-substituted divalent pyrimidine group; or an unsubstituted or aryl-substituted divalent triazine group.

[0081] In one embodiment of the present specification, L is a direct bond; a phenylene group; a biphenylene group; an anthracene group; a divalent pyridyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group and a biphenyl group; a divalent pyrimidine group which is unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group and a biphenyl group; or a divalent triazine group which is unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group and a biphenyl group.

[0082] In one embodiment of the present specification, Z may be a substituted or unsubstituted aryl group having 10 to 60 carbon atoms; or a substituted or unsubstituted phosphine oxide group, or represented by the following Chemical Formula 2.

[0083] [Chemical Formula 2]

[0084]

[0085] In Chemical Formula 2,

[0086] X1 to X3 are each CR or N, and at least one of them is N,

[0087] R, R21, and R22 are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and

[0088] Adjacent groups among X1 to X3, R21, and R22 may be bonded to each other to form a substituted or unsubstituted ring.

[0089] In one embodiment of the present specification, Z may be a substituted or unsubstituted aryl group having 10 to 60 carbon atoms; or a substituted or unsubstituted phosphine oxide group.

[0090] In one embodiment of the present specification, Z may be a substituted or unsubstituted aryl group having 10 to 40 carbon atoms; or a substituted or unsubstituted phosphine oxide group.

[0091] In one embodiment of the present specification, Z may be a substituted or unsubstituted aryl group having 10 to 20 carbon atoms; or a substituted or unsubstituted phosphine oxide group.

[0092] In one embodiment of the present specification, Z may be a substituted or unsubstituted aryl group having 10 to 20 carbon atoms; or an unsubstituted or alkyl-substituted phosphine oxide group.

[0093] In one embodiment of the present specification, Z may be a substituted or unsubstituted anthracene group; or an unsubstituted or alkyl-substituted phosphine oxide group.

[0094] In one embodiment of the present specification, Z may be an anthracene group which is unsubstituted or substituted with an aryl group or a phosphine oxide group; or an unsubstituted or substituted phosphine oxide group.

[0095] In one embodiment of the present specification, Z may be an anthracene group which is unsubstituted or substituted with an aryl group or a phosphine oxide group; or an unsubstituted or methyl-substituted phosphine oxide group.

[0096] In one embodiment of the present specification, when Z is a substituted or unsubstituted phosphine oxide group, Z may be represented by -P(=O)(R104)(R105), and R104 and R105 may each independently be hydrogen; deuterium; an alkyl group; or an aryl group.

[0097] In one embodiment of the present specification, Z is represented by -P(=O)(R104)(R105), and R104 and R105 may each independently be an alkyl group.

[0098] In one embodiment of the present specification, Z is represented by -P(=O)(R104)(R105), and R104 and R105 may each independently be an alkyl group having 1 to 10 carbon atoms.

[0099] In another embodiment of the present specification, Z may be represented by Chemical Formula 2.

[0100] In one embodiment of the present specification, Chemical Formula 2 may be represented by the following Chemical Formula 2-A.

[0101] [Chemical Formula 2-A]

[0102]

[0103] In Chemical Formula 2-A,

[0104] Each substituent has the same definition as in Chemical Formula 2.

[0105] In one embodiment of the present specification, one of X1 to X3 in Chemical Formula 2 is N and the rest are CR, and R, R21, and R22 are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and adjacent groups among R in X1 to X3, R21, and R22 may be bonded to each other to form a substituted or unsubstituted ring.

[0106] In one embodiment of the present specification, one of X1 to X3 is N and the rest are CR, and R, R21, and R22 are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, and adjacent groups among R in X1 to X3, R21, and R22 may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0107] In one embodiment of the present specification, one of X1 to X3 is N and the rest are CR, and R, R21, and R22 are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and adjacent groups among R in X1 to X3, R21, and R22 may be bonded to each other to form a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms.

[0108] In one embodiment of the present specification, one of X1 to X3 is N and the rest are CR, and R, R21, and R22 are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and adjacent groups among R in X1 to X3, R21, and R22 may be bonded to each other to form a substituted or unsubstituted aromatic heterocyclic ring having 6 to 60 carbon atoms.

[0109] In one embodiment of the present specification, one of X1 to X3 is N and the others are CR, and R, R21, and R22 are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and adjacent groups among R in X1 to X3, R21, and R22 may be bonded to each other to form a substituted or unsubstituted quinoline ring.

[0110] In one embodiment of the present disclosure, two of X1 to X3 are N and the other is CR, and R, R21, and R22 may each independently be hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0111] In one embodiment of the present specification, X1 to X3 are N, and R21 and R22 may each independently be hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0112] In one embodiment of the present specification, Chemical Formula 2 may be any one selected from the following structural formulas.

[0113]

[0114] In the structural formula, R31 and R32 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and R33 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0115] In one embodiment of the present specification, R31 to R32 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0116] In one embodiment of the present specification, R31 to R32 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.

[0117] In one embodiment of the present specification, R31 to R32 are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0118] In one embodiment of the present specification, R31 to R32 are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0119] In one embodiment of the present specification, R31 and R32 are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted terphenyl group.

[0120] In one embodiment of the present specification, R31 and R32 are each independently a phenyl group which is unsubstituted or substituted with a carbazolyl group, a biphenyl group, or a terphenyl group.

[0121] In one embodiment of the present specification, R33 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0122] In one embodiment of the present specification, R33 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

[0123] In one embodiment of the present specification, R33 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0124] In one embodiment of the present specification, R33 is hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0125] In one embodiment of the present specification, R33 is hydrogen; deuterium; or phenyl.

[0126] In one embodiment of the present specification, R33 is hydrogen; or phenyl.

[0127] In one embodiment of the present specification, Chemical Formula 2 may be any one selected from the following structural formulas.

[0128]

[0129] In the structural formula,

[0130] Each substituent has the same definition as described above.

[0131] In one embodiment of the present specification, R1 to R5 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0132] In one embodiment of the present specification, R1 to R5 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0133] In one embodiment of the present specification, R1 to R3 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0134] In one embodiment of the present specification, R1 to R3 are each independently hydrogen; deuterium; cyano; substituted or unsubstituted methyl; substituted or unsubstituted ethyl; or substituted or unsubstituted phenyl.

[0135] In one embodiment of the present specification, R1 to R3 are each independently hydrogen; deuterium; cyano; methyl; ethyl; or phenyl which is unsubstituted or substituted with cyano.

[0136] In one embodiment of the present specification, at least two of R1 to R3 are each independently a cyano group; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0137] In one embodiment of the present specification, at least two of R1 to R3 are each independently cyano; substituted or unsubstituted methyl; substituted or unsubstituted ethyl; or substituted or unsubstituted phenyl.

[0138] In one embodiment of the present specification, R4 is hydrogen.

[0139] In one embodiment of the present specification, R5 is hydrogen.

[0140] In one embodiment of the present specification, r is an integer from 0 to 3.

[0141] In one embodiment of the present specification, r is an integer from 1 to 3.

[0142] In one embodiment of the present specification, a and b are each an integer from 1 to 5.

[0143] In one embodiment of the present specification, a and b are each an integer from 1 to 3.

[0144] In one embodiment of the present specification, a and b are 1.

[0145] In another embodiment, a and b are 2.

[0146] In another embodiment, a and b are 3.

[0147] In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-4.

[0148] [Chemical Formula 1-1]

[0149]

[0150] [Chemical formula 1-2]

[0151]

[0152] [Chemical formula 1-3]

[0153]

[0154] [Chemical formula 1-4]

[0155]

[0156] In Chemical Formula 1-1 to Chemical Formula 1-4,

[0157] Each substituent has the same definition as in Chemical Formula 1.

[0158] In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2-1 to 2-3.

[0159] [Chemical Formula 2-1]

[0160]

[0161] [Chemical Formula 2-2]

[0162]

[0163] [Chemical formula 2-3]

[0164]

[0165] In Chemical Formula 2-1 to Chemical Formula 2-3,

[0166] R5, L, Z, r, a, and b have the same definitions as in Chemical Formula 1.

[0167] R11 to R13 are each independently a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0168] In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following compounds, but is not limited thereto.

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191] Furthermore, by introducing various substituents into the structure of Chemical Formula 1, compounds having unique properties of the introduced substituents can be synthesized. For example, by introducing substituents commonly used as hole injection layer materials, hole transfer layer materials, light-emitting layer materials, electron transport layer materials, and charge generation layer materials for manufacturing organic light-emitting devices into the core structure, materials that meet the requirements of each organic material layer can be synthesized.

[0192] In addition, by introducing various substituents into the structure of Chemical Formula 1, the energy band gap can be finely controlled, and at the same time, characteristics at the interface between organic materials are enhanced, and material applications can become diversified.

[0193] One embodiment of the present disclosure provides an organic light-emitting component, comprising: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer comprise one or more types of heterocyclic compounds represented by Chemical Formula 1.

[0194] In one embodiment of the present specification, one or more layers of the organic material layer include one type of heterocyclic compound represented by Chemical Formula 1.

[0195] In one embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

[0196] In another embodiment of the present specification, the first electrode may be a cathode, and the second electrode may be an anode.

[0197] In one embodiment of the present specification, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the blue organic light-emitting device. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in an electron transport layer or a hole blocking layer of the blue organic light-emitting device.

[0198] In one embodiment of the present specification, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the green organic light-emitting device. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in an electron transport layer or a hole blocking layer of the green organic light-emitting device.

[0199] In one embodiment of the present specification, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the red organic light-emitting device. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in an electron transport layer or a hole blocking layer of the red organic light-emitting device.

[0200] In addition to using the heterocyclic compound described above to form one or more organic material layers, the organic light-emitting device of this specification can be manufactured using commonly used organic light-emitting device manufacturing methods and materials.

[0201] When manufacturing an organic light-emitting device, the heterocyclic compound can be formed into an organic material layer via solution coating and vacuum deposition. In this article, solution coating refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating and the like, but is not limited thereto.

[0202] The organic material layer of the organic light-emitting device of the present disclosure may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic material layers are laminated. For example, the organic light-emitting device of the present disclosure may have a structure including a hole injection layer, a hole transport 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 device is not limited thereto and may include a small number of organic material layers.

[0203] In the organic light-emitting device of the present specification, the organic material layer includes an electron transport layer, and the electron transport layer may include the heterocyclic compound represented by Chemical Formula 1.

[0204] In the organic light-emitting device of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer may include the heterocyclic compound represented by Chemical Formula 1.

[0205] The organic light-emitting device of the present disclosure may further include one, two, or more than two 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, and a hole blocking layer.

[0206] Figures 1 to 5 The lamination sequence of electrodes and organic material layers of an organic light-emitting device according to one embodiment of the present invention is shown. However, the scope of the present invention is not limited to these figures, and structures of organic light-emitting devices known in the art can also be used in the present invention.

[0207] 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 this 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.

[0208] Figure 3 and Figure 4 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, an electron transport layer 305 and an electron injection layer 306, and according to Figure 4 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 this laminated structure, and if necessary, layers other than the light-emitting layer may not be included, and other required functional layers may be further added.

[0209] The organic material layer including the heterocyclic compound represented by Chemical Formula 1 may further include other materials as needed.

[0210] In addition, an organic light-emitting component according to one embodiment of the present specification includes an anode, a cathode, and two stacks disposed between two or more anodes and cathodes, wherein the two or more stacks each independently include a light-emitting layer, a charge generation layer is included between the two or more stacks, and the charge generation layer includes a heterocyclic compound represented by Chemical Formula 1.

[0211] In addition, an organic light-emitting device according to one embodiment of the present invention includes: an anode; a first stack disposed on the anode and including a first light-emitting layer; a charge generation layer disposed on the first stack; a second stack disposed on the charge generation layer and including a second light-emitting layer; and a cathode disposed on the second stack. In this context, the charge generation layer may include a heterocyclic compound represented by Chemical Formula 1.

[0212] An organic light-emitting component according to one embodiment of the present specification includes: a first electrode; a first stack disposed on the first electrode and including a first light-emitting layer; a charge generation layer disposed on the first stack; a second stack disposed on the charge generation layer and including a second light-emitting layer; and a second electrode disposed on the second stack, wherein the charge generation layer may include a heterocyclic compound represented by Chemical Formula 1.

[0213] An organic light-emitting component according to one embodiment of the present specification includes a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer includes two or more stacks, and the two or more stacks each independently include a light-emitting layer, a charge generation layer is included between the two or more stacks, and the charge generation layer may include a heterocyclic compound represented by Chemical Formula 1.

[0214] An organic light-emitting component according to one embodiment of the present specification includes a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer includes: a first stack including a first light-emitting layer; a charge generation layer disposed on the first stack; and a second stack disposed on the charge generation layer and including a second light-emitting layer, and the charge generation layer may include a heterocyclic compound represented by Chemical Formula 1.

[0215] In an organic light-emitting device according to one embodiment of the present disclosure, the charge generation layer includes an N-type charge generation layer, and the N-type charge generation layer includes the heterocyclic compound represented by Chemical Formula 1.

[0216] In the organic light-emitting device according to one embodiment of the present disclosure, the charge generation layer may further include a P-type charge generation layer.

[0217] As an organic light-emitting component according to one embodiment of the present specification, Figure 5 An organic light emitting device having a 2-stack tandem structure is shown in FIG. Figure 5 The organic light-emitting component includes a first hole injection layer 401, a first hole transport layer 402, a first electron blocking layer 403, a first stacked light-emitting layer 404, a first hole blocking layer 405, a first electron transport layer 406, an N-type charge generation layer 407, a P-type charge generation layer 408, a second hole injection layer 409, a second hole transport layer 410, a second electron blocking layer 411, a second stacked light-emitting layer 412, a second hole blocking layer 413, a second electron transport layer 414, and an electron injection layer 415.

[0218] In some cases, the Figure 5 The first electron blocking layer, the first hole blocking layer, the second hole blocking layer and the like are included in the embodiment of the present invention.

[0219] In an organic light-emitting device according to one embodiment of the present specification, materials other than the heterocyclic compound represented by 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.

[0220] A material having a relatively large work function can be used as the anode material, and a transparent conductive oxide, metal, conductive polymer, or similar material can be used as the anode material. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, and the like, but are not limited thereto.

[0221] A material having a relatively small work function can be used as the cathode material, and metals, metal oxides, conductive polymers, or similar materials can be used as the cathode material. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, and similar materials, but are not limited thereto.

[0222] Known hole injection materials can be used as the hole injection material, and for example, the following can be used: copper phthalocyanine compounds such as the copper phthalocyanine disclosed in U.S. Patent 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 Materials, 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.

[0223] As the hole transport material, pyrazoline derivatives, aromatic amine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like can be used, and low molecular weight materials or high molecular weight materials can also be used.

[0224] 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, diphenyldicyanide and its derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and its derivatives, and the like can be used. Polymer materials and low molecular weight materials can also be used as electron transport materials.

[0225] As an example of the electron injection material, LiF is generally used in the art, however, the present application is not limited thereto.

[0226] Materials that emit red, green, or blue light can be used as luminescent materials, and two or more luminescent materials can be mixed and used as needed. Here, two or more luminescent materials can be used by depositing them as separate supply sources or by premixing and depositing them as a single supply source. Furthermore, fluorescent materials can also be used as luminescent materials, but phosphorescent materials can also be used. As luminescent materials, materials that emit light by combining electrons and holes injected from the anode and cathode, respectively, can be used alone, but materials comprising a host material and a dopant material that contribute to light emission can also be used.

[0227] When mixing the light-emitting material host, the same series of hosts can be mixed, or hosts of different series can be mixed. For example, any two or more types of N-type host materials or P-type host materials can be selected and used as the host material of the light-emitting layer.

[0228] Depending on the materials used, the organic light-emitting device according to one embodiment of the present disclosure may be a top emission type, a bottom emission type, or a dual emission type.

[0229] The compound according to one embodiment of the present specification 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.

[0230] Hereinafter, this 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.

[0231] [Preparation Example 1] Preparation of Compound 9

[0232]

[0233] 1) Preparation of compound 9-1

[0234] After triethylamine (1000 ml) was introduced into 2-bromo-3-chlorobenzaldehyde (A) (100 g, 0.45 mol, 1 equivalent), ethynylbenzene (51.2 g, 0.50 mol, 1.1 equivalent), Pd(PPh 3 ) 2 Cl 2 (dichlorobis(triphenylphosphine)palladium(0)) (6.4 g, 0.009 mol, 0.02 equivalent) and CuI (0.86 g, 0.0045 mol, 0.01 equivalent), the mixture was stirred at 60° C. for 5 hours. The reaction was terminated by introducing water therein, and the resultant was extracted with dichloromethane (MC) and water. Thereafter, water was removed with anhydrous Na 2 CO 3 . The resultant was separated using a silica gel column to obtain compound 9-1 (85 g) with a yield of 77%.

[0235] 2) Preparation of compound 9-2

[0236] After compound 9-1 (170 g, 0.70 mol, 1 eq) and TsNHNH2 (p-toluenesulfonyl hydrazide) (144 g, 0.77 mol, 1.1 eq) were introduced into ethanol (EtOH) (3400 ml), the mixture was stirred at room temperature (RT) for 1 hour. The resulting solid was filtered and dried to obtain compound 9-2 (174 g) with a yield of 60%.

[0237] 3) Preparation of compound 9-3

[0238] After compound 9-2 (40 g, 0.097 mol, 1 eq) and AgOTf (silver trifluoromethanesulfonate) (3.8 g, 0.014 mol, 0.15 eq) were introduced into EtOH (800 ml), the mixture was stirred at 70°C for 2 hours. 1,2-Diphenylethanone (38.4 g, 0.19 mol, 2 eq) and K 3 PO 4 (62.3 g, 0.29 mol, 3 eq) were introduced thereto, and the resultant was stirred at 70°C for 7 hours. The reaction was terminated by the introduction of water, and the resultant was extracted with MC and water. Thereafter, the water was removed with anhydrous Na 2 CO 3 . The resultant was separated using a silica gel column to obtain compound 9-3 (62 g) in a 34% yield.

[0239] 4) Preparation of compound 9-4

[0240] Compound 9-3 (10 g, 0.023 mol, 1 equivalent), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (5.9 g, 0.035 mol, 1.5 equivalents), KOAc (potassium acetate) (6.8 g, 0.069 mol, 3 equivalents), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0)) (1.3 g, 0.0023 mol, 0.1 equivalent), and Xphos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) (2.2 g, 0.0046 mol, 0.2 equivalent) were added to 1,4-dioxane (100 ml) and stirred at 80° C. for 6 hours. The reaction was terminated by adding water, and the resultant was extracted with MC and water. Thereafter, water was removed with anhydrous Na 2 CO 3 . The resultant was separated using a silica gel column to obtain compound 9-4 (9 g) with a yield of 74%.

[0241] 5) Preparation of compound 9

[0242] Compound 9-4 (10 g, 0.019 mol, 1 eq), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (C) (7.4 g, 0.019 mol, 1 eq), K 3 PO 4 (8.1 g, 0.038 mol, 2 eq), and Pd(PPh 3 ) 4 (tetrakis(triphenylphosphine)palladium(0)) (11.1 g, 0.0009 mol, 0.05 eq) were added to 1,4-dioxane (100 ml) and H 2 O (25 ml), and the mixture was stirred at 80° C. for 6 hours. The resulting solid was filtered and dried to obtain compound 9 (11 g) with a yield of 81%.

[0243] The compounds were synthesized in the same manner as in Preparation Example 1, except that Intermediate A in Table 1 below was used instead of 2-bromo-3-chlorobenzaldehyde (A), Intermediate B in Table 1 below was used instead of 1,2-diphenylethanone (B), and Intermediate C in Table 1 below was used instead of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (C).

[0244] [Table 1]

[0245]

[0246]

[0247]

[0248]

[0249] The compounds were prepared in the same manner as in the Preparation Example, and the synthesis identification results are shown in Tables 2 and 3. Table 2 shows 1 Table 3 shows the measured values ​​of H NMR (CDCl 3 , 200 MHz), and Table 3 shows the measured values ​​of FD-mass spectrometry (FD-MS: field desorption mass spectrometry).

[0250] [Table 2]

[0251]

[0252] [Table 3]

[0253]

[0254] [Experimental Example]

[0255] <Experimental Example 1>

[0256] 1) Manufacturing Organic Light-Emitting Components - Comparative Example 1

[0257] A transparent indium tin oxide (ITO) electrode film obtained from glass used for OLEDs (manufactured by Samsung-Corning Co., Ltd.) was ultrasonically cleaned using trichloroethylene, acetone, ethanol, and distilled water for 5 minutes each, then stored in isopropyl alcohol and used. The ITO substrate was then mounted in a substrate holder of a vacuum deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)anilino)triphenylamine (2-TNATA) was introduced into a chamber within the vacuum deposition apparatus.

[0258]

[0259] Then, the chamber was evacuated until the vacuum level reached 10 -6, and then, by applying a current to the chamber, 2-TNATA was evaporated to deposit a 600 angstrom thick hole injection layer on the ITO substrate. The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was introduced into another chamber of the vacuum deposition apparatus and evaporated by applying a current to the chamber to deposit a 300 angstrom thick hole transport layer on the hole injection layer.

[0260]

[0261] After forming the hole injection layer and hole transport layer as described above, a blue-light-emitting material having the following structure was deposited thereon as the light-emitting layer. Specifically, in a side chamber of a vacuum deposition apparatus, H1 (a blue-light-emitting host material) was vacuum-deposited to a thickness of 200 angstroms, and D1 (a blue-light-emitting dopant material) was vacuum-deposited thereon at a concentration of 5% relative to the host material.

[0262]

[0263] Subsequently, a compound of the following structural formula E1 was deposited to a thickness of 300 angstroms as an electron transport layer.

[0264]

[0265] As an electron injection layer, lithium fluoride (LiF) was deposited to a thickness of 10 angstroms, and an Al cathode was used to a thickness of 1,000 angstroms, and thus an OLED was manufactured.

[0266] At the same time, in 10 -8 Support up to 10 -6 All organic compounds required for the manufacture of OLEDs are purified under vacuum by sublimation of the materials used in OLED manufacturing.

[0267] -Examples 1 to 23 and Comparative Examples 2 to 5

[0268] An organic electroluminescent element was manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 4 were used instead of E1 used in forming the electron transport layer.

[0269] 2) Evaluation of organic light-emitting components

[0270] The driving voltage, luminous efficiency, color coordinates (CIE), and service life of the blue organic light emitting device manufactured according to the present disclosure are measured and shown in Table 4 below.

[0271] [Table 4]

[0272]

[0273] As shown in Table 4, compared with Comparative Examples 1 to 5, the organic light-emitting device using the electron transport layer material of the blue organic light-emitting device of the present disclosure has a lower driving voltage and significantly improved luminous efficiency and service life.

[0274] This result is believed to be due to the fact that when a compound having appropriate length, strength, and flatness is used as an electron transport layer, the compound is produced in an excited state by receiving electrons under specific conditions. Specifically, when an excited state is formed in the hetero-skeleton site of the compound, the excitation energy will move to a stable state before the excited hetero-skeleton site undergoes other reactions. Therefore, the relatively stable compound can efficiently transport electrons without decomposing or destroying the compound. For reference, those compounds that are stable when excited are considered to be aryl or acene compounds or polycyclic hetero compounds.

[0275] Therefore, it is believed that the compounds of the present disclosure bring about excellent performance in all embodiments of driving, efficiency, and service life through enhanced electron transport properties or improved stability.

[0276] <Experimental Example 2>

[0277] 1) Manufacturing of organic light-emitting components

[0278] -Comparative Example 6

[0279] A transparent indium tin oxide (ITO) electrode film obtained from OLED glass (manufactured by Samsung Corning Co., Ltd.) was ultrasonically cleaned using trichloroethylene, acetone, ethanol, and distilled water for 5 minutes each, then stored in isopropyl alcohol and used. The ITO substrate was then mounted in a substrate holder of a vacuum deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)phenylamino)triphenylamine (2-TNATA) was introduced into a chamber within the vacuum deposition apparatus.

[0280]

[0281] Then, the chamber was evacuated until the vacuum level reached 10 -6 , and then, by applying a current to the chamber, 2-TNATA was evaporated to deposit a 600 angstrom thick hole injection layer on the ITO substrate. The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was introduced into another chamber of the vacuum deposition apparatus and evaporated by applying a current to the chamber to deposit a 300 angstrom thick hole transport layer on the hole injection layer.

[0282]

[0283] After forming the hole injection layer and hole transport layer as described above, a blue-light-emitting material having the following structure was deposited thereon as the light-emitting layer. Specifically, in a side chamber of a vacuum deposition apparatus, H1 (a blue-light-emitting host material) was vacuum-deposited to a thickness of 200 angstroms, and D1 (a blue-light-emitting dopant material) was vacuum-deposited thereon at a concentration of 5% relative to the host material.

[0284]

[0285] Subsequently, a compound of the following structural formula E1 was deposited to a thickness of 300 angstroms as an electron transport layer.

[0286]

[0287] As an electron injection layer, lithium fluoride (LiF) was deposited with a thickness of 10 angstroms, and an Al cathode with a thickness of 1,000 angstroms was used, and thus an OLED was manufactured. -8 Support up to 10 -6 All organic compounds required for the manufacture of OLEDs are purified under vacuum by sublimation of the materials used in OLED manufacturing.

[0288] -Examples 24 to 46 and Comparative Examples 7 to 10

[0289] An organic electroluminescent device was manufactured in the same manner as in Comparative Example 6, except that after forming the electron transport layer E1 with a thickness of 250 angstroms, a hole blocking layer with a thickness of 50 angstroms was formed on the electron transport layer using the compound shown in Table 5.

[0290] 2) Evaluation of organic light-emitting components

[0291] The driving voltage, luminous efficiency, color coordinates (CIE), and service life of the blue organic light emitting device manufactured according to the present disclosure are measured and shown in Table 5 below.

[0292] [Table 5]

[0293]

[0294] As can be seen from the results in Table 5, compared with Comparative Examples 6 to 10, the organic light-emitting device using the hole blocking layer material of the blue organic light-emitting device of the present disclosure has a lower driving voltage and significantly improved luminous efficiency and service life.

[0295] This result is believed to be due to the fact that when holes pass through the electron transport layer and reach the anode without being combined in the light-emitting layer, the efficiency and lifespan of the OLED are reduced. When a compound with a deep HOMO level is used as a hole-blocking layer to prevent this phenomenon, the holes that attempt to pass through the light-emitting layer and reach the cathode are blocked by the energy barrier of the hole-blocking layer.

[0296] Therefore, it is believed that the probability of holes and electrons forming excitons increases, and the possibility of emitting light in the light-emitting layer increases, and the compounds of the present disclosure bring excellent performance in all embodiments of driving, efficiency, and service life.

[0297] <Experimental Example 3>

[0298] 1) Manufacturing of organic light-emitting components

[0299] - Examples 47 to 69 and Comparative Examples 11 to 15

[0300] A 1,500-angstrom-thick glass substrate coated with an ITO thin film was ultrasonically cleaned with distilled water. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO in a UV cleaner for 5 minutes. The substrate was then transferred to a plasma cleaner (PT) and subjected to vacuum plasma treatment to enhance the ITO work function and remove residual film. The substrate was then transferred to a thermal deposition system for organic deposition.

[0301] On a transparent ITO electrode (anode), organic materials are formed in a 2-stack white organic light emitting device (WOLED) structure. For the first stack, TAPC is first thermally vacuum deposited to a thickness of 300 angstroms to form a hole transport layer. After the hole transport layer is formed, the light-emitting layer is thermally vacuum deposited thereon as follows. As the light-emitting layer, TCz1 (host) is doped with 8% of the blue phosphorescent dopant FIrpic and deposited to 300 angstroms. After forming a 400 angstrom electron transport layer using TmPyPB, the compounds described in Table 6 below are doped with 20% Cs2CO3 to form a 100 angstrom charge generation layer.

[0302] For the second stack, a hole injection layer is first formed by thermal vacuum depositing MoO3 to a thickness of 50 angstroms. A hole transport layer (common layer) is formed by doping TAPC with 20% MoO3 to 100 angstroms and depositing TAPC to 300 angstroms. A light-emitting layer is formed thereon by doping TCz1 (host) with 8% green phosphorescent dopant Ir(ppy)3 and depositing the resultant to 300 angstroms, and then a 600 angstrom electron transport layer is formed using TmPyPB. Finally, an electron injection layer is formed on the electron transport layer by depositing lithium fluoride (LiF) to a thickness of 10 angstroms, and then a cathode is formed on the electron injection layer by depositing an aluminum (Al) cathode to a thickness of 1,200 angstroms, thereby manufacturing an organic light-emitting component.

[0303] At the same time, in 10 -8 Support up to 10 -6 All organic compounds required for OLED manufacturing are purified by vacuum sublimation under the support for each material used in OLED manufacturing.

[0304]

[0305] 2) Driving voltage and luminous efficiency of organic light-emitting components

[0306] For each of the organic light-emitting devices manufactured as above, electroluminescence (EL) characteristics were measured using an M7000 manufactured by McScience Inc., and using the measurement results, T was measured using a service life measurement system (M6000) manufactured by McScience Inc. when the standard brightness was 3,500 cd / m². 95 The driving voltage, luminous efficiency, external quantum efficiency, and color coordinates (CIE) of the white organic light-emitting device manufactured according to the present disclosure are measured and shown in Table 6.

[0307] [Table 6]

[0308]

[0309] As can be seen from the results in Table 6, compared to Comparative Examples 11 to 15, the organic light-emitting device using the charge generation layer material of the 2-stack white organic light-emitting device of the present disclosure has a lower driving voltage and improved luminous efficiency.

[0310] This result is believed to be due to the fact that the compounds of the present disclosure, which are used as an N-type charge generation layer formed of the disclosed compounds having appropriate length, strength, and flatness, and an appropriate hetero compound capable of bonding to a metal, form an energy gap state in the N-type charge generation layer by doping it with an alkali metal or alkaline earth metal. Electrons generated by the P-type charge generation layer are easily injected into the electron transport layer through the energy gap state created in the N-type charge generation layer. As a result, the P-type charge generation layer can advantageously inject and transport electrons to the N-type charge generation layer, thereby reducing the driving voltage and improving the efficiency and lifespan of the organic light-emitting device.

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical formula 1] in, In Chemical Formula 1, R1 to R3 are each independently hydrogen; deuterium; cyano; unsubstituted or deuterium-substituted methyl; unsubstituted or deuterium-substituted ethyl; unsubstituted or deuterium-substituted phenyl; or unsubstituted or deuterium-substituted biphenyl; R4 and R5 are each independently hydrogen; or deuterium; L is a direct bond; unsubstituted or deuterium-substituted phenylene; or unsubstituted or deuterium-substituted biphenylene; and Z is represented by any of the following structural formulas; In the structural formula, R31 and R32 are each independently an unsubstituted or carbazolyl-substituted phenyl group; an unsubstituted or carbazolyl-substituted biphenyl group; or an unsubstituted or carbazolyl-substituted terphenyl group; R33 is hydrogen; deuterium; or unsubstituted or deuterium-substituted phenyl; r is an integer from 0 to 3; a and b are each an integer from 1 to 5; and When r, a and b are each 2 or more, the substituents in the brackets are the same as or different from each other.

2. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] In Chemical Formula 1-1 to Chemical Formula 1-4, Each substituent has the same definition as in Chemical Formula 1.

3. The heterocyclic compound according to claim 1, wherein at least two of R1 to R3 are each independently cyano; unsubstituted or deuterated methyl; unsubstituted or deuterated ethyl; unsubstituted or deuterated phenyl; or unsubstituted or deuterated biphenyl.

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

5. An organic light-emitting component, comprising: a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode, The organic material layer comprises one or more types of the heterocyclic compound according to any one of claims 1 to 4. 6 . The organic light-emitting device according to claim 5 , wherein the organic material layer comprises an electron transport layer, and the electron transport layer comprises the heterocyclic compound. 7 . The organic light-emitting device according to claim 5 , wherein the organic material layer comprises a hole blocking layer, and the hole blocking layer comprises the heterocyclic compound.

8. The organic light emitting device according to claim 5, further comprising a layer 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 and a hole blocking layer.

9. The organic light emitting component according to claim 5, comprising: A first stack, disposed on the first electrode and comprising a first light-emitting layer; a charge generation layer disposed on the first stack; and A second stack is disposed on the charge generating layer and includes a second light emitting layer, The second electrode is disposed on the second stack. 10 . The organic light emitting device according to claim 9 , wherein the charge generation layer comprises the heterocyclic compound. 11 . The organic light emitting device according to claim 10 , wherein the charge generation layer comprises an N-type charge generation layer, and the N-type charge generation layer comprises the heterocyclic compound.

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