Heterocyclic Compounds and Organic Light-Emitting Components Using the Same

Abstract

The present application provides a heterocyclic compound capable of significantly improving the lifespan, efficiency, electrochemical stability, and thermal stability of an organic light-emitting component, as well as an organic light-emitting component comprising the heterocyclic compound in an organic material layer.

Description

Technical Field

[0001] This application claims priority and the benefit of Korean Patent Application No. 10-2020-0078425, filed on Jun. 26, 2020, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

[0002] This application relates to a heterocyclic compound and an organic light-emitting device using the same. Background Art

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

[0004] An 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 such a structure, electrons and holes injected from the two electrodes are combined into pairs in the organic thin film, and light is emitted when the electrons and holes annihilate. The organic thin film may be formed as a single layer or multiple layers as needed.

[0005] The material of the organic thin film may have a light-emitting function as needed. For example, as the material of the organic thin film, a compound capable of forming a light-emitting layer alone by itself may be used, or a compound capable of acting as a host or a dopant of a host-dopant-based light-emitting layer may also be used. In addition, a compound capable of acting as a hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, etc. may also be used as the material of the organic thin film.

[0006] In order to enhance the efficiency, lifespan, or efficiency of the organic light-emitting device, there has been a continuous need to develop organic thin film materials.

[0007] [Patent Document]

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

[0009] Technical Problem

[0010] The present disclosure relates to providing a heterocyclic compound and an organic light-emitting device using the same.

[0011] Technical Solution

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

[0013] [Chemical Formula 1]

[0014]

[0015] In Chemical Formula 1,

[0016] R a is a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms,

[0017] R b is 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,

[0018] When R a is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, only one of R1, R2, and R4 to R7 is ―(La)p―A, and the remaining ones among R1 to R7 are the same as or different from each other and are each independently selected from the group consisting of 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; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0019] When R a is a halogen group; a cyano group; or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, only one of R1 to R7 is ―(La)p―A, and the remaining ones among R1 to R7 are the same as or different from each other and are each independently selected from the group consisting of 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; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0020] La is 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, p is an integer from 0 to 3, and when p is 2 or greater than 2, Las are the same as or different from each other,

[0021] A is a substituted or unsubstituted amino group, and

[0022] m is an integer from 0 to 8, and when m is 2 or greater than 2, R b are the same as or different from each other.

[0023] Another embodiment of the present application provides an organic light-emitting component, which includes: an anode; a cathode; and one or more organic material layers disposed between the anode and the cathode, wherein one or more of the organic material layers contain the heterocyclic compound represented by Chemical Formula 1.

[0024] Advantageous effects

[0025] A heterocyclic compound according to an embodiment of the present application can be used as a material for an organic material layer of an organic light-emitting device. The heterocyclic compound can be used as a material for a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a charge generation layer, and similar layers in an organic light-emitting device. Specifically, the heterocyclic compound represented by Chemical Formula 1 can be used as a material for the light-emitting layer of an organic light-emitting device. In addition, using the heterocyclic compound represented by Chemical Formula 1 in an organic light-emitting device can reduce the driving voltage of the device, enhance the light efficiency, and enhance the lifetime properties of the device through the thermal stability of the compound. BRIEF DESCRIPTION OF THE DRAWINGS

[0026] Figures 1 to 3 are diagrams each schematically showing a stacked structure of an organic light-emitting device according to an embodiment of the present application.

[0027] DESCRIPTION OF REFERENCE NUMERALS IN THE DRAWINGS

[0028] 100: Substrate

[0029] 200: Anode

[0030] 300: Organic material layer

[0031] 301: Hole injection layer

[0032] 302: Hole transport layer

[0033] 303: Light-emitting layer

[0034] 304: Hole blocking layer

[0035] 305: Electron transport layer

[0036] 306: Electron injection layer

[0037] 400: Cathode DETAILED DESCRIPTION

[0038] Hereinafter, the present application will be described in detail.

[0039] An embodiment of the present application provides a heterocyclic compound represented by the following Chemical Formula 1.

[0040] [Chemical Formula 1]

[0041]

[0042] In Chemical Formula 1,

[0043] R a is a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms,

[0044] R b is 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,

[0045] When R a is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, only one of R1, R2, and R4 to R7 is ―(La)p―A, and the rest of R1 to R7 are the same as or different from each other, and each independently is selected from the group consisting of 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; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0046] When R a is a halogen group; a cyano group; or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, only one of R1 to R7 is ―(La)p―A, and the rest of R1 to R7 are the same as or different from each other, and each independently is selected from the group consisting of 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; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0047] La is 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, p is an integer from 0 to 3, and when p is 2 or greater than 2, Las are the same as or different from each other,

[0048] A is a substituted or unsubstituted amino group, and

[0049] m is an integer from 0 to 8, and when m is 2 or greater than 2, R b are the same as or different from each other.

[0050] In the compound represented by Chemical Formula 1 having a specific substituent including a dibenzofuranyl group on fluorene, the π-π stacking of the aromatic ring is inhibited, and by having a dibenzofuranyl group having an amino group with hole properties as a substituent, a wide band gap and stability are obtained by having excellent hole transport properties. Therefore, using the compound represented by Chemical Formula 1 in an organic light-emitting device effectively reduces the driving voltage, and excellent efficiency and lifetime properties are obtained in the organic light-emitting device.

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

[0052] In this specification, "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of: deuterium; a halogen group; a cyano group; 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; -SiRR'R"; -P(=O)RR'; an alkylamine having 1 to 20 carbon atoms; a monocyclic or polycyclic arylamine having 6 to 60 carbon atoms; and a monocyclic or polycyclic heteroarylamine having 2 to 60 carbon atoms, or unsubstituted, or substituted by a substituent connecting two or more substituents selected from the substituents shown above, or unsubstituted, and R, R' and R" are the same as or different from each other, and each independently is hydrogen; deuterium; a halogen; 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.

[0053] In this specification, "the case where no substituent is specified in the 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, some hydrogen atoms may be deuterium.

[0054] In one embodiment of the present application, "the case where no substituent is specified in the chemical formula or compound structure" may mean that all positions that can be substituents can be hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms can be deuterium as an isotope, and herein, the content of deuterium can be 0% to 100%.

[0055] In one embodiment of the present application, in the case of "no substituent is specified in the chemical formula or compound structure", when deuterium is not explicitly excluded, hydrogen and deuterium can be mixed in the compound, for example, the deuterium content is 0% and the hydrogen content is 100%, or all substituents are hydrogen.

[0056] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, an element having deuterium formed by one proton and one neutron as its nucleus, and can be expressed as hydrogen-2, and the element symbol can also be written as D or 2 H.

[0057] In one embodiment of the present application, an isotope means an atom having the same atomic number (Z) but different mass numbers (A), and can also be interpreted as an element having the same number of protons but different numbers of neutrons.

[0058] In one embodiment of the present application, when the total number of substituents that a base compound can have is defined as T1, and the number of a specific substituent is defined as T2, the meaning of the content T% of the specific substituent can be defined as T2 / T1×100 = T%.

[0059] In other words, in one example, in a phenyl group represented by having a deuterium content of 20% means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and the number of deuteriums is 1 (T2 in the formula). In other words, a phenyl group having a deuterium content of 20% can be represented by the following structural formula.

[0060]

[0061] In addition, in one embodiment of the present application, "a phenyl group with a deuterium content of 0%" may mean a phenyl group that does not contain deuterium atoms, that is, a phenyl group having 5 hydrogen atoms.

[0062] In this specification, a halogen may be fluorine, chlorine, bromine or iodine.

[0063] In this specification, an alkyl group includes a straight-chain or branched-chain alkyl group 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 thereof may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-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, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto.

[0064] In this specification, alkenyl includes straight-chain or branched alkenyl having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkenyl may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples thereof 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-phenylethenyl-1-yl, 2-phenylethenyl-1-yl, 2,2-diphenylethenyl-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethenyl-1-yl, 2,2-bis(diphenyl-1-yl)ethenyl-1-yl, stilbenyl group, styryl, etc., but are not limited thereto.

[0065] In this specification, alkynyl includes straight-chain or branched alkynyl having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkynyl may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0066] In this specification, alkoxy may be straight-chain, branched-chain or cyclic. The number of carbon atoms in the alkoxy is not particularly limited, but is preferably 1 to 20. Specific examples thereof may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but are not limited thereto.

[0067] In this specification, cycloalkyl includes monocyclic or polycyclic cycloalkyl having 3 to 60 carbon atoms, and may be further substituted with other substituents. Herein, polycyclic means a group in which cycloalkyl is directly connected or fused with other cyclic groups. Herein, other cyclic groups may be cycloalkyl, but may also be different types of cyclic groups, such as heterocycloalkyl, aryl and heteroaryl. The number of carbon groups in the cycloalkyl may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0068] In this specification, heterocycloalkyl includes O, S, Se, N, or Si as a heteroatom, includes monocyclic or polycyclic heterocycloalkyl having 2 to 60 carbon atoms, and may be further substituted with other substituents. Herein, polycyclic means a group in which the heterocycloalkyl is directly linked or fused to other cyclic groups. Herein, the other cyclic group may be heterocycloalkyl, but may also be a different type of cyclic group, such as cycloalkyl, aryl, and heteroaryl. The number of carbon atoms of the heterocycloalkyl may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0069] In this specification, aryl includes monocyclic or polycyclic aryl having 6 to 60 carbon atoms, and may be further substituted with other substituents. Herein, polycyclic means a group in which the aryl is directly linked or fused to other cyclic groups. Herein, the other cyclic group may be aryl, but may also be a different type of cyclic group, such as cycloalkyl, heterocycloalkyl, and heteroaryl. Aryl includes spiro 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 aryl may include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, -yl, phenanthryl, perylenyl, fluoranthenyl, triphenylenyl, picenyl, pyrenyl, condensed tetraphenyl, condensed pentaphenyl, fluorenyl, indenyl, acenaphthylenyl, benzoindenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, its fused ring groups, etc., but are not limited thereto.

[0070] In this specification, the phosphine oxide group is represented by -P(=O)R101R102, and R101 and R102 are the same or different from each other, and may each independently be a substituent formed from at least one of 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 group may include diphenylphosphine oxide group, dinaphthylphosphine oxide group, and the like, but are not limited thereto.

[0071] In this specification, silyl is a substituent containing Si and directly linked with an Si atom as a radical, and is represented by -SiR104R105R106. R104 to R106 are the same or different from each other, and may each independently be a substituent formed from at least one of 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 silyl may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0072] In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0073] In the present specification, a spiro group is a group including a spiro structure and may have 15 to 60 carbon atoms. For example, the spiro group may include a structure in which 2,3-dihydro-1H-indenyl or cyclohexyl is spiro-bonded to a fluorenyl group. Specifically, the spiro group may include any of the groups having the following structural formulas.

[0074]

[0075] In the present specification, a heteroaryl group includes S, O, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms, and may be further substituted with other substituents. Herein, polycyclic means a group in which a heteroaryl group is directly connected or fused to another cyclic group. Herein, the other cyclic group may be a heteroaryl group, but may also be a different type of cyclic group, such as a cycloalkyl group, a heterocycloalkyl group, and an aryl group. The number of carbon atoms of the heteroaryl group 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, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, isoquinazolinyl, quinazolinyl, naphthyridinyl, acridinyl, phenanthridinyl, imidazopyridyl, phthalazinyl, triazaindenyl, indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuryl, dibenzothienyl, dibenzofuryl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, dibenzosilole group, spirobis(dibenzosilole group), dihydro phenoxazinyl, phenoxazinyl, phenanthridinyl, imidazopyridyl, thienyl, indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, indolinyl, 10,11-dihydro-dibenzo[b,f]azepinyl, 9,10-dihydroacridinyl, phenothiazinyl, phthalazinyl, naphthyridinyl, phenoxazinyl, 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]dihydroindolyl, 5,11-dihydroindeno[1,2-b]carbazolyl, and the like, but are not limited thereto.

[0076] In this specification, the amino group may be selected from the group consisting of monoalkylamino; monoarylamino; monoheteroarylamino; -NH2; dialkylamino; diarylamino; diheteroarylamino; alkylarylamino; alkylheteroarylamino; and arylheteroarylamino, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 30. Specific examples of the amino group may include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, dibiphenylamino, anthrylamino, 9-methyl-anthrylamino, diphenylamino, phenylnaphthylamino, xylanylamino, phenyltolylamino, triphenylamino, biphenylnaphthylamino, phenylbiphenylamino, biphenylfluorenylamino, phenyltriphenylenylamino, biphenyltriphenylenylamino and similar groups, but not limited thereto.

[0077] In this specification, arylene means an aryl group having two bonding sites, that is, a divalent group. Except that each arylene is a divalent group, the description of the aryl group provided above can be applied thereto. In addition, heteroarylene means a heteroaryl group having two bonding sites, that is, a divalent group. Except that each heteroarylene is a divalent group, the description of the heteroaryl group provided above can be applied thereto.

[0078] In this specification, "adjacent" groups may mean a substituent that substitutes an atom directly connected to the atom substituted by the corresponding substituent, a substituent that is spatially positioned closest to the corresponding substituent, or another substituent that substitutes the atom substituted by the corresponding substituent. For example, two substituents substituting the ortho position in a benzene ring and two substituents substituting the same carbon in an aliphatic ring can be understood as "adjacent" groups to each other.

[0079] The heterocyclic compound according to an embodiment of the present application is represented by Chemical Formula 1. More specifically, due to the core structure and structural properties having the substituents as described above, the heterocyclic compound represented by Chemical Formula 1 can be used as a material for the organic material layer of an organic light-emitting component.

[0080] In an embodiment of the present application, the compound represented by Chemical Formula 1 may have a deuterium content of greater than or equal to 0% and less than or equal to 100%.

[0081] In an embodiment of the present application, the compound represented by Chemical Formula 1 may have a deuterium content of greater than 0% and less than or equal to 100%.

[0082] In an embodiment of the present application, the compound represented by Chemical Formula 1 may have a deuterium content of greater than or equal to 10% and less than or equal to 100%.

[0083] In an embodiment of the present application, R of Chemical Formula 1 amay be a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0084] In one embodiment of the present application, R a may be a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

[0085] In one embodiment of the present application, R a may be a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0086] In one embodiment of the present application, R a may be a halogen group; a cyano group; a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

[0087] In another embodiment, R a may be a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

[0088] In another embodiment, R a is an unsubstituted or deuterium-substituted methyl group; or an unsubstituted or deuterium-substituted phenyl group.

[0089] In another embodiment, R a is a methyl group; or a phenyl group.

[0090] In another embodiment, R a is a methyl group.

[0091] In another embodiment, R a is a phenyl group.

[0092] In one embodiment of the present application, R of Formula 1 b may be 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.

[0093] In one embodiment of the present application, R b may be 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 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0094] In one embodiment of the present application, Rb may be 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 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0095] In another embodiment, R b is hydrogen; deuterium; a halogen group; a cyano group; or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms.

[0096] In another embodiment, R b is hydrogen; deuterium; or a halogen group.

[0097] In another embodiment, R b is hydrogen; or deuterium.

[0098] In another embodiment, R b is hydrogen.

[0099] In another embodiment, R b is deuterium.

[0100] In another embodiment, R b is 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.

[0101] In one embodiment of the present application, when R a is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, among R1 to R7 in Formula 1, only one of R1, R2, and R4 to R7 is ―(La)p―A, and the rest of R1 to R7 are the same or different from each other and are each independently selected from the group consisting of 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; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and when R a is a halogen group; a cyano group; or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, only one of R1 to R7 is ―(La)p―A, and the rest of R1 to R7 are the same or different from each other and may each independently be selected from the group consisting of 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; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0102] In one embodiment of the present application, when R aWhen R is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, among R1 to R7, only one of R1, R2 and R4 to R7 is ―(La)p―A, and the remaining ones among R1 to R7 are the same as or different from each other, and may each independently be selected from the group consisting of 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; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0103] In one embodiment of the present application, when R a is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, among R1 to R7, only one of R1, R2 and R4 to R7 is ―(La)p―A, and the remaining ones among R1 to R7 are the same as or different from each other, and may each independently be selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; 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.

[0104] In one embodiment of the present application, when R a is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, among R1 to R7, only one of R1, R2 and R4 to R7 is ―(La)p―A, and the remaining ones among R1 to R7 are the same as or different from each other, and may each independently be selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0105] When R a is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, the description and definition of R1 to R7 also apply when R a is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0106] In other words, when R a is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, only one of R1, R2 and R4 to R7 is ―(La)p―A, and the remaining ones among R1 to R7 are the same as or different from each other, and may each independently be selected from the group consisting of 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; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0107] Similarly, when R a is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, only one of R1, R2, and R4 to R7 is ―(La)p―A, and the remaining ones among R1 to R7 are the same as or different from each other and can each independently be selected from the group consisting of 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; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0108] In one embodiment of the present application, when R a is a halogen group; a cyano group; or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, among R1 to R7, only one of R1 to R7 is ―(La)p―A, and the remaining ones among R1 to R7 are the same as or different from each other and can each independently be selected from the group consisting of 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; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0109] In one embodiment of the present application, when R a is a halogen group; a cyano group; or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, among R1 to R7, only one of R1 to R7 is ―(La)p―A, and the remaining ones among R1 to R7 are the same as or different from each other and can each independently be selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; 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.

[0110] In one embodiment of the present application, when R a is a halogen group; a cyano group; or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, among R1 to R7, only one of R1 to R7 is ―(La)p―A, and the remaining ones among R1 to R7 are the same as or different from each other and can each independently be selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0111] When R a is a halogen group; a cyano group; or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, the description and definition of R1 to R7 also apply when Ra is a halogen group; a cyano group; or a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, or when R a is a halogen group; a cyano group; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0112] In other words, when R a is a halogen group; a cyano group; or a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, only one of R1 to R7 is ―(La)p―A, and the remaining ones among R1 to R7 are the same as or different from each other, and may each independently be selected from the group consisting of 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; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0113] Similarly, when R a is a halogen group; a cyano group; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, only one of R1 to R7 is ―(La)p―A, and the remaining ones among R1 to R7 are the same as or different from each other, and may each independently be selected from the group consisting of 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; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0114] In one embodiment of the present application, La is a direct bond; a substituted or unsubstituted arylene having 6 to 60 carbon atoms or a substituted or unsubstituted heteroarylene having 2 to 60 carbon atoms, p is an integer from 0 to 3, and when p is 2 or greater than 2, Las are the same as or different from each other, and A is a substituted or unsubstituted amino group.

[0115] In one embodiment of the present application, La is a direct bond; a substituted or unsubstituted arylene having 6 to 60 carbon atoms or a substituted or unsubstituted heteroarylene having 2 to 60 carbon atoms, p is an integer from 0 to 3, and when p is 2 or greater than 2, Las are the same as or different from each other.

[0116] In one embodiment of the present application, La may be a direct bond; a substituted or unsubstituted arylene having 6 to 40 carbon atoms or a substituted or unsubstituted heteroarylene having 2 to 40 carbon atoms.

[0117] In one embodiment of the present application, La may be a direct bond; or a substituted or unsubstituted arylene having 6 to 40 carbon atoms.

[0118] In one embodiment of the present application, La can be a direct bond; or a substituted or unsubstituted arylene having 6 to 20 carbon atoms.

[0119] In one embodiment of the present application, La is a direct bond.

[0120] In one embodiment of the present application, La is a phenylene group.

[0121] In one embodiment of the present application, A is a substituted or unsubstituted amino group.

[0122] In one embodiment of the present application, m in Chemical Formula 1 is an integer from 0 to 8, and when m is 2 or greater than 2, R b are the same as or different from each other.

[0123] In one embodiment of the present application, Chemical Formula 1 can be represented by any one of the following Chemical Formulas 2 to 7.

[0124] [Chemical Formula 2]

[0125]

[0126] [Chemical Formula 3]

[0127]

[0128] [Chemical Formula 4]

[0129]

[0130] [Chemical Formula 5]

[0131]

[0132] [Chemical Formula 6]

[0133]

[0134] [Chemical Formula 7]

[0135]

[0136] In Chemical Formulas 2 to 7,

[0137] R a1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms,

[0138] L1 and L2 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted arylene having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 60 carbon atoms,

[0139] Ar1 and Ar2 are the same as or different from each other and 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,

[0140] R 11 To R 17 are the same as or different from each other and are each independently selected from the group consisting of 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; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and

[0141] a and b are 0 or 1, and L a ,p,R b and m have the same definitions as in Chemical Formula 1.

[0142] When R of chemical formula 1 a In the case where the compound is an aryl group, the π-π stacking of the aromatic ring can be further suppressed. Therefore, the use of the compound represented by Chemical Formulas 2 to 7 in an organic light-emitting device can reduce the driving voltage of the organic light-emitting device. In other words, it is more effective in preventing the problem of device property degradation that may be caused by the high driving voltage of the organic light-emitting device.

[0143] In one embodiment of the present application, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 8 to 14.

[0144] [Chemical formula 8]

[0145]

[0146] [Chemical formula 9]

[0147]

[0148] [Chemical formula 10]

[0149]

[0150] [Chemical formula 11]

[0151]

[0152] [Chemical formula 12]

[0153]

[0154] [Chemical formula 13]

[0155]

[0156] [Chemical Formula 14]

[0157]

[0158] In Chemical Formulas 8 to 14,

[0159] R a2 is a halogen group; a cyano group; or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, and L1 and L2 are the same as or different from each other, and each independently is 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,

[0160] Ar1 and Ar2 are the same as or different from each other, and each independently is 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,

[0161] R 11 to R 17 are the same as or different from each other, and each independently is selected from the group consisting of 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; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and

[0162] a and b are 0 or 1, and L a , p, R b and m have the same definitions as in Chemical Formula 1.

[0163] When a compound represented by Chemical Formulas 8 to 14 corresponding to the case where R a in Chemical Formula 1 is a halogen group; a cyano group; or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms instead of an aryl group is used in an organic light-emitting device, due to the steric hindrance present in the structure of the compound, a higher T1 value is obtained, and a device having more excellent driving and efficiency can be obtained. Herein, the T1 value means the energy level value in the triplet state.

[0164] In one embodiment of the present application, L1 and L2 in Chemical Formulas 2 to 14 are the same as or different from each other, and each may 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.

[0165] In one embodiment of the present application, L1 and L2 of Formulae 2 to 14 are the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted arylene having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroarylene having 2 to 40 carbon atoms.

[0166] In one embodiment of the present application, L1 and L2 are the same as or different from each other, and may each independently be a direct bond; or a substituted or unsubstituted arylene having 6 to 40 carbon atoms.

[0167] In one embodiment of the present application, L1 and L2 are the same as or different from each other, and may each independently be a direct bond; or a substituted or unsubstituted arylene having 6 to 20 carbon atoms.

[0168] In one embodiment of the present application, L1 and L2 are the same as or different from each other, and may each independently be a direct bond; or a substituted or unsubstituted phenylene.

[0169] In one embodiment of the present application, L1 is a direct bond.

[0170] In one embodiment of the present application, L1 is phenylene.

[0171] In one embodiment of the present application, L2 is a direct bond.

[0172] In one embodiment of the present application, L2 is phenylene.

[0173] In one embodiment of the present application, Ar1 and Ar2 of Formulae 2 to 14 are the same as or different from each other, and may each independently be 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.

[0174] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and may each independently be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0175] In one embodiment of the present application, Ar1 and Ar2 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.

[0176] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each may independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a fluorenyl group unsubstituted or substituted with one or more members selected from the group consisting of deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 10 carbon atoms; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted spirobifluorenyl group.

[0177] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each may independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a fluorenyl group unsubstituted or substituted with one or more members selected from the group consisting of deuterium, methyl, and phenyl; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted spirobifluorenyl group.

[0178] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each may independently be an unsubstituted or deuterium-substituted phenyl group; an unsubstituted or deuterium-substituted biphenyl group; an unsubstituted or deuterium-substituted terphenyl group; an unsubstituted or deuterium-substituted naphthyl group; a fluorenyl group unsubstituted or substituted with one or more members selected from the group consisting of deuterium, an unsubstituted or deuterium-substituted methyl group, and an unsubstituted or deuterium-substituted phenyl group; an unsubstituted or deuterium-substituted dibenzofuranyl group; an unsubstituted or deuterium-substituted dibenzothiophenyl group; or an unsubstituted or deuterium-substituted spirobifluorenyl group.

[0179] According to one embodiment of the present application, Formula 1 may be represented by any one of the following compounds, but is not limited thereto.

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201] In addition, by introducing various substituents into the structure of Formula 1, compounds having unique properties of the introduced substituents can be synthesized. For example, by introducing substituents that are 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, materials that meet the requirements of each organic material layer can be synthesized.

[0202] In addition, by introducing various substituents into the structure of Formula 1, the band gap can be precisely controlled, and at the same time, the properties at the interface between organic materials can be enhanced, and the material applications can become diversified.

[0203] At the same time, the heterocyclic compound has a high glass transition temperature (Tg) and excellent thermal stability. This increase in thermal stability becomes an important factor in providing driving stability for the component.

[0204] The heterocyclic compound according to an embodiment of the present application can be prepared using a multi-step chemical reaction. First, some intermediate compounds are prepared, and the heterocyclic compound of Formula 1 can be prepared from the intermediate compounds. More specifically, the heterocyclic compound according to an embodiment of the present application can be prepared based on the preparation examples described later.

[0205] Another embodiment of the present application provides an organic light-emitting component comprising a heterocyclic compound represented by Chemical Formula 1. The "organic light-emitting component" can be represented by terms such as "organic light-emitting diode", "OLED", "OLED component", and "organic electroluminescent component".

[0206] The heterocyclic compound can be formed into an organic material layer using a solution coating method and a vacuum deposition method. Herein, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spray method, rollcoating, etc., but is not limited thereto.

[0207] Specifically, an organic light-emitting component according to an embodiment of the present application includes an anode, a cathode, and one or more organic material layers disposed between the anode and the cathode, and one or more of the organic material layers contain a heterocyclic compound represented by Chemical Formula 1. When the organic material layer contains the heterocyclic compound represented by Chemical Formula 1, the organic light-emitting component has excellent luminous efficiency and lifespan.

[0208] In addition, the organic material layer includes a hole transport layer, and the hole transport layer contains a heterocyclic compound represented by Chemical Formula 1. When the organic material layer contains the heterocyclic compound represented by Chemical Formula 1 in the hole transport layer, the organic light-emitting component has more excellent luminous efficiency and lifespan.

[0209] In the organic light-emitting component of the present application, the organic material layer includes an electron blocking layer, and the electron blocking layer may contain the heterocyclic compound as a host material of the light-emitting material.

[0210] The organic light-emitting component 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 blocking layer, an electron injection layer, an electron transport layer, a hole assisting layer, and a hole blocking layer.

[0211] In the organic light-emitting component of the present application, the light-emitting layer may contain two or more host materials.

[0212] In the organic light-emitting component of the present application, two or more host materials may be premixed and used as the light-emitting layer. Premixing means placing and mixing two or more host materials of the light-emitting layer in one supply source before depositing on the organic material layer.

[0213] In the organic light-emitting component of the present application, the light-emitting layer may include two or more host materials, and each of the two or more host materials may include one or more p-type host materials and n-type host materials.

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

[0215] Figures 1 to 3 The stacking order of the electrodes and the organic material layer of the organic light-emitting component according to an embodiment of the present application is shown. However, the scope of the present application is not limited to these figures, and the structures of organic light-emitting components known in the art can also be used in the present application.

[0216] Figure 1 An organic light-emitting component is shown in which the anode (200), the organic material layer (300), and the cathode (400) are continuously stacked on the substrate (100). However, the structure is not limited to this structure, and as Figure 2 shown, an organic light-emitting component in which the cathode, the organic material layer, and the anode are continuously stacked on the substrate can also be obtained.

[0217] Figure 3 The case where the organic material layer is multilayer is shown. The organic light-emitting component according to Figure 3 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 stacking structure, and according to needs, layers other than the light-emitting layer may not be included, and other required functional layers may be further added.

[0218] In the organic light-emitting component according to an embodiment of the present application, the materials other than the heterocyclic compound of Chemical Formula 1 are shown below. However, these are only for illustrative purposes and do not limit the scope of the present application, and can be replaced by materials known in the art.

[0219] As the anode material, a material having a relatively large work function can be used, and transparent conductive oxides, metals, conductive polymers, etc. can be used. 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] (PEDT), polypyrrole, and polyaniline, etc., but not limited thereto.

[0220] As the cathode material, a material having a relatively small work function can be used, and metals, metal oxides, conductive polymers, etc. can be used. 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; multilayered structure materials such as LiF / Al or LiO2 / Al, etc., but not limited thereto.

[0221] As the hole injection material, known hole injection materials can be used, and for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 can be used; or starburst amine derivatives such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4',4”-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), or 1,3,5-tris[4-(3-methylphenylanilino)phenyl]benzene (m-MTDAPB) described in [Advanced Material, 6, p. 677 (1994)], polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid, or polyaniline / poly(4-styrene-sulfonate) and the like as conductive polymers having solubility.

[0222] As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyl diamine derivatives, etc. can be used, and low molecular weight or high molecular weight materials can also be used.

[0223] As the electron transport material, metal complexes such as oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and its derivatives, etc. can be used, and polymer materials and low-molecular materials can also be used.

[0224] As an example of the electron injection material, LiF is usually used in this technology. However, the present application is not limited thereto.

[0225] As the light-emitting material, red, green or blue light-emitting materials can be used, and if necessary, two or more light-emitting materials can be mixed and used. In addition, fluorescent materials can also be used as the light-emitting material. However, phosphorescent materials can also be used. As the light-emitting material, a material that emits light by bonding electrons and holes injected from the anode and cathode respectively can be used alone. However, a material having a host material and a dopant material that participate in light emission together can also be used.

[0226] Depending on the materials used, the organic light-emitting device according to an embodiment of the present application can be a top-emission type, a bottom-emission type, or a dual-emission type.

[0227] The heterocyclic compound according to an embodiment of the present application can also be used in organic electronic devices, including organic solar cells, organic photoconductors, organic transistors, etc., under a similar principle to that used in organic light-emitting devices.

[0228] Hereinafter, the present specification will be described in more detail with reference to examples. However, these are for illustrative purposes only, and the scope of the present application is not limited thereto.

[0229] <Preparation Example 1> Preparation of Compound A1-2

[0230]

[0231] 1) Preparation of Compound A1-2-3

[0232] 4-Bromo-6-chlorodibenzofuran (A) (50 g, 0.178 mol, 1.0 eq) was introduced into tetrahydrofuran (hereinafter referred to as THF) (750 mL), and after replacing with N2, n-BuLi (12.5 g, 0.195 mol, 1.1 eq) was added dropwise thereto at 0 °C, and the mixture was stirred for 30 minutes. Thereafter, N,N-dimethylacetamide (17 g, 0.195 mol, 1.1 eq) was added dropwise thereto, and the resulting mixture was stirred at room temperature for 3 hours (h). Then, the reaction was terminated by introducing water (distilled water) thereto, and the resulting mixture was extracted with chloromethane (hereinafter, MC) and water. Thereafter, water was removed using anhydrous MgSO4. After removing water, the resulting mixture was separated using a silica gel column to obtain compound A1-2-3 (41 g) in 84% yield.

[0233] 2) Preparation of compound A1-2-2

[0234] Compound A1-2-3 (41 g, 0.15 mol, 1 eq) was introduced into THF (600 mL), and after replacing with N2, the mixture was stirred at 0 °C. MeLi (B) (3.7 g, 0.17 mol, 1.1 eq) was slowly added dropwise thereto, and the resulting mixture was stirred at 0 °C for 2 hours. Then, the reaction was terminated by introducing water (distilled water) thereto, and the resulting mixture was extracted with MC and water. Thereafter, water was removed using anhydrous MgSO4. After removing water, the resulting mixture was separated using a silica gel column to obtain compound A1-2-2 (20 g) in 54% yield.

[0235] 3) Preparation of compound A1-2-1

[0236] 2-Bromo-1,1'-biphenyl (21 g, 0.09 mol, 1.1 eq) was introduced into THF (40 mL), and after replacing with N2, n-BuLi 2.5 mol / L (M) (36 mL, 0.09 mol, 1.1 eq) was added dropwise thereto at 0 °C, and the mixture was stirred for 1 hour. Compound A1-2-1 (20 g, 0.08 mol, 1 eq) dissolved in THF (600 mL) was slowly added dropwise to the reaction material, and the resulting mixture was stirred at room temperature (RT) for 6 hours. Then, the resulting mixture was extracted with EA and water. Thereafter, HCl (20 mL) and acetic acid (200 mL) were introduced thereto, and the resulting mixture was stirred at 110 °C for 6 hours. After the reaction was completed, water was introduced thereto, and the resulting solid was filtered to obtain compound A1-2-1 (20 g) in 60% yield.

[0237] 4) Preparation of compound A1-2

[0238] Compound A1-2-1 (20 g, 0.05 mol, 1 equiv), N-phenyl-[1,1'-biphenyl]-4-amine (C) (19 g, 0.06 mol, 1.1 equiv), Nat-BuO (9.6 g, 0.1 mol, 2 equiv), Pd2(dba)3 (2.3 g, 0.0025 mol, 0.05 equiv), and t-Bu3P (2.3 mL, 0.005 mol, 0.1 equiv) were introduced into toluene (200 mL), and the mixture was stirred at 110 °C for 6 h. Then, the reaction was terminated by introducing water (distilled water) thereto, and the resultant was extracted with MC and water. Thereafter, the water was removed using anhydrous MgSO4. After removing the water, the resultant was separated using a silica gel column to obtain compound A1-2 (25.6 g) in 77% yield.

[0239] 5) Preparation of the compounds in Table 1

[0240] The compounds in Table 1 below were synthesized in the same manner as in Preparation Example 1, except that intermediate A in Table 1 below was used instead of 4-bromo-6-chlorodibenz[b,d]furan (A), and intermediate B and C in Table 1 below were used instead of MeLi (B) and N-phenyl-[1,1'-biphenyl]-4-amine (C), respectively.

[0241] [Table 1]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252] <Preparation Example 2> Preparation of Compound A1-51

[0253]

[0254] 1) Preparation of Compound A1-2-3

[0255] After dissolving compound A1-2-1(D) (10 g, 26.26 mmol) and (4-(bis([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid (E) (11.59 g, 26.26 mmol) in 1,4-dioxane (100 mL) and distilled water (20 mL), Pd(dba)2 (0.75 g, 1.31 mmol), xphos (1.25 g, 2.63 mmol) and K2CO3 (9.07 g, 65.64 mmol) were introduced therein, and the resulting mixture was stirred under reflux for 12 hours. After completion of the reaction, the reaction solution was extracted with dichloromethane and distilled water, and after drying the organic layer with anhydrous MgSO4, the solvent was removed using a rotary evaporator. The resulting product was purified by column chromatography using dichloromethane and hexane as eluents to obtain compound A1-51 (14 g, 72%).

[0256] 2) Preparation of the compounds in Table 2

[0257] The compounds in Table 2 were synthesized in the same manner as in Preparation Example 2, except that intermediate D in Table 2 below was used instead of compound A1-2-1(D) and intermediate E in Table 2 below was used instead of (4-(bis([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid (E).

[0258] [Table 2]

[0259]

[0260] <Preparation Example 3> Preparation of Compound D-5

[0261]

[0262] 1) Preparation of Compound D-5

[0263] Compound A4-2 (10 g, 14.17 mmol), trifluoromethanesulfonic acid (3.19 g, 21.25 mmol) and D6-benzene (200 mL) were introduced into a reaction flask, and then the mixture was stirred under reflux for 5 hours. After completion of the reaction, the reaction was terminated by introducing water therein, and the resulting product was extracted with dichloromethane and distilled water. After drying the organic layer with anhydrous MgSO4, the solvent was removed using a rotary evaporator, and the resulting product was purified by column chromatography using dichloromethane and hexane as eluents to obtain compound D-5 (9 g, 87%). The average value of 26 deuterium substitutions was identified by LC / MS analysis.

[0264] <Preparation Example 4> Preparation of Compound D-11

[0265]

[0266] 1) Preparation of Compound D-11

[0267] Compound A2-54 (10 g, 14.17 mmol), trifluoromethanesulfonic acid (3.19 g, 21.25 mmol), and D6-benzene (200 mL) were introduced into a reaction flask and then stirred under reflux for 5 hours. After the reaction was completed, the reaction was terminated by introducing water into it, and the resulting mixture was extracted with dichloromethane and distilled water. After drying the organic layer with anhydrous MgSO4, the solvent was removed using a rotary evaporator, and the resulting product was purified by column chromatography using dichloromethane and hexane as the eluent to obtain Compound D-11 (8 g, 78%). By LC / MS analysis, the average value of 22 deuterium substitutions was identified.

[0268] The compounds described in this specification were prepared in the same manner as in the Preparation Examples, and for the synthetic identification results of the prepared compounds, 1 1H nuclear magnetic resonance (NMR) (CDCl3, 200 MHz) and FD-mass spectrometry (FD-MS: field desorption mass spectrometry) were used, and the measured values are shown in Tables 3 and 4 below. Table 3 below shows the 1 measured values of 1H NMR (CDCl3, 200 MHz) of some of the prepared compounds, and Table 4 below shows the measured values of FD-mass spectrometry (FD-MS: field desorption mass spectrometry) of the prepared compounds.

[0269] [Table 3]

[0270]

[0271]

[0272]

[0273]

[0274] [Table 4]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280] [Experimental Example]

[0281] <Experimental Example 1>

[0282] (1) Fabricate an organic light-emitting component

[0283] Use trichloroethylene, acetone, ethanol, and distilled water to ultrasonically clean a transparent indium tin oxide (ITO) electrode film obtained from glass for organic light-emitting components (manufactured by Samsung-Corning Co., Ltd.) for 5 minutes each continuously, store the transparent ITO electrode film in isopropyl alcohol, and use it. Next, mount the ITO substrate in the substrate folder of a vacuum deposition device, and introduce the following 4,4',4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) into a cell in the vacuum deposition device.

[0284]

[0285] Subsequently, evacuate the chamber until the vacuum degree therein reaches 10 -6 Torr, and then evaporate 2-TNATA by applying current to the cell to deposit a hole injection layer with a thickness of 600 Å on the ITO substrate. Introduce the following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) into another cell in the vacuum deposition device, and evaporate it by applying current to deposit a hole transport layer with a thickness of 300 Å on the hole injection layer.

[0286]

[0287] After forming the hole injection layer and the hole transport layer as described above, deposit a blue light-emitting material having the following structure as the light-emitting layer. Specifically, in a cell on one side of the vacuum deposition device, vacuum deposit the blue light-emitting host material H1 to a thickness of 200 Å, and vacuum deposit the blue light-emitting dopant material D1 relative to the host material at 5 wt% thereon.

[0288]

[0289] Subsequently, deposit a compound of the following structural formula E1 to a thickness of 300 Å as the electron transport layer.

[0290]

[0291] As the electron injection layer, deposit lithium fluoride (LiF) to a thickness of 10 Å, and deposit the Al cathode to a thickness of 1,000 Å, and thus, an organic light-emitting component (Comparative Example 1) was fabricated.

[0292] Meanwhile, by placing each material used in the manufacture of the organic light-emitting component under a vacuum of 10 -8 Torr to 10 -6 Torr, all the organic compounds required for manufacturing the OLED component were purified by vacuum sublimation.

[0293] Except for using the compounds described in Table 5 below instead of NPB used when forming the hole transport layer in the manufacturing process of the organic light-emitting component (Comparative Example 1), organic light-emitting components (Comparative Example 2 and Examples 1 to 75) were additionally manufactured in the same manner as in the manufacturing process of the organic light-emitting component (Comparative Example 1).

[0294] The compound (HTL1) used when forming the hole transport layer in Comparative Example 2 is as follows.

[0295]

[0296] 2) Driving voltage and luminous efficiency of the organic light-emitting component

[0297] For each of the above-manufactured organic light-emitting components (Comparative Examples 1 and 2 and Examples 1 to 75), the electroluminescent (EL) properties were measured using an M7000 manufactured by McScience Inc., and using the measurement results, the time T (unit: h, time) taken for the brightness to become 95% of the initial brightness when the standard brightness was 700 candela per square meter (cd / m 2 ) was measured by a lifetime measurement system (M6000) manufactured by McScience Inc. 95 (Unit: h, time).

[0298] The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the manufactured organic light-emitting components according to the above measurement method are shown in Table 5 below.

[0299] [Table 5]

[0300]

[0301]

[0302]

[0303] As can be seen from the results in Table 5, compared with Comparative Examples 1 and 2 (which are organic light-emitting components that do not use the compound represented by Chemical Formula 1 disclosed herein as the material for the hole transport layer), Examples 1 to 75 (which are organic light-emitting components that use the compound represented by Chemical Formula 1 disclosed herein as the material for the hole transport layer) have a lower driving voltage and significantly improved luminous efficiency and lifetime.

[0304] When comparing the hole transport layer material NPB of Comparative Example 1 with the compound represented by Chemical Formula 1 disclosed herein, the hole transport layer materials having an arylamino group in Examples 1 to 75 are similar. However, the compound represented by Chemical Formula 1 disclosed herein is different in that the arylamino group is substituted with a substituent having a fluorene group and a dibenzofuran group attached thereto. By substituting the arylamino group with a substituent having a fluorene group and a dibenzofuran group attached thereto as described above, π-π stacking of the aromatic rings is suppressed, and this is regarded as preventing deterioration of device properties by increasing the driving voltage of the organic light-emitting device.

[0305] In addition, when comparing the hole transport layer material HTL1 of Comparative Example 2 with the compound represented by Chemical Formula 1 disclosed herein, the hole transport layer materials in Examples 1 to 75 (having a substituent having a fluorene group and a dibenzofuran group attached thereto as the arylamino group) are similar. However, HTL1 of Comparative Example 2 and the compound represented by Chemical Formula 1 disclosed herein are different in the substitution position.

[0306] The amino group of the compound represented by Chemical Formula 1 disclosed herein is substituted based on the dibenzofuran group, which results in a higher hole mobility compared to when the amino group is substituted based on the fluorene group as in HTL1 of Comparative Example 2. And through the amino group substituted based on the dibenzofuran group, the electron cloud distribution of the highest occupied molecular orbital (HOMO) of the compound disclosed herein is distributed to the dibenzofuran group, thereby generating an appropriate energy level. Therefore, it is considered that excellent results are obtained in terms of driving voltage, efficiency, and lifetime by increasing the charge balance between holes and electrons in the light-emitting layer.

[0307] <Experimental Example 2>

[0308] (1) Fabricating an organic light-emitting device

[0309] The transparent ITO electrode film obtained from glass for organic light-emitting devices (manufactured by Samsung-Corning Co., Ltd.) was ultrasonically cleaned continuously in trichloroethylene, acetone, ethanol, and distilled water for 5 minutes each, and the transparent ITO electrode film was stored in isopropyl alcohol and used. Next, the ITO substrate was mounted in the substrate holder of a vacuum deposition apparatus, and 4,4',4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was introduced into the unit in the vacuum deposition apparatus.

[0310]

[0311] Subsequently, the chamber was evacuated until the vacuum degree therein reached 10 -6It is carried, and then 2-TNATA is evaporated by applying current to the unit to deposit a hole injection layer with a thickness of 600 Å on the ITO substrate. The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) is introduced into another unit in the vacuum deposition equipment and evaporated by applying current to the unit to deposit a hole transport layer with a thickness of 300 Å on the hole injection layer.

[0312]

[0313] After forming the hole injection layer and the hole transport layer as described above, a blue light-emitting material having the following structure is deposited thereon as the light-emitting layer. Specifically, in one unit of the vacuum deposition equipment, the blue light-emitting host material H1 is vacuum-deposited to a thickness of 200 Å, and the blue light-emitting dopant material D1 is vacuum-deposited thereon at 5 wt% relative to the host material.

[0314]

[0315] Subsequently, a compound of the following structural formula E1 is deposited to a thickness of 300 Å as the electron transport layer.

[0316]

[0317] As the electron injection layer, lithium fluoride (LiF) is deposited to a thickness of 10 Å, and an Al cathode is applied to a thickness of 1,000 Å, and thus, an organic light-emitting component (Comparative Example 3) is manufactured.

[0318] Meanwhile, each material used for manufacturing the organic light-emitting component is vacuum sublimation purified at 10 -8 torr to 10 -6 torr to purify all the organic compounds required for manufacturing the OLED component.

[0319] An organic electroluminescent component (Examples 76 to 150 and Comparative Example 4) was additionally manufactured in the same manner as the manufacturing process of the organic light-emitting component (Comparative Example 3), except that after forming the hole transport layer NPB to a thickness of 250 Å, an electron blocking layer with a thickness of 50 Å was formed on the hole transport layer using the compounds shown in Table 6 below.

[0320] 2) Driving voltage and luminous efficiency of the organic light-emitting component

[0321] For each of the above - manufactured organic light - emitting components (Comparative Examples 3 and 4 and Examples 76 to 150), the electroluminescence (EL) properties were measured using an M7000 manufactured by McScience Co., Ltd. And using the measurement results, the time T taken for the luminance to become 95% of the initial luminance when the standard luminance is 700 candela per square meter was measured by a lifetime measurement system (M6000) manufactured by McScience Co., Ltd. 95 (Unit: h, time).

[0322] The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the manufactured organic light - emitting components according to the above - mentioned measurement method are shown in Table 6 below.

[0323] [Table 6]

[0324]

[0325]

[0326]

[0327]

[0328] As can be seen from the results in Table 6, compared with Comparative Examples 3 and 4 (which are organic light - emitting components using NPB and HTL1 compounds as electron - blocking layer materials), Examples 76 to 150 (which are organic light - emitting components using the compound represented by Chemical Formula 1 disclosed herein as the hole - blocking layer material) have a lower driving voltage and significantly improved luminous efficiency and lifetime.

[0329] Generally, when electrons pass through the hole - transport layer and migrate to the anode without combining in the light - emitting layer, the efficiency and lifetime of the organic light - emitting component decrease. Herein, when a compound having a high Lowest Unoccupied Molecular Orbital (LUMO) energy level is used as the electron - blocking layer, the electrons that migrate to the anode after passing through the light - emitting layer are blocked by the energy barrier of the electron - blocking layer, and the phenomenon of reducing the efficiency and lifetime of the organic light - emitting component can be prevented. In other words, when a compound having a high Lowest Unoccupied Molecular Orbital (LUMO) energy level is used as the electron - blocking layer, holes and electrons are more likely to form excitons, which increases the possibility of light emission in the light - emitting layer.

[0330] Therefore, with the compounds of the present disclosure having a higher LUMO energy level and a wider bandgap compared to the compounds of Comparative Examples 3 and 4, when the compounds of the present disclosure are used as an electron blocking layer of an organic light-emitting device, excellent electron blocking ability is obtained, and it is considered that charge balance is formed by holes and electrons and thus light emission occurs inside the light-emitting layer rather than at the interface of the hole transport layer, and excellent results are obtained in all aspects such as driving, efficiency, and lifetime.

Claims

1. A heterocyclic compound represented by any one of the following Chemical Formulas 8 to 14: [Chemical Formula 8] [Chemical Formula 9] [Chemical Formula 10] [Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] Among them, In Chemical Formulas 8 to 14, R a2 is a methyl group which is unsubstituted or substituted by at least one deuterium; R b is hydrogen; or deuterium; L1 and L2 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted phenylene; Ar1 and Ar2 are the same as or different from each other and may each independently be an unsubstituted or deuterium-substituted phenyl; an unsubstituted or deuterium-substituted biphenyl; an unsubstituted or deuterium-substituted terphenyl; an unsubstituted or deuterium-substituted naphthyl; an unsubstituted or deuterium-substituted triphenylene; an unsubstituted or deuterium-substituted phenanthryl; a fluorene group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an unsubstituted or deuterium-substituted methyl, and an unsubstituted or deuterium-substituted phenyl; an unsubstituted or deuterium-substituted dibenzofuranyl; an unsubstituted or deuterium-substituted dibenzothiophenyl; or an unsubstituted or deuterium-substituted spirobifluorene group; R 11 to R 17 are the same as or different from each other, and each independently is selected from the group consisting of hydrogen; or deuterium; a and b are 0 or 1; La is a direct bond; a substituted or unsubstituted phenylene, p is an integer from 0 to 3, and when p is 2 or greater than 2, Las are the same as or different from each other; and m is an integer from 0 to 8, and when m is 2 or greater than 2, R b are the same as or different from each other.

2. The heterocyclic compound according to claim 1, wherein the substituted or unsubstituted means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; 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; -SiRR′R”; -P(=O)RR'; an alkylamine having 1 to 20 carbon atoms; a monocyclic or polycyclic arylamine having 6 to 60 carbon atoms; and a monocyclic or polycyclic heteroarylamine having 2 to 60 carbon atoms, or unsubstituted, or substituted with a substituent connecting two or more of the above-mentioned substituents, or unsubstituted, and R, R′, and R” are the same as or different from each other and are each independently hydrogen; deuterium; a halogen; 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.

3. The heterocyclic compound according to claim 1, wherein the compound represented by any one of Chemical Formulas 8 to 14 has a deuterium content of greater than or equal to 10% and less than or equal to 100%.

4. The heterocyclic compound according to claim 1, wherein any one of Chemical Formulas 8 to 14 is represented by any one of the following compounds:

5. An organic light-emitting device, comprising: an anode; a cathode; and one or more organic material layers disposed between the anode and the cathode, One or more of the organic material layers contain a heterocyclic compound as described in any one of claims 1 to 4.

6. The organic light-emitting assembly according to claim 5, wherein the organic material layer includes a hole transport layer, and the hole transport layer contains the heterocyclic compound.

7. The organic light-emitting assembly according to claim 5, wherein the organic material layer includes an electron blocking layer, and the electron blocking layer contains the heterocyclic compound.

8. The organic light-emitting assembly according to claim 5, 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 blocking layer, an electron injection layer, an electron transport layer, a hole assist layer and a hole blocking layer.

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