Heterocyclic compound and organic light-emitting device including the same

Abstract

To provide a heterocyclic compound and an organic light-emitting device comprising the same.SOLUTION: The present invention relates to a heterocyclic compound represented by Formula 1, where Z is an anthracenyl group unsubstituted or substituted with a naphthyl or biphenyl group or is a phosphine oxide group unsubstituted or substituted with an alkyl group.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present specification relates to a heterocyclic compound and an organic light-emitting device including the same.

[0002] This specification claims the benefit of the filing date of Korean Patent Application No. 10-2019-0158383, filed with the Korean Intellectual Property Office on December 2, 2019, the entire contents of which are incorporated herein by reference. [Background technology]

[0003] 2. Description of the Related Art An electroluminescent device is a type of self-luminous display device, and has advantages such as a wide viewing angle, excellent contrast, and fast response speed.

[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 an organic light-emitting device with this structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs, and then annihilate, emitting light. The organic thin film can be composed of 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, the material of the organic thin film may be a compound that can constitute an emitting layer by itself, or a compound that functions as a host or dopant in a host-dopant emitting layer. In addition, the material of the organic thin film may be a compound that functions as a hole injection, hole transport, electron block, hole block, electron transport, electron injection, etc.

[0006] To improve the performance, lifetime or efficiency of organic light-emitting devices, there is a continuing need to develop materials for organic thin films. Summary of the Invention [Problem to be solved by the invention]

[0007] The present specification provides a heterocyclic compound and an organic light-emitting device including the same. [Means for solving the problem]

[0008] In one embodiment of the present specification, there is provided a heterocyclic compound represented by the following formula 1: [ka]

[0009] In the formula 1, R1 to R5 each independently represent 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; L 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; 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 formula 2: [ka] In the formula 2, X1 to X3 are each CR or N, and at least one is N; 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; adjacent groups among X1 to X3, R21 and R22 may be bonded to each other to form a substituted or unsubstituted ring; r is an integer from 0 to 3, a and b are each an integer of 1 to 5, When r, a, and b are each 2 or more, the substituents in parentheses are the same or different.

[0010] Furthermore, according to one embodiment of the present application, there is provided an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer contains one or more heterocyclic compounds represented by Formula 1. [Effects of the Invention]

[0011] The heterocyclic compounds described herein can be used as organic layer materials in organic light-emitting devices. The heterocyclic compounds can serve as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. In particular, the heterocyclic compounds can be used as electron transport layer materials, hole blocking layer materials, and charge generation layer materials in organic light-emitting devices.

[0012] Formula 1 has a pyrazolo[5,1-a]isoquinoline core structure, and the benzene ring is substituted with a substituent, including pyridine, pyrimidine, triazine, phenanthroline, or anthracene. The pyridine or pyrazole ring has a substituent, which allows the azine functional group to have excellent electron-pull properties, improving the electron flow and electron transport ability of the electron transport layer. Furthermore, the combination of the azine moiety with a substituent that enhances hole-blocking properties increases the planarity and glass transition temperature of the azine derivative, thereby enhancing the thermal stability of the compound. The electron transport ability and hole-blocking ability can be improved by adjusting the band gap and triplet state energy level (T1).

[0013] In addition, when the heterocyclic compound of Formula 1 is used as a material for the electron transport layer or hole blocking layer of an organic light-emitting device, the driving voltage of the device can be reduced, the light efficiency can be improved, and the life characteristics of the device can be improved. [Brief explanation of the drawings]

[0014] [Figure 1]1 is a diagram schematically illustrating a stack structure of an organic light-emitting device according to an embodiment of the present application. [Figure 2] 1 is a diagram schematically illustrating a stack structure of an organic light-emitting device according to an embodiment of the present application. [Figure 3] 1 is a diagram schematically illustrating a stack structure of an organic light-emitting device according to an embodiment of the present application. [Figure 4] 1 is a diagram schematically illustrating a stack structure of an organic light-emitting device according to an embodiment of the present application. [Figure 5] 1 is a diagram schematically illustrating a stack structure of an organic light-emitting device according to an embodiment of the present application. DETAILED DESCRIPTION OF THE INVENTION

[0015] The present specification will be explained in more detail below.

[0016] In this specification, when a part is said to "comprise" a certain component, this does not mean that it excludes other components, but that it may further include other components, unless otherwise specified.

[0017] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different.

[0018] In this specification, [ka] means the position to be substituted.

[0019] In this specification, the term "substituted or unsubstituted" means that the group is substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; a C1 to C60 linear or branched alkyl group; a C2 to C60 linear or branched alkenyl group; a C2 to C60 linear 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 silyl group; a phosphine oxide group; and an amine group, or a substituent formed by linking two or more substituents selected from the above-mentioned exemplary substituents.

[0020] In this specification, when "no substituent is shown in the chemical formula or compound structure," it means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0021] In one embodiment of the present application, "when no substituent is shown in the chemical formula or compound structure," can mean that all positions substitutable as substituents are hydrogen or deuterium. In other words, in the case of deuterium, which is an isotope of hydrogen, some hydrogen atoms may be deuterium, which is an isotope of hydrogen, and in this case, the content of deuterium may be 0% to 100%.

[0022] In one embodiment of the present application, when "substituents are not shown in the chemical formula or structure of a compound," if the deuterium content is 0%, the hydrogen content is 100%, and the substituents do not clearly exclude hydrogen and deuterium, hydrogen and deuterium may be used together in the compound.

[0023] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, and is an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, and can be represented as hydrogen-2, and its atomic symbol is D or 2 It can also be written as H.

[0024] In one embodiment of the present application, isotopes refer to atoms with the same atomic number (Z) but different mass numbers (A). Isotopes can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0025] In one embodiment of the present application, the content T% of a specific substituent can be defined as T2 / T1×100=T%, where T1 is the total number of substituents that the base compound may have and T2 is the number of specific substituents among them.

[0026] That is, in one example: [ka] In a phenyl group represented by the formula, a deuterium content of 20% can be expressed as 20% when the total number of substituents that the phenyl group can have is 5 (T1 in the formula), of which the number of deuterium is 1 (T2 in the formula). That is, a phenyl group with a deuterium content of 20% can be represented by the following structural formula.

[0027] [ka]

[0028] In one embodiment of the present application, a "phenyl group having a deuterium content of 0%" can mean a phenyl group that does not contain a deuterium atom, that is, a phenyl group that has 5 hydrogen atoms.

[0029] In this specification, the halogen may be fluorine, chlorine, bromine or iodine.

[0030] In this specification, the alkyl group includes a straight 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 include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, and a heptyl group. , n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but are not limited to these.

[0031] In this specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms and may be further substituted with other substituents. The number of carbon atoms in the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples include a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group, but are not limited to these.

[0032] In this specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The alkynyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms.

[0033] In this specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms and may be further substituted with other substituents. Here, "polycyclic" refers to a group in which a cycloalkyl group is directly bonded to or condensed with another cyclic group. Here, the other cyclic group may be a cycloalkyl group, but may also be other types of cyclic groups, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples of the cycloalkyl group include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0034] In this specification, the heterocycloalkyl group contains O, S, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, the term "polycyclic group" refers to a group in which the heterocycloalkyl group is directly bonded to or condensed with another cyclic group. Here, the other cyclic group may be a heterocycloalkyl group, but may also be other types of cyclic groups, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 20.

[0035] In this specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic ring means a group in which an aryl group is directly bonded to or condensed with another cyclic group. Here, the other cyclic group may be an aryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or a heteroaryl group. The aryl group includes a spiro group. The number of carbon atoms in the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group include, but are not limited to, a phenyl group, a biphenyl group, a triphenyl group (a terphenyl group), a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and fused ring groups thereof.

[0036] In this specification, the terphenyl group may be selected from the following structural formulas: [ka]

[0037] In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0038] When the fluorenyl group is substituted, [ka] It may be, but is not limited to, the above.

[0039] In this specification, the heteroaryl group contains O, S, SO2, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic ring refers to a group in which the heteroaryl group is directly bonded to or fused with another cyclic group. Here, the other cyclic group may be a heteroaryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or an aryl group. The number of carbon atoms in the heteroaryl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 25. Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, an oxadiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, a tetrazolyl group, a pyranyl group, a pyranyl group, a pyranyl group, a pyrazin ... nyl group, thiazinyl group, dioxinyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyl group, naphthyridyl group, acridinyl group, phenanthridinyl group, imidazopyridinyl group, diazanaphthalenyl group, triazaindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzyl group, Benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilole group, spirobi(dibenzosilole), dihydrophenazinyl group, phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group zolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiazinyl group, phthalazinyl group, naphthyridinyl group, phenanthrolinyl group, benzo[c][1,2,5]thiadiazolyl group, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl group, pyrido[1,2-b]indazolyl group, pyrido[1,2-a]imidazo[1,2-e]indolinyl group, benzofuro[2,3-d]pyrimidyl group; benzothieno[2,3-d]pyrimidyl group; benzofuro[2,3-a]carbazolyl group, benzothieno[2,3-a]carbazolyl group, 1,3-dihydroindolo[2,3-a]carbazolyl group, benzofuro[3,2-a]carbazolyl group, benzothieno[3,2-a]carbazolyl group, 1,3-dihydroindolo[3,2-a]carbazolyl group, benzofuro[2,3-b]carbazolyl group, benzothieno[2,3-b]carbazolyl group, 1,3-dihydroindolo[2,3-b]carbazolyl group, benzofuro[3,2-b]carbazolyl group, benzothieno[3,2-b]carbazolyl group, 1,3-dihydroindolo[3,2 -b]carbazolyl group, benzofuro[2,3-c]carbazolyl group, benzothieno[2,3-c]carbazolyl group, 1,3-dihydroindolo[2,3-c]carbazolyl group, benzofuro[3,2-c]carbazolyl group, benzothieno[3,2-c]carbazolyl group, 1,3-dihydroindolo[3,2-c]carbazolyl group, 1,3-dihydroindeno[2,1-b]carbazolyl group, Examples of dihydroindenocarbazolyl include, but are not limited to, a 5,11-dihydroindeno[1,2-b]carbazolyl group, a 5,12-dihydroindeno[1,2-c]carbazolyl group, a 5,8-dihydroindeno[2,1-c]carbazolyl group, a 7,12-dihydroindeno[1,2-a]carbazolyl group, and a 11,12-dihydroindeno[2,1-a]carbazolyl group.

[0040] In this specification, when a group is substituted with a carbazole group, it includes both cases where a carbon atom of the carbazole is bonded to the substitution position or where a nitrogen atom of the carbazole is bonded to the substitution position.

[0041] In this specification, a silyl group refers to a substituent containing Si and having the Si atom directly bonded as a radical, and is represented by -Si(R101)(R102)(R103), where R101 to R103 may be the same or different and each independently represent 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 heteroaryl group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0042] In this specification, the phosphine oxide group is represented by -P(=O)(R104)(R105), where R104 and R105 may be the same or different and each independently represent at least one substituent selected from the group consisting of 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 aryl group may be any of the above-mentioned examples. Examples of the phosphine oxide group include, but are not limited to, a dimethylphosphine oxide group, a diphenylphosphine oxide group, and a dinaphthylphosphine oxide group.

[0043] In this specification, the amine group is represented by -N(R106)(R107), where R106 and R107 may be the same or different and each independently may be a substituent consisting of 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 heteroaryl group. The amine group may be selected from the group consisting of -NH2, a monoalkylamine group, a monoarylamine group, a monoheteroarylamine group, a dialkylamine group, a diarylamine group, a diheteroarylamine group, an alkylarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group. The number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group.

[0044] In this specification, the arylene group may be any of the aryl groups listed above, except that the arylene group is a divalent group.

[0045] In this specification, the heteroarylene group may be any of the heteroarylene groups exemplified above, except that the heteroarylene group is a divalent group.

[0046] As used herein, the term "adjacent" refers to a substituent substituted on an atom directly bonded to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring can be interpreted as groups "adjacent" to each other.

[0047] The aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, or aromatic heterocycle that can be formed by adjacent groups can have the structures exemplified by the above-mentioned cycloalkyl group, aryl group, cycloheteroalkyl group, and heteroaryl group, except that they are not monovalent groups.

[0048] In one embodiment of the present specification, there is provided a heterocyclic compound represented by the above formula 1.

[0049] In one embodiment of the present specification, L 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.

[0050] In one embodiment of the present specification, L is a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

[0051] In one embodiment of the present specification, L is a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0052] 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 anthracenylene group; a divalent pyridine group substituted or unsubstituted with an aryl group; a divalent pyrimidine group substituted or unsubstituted with an aryl group; or a divalent triazine group substituted or unsubstituted with an aryl group.

[0053] In one embodiment of the present specification, L is a direct bond; a phenylene group; a biphenylene group; an anthracenylene group; a divalent pyridine group substituted or unsubstituted with one or more substituents selected from a phenyl group and a biphenyl group; a divalent pyrimidine group substituted or unsubstituted with one or more substituents selected from a phenyl group and a biphenyl group; or a divalent triazine group substituted or unsubstituted with one or more substituents selected from a phenyl group and a biphenyl group.

[0054] In one embodiment of the present specification, Z is a substituted or unsubstituted aryl group having 10 to 60 carbon atoms; or a substituted or unsubstituted phosphine oxide group, or can be represented by the following formula 2. [ka]

[0055] In the formula 2, X1 to X3 are each CR or N, and at least one is N; 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; Adjacent groups among X1 to X3, R21 and R22 can be bonded to each other to form a substituted or unsubstituted ring.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] In one embodiment of the present specification, Z may be a substituted or unsubstituted aryl group having 10 to 20 carbon atoms; or a phosphine oxide group substituted or unsubstituted with an alkyl group.

[0060] In one embodiment of the present specification, Z may be a substituted or unsubstituted anthracenyl group; or a phosphine oxide group substituted or unsubstituted with an alkyl group.

[0061] In one embodiment of the present specification, Z may be an anthracenyl group substituted or unsubstituted with an aryl group or a phosphine oxide group; or a phosphine oxide group substituted or unsubstituted with an alkyl group.

[0062] In one embodiment of the present specification, Z may be an anthracenyl group substituted or unsubstituted with an aryl group or a phosphine oxide group; or a phosphine oxide group substituted or unsubstituted with a methyl group.

[0063] In one embodiment of the present specification, when Z is a substituted or unsubstituted phosphine oxide group, it can be represented by -P(=O)(R104)(R105), where R104 and R105 may each independently be hydrogen; deuterium; an alkyl group; or an aryl group.

[0064] 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.

[0065] 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.

[0066] In still another embodiment of the present specification, Z can be represented by formula 2 above.

[0067] In one embodiment of the present specification, the formula 2 may be represented by the following formula 2-A. [ka]

[0068] In the formula 2-A, the definitions of each substituent are the same as those in the formula 2.

[0069] In one embodiment of the present specification, one of X1 to X3 in the formula 2 is N, and the rest are CR; R, R21, and R22 each independently represent 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, R21, and R22 of X1 to X3 can be bonded to each other to form a substituted or unsubstituted ring.

[0070] In one embodiment of the present specification, one of X1 to X3 is N and the rest are CR, and R, R21, and R22 each independently represent 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, R21, and R22 of X1 to X3 can be bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle.

[0071] In one embodiment of the present specification, one of X1 to X3 is N and the rest are CR, and R, R21, and R22 each independently represent 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, R21, and R22 of X1 to X3 can be bonded to each other to form a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms.

[0072] In one embodiment of the present specification, one of X1 to X3 is N and the rest are CR, and R, R21, and R22 each independently represent 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, R21, and R22 of X1 to X3 can be bonded to each other to form a substituted or unsubstituted aromatic heterocycle having 6 to 60 carbon atoms.

[0073] In one embodiment of the present specification, one of X1 to X3 is N and the rest are CR, and R, R21, and R22 each independently represent 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, R21, and R22 of X1 to X3 can be bonded to each other to form a substituted or unsubstituted quinoline ring.

[0074] In one embodiment of the present specification, two of X1 to X3 are N, and the remaining one is CR, and R, R21, and R22 may each independently represent 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.

[0075] In one embodiment of the present specification, X1 to X3 are N, and R21 and R22 may each independently represent 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.

[0076] In one embodiment of the present specification, the formula 2 may be any one selected from the following structural formulas. [ka]

[0077] 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.

[0078] In one embodiment of the present specification, R31 and 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.

[0079] In one embodiment of the present specification, R31 and 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.

[0080] In one embodiment of the present specification, R31 and R32 each independently represent 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.

[0081] In one embodiment of the present specification, R31 and R32 each independently represent a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0082] In one embodiment of the present specification, R31 and R32 each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted terphenyl group.

[0083] In one embodiment of the present specification, R31 and R32 each independently represent a phenyl group unsubstituted or substituted with a carbazole group; a biphenyl group; or a terphenyl group.

[0084] In one embodiment of the present specification, R33 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0085] In one embodiment of the present specification, R33 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

[0086] In one embodiment of the present specification, R33 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0087] In one embodiment of the present specification, R33 is hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0088] In one embodiment of the present specification, R33 is hydrogen; deuterium; or a phenyl group.

[0089] In one embodiment of the present specification, R33 is hydrogen; or a phenyl group.

[0090] In one embodiment of the present specification, the formula 2 may be any one selected from the following structural formulas. [ka]

[0091] In the structural formula, the definitions of the respective substituents are as described above.

[0092] 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.

[0093] 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.

[0094] 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.

[0095] In one embodiment of the present specification, R1 to R3 are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; or a substituted or unsubstituted phenyl group.

[0096] In one embodiment of the present specification, R1 to R3 are each independently hydrogen; deuterium; a cyano group; a methyl group; an ethyl group, or a phenyl group unsubstituted or substituted with a cyano group.

[0097] 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.

[0098] In one embodiment of the present specification, at least two of R1 to R3 are each independently a cyano group; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; or a substituted or unsubstituted phenyl group.

[0099] In one embodiment of the present specification, R4 is hydrogen.

[0100] In one embodiment of the present specification, R5 is hydrogen.

[0101] In one embodiment of the present specification, the r is an integer of 0 to 3.

[0102] In one embodiment of the present specification, the r is an integer of 1 to 3.

[0103] In one embodiment of the present specification, a and b are each an integer of 1 to 5.

[0104] In one embodiment of the present specification, a and b are each an integer of 1 to 3.

[0105] In one embodiment of the present specification, a and b are 1.

[0106] In yet another embodiment, a and b are 2.

[0107] In yet other embodiments, a and b are 3.

[0108] In one embodiment of the present specification, the formula 1 can be represented by any of the following formulas 1-1 to 1-4. [ka] [ka] [ka] [ka]

[0109] In the formulas 1-1 to 1-4, the definitions of the respective substituents are the same as those in formula 1.

[0110] In one embodiment of the present specification, the formula 1 can be represented by any of the following formulas 2-1 to 2-3. [ka] [ka] [ka]

[0111] In the formulas 2-1 to 2-3, The definitions of R5, L, Z, r, a, and b are the same as those of Formula 1 above, R11 to R13 each independently represent 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.

[0112] In one embodiment of the present specification, the formula 1 can be represented by any of the following compounds, but is not limited to these.

[0113] [ka] TIFF0007759671000020.tif198165 TIFF0007759671000021.tif199165 TIFF0007759671000022.tif192165 TIFF0007759671000023.tif167165 TIFF0007759671000024.tif181165 TIFF0007759671000025.tif199165 TIFF0007759671000026.tif202165 TIFF0007759671000027.tif198165 TIFF0007759671000028.tif208165 TIFF0007759671000029.tif204165 TIFF0007759671000030.tif180165 TIFF0007759671000031.tif190165 TIFF0007759671000032.tif222165 TIFF0007759671000033.tif210165 TIFF0007759671000034.tif187165 TIFF0007759671000035.tif187165 TIFF0007759671000036.tif204165 TIFF0007759671000037.tif212165 TIFF0007759671000038.tif221165 TIFF0007759671000039.tif222165 TIFF0007759671000040.tif114165

[0114] Furthermore, heterocyclic compounds having properties specific to the introduced substituents can be synthesized by introducing various substituents into the structure of Formula 1. For example, by introducing into the core structure substituents that are primarily used in hole injection layer materials, hole transport layer materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light emitting devices, materials that satisfy the requirements for each organic layer can be synthesized.

[0115] Furthermore, by introducing various substituents into the structure of Formula 1, it is possible to finely adjust the energy band gap, while improving the properties at the interface between organic materials, thereby diversifying the applications of the material.

[0116] In one embodiment of the present specification, the device includes the first electrode; the second electrode; and one or more organic layers provided between the first electrode and the second electrode, and at least one of the organic layers contains one or more heterocyclic compounds represented by Formula 1.

[0117] In one embodiment of the present specification, at least one of the organic layers contains one kind of heterocyclic compound represented by formula 1 above.

[0118] In one embodiment of the present specification, the first electrode may be an anode and the second electrode may be a cathode.

[0119] In still other embodiments herein, the first electrode may be a cathode and the second electrode may be an anode.

[0120] 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 Formula 1 may be used as a material for the blue organic light-emitting device. For example, the heterocyclic compound represented by Formula 1 may be contained in an electron transport layer or a hole blocking layer of the blue organic light-emitting device.

[0121] 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 Formula 1 may be used as a material for the green organic light-emitting device. For example, the heterocyclic compound represented by Formula 1 may be contained in an electron transport layer or a hole blocking layer of the green organic light-emitting device.

[0122] 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 Formula 1 may be used as a material for the red organic light-emitting device. For example, the heterocyclic compound represented by Formula 1 may be contained in an electron transport layer or a hole blocking layer of the red organic light-emitting device.

[0123] The organic light-emitting device of the present specification can be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the heterocyclic compound described above.

[0124] The heterocyclic compound may be formed into an organic layer by a solution coating method as well as a vacuum deposition method during fabrication of an organic light emitting device, including, but not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, and roll coating.

[0125] The organic material layer of the organic light-emitting device of the present specification may have a single-layer structure or a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto and may include a fewer number of organic material layers.

[0126] In the organic light-emitting device of the present specification, the organic material layer may include an electron transport layer, and the electron transport layer may include the heterocyclic compound represented by Formula 1 above.

[0127] In the organic light-emitting device of the present specification, the organic material layer may include a hole-blocking layer, and the hole-blocking layer may include a heterocyclic compound represented by Formula 1 above.

[0128] The organic light-emitting device of the present invention may further include one or more layers selected from the group consisting of a light-emitting layer, a hole-injection layer, a hole-transport layer, an electron-injection layer, an electron-transport layer, an electron-blocking layer, and a hole-blocking layer.

[0129] 1 to 5 illustrate examples of the stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present specification. However, these drawings are not intended to limit the scope of the present application, and structures of organic light-emitting devices known in the art can also be applied to the present application.

[0130] 1 shows an organic light emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, the present invention is not limited to this structure, and an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate, as shown in FIG.

[0131] 3 and 4 illustrate examples in which the organic material layer has multiple layers. The organic light-emitting device of Fig. 3 includes a hole injection layer 301, a hole transport layer 302, an emitting layer 303, an electron transport layer 305, and an electron injection layer 306, while the organic light-emitting device of Fig. 4 includes a hole injection layer 301, a hole transport layer 302, an emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited to such a stacked structure. Layers other than the emitting layer may be omitted as needed, and other necessary functional layers may be further added.

[0132] The organic layer containing the heterocyclic compound represented by formula 1 may further contain other substances as necessary.

[0133] Furthermore, an organic light-emitting device according to one embodiment of the present specification includes an anode, a cathode, and two or more stacks provided between the anode and the cathode, each of the two or more stacks independently including an emitting layer, and a charge generation layer between the two or more stacks, the charge generation layer including the heterocyclic compound represented by Formula 1.

[0134] An organic light-emitting device according to one embodiment of the present specification includes an anode, a first stack including a first light-emitting layer disposed on the anode, a charge generation layer disposed on the first stack, a second stack including a second light-emitting layer disposed on the charge generation layer, and a cathode disposed on the second stack, wherein the charge generation layer may include a heterocyclic compound represented by Formula 1.

[0135] An organic light-emitting device according to one embodiment of the present specification may include a first electrode; a first stack provided on the first electrode and including a first light-emitting layer; a charge generation layer provided on the first stack; a second stack provided on the charge generation layer and including a second light-emitting layer; and the charge generation layer may include a heterocyclic compound represented by Formula 1.

[0136] An organic light-emitting device according to one embodiment of the present specification includes a first electrode; a second electrode; and an organic layer provided between the first electrode and the second electrode, the organic layer including two or more stacks, each of the two or more stacks independently including an emitting layer, and a charge is generated between the two or more stacks, and the charge generation layer includes a heterocyclic compound represented by Formula 1.

[0137] An organic light-emitting device according to one embodiment of the present specification includes a first electrode; a second electrode; and an organic layer provided between the first electrode and the second electrode, the organic layer including a first stack including a first light-emitting layer; a charge generation layer provided on the first stack; and a second stack including a second light-emitting layer provided on the charge generation layer, and the charge generation layer includes a heterocyclic compound represented by Formula 1.

[0138] In the organic light-emitting device according to one embodiment of the present specification, the charge generation layer includes an N-type charge generation layer, and the N-type charge generation layer includes the heterocyclic compound represented by Formula 1 above.

[0139] In the organic light emitting device according to one embodiment of the present specification, the charge generation layer may further include a P-type charge generation layer.

[0140] As an organic light emitting device according to one embodiment of the present specification, an organic light emitting device having a 2-stack tandem structure is exemplarily shown in FIG. 5 below.

[0141] In this case, the first electron blocking layer, the first hole blocking layer, and the second hole blocking layer shown in FIG. 5 below may be omitted in some cases.

[0142] In an organic light-emitting device according to one embodiment of the present application, materials other than the hetero compound represented by Formula 1 are exemplified below, but these are for illustrative purposes only and are not intended to limit the scope of the present application, and may be substituted with materials known in the art.

[0143] The anode material may be a material with a relatively large work function, such as a transparent conductive oxide, a metal, or a conductive polymer. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0144] The cathode material may be a material with a relatively low work function, such as a metal, a metal oxide, or a conductive polymer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structure materials such as LiF / Al or LiO / Al.

[0145] As the hole injection material, known hole injection materials can be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429 or starburst type amine derivatives described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), soluble conductive polymer polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic acid), Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / Camphor sulfonic acid, or polyaniline / Poly(4-styrenesulfonate), etc. can be used.

[0146] As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used, and low-molecular or high-molecular materials can also be used.

[0147] Examples of electron transport materials that can be used include 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, and metal complexes of 8-hydroxyquinoline and its derivatives. Not only low molecular weight materials but also high molecular weight materials can be used.

[0148] As the electron injection material, for example, LiF is typically used in the industry, but the present application is not limited thereto.

[0149] The light-emitting material may be a red, green, or blue light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. In this case, the two or more light-emitting materials may be deposited as separate sources or premixed and deposited as a single source. The light-emitting material may be a fluorescent material or a phosphorescent material. The light-emitting material may be a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, or a material in which both the host material and the dopant material contribute to light emission.

[0150] When a mixture of hosts for light-emitting materials is used, the mixture may be of the same series or different series. For example, two or more of n-type host materials or p-type host materials may be selected and used as the host material for the light-emitting layer.

[0151] The organic light emitting device according to an embodiment of the present specification may be a top-emitting type, a back-emitting type, or a dual-emitting type depending on the materials used.

[0152] The compound according to an embodiment of the present specification can also function in organic electronic devices such as organic solar cells, organic photoreceptors, and organic transistors based on the same principles as those applied to organic light-emitting devices. [Example]

[0153] The present specification will be described in more detail below through embodiments, which are merely for the purpose of illustrating the present application and are not intended to limit the scope of the present application.

[0154] [Production Example 1] Production of Compound 9 [ka]

[0155] 1) Preparation of Compound 9-1 2-Bromo-3-chlorobenzaldehyde (A) (100 g, 0.45 mol, 1 eq), ethynylbenzene (51.2 g, 0.50 mol, 1.1 eq), Pd(PPh3)2Cl2 (bis(triphenylphosphine)palladium(0) dichloride) (6.4 g, 0.009 mol, 0.02 eq), CuI (0.86 g, 0.0045 mol, 0.01 eq), and triethylamine (1000 mL) were added and stirred at 60 °C for 5 h. After the reaction was terminated by adding water, the mixture was extracted with methylene chloride (MC) and water. The water was then removed with anhydrous Na2CO3. Compound 9-1 (85 g, 77% yield) was obtained by separation on a silica gel column.

[0156] 2) Preparation of Compound 9-2 Compound 9-1 (170 g, 0.70 mol, 1 eq) and TsNHNH2 (p-toluenesulfonylhydrazide) (144 g, 0.77 mol, 1.1 eq) were added to ethanol (EtOH) (3400 ml) and stirred at room temperature for 1 hour. The resulting solid was filtered and dried to give compound 9-2 (174 g, 60% yield).

[0157] 3) Preparation of Compound 9-3 Compound 9-2 (40 g, 0.097 mol, 1 eq) and AgOTf (silver trifluoromethanesulfonate) (3.8 g, 0.014 mol, 0.15 eq) were added to EtOH (800 ml) and stirred at 70 °C for 2 hours. 1,2-diphenylethanone (B) (38.4 g, 0.19 mol, 2 eq) and K3PO4 (62.3 g, 0.29 mol, 3 eq) were added and stirred at 70 °C for 7 hours. After the reaction was terminated by adding water, the mixture was extracted with MC and water. Water was then removed with anhydrous Na2CO3. Compound 9-3 (62 g, 34% yield) was obtained by separation on a silica gel column.

[0158] 4) Preparation of Compound 9-4 Compound 9-3 (10 g, 0.023 mol, 1 eq), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (5.9 g, 0.035 mol, 1.5 eq), KOAc (potassium acetate) (6.8 g, 0.06 The resulting mixture was stirred at 80°C for 6 hours in a 100 ml solution of 9 mol (3 eq), Pd(dba)2 (bis(dibenzylideneacetone)palladium(0)) (1.3 g, 0.0023 mol, 0.1 eq), Xphos (2-dicyclohexylphospino-2',4',6'-triisopropylbiphenyl) (2.2 g, 0.0046 mol, 0.2 eq), and 1,4-dioxane (100 ml). The mixture was quenched by adding water, and then extracted with MC and water. The water was then removed with anhydrous Na2CO3. Compound 9-4 (9 g, 74% yield) was obtained by separation on a silica gel column.

[0159] 5) Preparation of Compound 9 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), KPO (8.1 g, 0.038 mol, 2 eq), and Pd(PPh) (tetrakis(triphenylphosphine)palladium(0)) (11.1 g, 0.0009 mol, 0.05 eq) were added to 1,4-dioxane (100 ml) and HO (25 ml) and stirred at 80 °C for 6 h. The resulting solid was filtered and dried to give compound 9 (11 g, 81% yield).

[0160] Compounds were synthesized in the same manner as in Production Example 1, except that intermediate A in Table 1 below was used in place of 2-bromo-3-chlorobenzaldehyde (A), intermediate B in Table 1 below was used in place of 1,2-diphenylethanone (B), and intermediate C in Table 1 below was used in place of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (C).

[0161] [Table 1] TIFF0007759671000043.tif217161 TIFF0007759671000044.tif222161 TIFF0007759671000045.tif83161

[0162] The compounds were produced in the same manner as in the above production examples, and the synthesis confirmation results are shown in Tables 2 and 3. 1 Table 3 shows the results of measurements by FD-MS (Field desorption mass spectrometry).

[0163] [Table 2] JPEG0007759671000047.jpg162161

[0164] [Table 3]

[0165] [Experimental Example] <Experimental Example 1> 1) Fabrication of organic light-emitting devices Comparative Example 1 A transparent electrode ITO (indium tin oxide) thin film obtained from OLED glass (Samsung Corning) was ultrasonically cleaned using trichloroethylene, acetone, ethanol, and distilled water, respectively, for 5 minutes each, and then stored in isopropanol before use. Next, the ITO substrate was placed in a substrate holder of a vacuum deposition system, and 4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell inside the vacuum deposition system. [ka]

[0166] Then, the vacuum in the chamber was reduced to 10 -6 After evacuating the chamber to 1000 torr, a current was applied to the cell to evaporate 2-TNATA, depositing a 600 Å-thick hole-injection layer on the ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell in the vacuum evaporation system, and a current was applied to the cell to evaporate it, depositing a 300 Å-thick hole-transport layer on the hole-injection layer. [ka]

[0167] After forming the hole injection layer and hole transport layer in this way, a blue light-emitting material with the following structure was deposited thereon as an emitting layer: Specifically, a blue light-emitting host material H1 was vacuum-deposited in one cell of a vacuum deposition apparatus to a thickness of 200 Å, and a blue light-emitting dopant material D1 was vacuum-deposited thereon at a concentration of 5% relative to the host material. [ka]

[0168] Next, as an electron transport layer, a compound of the following structural formula E1 was vapor-deposited to a thickness of 300 Å. [ka]

[0169] An OLED device was fabricated by depositing lithium fluoride (LiF) to a thickness of 10 Å as an electron injection layer and forming an Al cathode to a thickness of 1,000 Å.

[0170] On the other hand, all organic compounds required for manufacturing OLED elements are 10 -8 ~10 -6 It was purified by vacuum sublimation under torr and used for OLED fabrication.

[0171] Examples 1 to 23 and Comparative Examples 2 to 5 An organic electroluminescent device was produced 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.

[0172] 2) Evaluation of organic light-emitting devices The driving voltage, luminous efficiency, color coordinate (CIE), and lifespan of the blue organic light emitting device manufactured according to the present invention were measured, and the results are shown in Table 4.

[0173] [Table 4] TIFF0007759671000054.tif31161

[0174] As can be seen from the results in Table 4, the organic light-emitting device using the electron transport layer material for the blue organic light-emitting device of the present invention had a lower driving voltage and significantly improved luminous efficiency and lifespan compared to Comparative Examples 1 to 5.

[0175] The reason for this result is believed to be that when the invented compound having appropriate length, strength, and flat properties is used as an electron transport layer, it receives electrons under certain conditions to form an excited state compound, and in particular, when an excited state of the hetero skeletal portion of the compound is formed, the excited energy should be transferred to a stable state before the excited hetero skeletal portion undergoes a different reaction, and the relatively stable compound can efficiently transfer electrons without decomposition or destruction of the compound. For reference, compounds that have a stable state when excited are thought to be aryl, acene compounds, or polycyclic hetero compounds.

[0176] Therefore, it is believed that the compound of the present invention has improved electron-transporting properties or stability, and is excellent in all aspects of operation, efficiency, and lifespan.

[0177] <Experimental Example 2> 1) Fabrication of organic light-emitting devices Comparative Example 6 A transparent electrode ITO thin film obtained from OLED glass (Samsung Corning) was ultrasonically cleaned using trichloroethylene, acetone, ethanol, and distilled water, respectively, for 5 minutes each, and then stored in isopropanol before use. Next, the ITO substrate was placed in a substrate holder in a vacuum deposition system, and 4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell inside the vacuum deposition system. [ka]

[0178] Then, the vacuum in the chamber was reduced to 10 -6 After evacuating the chamber to 1000 volts, a current was applied to the cell to evaporate 2-TNATA, depositing a 600 Å-thick hole-injection layer on the ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell in the vacuum evaporation system, and a current was applied to the cell to evaporate it, depositing a 300 Å-thick hole-transport layer on the hole-injection layer. [ka]

[0179] After forming the hole injection layer and hole transport layer in this way, a blue light-emitting material with the following structure was deposited thereon as an emitting layer: Specifically, a blue light-emitting host material H1 was vacuum-deposited in one cell of a vacuum deposition apparatus to a thickness of 200 Å, and a blue light-emitting dopant material D1 was vacuum-deposited on top of that at a concentration of 5% relative to the host material. [ka]

[0180] Next, as an electron transport layer, a compound of the following structural formula E1 was vapor-deposited to a thickness of 300 Å. [ka]

[0181] The OLED device was fabricated by depositing lithium fluoride (LiF) to a thickness of 10 Å as the electron injection layer and by depositing an Al cathode to a thickness of 1,000 Å. Meanwhile, all organic compounds required for the fabrication of the OLED device were deposited in a thickness of 10 Å. -8 ~10 -6It was purified by vacuum sublimation under torr and used for OLED fabrication.

[0182] Examples 24 to 46 and Comparative Examples 7 to 10 An organic electroluminescent device was fabricated in the same manner as in Comparative Example 6, except that an electron transport layer E1 was formed to a thickness of 250 Å, and then a hole blocking layer containing the compound shown in Table 5 was formed to a thickness of 50 Å on the electron transport layer.

[0183] 2) Evaluation of organic light-emitting devices The driving voltage, luminous efficiency, color coordinate (CIE), and lifespan of the blue organic light emitting device manufactured according to the present invention were measured, and the results are shown in Table 5.

[0184] [Table 5] TIFF0007759671000060.tif32161

[0185] As can be seen from the results in Table 5, the organic light-emitting device using the hole-blocking layer material for the blue organic light-emitting device of the present invention had a lower driving voltage and significantly improved luminous efficiency and lifespan compared to Comparative Examples 6 to 10.

[0186] The reason for this is that holes are not bound in the light-emitting layer and move to the cathode through the electron transport layer, which reduces the efficiency and lifespan of the OLED device. To prevent this, if a compound with a deep HOMO level is used as a hole-blocking layer, holes that attempt to move to the cathode through the light-emitting layer are blocked by the energy barrier of the hole-blocking layer.

[0187] Therefore, the probability that holes and electrons form excitons increases, and the probability that light is emitted from the light-emitting layer increases, which is considered to be excellent in all respects of operation, efficiency, and lifespan of the organic light-emitting device.

[0188] <Experimental Example 3> 1) Fabrication of organic light-emitting devices Examples 47 to 69 and Comparative Examples 11 to 15 A glass substrate coated with a thin ITO film at a thickness of 1500 Å was ultrasonically cleaned with distilled water. After the distilled water cleaning, it 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 plasma treated in a vacuum to remove the ITO work function and residual film, before being transferred to a thermal evaporation system for organic deposition.

[0189] A two-stack WOLED (White Organic Light Device) structure was formed on the ITO transparent electrode (anode). For the first stack, TAPC was first thermally evaporated to a thickness of 300 Å to form a hole transport layer. After the hole transport layer was formed, an emitting layer was then thermally evaporated on top of it as follows: The emitting layer was formed by doping 8% of FIrpic, a blue phosphorescent material, into the host TCz1 and depositing it at 300 Å. The electron transport layer was formed at 400 Å using TmPyPB, and then a charge generation layer was formed at 100 Å by doping 20% ​​of Cs2CO3 with the compound listed in Table 6 below.

[0190] The second stack was first formed by thermal vacuum deposition of MoO3 to a thickness of 50 Å to form a hole injection layer. The common layer, the hole transport layer, was formed by depositing TAPC with 20% MoO3 to a thickness of 100 Å, followed by deposition of TAPC to a thickness of 300 Å. し On top of that, the light-emitting layer is a host TC Z 1 was doped with 8% Ir(ppy)3, a green phosphorescent dopant, and vapor-deposited to a thickness of 300 Å. Then, a 600 Å electron transport layer was formed using TmPyPB. Finally, lithium fluoride (LiF) was vapor-deposited to a thickness of 10 Å on the electron transport layer to form an electron injection layer. An aluminum (Al) cathode was vapor-deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby fabricating an organic light-emitting device.

[0191] On the other hand, all organic compounds required for manufacturing OLED elements are 10 -8 ~10 -6It was purified by vacuum sublimation under torr and used for OLED fabrication. [ka]

[0192] 2) Driving voltage and luminous efficiency of organic light-emitting devices The electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured using the M7000 manufactured by Mac Science, and the reference luminance was measured using the lifespan measurement device (M6000) manufactured by Mac Science. 2 When T 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 invention were measured, and the results are shown in Table 6.

[0193] [Table 6] TIFF0007759671000063.tif31161

[0194] As can be seen from the results in Table 6, the organic light-emitting devices using the charge generating layer materials of the two-stack white organic light-emitting devices of the present invention had lower driving voltages and improved luminous efficiency compared to Comparative Examples 11 to 15.

[0195] The reason for these results is believed to be that the compound of the present invention, used as an N-type charge generation layer consisting of an inventive skeleton with appropriate length, strength, and flatness characteristics and an appropriate heterocyclic compound capable of bonding to a metal, was doped with an alkali metal or alkaline earth metal to form a gap state in the N-type charge generation layer, which facilitates electron injection into the electron transport layer through the gap state formed in the N-type charge generation layer. Therefore, the P-type charge generation layer can improve electron injection and electron transport in the N-type charge generation layer, which is believed to result in lower driving voltage and improved efficiency and lifespan of the organic light emitting device. [Explanation of symbols]

[0196] 100... Substrate 200...Anode 300...organic layer 301 Hole injection layer 302 Hole transport layer 303 Light-emitting layer 304: Hole blocking layer 305...electron transport layer 306...electron injection layer 400...Cathode

Claims

1. A heterocyclic compound represented by the following formula 1: 【Chemical 1】 In the formula 1, at least two of R1 to R3 are each independently a cyano group; an alkyl group having 1 to 10 carbon atoms which is substituted or unsubstituted with a substituent selected from the group consisting of deuterium and a cyano group; or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with a substituent selected from the group consisting of deuterium and a cyano group, and the rest are hydrogen or deuterium; R4 and R5 are each independently hydrogen or deuterium; L 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; Z is an anthracenyl group substituted or unsubstituted with a naphthyl group or a biphenyl group; a phosphine oxide group substituted or unsubstituted with an alkyl group, or any one selected from the following structural formulas: 【Chemistry 7】 In the structural formula: R31 and R32 each independently represent 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; R33 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; r is an integer from 0 to 3; a and b are each an integer from 1 to 5; When r, a and b are each 2 or more, the substituents in parentheses may be the same or different.

2. The heterocyclic compound according to claim 1, wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-4: 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 In the formulas 1-1 to 1-4, the definitions of R1 to R4, L, Z, a, and b are the same as those in formula 1.

3. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any of the following compounds: 【Chemistry 8】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

4. An organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer provided between the first electrode and the second electrode, The organic light-emitting device, wherein the organic layer contains one or more heterocyclic compounds according to any one of claims 1 to 3.

5. The organic layer includes an electron transport layer, The organic light-emitting device according to claim 4 , wherein the electron transport layer contains the heterocyclic compound.

6. The organic layer includes a hole blocking layer, The organic light-emitting device according to claim 4 , wherein the hole-blocking layer contains the heterocyclic compound.

7. The organic light-emitting element described in Claim 4, further comprising one layer selected from the group consisting of an 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.

8. The organic light-emitting element comprises: a first stack provided on the first electrode and including a first light-emitting layer; a charge-generating layer provided on the first stack; and a second stack provided on the charge-generating layer and including a second light-emitting layer; The organic light-emitting device according to claim 4 , wherein the second electrode is provided on the second stack.

9. The organic light-emitting element described in Claim 8, wherein the charge generation layer contains the heterocyclic compound.

10. The organic light-emitting element described in Claim 9, wherein the charge generation layer includes an N-type charge generation layer, and the N-type charge generation layer includes the heterocyclic compound.

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