Heterocyclic compound and organic light emitting device comprising same

Abstract

To provide a heterocyclic compound and an organic light-emitting element containing the same.SOLUTION: According to an embodiment of the present invention, a heterocyclic compound represented by a specific chemical formula is provided. The organic light-emitting device includes a first electrode, an organic layer, and a second electrode, wherein the organic layer includes the heterocyclic compound described above.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] (CROSS-REFERENCE TO RELATED APPLICATIONS AND PRIORITY CLAIMS) This application claims the benefit of priority based on Korean Patent Application No. 10-2024-0094507, filed on July 17, 2024, the entire contents of which are incorporated herein by reference.

[0002] FIELD OF THE INVENTION The present disclosure relates to heterocyclic compounds and organic light-emitting devices containing the same. [Background technology]

[0003] An organic light emitting display (OLED) device includes organic light emitting elements that emit light. Because OLED displays do not require a separate light source, they offer a wide viewing angle, fast response speed, and improved contrast and brightness.

[0004] In an organic light-emitting device, an organic light-emitting layer is formed for each pixel, and the organic light-emitting layer can be interposed between opposing electrodes. Holes and electrons injected from each electrode recombine in the organic light-emitting layer to generate excitons, which then emit light by releasing energy.

[0005] In order to realize organic light-emitting devices with high efficiency and long life, materials to be applied to the organic light-emitting layer have been researched. Summary of the Invention [Problem to be solved by the invention]

[0006] One object of the present disclosure is to provide novel heterocyclic compounds.

[0007] One object of the present disclosure is to provide an organic light-emitting device containing the heterocyclic compound. [Means for solving the problem]

[0008] The heterocyclic compound according to the present disclosure is represented by the following chemical formula 1: [ka] In the above Chemical Formula 1, one of R1 to R8 is a substituent represented by the following Chemical Formula 2: the remainders are each independently selected from the group consisting of hydrogen; deuterium; halogen; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; -SiRR'R"; and -P(=O)RR'; R, R', and R" are each independently hydrogen; deuterium; -CN; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 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; [ka] In the above chemical formula 2, R 11 and R 12 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, L1, L2, and L3 each independently represent 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; a, b, and c each independently represent 0 or an integer of 1 to 5; When a is an integer of 2 to 5, a plurality of L1's may be the same or different, When b is an integer of 2 to 5, a plurality of L2's may be the same or different, When c is an integer of 2 to 5, multiple L3s are the same or different, R9 and R 10 Either one of the two is -(L4)nR 13 and the other is hydrogen or deuterium, L4 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; n is an integer of 1 to 5, and when n is an integer of 2 to 5, multiple L4s are the same or different, R 13 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, * indicates the bonding site with the adjacent atom.

[0009] The organic light-emitting device according to the present disclosure includes a first electrode, a second electrode disposed on the first electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein one or more of the organic layers contains the heterocyclic compound. [Effects of the Invention]

[0010] The heterocyclic compound according to the present disclosure can be used as a material for the organic layer of an organic light-emitting device. The heterocyclic compound includes a five-ring fused ring structure containing a benzofuran moiety, and an aryl group attached to the third ring and an aminoaryl group attached to the terminal ring, thereby enabling the compound to have suitable hole or electron mobility. This improves the stability of the compound, preventing decomposition or deformation of the compound when the organic light-emitting device is driven, and allowing for efficient transport of electrons or holes.

[0011] In addition, the band gap can be adjusted by adjusting the bonding position of the substituent of the heterocyclic compound, and the heterocyclic compound can be suitable for use as a material for a hole transport layer, a hole transport assisting layer, or an electron blocking layer of an organic light emitting device.

[0012] An organic light emitting device including the heterocyclic compound may have a low driving voltage, high device efficiency, or improved life characteristics. [Brief explanation of the drawings]

[0013] [Figure 1] FIG. 1 is a diagram schematically illustrating a layered structure of an organic light-emitting device according to an embodiment of the present disclosure. [Figure 2] FIG. 2 is a diagram schematically illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present disclosure. [Figure 3] FIG. 3 is a diagram schematically illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present disclosure. DETAILED DESCRIPTION OF THE INVENTION

[0014] Exemplary embodiments of the present disclosure will now be described in detail with reference to the accompanying drawings, which are merely illustrative and not limiting of the present disclosure.

[0015] In this specification, unless otherwise specified, when a part "comprises" a certain component, it does not exclude other components and means that it may further include other components.

[0016] In this specification, "*" in a chemical formula indicates the position of binding.

[0017] As used herein, "substitution" means that any hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent. The position of 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, "substituted or unsubstituted" means deuterium; a halogen group; -CN; an alkyl group having 1 to 60 carbon atoms; an alkenyl group having 2 to 60 carbon atoms; an alkynyl group having 2 to 60 carbon atoms; a haloalkyl group having 1 to 60 carbon atoms; an alkoxy group having 1 to 60 carbon atoms; an aryloxy group having 6 to 60 carbon atoms; an alkylthioxy group having 1 to 60 carbon atoms; an arylthioxy group having 6 to 60 carbon atoms; an alkylsulfoxy group having 1 to 60 carbon atoms; an arylsulfoxy group having 6 to 60 carbon atoms; a cycloalkyl group having 3 to 60 carbon atoms; a heterocycloalkyl group having 2 to 60 carbon atoms; a cycloalkyl group having 6 to 60 carbon atoms; a hetero ... R, R', and R" are each independently a substituent consisting of at least one of hydrogen; deuterium; a halogen atom; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group.

[0019] 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 Since H, Deuterium) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0020] In this specification, "when no substituent is shown in the chemical formula or compound structure," may mean that all positions substitutable as substituents are hydrogen or deuterium. In other words, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be deuterium, which is also an isotope. In this case, the deuterium content may be 0% to 100%.

[0021] If no substituents are indicated in the chemical formula or structure of a compound, the deuterium content is 0%, the hydrogen content is 100%, and if none of the substituents explicitly exclude deuterium, such as hydrogen, then a mixture of hydrogen and deuterium may be used in the compound.

[0022] Deuterium is an isotope of hydrogen, and has a deuteron nucleus, which consists of one proton and one neutron. It can be expressed as hydrogen-2 and its atomic symbol is D or 2 It can be written as H.

[0023] An isotope is an atom with the same atomic number (Z) but a different mass number (A). Isotopes can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0024] In this specification, the content T% of specific substituents 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.

[0025] In one example, [ka] In a phenyl group represented by the formula (I), 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). In other words, a phenyl group having a deuterium content of 20% can be expressed by the following structural formula.

[0026] [ka]

[0027] Also, a "phenyl group with a deuterium content of 0%" can mean a phenyl group having five hydrogen atoms and no deuterium atoms.

[0028] As used herein, halogen may be fluorine, chlorine, bromine, or iodine.

[0029] In this specification, an 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, 1 to 40, or 1 to 20. For example, 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-ethyl ... Examples of alkyl groups include, but are not limited to, butyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl groups.

[0030] In this specification, the term "alkenyl group" refers to a straight or branched chain alkenyl group having 2 to 60 carbon atoms, which may be further substituted with other substituents. The alkenyl group may have 2 to 60, 2 to 40, or 2 to 20 carbon atoms. Examples of alkenyl groups include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, and styrenyl groups.

[0031] In this specification, an alkynyl 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 alkynyl group may be 2 to 60, 2 to 40, or 2 to 20.

[0032] As used herein, haloalkyl refers to an alkyl group substituted with a halogen group, such as, but not limited to, -CF3, -CF2CF3, and the like.

[0033] In this specification, the term "cycloalkyl group" refers to a monocyclic or polycyclic group having 3 to 60 carbon atoms, which may be further substituted with other substituents. Here, "polycyclic" refers to a group in which a cycloalkyl group is directly linked 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, 3 to 40, or 5 to 20. 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, a heterocycloalkyl group contains at least one heteroatom selected from O, S, Se, N, and Si, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, which may be further substituted with other substituents. Here, "polycyclic" refers to a group in which a heterocycloalkyl group is directly linked 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, 2 to 40, or 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, "polycyclic" means a group in which an aryl group is directly linked 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, 6 to 40, or 6 to 25. Specific examples of the aryl group include, but are not limited to, a phenyl group, a biphenyl 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 structures:

[0037] [ka]

[0038] As used herein, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0039] The substituted fluorenyl group can be represented by the following structural formulas, but is not limited thereto.

[0040] [ka]

[0041] In this specification, an alkoxy group is represented by -O(R101), and the above-mentioned examples of alkyl groups can be applied to R101.

[0042] In this specification, the aryloxy group is represented by -O(R102), and the above-mentioned examples of the aryl group can be applied to R102.

[0043] In this specification, an alkylthioxy group is represented by -S(R103), and the above-mentioned examples of alkyl groups can be applied to R103.

[0044] In this specification, an arylthioxy group is represented by -S(R104), and the above-mentioned examples of the aryl group can be applied to R104.

[0045] In this specification, the alkylsulfoxy group is represented by -S(=O)2(R105), and the alkyl groups mentioned above can be applied to R105.

[0046] In this specification, the arylsulfoxy group is represented by -S(=O)2(R106), and the above-mentioned examples of the aryl group can be applied to R106.

[0047] In this specification, the heteroaryl group contains at least one heteroatom selected from S, O, Se, N, and Si, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, which may be further substituted with other substituents. Here, the "polycyclic" refers to a group in which a heteroaryl group is directly linked to or fused with another cyclic group. 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, 2 to 40, or 3 to 25.Examples of the heteroaryl group include a pyridine group, a pyrrole group, a pyrimidine group, a pyridazine group, a furan group, a thiophene group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, a triazole group, a furazan group, an oxadiazole group, a thiadiazole group, a dithiazole group, a tetrazolyl group, a pyran group, a thiopyran group, a diazine group, an oxazine group, a thiazine group, a dioxin group, a triazine group, a tetrazine group, and a quinoline group. group, isoquinoline group, quinazoline group, isoquinazoline group, quinozoline group, naphthyridine group, acridine group, phenanthridine group, imidazopyridine group, diazanaphthalene group, triazaindene group, indole group, indolizine group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazole group, benzocarbazole group, dibenzocarbazole group, phenazine group, dibenzosilole group, spirobi(dibenzosilole), dihydrophenazine group, phenoxazine group, phenanthridine group, thienyl group, indolo[2,3-a]carbazole group, indolo[2,3-b]carbazole group, indoline group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridine group, phenantrazine group, phenothiathiazine group, phthalazine group, phenanthroline group, naphthobenzofuran group, naphthobenzothiophene group Examples of the dihydrobenzo[b]thiophene group include, but are not limited to, a benzo[c][1,2,5]thiadiazole group, a 2,3-dihydrobenzo[b]thiophene group, a 2,3-dihydrobenzofuran group, a 5,10-dihydrodibenzo[b,e][1,4]azasiline group, a pyrazolo[1,5-c]quinazoline group, a pyrido[1,2-b]indazole group, a pyrido[1,2-a]imidazo[1,2-e]indoline group, and a 5,11-dihydroindeno[1,2-b]carbazole group.

[0048] In this specification, when a substituent is a carbazole group, it means that it is bonded to the nitrogen or carbon of the carbazole.

[0049] Herein, when the carbazole group is substituted, it may be substituted with additional substituents on the nitrogen or carbon of the carbazole.

[0050] As used herein, examples of benzocarbazole groups may be any one of the following structures:

[0051] [ka]

[0052] As used herein, examples of dibenzocarbazole groups may be any one of the following structures:

[0053] [ka]

[0054] As used herein, examples of naphthobenzofuran groups may be any one of the following structures:

[0055] [ka]

[0056] As used herein, examples of naphthobenzothiophene groups may be any one of the following structures:

[0057] [ka]

[0058] Among the substituents, -SiRR'R" is a silyl group, which is a substituent containing Si and in which the Si atom is directly linked as a radical. R, R' and R" may be the same or different from one another and may each independently 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; a heterocycloalkyl group; an aryl group; and a heteroaryl group. Examples of silyl groups include: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] These include, but are not limited to:

[0059] Among the substituents, -P(=O)RR' is a phosphine oxide group, and R and R' 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, a heterocycloalkyl group, an aryl group, and a heteroaryl group, or may be an alkyl group or an aryl group. The alkyl group and the aryl group can be the same as or different from the alkyl group and the aryl group. For example, the phosphine oxide group may be, but is not limited to, a dimethylphosphine oxide group, a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like.

[0060] Among the substituents, -NRR' is an amine group, and R and R' 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, a heterocycloalkyl group, an aryl group, and a heteroaryl group. The amine group can 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 preferably is 1 to 30. 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.

[0061] In this specification, the arylene group is a divalent group, but the examples of the aryl group described above can be applied.

[0062] In this specification, the heteroarylene group is a divalent group, but the examples of the heteroaryl group described above can be applied.

[0063] As used herein, the term "adjacent" groups may refer to a substituent substituted on an atom directly linked 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.

[0064] The hydrocarbon ring and hetero ring capable of forming the adjacent group include an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aliphatic hetero ring, and an aromatic hetero ring, and the structures exemplified above as the cycloalkyl group, aryl group, heterocycloalkyl group, and heteroaryl group, respectively, can be applied, except that the ring is not a monovalent group.

[0065] In general, hydrogen-bonded compounds and deuterium-substituted compounds exhibit different thermodynamic behaviors because the mass of the deuterium atom is twice as large as that of hydrogen, and the difference in atomic mass results in deuterium having lower vibrational energy.

[0066] In addition, the single bond dissociation energy (BDE) between carbon and deuterium is higher than that between carbon and hydrogen. Therefore, the structure substituted with deuterium increases the thermal stability of the molecule, which has the effect of improving the lifespan of devices using it.

[0067] When a compound is deposited on a silicon wafer, materials containing deuterium tend to be packed closer together with tighter intermolecular distances. Also, when observing the thin film surface using an atomic force microscope (AFM), it can be seen that thin films made with compounds containing deuterium are deposited with a more uniform surface without any aggregation.

[0068] The heterocyclic compound of Chemical Formula 1 of the present disclosure has a deuterium substitution rate of more than 0% to 100%. When deuterium is substituted, the ground state energy is lower than that of a hydrogen-substituted compound, and as the carbon-deuterium bond length shortens, the molecular hardcore volume (MHV) decreases. This reduces the electrical polarization (EP) and weakens intermolecular interactions, resulting in a more stable stacking structure during device fabrication.

[0069] This property creates an amorphous state in the thin film and reduces the crystallinity. In other words, the heterocyclic compound of Chemical Formula 1 is effective in improving the heat resistance of OLED devices, thereby improving their lifespan and driving characteristics.

[0070] The heterocyclic compound according to the present disclosure is represented by the following chemical formula 1:

[0071] [ka]

[0072] In Chemical Formula 1, one of R1 to R8 is a substituent represented by Chemical Formula 2 below, and the rest are each independently selected from the group consisting of hydrogen; deuterium; halogen; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; -SiRR'R"; and -P(=O)RR'.

[0073] R, R', and R" are each independently hydrogen; deuterium; -CN; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 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.

[0074] [ka]

[0075] In the above chemical formula 2, R 11 and R 12 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.

[0076] L1, L2 and L3 each independently represent 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.

[0077] a, b, and c each independently represent 0 or an integer of 1 to 5.

[0078] When a is an integer of 2 to 5, the multiple L1s may be the same or different.

[0079] When b is an integer of 2 to 5, the multiple L2s may be the same or different.

[0080] When c is an integer of 2 to 5, the multiple L3s may be the same or different.

[0081] R9 and R 10 Either one of -L4-R 13 and the other is hydrogen or deuterium.

[0082] L4 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.

[0083] R 13 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0084] * indicates the bonding site with the adjacent atom.

[0085] According to an exemplary embodiment, one of R1 to R8 in Chemical Formula 1 is a substituent represented by Chemical Formula 2. The substituent represented by Chemical Formula 2 is an arylamine group, and may be bonded to a terminal ring of the five-ring fused ring in Chemical Formula 1.

[0086] According to an exemplary embodiment, one of R1 to R4 in Chemical Formula 1 may be a substituent represented by Chemical Formula 2.

[0087] According to an exemplary embodiment, one of R5 to R8 in Chemical Formula 1 may be a substituent represented by Chemical Formula 2.

[0088] According to an exemplary embodiment, in Formula 2, R 11 and R 12 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. 11 and R 12 R may each independently be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms. 11 and R 12 may be the same or different from each other.

[0089] For example, in the above-mentioned Chemical Formula 2, R 11 and R 12may each 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 substituted or unsubstituted anthryl group; a substituted or unsubstituted dimethylfluorenyl group; a substituted or unsubstituted diethylfluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted furan group; a substituted or unsubstituted thiophene group; a substituted or unsubstituted benzofuran group; a substituted or unsubstituted benzothiophene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted carbazole group; or a combination thereof.

[0090] For example, in the above-mentioned Chemical Formula 2, R 11 and R 12 may each independently be a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; a deuterium-substituted or unsubstituted terphenyl group; a deuterium-substituted or unsubstituted naphthyl group; a deuterium-substituted or unsubstituted dimethylfluorenyl group; a deuterium-substituted or unsubstituted diphenylfluorenyl group; a deuterium-substituted or unsubstituted spirobifluorenyl group; a deuterium-substituted or unsubstituted furan group; a deuterium-substituted or unsubstituted thiophene group; a deuterium-substituted or unsubstituted benzofuran group; a deuterium-substituted or unsubstituted benzothiophene group; a deuterium-substituted or unsubstituted dibenzofuran group; a deuterium-substituted or unsubstituted dibenzothiophene group; a deuterium-substituted or unsubstituted anthryl group; a deuterium-substituted or unsubstituted carbazole group; or a combination thereof.

[0091] According to exemplary embodiments, in Chemical Formula 2, L1, L2, and L3 may each independently represent 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. According to some embodiments, in Chemical Formula 2, L1, L2, and L3 may each independently represent 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 15 carbon atoms. L1, L2, and L3 may be the same or different.

[0092] According to an exemplary embodiment, in Chemical Formula 2, L1, L2, and L3 may each independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 10 carbon atoms, such as a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthalene group.

[0093] According to an exemplary embodiment, in the above Chemical Formula 2, L1, L2, and L3 may each independently be a direct bond or an arylene group having 6 to 20 carbon atoms and which may or may not be substituted with deuterium.

[0094] According to an exemplary embodiment, L1, L2, and L3 may each independently be a direct bond, a deuterium-substituted or unsubstituted phenylene group, or a deuterium-substituted or unsubstituted naphthylene group.

[0095] According to an exemplary embodiment, in Chemical Formula 2, a, b, and c are each independently 0 or an integer of 1-5.

[0096] In the above chemical formula 2, when a is an integer of 2 to 5, multiple L1s are the same or different from each other; when b is an integer of 2 to 5, multiple L2s are the same or different from each other; and when c is an integer of 2 to 5, multiple L3s are the same or different from each other.

[0097] According to an exemplary embodiment, in Chemical Formula 2, a, b, and c may each independently be 0, 1, or 2.

[0098] According to an exemplary embodiment, the chemical formula 2 can be represented by any one of the following chemical formulas 2-1 to 2-8.

[0099] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0100] In the above chemical formulas 2-1 to 2-8, L2, L3, b, c, R 11 and R 12 is as defined in Chemical Formula 2 above.

[0101] In the above chemical formulas 2-1 to 2-8, R a , R b , R b ' and R c may each be hydrogen or deuterium. p, q and r are each independently 0 or an integer of 1 to 4, and q' may be 0 or an integer of 1 to 8.

[0102] According to an exemplary embodiment, p may be 0, 3 or 4.

[0103] According to an exemplary embodiment, q may be 0, 3 or 4.

[0104] According to an exemplary embodiment, q' may be 0, 1, 2, 3, 7 or 8.

[0105] According to an exemplary embodiment, r may be 0, 3 or 4.

[0106] According to an exemplary embodiment, when p, q, q′, and r are each independently an integer greater than or equal to 2, a plurality of R a , R b , R b ' and R c may be the same or different.

[0107] According to an exemplary embodiment, the remaining R1 to R8 in Chemical Formula 1 that are not in Chemical Formula 2 are each independently selected from the group consisting of hydrogen; deuterium; halogen; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; -SiRR'R"; and -P(=O)RR'.

[0108] According to an exemplary embodiment, in Chemical Formula 1, one of R1 to R4 is a substituent represented by Chemical Formula 2, and the remaining R5 to R8 may each independently be selected from the group consisting of hydrogen; deuterium; halogen; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; -SiRR'R"; and -P(=O)RR'.

[0109] According to an exemplary embodiment, in Chemical Formula 1, one of R5 to R8 is a substituent represented by Chemical Formula 2, and the remaining R1 to R4 may each independently be selected from the group consisting of hydrogen; deuterium; halogen; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; -SiRR'R"; and -P(=O)RR'.

[0110] According to an exemplary embodiment, in Chemical Formula 1, the remaining R1 to R8 that are not in Chemical Formula 2 may each independently be hydrogen or deuterium.

[0111] According to an exemplary embodiment, in Chemical Formula 1, the remaining R1 to R4 that are not in Chemical Formula 2 and R5 to R8 may each independently be hydrogen or deuterium.

[0112] According to an exemplary embodiment, in Chemical Formula 1, the remaining R5 to R8 that are not in Chemical Formula 2 and R1 to R4 may each independently be hydrogen or deuterium.

[0113] According to an exemplary embodiment, in Formula 1, R and R 10 Either one of the two is -(L4)mR 13 and the other is hydrogen or deuterium.

[0114] In an exemplary embodiment, R9 is -(L4)nR 13 and R 10 may be hydrogen or deuterium.

[0115] In an exemplary embodiment, R 10 Ha-(L4)nR 13 and R9 may be hydrogen or deuterium.

[0116] n may be an integer of 1 to 5. In some embodiments, n may be 1 or 2. For example, when n is an integer of 2 to 5, multiple L4s may be the same or different from each other.

[0117] L4 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.

[0118] In an exemplary embodiment, L4 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.

[0119] In an exemplary embodiment, L4 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 15 carbon atoms.

[0120] In exemplary embodiments, L4 may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0121] In exemplary embodiments, L4 can be a direct bond; a deuterium-substituted or unsubstituted phenylene group; or a deuterium-substituted or unsubstituted biphenylene group.

[0122] R 13 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0123] In an exemplary embodiment, R 13 is 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.

[0124] In an exemplary embodiment, R 13 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms.

[0125] In an exemplary embodiment, R 13 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted anthracene group; a substituted or unsubstituted triphenylene group; or a combination thereof.

[0126] In an exemplary embodiment, R 13 may be a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted naphthyl group; a deuterium-substituted or unsubstituted biphenyl group; a deuterium-substituted or unsubstituted anthracene group; a deuterium-substituted or unsubstituted triphenylene group; or a combination thereof.

[0127] In an exemplary embodiment, R and R 10One of them may be represented by any one of the following chemical formulas 3-1 to 3-6, and the remaining one may be hydrogen or deuterium.

[0128] [ka] [ka] [ka] [ka] [ka] [ka]

[0129] In the above chemical formulas 3-1 to 3-6, R d , R d1 , R d2 , R d3 , R e and R f are hydrogen or deuterium, respectively.

[0130] In Chemical Formula 3-1 to Chemical Formula 3-6, s may be 0 or an integer of 1 to 4. s1 may be 0 or an integer of 1 to 3, and s2 and s3 may each independently be 0 or an integer of 1 to 4. t may be 0 or an integer of 1 to 5. u may be 0 or an integer of 1 to 5.

[0131] According to an exemplary embodiment, s may be 0, 1, 2, 3 or 4.

[0132] According to an exemplary embodiment, s1 may be 0, 1, 2 or 3.

[0133] According to an exemplary embodiment, s2 may be 0, 1, 2, 3 or 4.

[0134] According to an exemplary embodiment, s3 may be 0, 1, 2, 3 or 4.

[0135] According to an exemplary embodiment, t may be 0, 1, 2, 3, 4 or 5.

[0136] According to an exemplary embodiment, u may be 0, 1, 2, 3, 4 or 5.

[0137] According to an exemplary embodiment, when s, s1, s2, s3, t, and u are each independently an integer greater than or equal to 2, a plurality of R d , R d1 , R d2 , R d3 , R e and R f may be the same or different from each other.

[0138] According to an exemplary embodiment, one of R1 to R4 is a substituent represented by Formula 2, and the remaining R5 to R8 may each independently be hydrogen or deuterium. 13 and R 10 may be hydrogen or deuterium. The heterocyclic compound may include an arylamine group bonded to the terminal ring closer to the carbon atom to which the substituent of the third ring of the five-ring fused structure is bonded. This facilitates intermolecular interactions and allows the band gap to be adjusted to a desired value.

[0139] In an exemplary embodiment, the heterocyclic compound can be represented by the following Chemical Formula 1-1:

[0140] [ka]

[0141] In the above Chemical Formula 1-1, one of R1 to R4 is a substituent represented by the above Chemical Formula 2, and the rest may each independently be hydrogen or deuterium.

[0142] R5 to R8 and R 10 may each independently be hydrogen or deuterium.

[0143] L4 may be a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0144] n is an integer of 1 to 5, and when n is an integer of 2 to 5, multiple L4s may be the same or different.

[0145] R 13 may 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.

[0146] In exemplary embodiments, the heterocyclic compound can contain one nitrogen atom in the molecule. In some embodiments, the heterocyclic compound may not contain any nitrogen atoms other than the nitrogen atom contained in Chemical Formula 2.

[0147] For example, one of R1 to R8 in Chemical Formula 1 is a substituent represented by Chemical Formula 2, and the remaining R9 and R 10 may not contain a nitrogen atom.

[0148] For example, the heterocyclic compound may not contain a nitrogen-containing heteroaryl group.

[0149] This can improve the carrier balance of the heterocyclic compound, and can appropriately realize capacitance characteristics due to excess electrons.

[0150] According to an exemplary embodiment, the deuterium content of the compound of Formula 1 may be 0%, or may be greater than 0 and less than or equal to 100%.

[0151] According to an exemplary embodiment, the deuterium content of the compound of Formula 1 may be 0%, or may be 5% to 100%.

[0152] According to an exemplary embodiment, the deuterium content of the compound of Formula 1 may be 0%, or may be 10% to 100%.

[0153] According to an exemplary embodiment, the deuterium content of the compound of Formula 1 may be 0%, or may be 15% to 100%.

[0154] According to an exemplary embodiment, the deuterium content of the compound of Formula 1 may be 0%, or may be 20% to 100%.

[0155] According to an exemplary embodiment, the deuterium content of the compound of Formula 1 may be 0%, or may be 25% to 100%.

[0156] According to an exemplary embodiment, the deuterium content of the compound of Formula 1 may be 0%, or may be 30% to 100%.

[0157] According to an exemplary embodiment, the deuterium content of the compound of Formula 1 may be 0%, or 50% to 100%.

[0158] According to an exemplary embodiment, the deuterium content of the compound of Formula 1 may be 0%, or 70% to 100%.

[0159] According to an exemplary embodiment, the deuterium content of the compound of Formula 1 may be 0%, or 90% to 100%.

[0160] According to an exemplary embodiment, the compound of Formula 1 may have a deuterium content of 0%.

[0161] According to an exemplary embodiment, the deuterium content of the compound of Formula 1 may be 30% to 100%.

[0162] According to an exemplary embodiment, the deuterium content of the compound of Formula 1 may be 50% to 100%.

[0163] According to an exemplary embodiment, the deuterium content of the compound of Formula 1 may be 70% to 100%.

[0164] According to an exemplary embodiment, the deuterium content of the compound of Formula 1 may be 90% to 100%.

[0165] The heterocyclic compound can be represented by any one of the following chemical formulas:

[0166] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0167] In one embodiment of the present disclosure, there is provided an organic light-emitting device including a first electrode, a second electrode provided opposite to the first electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers includes a heterocyclic compound represented by Chemical Formula 1.

[0168] In an exemplary embodiment, one or more of the organic layers may contain one type of heterocyclic compound represented by Chemical Formula 1 above.

[0169] In an exemplary embodiment, one or more of the organic layers may contain two or more heterocyclic compounds represented by Chemical Formula 1.

[0170] In an exemplary embodiment, the first electrode may be an anode and the second electrode may be a cathode, or the first electrode may be a cathode and the second electrode may be an anode.

[0171] In an exemplary embodiment, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound of Chemical Formula 1 may be used as a material for the blue organic light emitting device.

[0172] In an exemplary embodiment, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the green organic light-emitting device.

[0173] In an exemplary embodiment, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the red organic light-emitting device.

[0174] In this specification, the details of the heterocyclic compound represented by Chemical Formula 1 are as described above.

[0175] The organic light-emitting device can be manufactured by a conventional method and materials for manufacturing an organic light-emitting device, except that one or more organic material layers are formed using the heterocyclic compound described above.

[0176] The heterocyclic compound may be formed as 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.

[0177] The organic material layer of the organic light emitting device 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 may have a structure including a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, an electron injection layer, etc. However, the structure of the organic light emitting device is not limited thereto and may include a fewer or greater number of organic material layers.

[0178] The organic material layer of the organic light emitting device may include a light emitting layer, and the light emitting layer may include the heterocyclic compound.

[0179] The light-emitting layer includes a host material, and the host material may include the heterocyclic compound.

[0180] According to an exemplary embodiment, the organic material layers of the organic light-emitting device include a hole transport layer (Host Transfer Layer: HTL), a hole transport auxiliary layer (Prime HTL), and an electron blocking layer (Electron Blocking Layer: EBL), and at least one of the hole transport layer, the hole transport auxiliary layer, and the electron blocking layer may include a heterocyclic compound represented by Chemical Formula 1.

[0181] According to an exemplary embodiment, the organic layer includes a hole transport layer (Host transfer layer: HTL) and a hole transport auxiliary layer (Prime HTL), and at least one of the hole transport layer and the hole transport auxiliary layer can include the heterocyclic compound.

[0182] According to an exemplary embodiment, the organic layer includes an electron blocking layer (EBL), and the electron blocking layer may include the heterocyclic compound.

[0183] According to an exemplary embodiment, the organic layer includes a hole transport layer, an emitting layer, or an electron blocking layer, and the hole transport layer, the emitting layer, or the electron blocking layer may include the heterocyclic compound.

[0184] According to an exemplary embodiment, the organic layer includes a hole transport layer or a hole transport auxiliary layer, and the hole transport layer or the hole transport auxiliary layer may include the compound.

[0185] According to an exemplary embodiment, the organic layer may further include a light-emitting auxiliary layer or an N-type charge-generating layer (N-CGL).

[0186] According to an exemplary embodiment, the anode material may have a relatively high work function, such as a transparent conductive oxide, a metal, or a conductive polymer. 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.

[0187] The cathode material may be a material with a relatively low work function, such as a metal, a metal oxide, or a conductive polymer. 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 structures such as LiF / Al or LiO2 / Al.

[0188] As the material for the hole injection layer, known materials for hole injection layers 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), 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA), or 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.

[0189] Materials for the hole transport layer include pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc., and low-molecular-weight or high-molecular-weight materials can also be used. Materials for the electron transport layer 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, and not only low-molecular-weight materials but also high-molecular-weight materials can be used.

[0190] As a material for the electron injection layer, for example, LiF is typically used in the industry, but the present application is not limited to this.

[0191] 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, two or more light-emitting materials may be deposited as separate supply sources or may be premixed and deposited as a single supply 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.

[0192] When a mixture of hosts of light-emitting materials is used, hosts of the same series may be mixed, or hosts of different series may be mixed. For example, two or more of n-type host materials or p-type host materials may be selected and used as the host material of the light-emitting layer.

[0193] According to exemplary embodiments, the organic light emitting device may be top-emitting, bottom-emitting, or double-sided emitting, depending on the materials used.

[0194] According to exemplary embodiments, the heterocyclic compounds may also function in organic electronic devices such as organic solar cells, organic photoreceptors, and organic transistors, based on principles similar to those applied to organic light-emitting devices.

[0195] The organic light emitting device 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.

[0196] The organic light emitting device may further include one or more layers selected from the group consisting of an emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, a charge generation layer, an electron transport layer, and an electron injection layer.

[0197] 1 to 3 illustrate examples of the stacking order of electrodes and organic material layers of an organic light-emitting device according to an embodiment of the present application. 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.

[0198] 1 shows an organic light-emitting device in which an anode 200, an organic 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 may also be used in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate, as shown in FIG.

[0199] FIG. 3 illustrates a case where the organic layer is a multi-layer.

[0200] 3 includes a hole injection layer 301, a hole transport layer 302, an emitting layer 303, an electron transport layer 304, and an electron injection layer 305. However, the scope of the present application is not limited to such a stacked structure, and the remaining layers except for the emitting layer may be omitted, or other functional layers may be further added.

[0201] The organic layer containing the heterocyclic compound of Formula 1 may further contain other materials as needed.

[0202] According to an exemplary embodiment, a method for manufacturing the organic light emitting device may be provided.

[0203] According to an exemplary embodiment, a substrate may be prepared. A first electrode may be formed on the substrate. One or more organic material layers may be formed on the first electrode. A second electrode may be formed on the organic material layer to manufacture an organic light-emitting device.

[0204] The organic layer can be formed using a composition for an organic layer containing the heterocyclic compound represented by Chemical Formula 1.

[0205] The present invention will be further described below with reference to specific experimental examples. The examples and comparative examples included in the experimental examples are merely illustrative of the present invention and do not limit the scope of the appended claims. It is obvious to those skilled in the art that various changes and modifications to the examples are possible within the scope and technical idea of ​​the present invention, and it is natural that such changes and modifications also fall within the scope of the appended claims.

[0206] Manufacturing Example 1 [ka] 1) Preparation of Compound 001-P5 3-iodo-2-methoxydibenzofuran (20 g, 60.47 mmol, 1 eq (equivalent)), phenylboronic acid (A) (9.03 g, 72.57 mmol, 1.2 eq), potassium carbonate (K2CO3) (20.89 g, 151.18 mmol, 2.5 eq), and tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (3.49 g, 3.02 mmol, 0.05 eq) were added to a mixture of 1,4-dioxane (200 ml) and deionized water (Di-Water) (70 ml) and stirred at 100 °C for 6 hours. After removing water and separating on a silica gel column, 10 g of compound 001-P5 was obtained in a yield of 60.28%.

[0207] 2) Preparation of Compound 001-P4 Compound 001-P5 (10 g, 36.46 mmol, 1 eq) and boron tribromide (BBr) (5.19 ml, 54.68 mmol, 1.5 eq) were added to dichloromethane (100 ml) and stirred at room temperature for 1 hour. The organic layer was extracted with dichloromethane and water, and then the water was removed with magnesium sulfate (MgSO). The extract was then separated on a silica gel column to obtain 7.4 g of compound 001-P4 in 77.9% yield.

[0208] 3) Preparation of Compound 001-P3 Compound 001-P4 (7.4 g, 36.46 mmol, 1 eq) and N-bromosuccinimide (NBS) (5.57 g, 31.27 mmol, 1.1 eq) were added to dimethylformamide (DMF) (74 ml) and stirred at 80 °C for 4 hours. After the reaction was completed, deionized water (Di water) (74 ml) was added. The precipitated solid was filtered to remove the solvent and residual water, yielding 7.2 g of compound 001-P3 in 74.67% yield.

[0209] 4) Preparation of Compound 001-P2 Compound 001-P3 (7.2 g, 21.23 mmol, 1 eq), 3-chloro-2-fluorophenylboronic acid (B) (4.07 g, 23.35 mmol, 1.1 eq), potassium carbonate (K2CO3) (20.89 g, 151.18 mmol, 2.5 eq), and tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (3.49 g, 3.02 mmol, 0.05 eq) were added to a mixture of 1,4-dioxane (200 ml) and deionized water (Di-Water) (70 ml) and stirred at 100 °C for 6 h. After removing water, the mixture was separated on a silica gel column to obtain 7 g of compound 001-P2 in a yield of 84.81%.

[0210] 5) Preparation of Compound 001-P1 Compound 001-P2 (7 g, 18 mmol, 1 eq) and cesium carbonate (Cs2CO3) (11.73 g, 36.01 mmol, 2 eq) were added to N,N-dimethylacetamide (DMA) (110 ml) and stirred at 150 °C for 3 hours. The organic layer was extracted with methylene chloride (MC) and water, and then the water was removed with magnesium sulfate (MgSO4). The mixture was then separated on a silica gel column to obtain 6.1 g of compound 001-P1 in 91.8% yield.

[0211] 6) Preparation of Compound 001 Compound 001-P1 (6.1 g, 16.54 mmol, 1 eq), N-phenylaniline (C) (2.8 g, 16.54 mmol, 1 eq), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) (0.76 g, 0.83 mmol, 0.05 eq), Xphos (0.79 g, 1.65 mmol, 0.1 eq), sodium tert-butoxide (NaOtBu) (3.97 g, 41.35 mmol, 2.5 eq), and toluene (6.1 ml) were mixed and stirred at 100 °C for 1 h. After the reaction was completed, the mixture was concentrated and separated on a silica gel column to obtain 7 g of compound 001 in 84.38% yield.

[0212] Compounds were synthesized in a similar manner, except that intermediate A in Table 1 below was used in place of phenylboronic acid (A) in 1), intermediate B in Table 1 below was used in place of 3-chloro-2-fluorophenylboronic acid (B) in 3), and intermediate C in Table 1 below was used in place of N-phenylaniline (C) in 6).

[0213] [Table 1-1] [Table 1-2]

[0214] Manufacturing Example 2 [ka] Compound 001-P1 (10 g, 27.11 mmol, 1 eq) of Preparation Example 1-5), 4,4,5,5-tetramethyl-N,N-bis(4-phenylphenyl)-1,3,2-dioxaborolan-2-amine (C) (12.13 g, 27.11 mmol, 1 eq), tetramethyl-N,N-bis(4-phenylphenyl)-1,3,2-dioxaborolan-2-amine, Tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (1.57 g, 1.36 mmol, 0.05 eq) and potassium carbonate (K2CO3) (9.37 g, 67.79 mmol, 2.5 eq) were added to a mixture of 1,4-dioxane (100 ml) and water (30 ml) and stirred at 100 °C for 6 hours. The organic layer was extracted with methylene chloride (MC) and water, and then the water was removed with magnesium sulfate (MgSO4). After separation on a silica gel column, 13.5 g of compound 033 was obtained in 76.16% yield.

[0215] Compounds were synthesized in a similar manner, except that in 1) of Production Example 1, Intermediate A in Table 2 below was used instead of phenylboronic acid (A), in 3) of Production Example 1, Intermediate B in Table 2 below was used instead of 3-chloro-2-fluorophenylboronic acid (B), and in 3) of Production Example 1, Intermediate C in Table 2 below was used instead of 4,4,5,5-tetramethyl-N,N-bis(4-phenylphenyl)-1,3,2-dioxaborolan-2-amine (C).

[0216] [Table 2-1] [Table 2-2]

[0217] Manufacturing Example 3 [ka] Compound 001 (5 g, 9.97 mmol) was placed in 50 mL of C6D6 and purged with nitrogen for 2 hours to prepare a reaction mixture. 6.27 mL of trifluoromethanesulfonic acid (69.78 mmol, 7 eq) was added dropwise to the reaction mixture via syringe, and the reaction mixture was heated under reflux for 2 hours. After cooling to room temperature, 50 mL of deuterium oxide was added for extraction, and the organic layer was dried over anhydrous magnesium sulfate (MgSO4) and concentrated on a rotary evaporator, followed by ethylene acetate (EA) slurry to give compound 137 (3.7 g, 70.7%). Compounds were synthesized in the same manner as in Production Example 3, except that the reaction compounds, reaction temperature and time, and equivalent amount of triflic acid (trifluoromethanesulfonic acid) were changed as shown in Table 3 below.

[0218] [Table 3]

[0219] The compounds in Tables 1 to 3 1 Measurements were performed using 1 H NMR (DMSO, 300 MHz) and FD-mass spectrometry (FD-MS), and the synthesis confirmation results are shown in Tables 4 and 5 below, respectively.

[0220] [Table 4-1] [Table 4-2]

[0221] [Table 5-1] [Table 5-2]

[0222] Manufacture of organic light-emitting element 1 A transparent electrode ITO thin film on an OLED glass substrate (manufactured by Samsung Corning) was ultrasonically cleaned using trichloroethylene, acetone, ethanol, and distilled water, successively, for 5 minutes each, and then stored in isopropanol before use. Next, the substrate was placed on the substrate holder of a vacuum deposition system, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell inside the vacuum deposition system.

[0223] [ka]

[0224] Next, the vacuum in the chamber was reduced to 10 -6 After evacuating the cell to torr, a current was applied to the cell to evaporate 2-TNATA, depositing a 600 Å thick hole-injection layer on the ITO thin film (anode).

[0225] The compound of formula 001 was placed in another cell in the vacuum deposition apparatus, and a current was applied to the cell to cause evaporation, thereby depositing a hole transport layer having a thickness of 300 Å on the hole injection layer.

[0226] A blue light-emitting material was deposited on the hole-transporting layer by the following method to form an emitting layer: Specifically, a blue light-emitting host material, a compound represented by the following structural formula 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, a compound represented by the following structural formula D1, was vacuum-deposited thereon in an amount of 5 parts by weight per 100 parts by weight of the blue light-emitting host material.

[0227] [ka] [ka]

[0228] On the light-emitting layer, a compound represented by the following structural formula E1 was vapor-deposited to a thickness of 300 Å as an electron transport layer.

[0229] [ka]

[0230] An OLED device was manufactured by depositing lithium fluoride (LiF) as an electron injection layer to a thickness of 10 Å on the electron transport layer and depositing an Al cathode to a thickness of 1,000 Å.

[0231] All organic compounds required for manufacturing the OLED device are 100% by material. -6 ~10 -8 It was purified by vacuum sublimation under torr and used for OLED fabrication.

[0232] An organic electroluminescent device was prepared in the same manner as above, except that the compound of Formula 001 used in forming the hole transport layer was replaced with the compound shown in Table 6 below.

[0233] Experimental Example 1 The electroluminescence (EL) characteristics of the organic light-emitting device were measured using an M7000 manufactured by Mac Science, and the measurement results were used to determine whether the reference luminance was 700 cd / m or less using a lifetime measurement device (M6000) manufactured by Mac Science. 2 T when 95 was measured. The driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light emitting device were measured, and the results are shown in Table 6.

[0234] [Table 6]

[0235] [ka]

[0236] Referring to Table 6, the blue organic light-emitting device having a hole transport layer incorporating the heterocyclic compound of the present disclosure exhibited lower driving voltage, higher luminous efficiency, and improved lifetime compared to the organic light-emitting device of the comparative example.

[0237] The organic light emitting device of the Example exhibited a T95 lifetime characteristic of 80 or more and an improved driving efficiency with a driving voltage of 4.90 V or less. In contrast, the organic light emitting device of the Comparative Example exhibited a T95 lifetime characteristic of 66 or less and an efficiency inferior to that of the organic light emitting device of the Example with a driving voltage of 5.08 V or more.

[0238] The compound used in the hole transport layer of the example contains an arylamine group bonded to the first ring and an aryl group bonded to the third ring of the five-fused ring structure, unlike the compounds used in Comparative Examples 1 to 4. This may be due to the fact that the intermolecular carrier mobility due to intermolecular interactions is higher than that of the compounds used in Comparative Examples 1 to 4.

[0239] Furthermore, the compounds used in the hole transport layers of the Examples exhibit improved carrier balance compared to the compounds used in Comparative Examples 5 to 7. The compounds used in Comparative Examples 5 to 7 have too strong electron transport (ET) properties for use in hole transport layers, and may not adequately realize capacitance characteristics due to excess electrons. As a result, they may exhibit inferior characteristics compared to the compounds used in the hole transport layers of the Examples.

[0240] The compound used in Comparative Example 8 may have an energy level that is less suitable for use in a hole transport layer than the compounds used in the hole transport layers of the Examples.

[0241] Fabrication of organic light-emitting element 2 Organic light-emitting device 2 was produced in the same manner as in the production of organic light-emitting device 1, except that the hole transport layer was formed as follows.

[0242] N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell in the vacuum deposition apparatus, and a current was applied to the cell to evaporate it, forming a hole-transporting layer with a thickness of 250 Å. Subsequently, an electron-blocking layer with a thickness of 50 Å containing a compound shown in Table 7 was formed on the hole-transporting layer.

[0243] Experimental Example 2 The T95, driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the organic light-emitting device were measured in the same manner as in Experimental Example 1, and are shown in Table 7. The LUMO level and T1 level of some compounds are also shown in Table 8.

[0244] [Table 7]

[0245] [Table 8]

[0246] [ka]

[0247] As can be seen from Table 7, the blue organic light-emitting device having an electron blocking layer incorporating the heterocyclic compound of the present disclosure exhibited lower driving voltage, higher luminous efficiency, and improved lifetime compared to the organic light-emitting device of the comparative example.

[0248] The organic light emitting device of the Example exhibited improved driving efficiency with a T95 lifetime characteristic of 81 or more and a driving voltage of 4.89 V or less. In contrast, the organic light emitting device of the Comparative Example exhibited a T95 lifetime characteristic of 66 or less and a driving voltage of 5.21 V or more, showing a lower efficiency than the organic light emitting device of the Example.

[0249] The compounds used in the electron blocking layers of the examples differ from the compounds used in Comparative Examples 9 to 13 in that they contain an arylamine group bonded to the first ring and an aryl group bonded to the third ring of the five-fused ring system.

[0250] As can be seen from Table 8, the compounds used in the electron blocking layers of the Examples generally achieve higher T1 levels than the compounds used in the electron blocking layers of the Comparative Examples. This prevents triplet energy generated from the emitting layer from transferring to the electron blocking layer, significantly improving the driving efficiency and lifetime of the organic light-emitting device. Furthermore, the compounds used in the electron blocking layers of the Examples have appropriate LUMO levels, making them suitable for forming an electron blocking layer. They can efficiently transport holes transported from the hole transport layer to the emitting layer while preventing electron migration.

[0251] This may be due to the fact that the compounds of the examples have higher intermolecular carrier mobility due to intermolecular interactions compared to the compounds used in Comparative Examples 9 to 13.

[0252] In addition, the compound used in the electron blocking layer of the Examples may have an improved carrier balance compared to the compound used in Comparative Example 14. The compound used in Comparative Example 14 has too strong electron transport (ET) properties for use in the hole transport layer, and may not adequately realize capacitance characteristics due to excess electrons. Therefore, it may exhibit inferior characteristics compared to the compound used in the hole transport layer of the Examples.

[0253] The compound used in Comparative Example 15 may have an energy level that is less suitable for use in a hole transport layer than the compounds used in the hole transport layers of the Examples.

[0254] The compound used in Comparative Example 16 has a structure in which two aryl groups are bonded to the third ring of a five-fused ring system, which can inhibit intermolecular interactions and result in properties inferior to those of the compounds used in the electron blocking layers of the Examples.

[0255] From the above results, it can be seen that the heterocyclic compound of the present disclosure can improve the driving, efficiency, and life characteristics of the organic light-emitting device.

[0256] The foregoing is merely illustrative of the application of the principles of the present disclosure, and other arrangements may still be included without departing from the scope of the present invention. [Explanation of symbols]

[0257] 100: Substrate 200:Anode 300:Organic layer 301: Hole injection layer 302: Hole transport layer 303: Light-emitting layer 304: Electron transport layer 305: Electron injection layer 400: Cathode

Claims

1. A heterocyclic compound represented by the following chemical formula 1: 【Chemistry 1】 In the above formula 1, R １ ~R ８ One of the groups is a substituent represented by the following chemical formula 2: the remainders are each independently selected from the group consisting of hydrogen; deuterium; a halogen; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; -SiRR'R"; and -P(=O)RR'; R, R', and R" are each independently hydrogen; deuterium; -CN; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 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; 【Chemistry 2】 In the above chemical formula 2, R １１ and R １２ 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, L １ , L ２ and L ３ each independently represents 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; a, b, and c each independently represent 0 or an integer from 1 to 5; When a is an integer of 2 to 5, a plurality of L １ are the same or different from each other, When b is an integer of 2 to 5, a plurality of L ２ are the same or different from each other, When c is an integer of 2 to 5, a plurality of L ３ are the same or different from each other, R ９ and R １０ Either one of -(L ４ ) n-R １３ and the other is hydrogen or deuterium, L ４ represents 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; n is an integer of 1 to 5, and when n is an integer of 2 to 5, a plurality of L ４ are the same or different from each other, R １３ is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, * indicates a bonding site with an adjacent atom.

2. In the above Chemical Formula 2, L １ , L ２ and L ３ each independently represents a direct bond or a substituted or unsubstituted arylene group having 6 to 10 carbon atoms; 2. The heterocyclic compound according to claim 1, wherein a, b, and c are each independently 0, 1, or 2.

3. The heterocyclic compound according to claim 1, represented by the following chemical formula 1-1: 【Transformation 3】 In the above chemical formula 1-1, R １ ~R ４ one of which is a substituent represented by Chemical Formula 2, and the rest are each independently hydrogen or deuterium; R ５ ~R ８ and R １０ are each independently hydrogen or deuterium, L ４ represents 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, n is an integer of 1 to 5, and when n is an integer of 2 to 5, a plurality of L ４ are the same or different from each other, R １３ is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

4. In the above Chemical Formula 1, R ９ and R １０ Either one of -(L ４ ) n-R １３ and the other is hydrogen or deuterium, L ４ represents a direct bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; n is an integer of 1 to 5, and when n is an integer of 2 to 5, a plurality of L ４ are the same or different from each other, R １３ is 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.

5. The heterocyclic compound according to claim 1, wherein the chemical formula 2 is represented by any one of the following chemical formulas 2-1 and 2-5: 【Chemistry 4】 【Transformation 5】 In the above chemical formulas 2-1 and 2-5, R １１ , R １２ , L ２ , L ３ , b and c are as defined in Chemical Formula 2 above, and R ｃ are each hydrogen or deuterium, r is 0 or an integer from 1 to 4, When r is an integer of 2 or more, a plurality of R ｃ are the same or different.

6. 2. The heterocyclic compound according to claim 1, wherein the deuterium content of the heterocyclic compound is 0 or more than 0 and 100% or less.

7. The heterocyclic compound according to claim 1, which is represented by any one of the following chemical formulas: 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】

8. A first electrode; a second electrode disposed on the first electrode; one or more organic layers interposed between the first electrode and the second electrode; An organic light-emitting device, wherein one or more of the organic layers comprises the heterocyclic compound according to claim 1 .

9. 9. The organic light-emitting device according to claim 8, wherein the organic layer comprises an emitting layer, a hole transport layer disposed between the first electrode and the emitting layer, and an electron transport layer disposed between the emitting layer and the second electrode.

10. 10. The organic light-emitting device according to claim 9, wherein the hole transport layer includes a hole injection layer, a hole transport layer, a hole transport assisting layer, and an electron blocking layer, and at least one of the hole transport layer, the hole transport assisting layer, and the electron blocking layer includes the heterocyclic compound.

11. The organic light-emitting device according to claim 9 , wherein the electron transport layer further comprises one or more layers selected from the group consisting of an electron injection layer, an electron transport layer, and an electron blocking layer.

12. 9. The organic light-emitting device according to claim 8, wherein the organic layer further comprises one or more layers selected from the group consisting of an emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

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