Heterocyclic compound and organic light-emitting element comprising same

Abstract

The present specification relates to a heterocyclic compound and an organic light-emitting element comprising same.

Description

Heterocyclic compound and organic light-emitting device containing the same

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

[0002] This application claims the benefit of Korean Patent Application No. 10-2023-0159570, filed with the Korean Intellectual Property Office on November 16, 2023, the entire contents of which are incorporated herein by reference.

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

[0004] Organic light-emitting devices are structured by placing an organic thin film between two electrodes. When voltage is applied to an organic light-emitting device of this structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs, and then disappear, emitting light. The organic thin film may 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 organic thin film material may be a compound that can form a light-emitting layer on its own, or a compound that can act as a host or dopant in a host-dopant light-emitting layer. In addition, the material of the organic thin film may be a compound that can perform functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection.

[0006] To improve the performance, efficiency, and lifespan of organic light-emitting devices, the development of materials for organic thin films is continuously required.

[0007] The present invention seeks to provide a heterocyclic compound and an organic light-emitting device comprising the same.

[0008] In one embodiment of the present application, a heterocyclic compound represented by the following chemical formula 1 is provided.

[0009] [Chemical Formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] X is O or S,

[0013] L1 and L2 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted C6 to C60 arylene group,

[0014] R1 and R2 are the same or different, and each independently represents a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or are represented by the following chemical formula 2,

[0015] One of the above R1 and R2 is represented by the following chemical formula 2, and the other is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0016] Ra, Rb and Rc are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0017] p is an integer from 0 to 4, and when p is 2 or greater, the substituents in the parentheses are the same or different from each other,

[0018] q is an integer from 0 to 2, and when q is 2, the substituents in the parentheses are the same or different from each other,

[0019] r is an integer from 0 to 4, and when r is 2 or greater, the substituents in the parentheses are the same or different from each other,

[0020] [Chemical Formula 2]

[0021]

[0022] In the above chemical formula 2,

[0023] L3 and L4 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted C6 to C60 arylene group,

[0024] R3 and R4 are the same or different, and each independently represent a condensed ring group of a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring and a C3 to C60 aliphatic hydrocarbon ring group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0025] One of the above R1 and R2 is represented by the above chemical formula 2, and the other one of R1 and R2 and at least one of R3 and R4 is substituted with two or more substituted or unsubstituted C1 to C60 branched-chain alkyl groups.

[0026] In addition, in one embodiment of the present application, an organic light-emitting device is provided, including a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers includes a heterocyclic compound represented by the above-described chemical formula 1.

[0027] The heterocyclic compound described herein can be used as an organic layer material of an organic light-emitting device. That is, it can play the role of a hole transport material, an electron blocking material, etc. in an organic light-emitting device.

[0028] Specifically, when used in the organic layer of an organic light-emitting device, the device can achieve significantly improved operation, efficiency, and lifespan.

[0029] Figures 1 to 4 are schematic drawings showing the laminated structure of an organic light-emitting device according to one embodiment of the present application.

[0030] [Explanation of symbols]

[0031] 100: Substrate

[0032] 200: Bipolar

[0033] 300: Organic layer

[0034] 301: Hole injection layer

[0035] 302: Hole transport layer

[0036] 303: Emissive layer

[0037] 304: Electron transport layer

[0038] 305: Electron injection layer

[0039] 306: Electronic barrier layer

[0040] 307: Static low-level layer

[0041] 400: Cathode

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

[0043] In this specification, when a part is said to "include" a component, this does not mean that it excludes other components, but rather that it may include other components, unless specifically stated otherwise.

[0044] In this specification, the chemical formula means the position where it is combined.

[0045] In this specification, n in Cn means carbon number. That is, for example, C6 to C60 means carbon number 6 to carbon number 60.

[0046] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where a hydrogen atom is substituted, i.e., a position where a substituent can be substituted, and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0047] In this specification, "substituted or unsubstituted" means deuterium; halogen group; -CN; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C1 to C60 haloalkyl group; C1 to C60 alkoxy group; C6 to C60 aryloxy group; C1 to C60 alkylthioxy group; C6 to C60 arylthioxy group; C1 to C60 alkylsulfoxy group; C6 to C60 arylsulfoxy group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; C6 to C60 aryl group; C2 to C60 heteroaryl group; -SiRR'R"; -P(=O)RR'; and -NRR', or a substituent in which two or more substituents selected from the above-mentioned substituents are connected, means substituted or unsubstituted, and R, R' and R" are each independently a substituent composed 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.

[0048] In this specification, "when no substituent is indicated in the chemical formula or compound structure" 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.

[0049] In one embodiment of the present application, "when no substituent is indicated in the chemical formula or compound structure" may mean that all positions that can be substituted are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the deuterium content may be 0% to 100%.

[0050] In one embodiment of the present application, in the case where "no substituent is indicated in the chemical formula or compound structure", if the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents are hydrogen, etc., and deuterium is not explicitly excluded, hydrogen and deuterium may be used in combination in the compound.

[0051] In one embodiment of the present application, deuterium is an element having a deuteron, which is one of the isotopes of hydrogen and is composed of one proton and one neutron, as its nucleus, and can be expressed as hydrogen-2, and its element symbol is D or 2 It can also be written as H.

[0052] In one embodiment of the present application, an isotope means an atom having the same atomic number (Z) but a different mass number (A). An isotope can also be interpreted as an element having the same number of protons but a different number of neutrons.

[0053] In one embodiment of the present application, the meaning of the content T% of a specific substituent can be defined as T2 / T1Х100 = T% when the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2.

[0054] That is, in one example, In the phenyl group represented by , the content of deuterium of 20% means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and if the number of deuterium among them is 1 (T2 in the formula), it can be expressed as 20%. In other words, the content of deuterium of 20% in the phenyl group can be expressed by the structural formula below.

[0055]

[0056] Additionally, in one embodiment of the present application, the term “phenyl group having a deuterium content of 0%” may mean a phenyl group that does not contain deuterium atoms, i.e., has 5 hydrogen atoms.

[0057] In this specification, halogen may be fluorine, chlorine, bromine or iodine.

[0058] In the present specification, an alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The alkyl group may have 1 to 60 carbon atoms, specifically 1 to 40 carbon atoms, and more specifically 1 to 20 carbon atoms. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl 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, There are, but are not limited to, these.

[0059] In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms. Specific examples include, but are not limited to, 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.

[0060] In the present specification, an alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkynyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms.

[0061] In this specification, a haloalkyl group means an alkyl group substituted with a halogen group, and specific examples include, but are not limited to, -CF3, -CF2CF3, etc.

[0062] In this specification, an alkoxy group is represented as -O(R101), and examples of the alkyl group described above can be applied to R101.

[0063] In this specification, the aryloxy group is represented as -O(R102), and R102 can be applied to the examples of the aryl group described above.

[0064] In this specification, the alkylthioxy group is represented as -S(R103), and examples of the alkyl group described above can be applied to R103.

[0065] In this specification, the arylthioxy group is represented as -S(R104), and R104 can be applied to the examples of the aryl group described above.

[0066] In this specification, an alkylsulfoxy group is represented as -S(=0)2(R105), and examples of the alkyl group described above can be applied to R105.

[0067] In this specification, an arylsulfoxy group is represented as -S(=0)2(R106), and examples of the aryl group described above can be applied to R106.

[0068] In the present specification, a cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The cycloalkyl group may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, and more specifically 5 to 20 carbon atoms. Specifically, there are, 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, a cyclooctyl group, etc.

[0069] In the present specification, a heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, etc. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

[0070] In the present specification, an aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, etc. The aryl group includes a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 25 carbon atoms. Specific examples of the above 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 condensed ring groups thereof.

[0071] In this specification, the terphenyl group may be selected from the following structures.

[0072]

[0073] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0074] When the above fluorenyl group is substituted, it may have any of the following structures, but is not limited thereto.

[0075]

[0076] In the present specification, a heteroaryl group includes S, O, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic ring means a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms.Specific examples of the above 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, a quinoline group, an isoquinoline group, a quinazoline group, an isoquinazoline group, a quinozoline group, a naphthyridine group, an acridine group, a phenanthridine group, an imidazopyridine group, a diazanaphthalene group, a triazaindene group, an indole group, an indolizine group, a 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, phenanthrazine group, phenothiathiazine group, phthalazine group, phenanthroline group, naphthobenzofuran group, naphthobenzothiophene group, benzo[c][1,2,5]thiadiazole group, Examples thereof include, but are not limited to, 2,3-dihydrobenzo[b]thiophene group, 2,3-dihydrobenzofuran group, 5,10-dihydrodibenzo[b,e][1,4]azacillin group, pyrazolo[1,5-c]quinazoline group, pyrido[1,2-b]indazole group, pyrido[1,2-a]imidazo[1,2-e]indolin group, and 5,11-dihydroindeno[1,2-b]carbazole group.

[0077] In the present specification, when the substituent is a carbazole group, it means that it is bonded to the nitrogen or carbon of the carbazole.

[0078] In the present specification, when a carbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole.

[0079] In the present specification, the benzocarbazole group may have any of the following structures.

[0080]

[0081] In the present specification, the dibenzocarbazole group may have any of the following structures.

[0082]

[0083] In the present specification, the naphthobenzofuran group may have any of the following structures.

[0084]

[0085] In the present specification, the naphthobenzothiophene group may have any of the following structures.

[0086]

[0087] In the present specification, a silyl group is a substituent that contains Si and is directly connected to the Si atom as a radical, and is represented by -Si(R107)(R108)(R109), and R107 to R109 are the same as or different from each other, and may each independently be a substituent composed 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.

[0088] A specific example of a cylinder is (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group), but is not limited thereto.

[0089] In the present specification, a phosphine oxide group is represented by -P(=O)(R110)(R111), and R110 and R111 are the same as or different from each other, and can each independently be a substituent composed 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. Specifically, it can be substituted with an alkyl group or an aryl group, and the above-described examples can be applied to the alkyl group and the aryl group. For example, the phosphine oxide group includes, but is not limited to, a dimethylphosphine oxide group, a diphenylphosphine oxide group, and dinaphthylphosphine oxide.

[0090] In the present specification, an amine group is represented by -N(R112)(R113), and R112 and R113 are the same as or different from each other, and can each independently be a substituent composed 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. 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, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the above 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, 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.

[0091] In the present specification, the arylene group may be applied to the examples of the aryl group described above, except that it is a divalent group.

[0092] In the present specification, the heteroarylene group may be applied to the examples of the heteroaryl group described above, except that it is divalent.

[0093] As used herein, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent sterically closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

[0094] Hydrocarbon rings and heterocycles that adjacent groups can form include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles, and structures exemplified by the aforementioned cycloalkyl groups, aryl groups, heterocycloalkyl groups, and heteroaryl groups can be applied to the rings, except that they are not monovalent groups.

[0095] In the present specification, the condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring is a structure in which the above-mentioned aromatic hydrocarbon ring and the above-mentioned aliphatic hydrocarbon ring are condensed. For example, there are tetrahydronaphthalene group, tetrahydroanthracene group, 1,2,3,4-tetrahydro-1,4-methanonaphthalene group, 1,2,3,4-tetrahydro-1,4-ethanonaphthalene group, but are not limited thereto. More specifically, the condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring is or , and R301 to R304 may be a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, and R305 may be hydrogen or a substituted or unsubstituted alkyl group, but is not limited thereto.

[0096] In one embodiment of the present application, a group not indicated as a substituent; or a group indicated as hydrogen may all mean that it can be substituted with deuterium. That is, hydrogen; or deuterium may indicate that they are mutually substitutable.

[0097] Compounds bonded with hydrogen and those substituted with deuterium generally exhibit different thermodynamic behaviors. This is because the mass of a deuterium atom is twice that of hydrogen. This difference in atomic mass gives deuterium the characteristic of having lower vibrational energy.

[0098] Additionally, the single bond dissociation energy (BDE) of carbon and deuterium is higher than that of carbon and hydrogen. Therefore, structures substituted with deuterium have increased thermal stability of the molecule, which has the effect of improving the lifespan of devices utilizing them.

[0099] When compounds are deposited on silicon wafers, substances containing deuterium tend to pack more tightly between molecules. Furthermore, observing the thin film surface with an atomic force microscope (AFM) reveals that thin films made with deuterium-containing compounds are deposited on a more uniform surface, with no aggregations.

[0100] In one embodiment of the present application, a heterocyclic compound represented by the following chemical formula 1 is provided.

[0101] [Chemical Formula 1]

[0102]

[0103] In the above chemical formula 1,

[0104] X is O or S,

[0105] L1 and L2 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted C6 to C60 arylene group,

[0106] R1 and R2 are the same or different, and each independently represents a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or are represented by the following chemical formula 2,

[0107] One of the above R1 and R2 is represented by the following chemical formula 2, and the other is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0108] Ra, Rb and Rc are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0109] p is an integer from 0 to 4, and when p is 2 or greater, the substituents in the parentheses are the same or different from each other,

[0110] q is an integer from 0 to 2, and when q is 2, the substituents in the parentheses are the same or different from each other,

[0111] r is an integer from 0 to 4, and when r is 2 or greater, the substituents in the parentheses are the same or different from each other,

[0112] [Chemical Formula 2]

[0113]

[0114] In the above chemical formula 2,

[0115] L3 and L4 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted C6 to C60 arylene group,

[0116] R3 and R4 are the same or different, and each independently represent a condensed ring group of a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring and a C3 to C60 aliphatic hydrocarbon ring group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0117] One of the above R1 and R2 is represented by the above chemical formula 2, and the other one of R1 and R2 and at least one of R3 and R4 is substituted with two or more substituted or unsubstituted C1 to C60 branched-chain alkyl groups.

[0118] The heterocyclic compound represented by the above chemical formula 1 has a two-substituted structure of arylamine and aryl group / heteroaryl group, and at this time, by introducing at least two or more branched alkyl groups, for example, two or more tert-butyl groups, within the two-substituted structure, it has the characteristic of fast hole mobility and has the property of an appropriate HOMO level, thereby delocalizing the energy level and stabilizing the HOMO energy, while effectively preventing electrons from flowing over from the opposite side of the electron transport layer.

[0119] In the above chemical formula 2 means a position connected to L1 or L2 of the above chemical formula 1.

[0120] In one embodiment of the present application, one of R1 and R2 may be represented by the chemical formula 2, and the other one of R1 and R2, and at least one of R3 and R4 may be substituted with two or more substituted or unsubstituted C1 to C60 branched alkyl groups at the meta position to each other.

[0121] When the alkyl groups of the above two or more substituted or unsubstituted C1 to C60 branched chains are substituted at the meta position, it can be helpful in maintaining high triplet energy, lowering symmetry, reducing crystallinity, and improving solubility.

[0122] In one embodiment of the present application, the chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-4.

[0123] [Chemical Formula 1-1]

[0124]

[0125] [Chemical Formula 1-2]

[0126]

[0127] [Chemical Formula 1-3]

[0128]

[0129] [Chemical Formula 1-4]

[0130]

[0131] In the above chemical formulas 1-1 to 1-4,

[0132] The definitions of L1, L2, R1, R2, Ra, Rb, Rc, p, q and r are the same as those in the chemical formula 1 described above.

[0133] In one embodiment of the present application, the chemical formula 2 may be represented by the following chemical formula A or B.

[0134] [Chemical Formula A]

[0135]

[0136] [Chemical Formula B]

[0137]

[0138] In the above chemical formulas A and B,

[0139] The definitions of R4, L3 and L4 are the same as those in the chemical formula 1 described above,

[0140] R5 to R13 are the same or different and are each independently hydrogen; deuterium; or a substituted or unsubstituted C1 to C60 branched-chain alkyl group,

[0141] R14 and R15 are the same or different, and each independently represents a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group,

[0142] Rd is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0143] s is an integer from 0 to 3, and when s is 2 or greater, the substituents in the parentheses are the same or different from each other,

[0144] At least two of R5 to R9 are substituted or unsubstituted C1 to C60 branched alkyl groups, and at least two of R10 to R13 are substituted or unsubstituted C1 to C60 branched alkyl groups.

[0145] In one embodiment of the present application, among R5 to R9, R6 and R8 are substituted or unsubstituted C1 to C60 branched alkyl groups and the remainder is hydrogen; or deuterium, among R10 to R13, R10 and R12 are substituted or unsubstituted C1 to C60 branched alkyl groups and the remainder is hydrogen; or deuterium, or among R10 to R13, R11 and R13 are substituted or unsubstituted C1 to C60 branched alkyl groups and the remainder is hydrogen; or deuterium.

[0146] In one embodiment of the present application, among R5 to R9, R6 and R8 are substituted or unsubstituted C1 to C60 branched alkyl groups and the remainder is hydrogen; or deuterium, among R10 to R13, R10 and R12 are substituted or unsubstituted C1 to C60 branched alkyl groups and the remainder is hydrogen; or deuterium, or among R10 to R13, R11 and R13 are substituted or unsubstituted C1 to C60 branched alkyl groups and the remainder is hydrogen; or deuterium.

[0147] In one embodiment of the present application, R5 to R13 may be the same as or different from each other, and may each independently be hydrogen; deuterium; or a tert-butyl group substituted or unsubstituted with a tert-butyl group substituted or unsubstituted with deuterium.

[0148] In one embodiment of the present application, R5 to R13 are the same as or different from each other, and each independently represent hydrogen; deuterium; tert-butyl group; or It could be.

[0149] In one embodiment of the present application, R14 and R15 are the same as or different from each other, and each independently represents a substituted or unsubstituted C1 to C40 alkyl group; or a substituted or unsubstituted C6 to C40 aryl group, or may combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle.

[0150] In another embodiment, R14 and R15 are the same as or different from each other, and each independently represents a substituted or unsubstituted methyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; ; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group, or may be combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

[0151] In another embodiment, R14 and R15 are the same or different, and each independently represent a methyl group; ; or a phenyl group, or may be combined with each other to form a fluorenyl group.

[0152] In one embodiment of the present application, at least two of R5 to R9 may be tert-butyl groups substituted or unsubstituted with tert-butyl groups substituted or unsubstituted with deuterium, and at least two of R10 to R13 may be tert-butyl groups substituted or unsubstituted with tert-butyl groups substituted or unsubstituted with deuterium.

[0153] In one embodiment of the present application, at least two of R5 to R9 are tert-butyl groups or and at least two of R10 to R13 are tert-butyl groups or It could be.

[0154] In one embodiment of the present application, among R5 to R9, R6 and R8 are tert-butyl groups substituted or unsubstituted with a tert-butyl group substituted or unsubstituted with a deuterium substituted or unsubstituted and the remainder are hydrogen; or deuterium, among R10 to R13, R10 and R12 are tert-butyl groups substituted or unsubstituted with a deuterium substituted or unsubstituted tert-butyl group, and the remainder are hydrogen; or deuterium, or among R10 to R13, R11 and R13 are tert-butyl groups substituted or unsubstituted with a deuterium substituted or unsubstituted tert-butyl group, and the remainder are hydrogen; or deuterium.

[0155] In one embodiment of the present application, among R5 to R9, R6 and R8 are tert-butyl groups or and the remainder is hydrogen; or deuterium, and among R10 to R13, R10 and R12 are tert-butyl groups or and the remainder is hydrogen; or deuterium, or among R10 to R13, R11 and R13 are tert-butyl groups or and the rest may be hydrogen; or deuterium.

[0156] In one embodiment of the present application, X is O.

[0157] In another embodiment, X is S.

[0158] In one embodiment of the present application, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

[0159] In another embodiment, L1 and L2 are the same as or different from each other, and each independently may be a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0160] In another embodiment, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0161] In another embodiment, L1 and L2 may each independently be a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylene group substituted or unsubstituted with deuterium; or a naphthylene group substituted or unsubstituted with deuterium.

[0162] In another embodiment, L1 and L2 may each independently be a direct bond; or a phenylene group substituted or unsubstituted with deuterium.

[0163] In one embodiment of the present application, R1 and R2 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or a group represented by the above chemical formula 2.

[0164] In another embodiment, R1 and R2 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; or a group represented by the above chemical formula 2.

[0165] In another embodiment, R1 and R2 may be the same as or different from each other, and each independently represent a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a group represented by the above chemical formula 2.

[0166] In another embodiment, R1 and R2 may be the same as or different from each other, and each independently represent a butyl group unsubstituted or substituted with deuterium; a phenyl group unsubstituted or substituted with deuterium or a branched alkyl group substituted or unsubstituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium; a dibenzofuran group unsubstituted or substituted with deuterium; a dibenzothiophene group unsubstituted or substituted with deuterium; or a group represented by the above chemical formula 2.

[0167] In another embodiment, R1 and R2 may be the same as or different from each other, and each independently represent a tert-butyl group substituted or unsubstituted with deuterium; a phenyl group substituted or unsubstituted with deuterium or a tert-butyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a dibenzothiophene group substituted or unsubstituted with deuterium; or a group represented by the above chemical formula 2.

[0168] In another embodiment, R1 and R2 are the same or different from each other, and each independently represents a tert-butyl group; deuterium, a tert-butyl group, or A phenyl group substituted or unsubstituted with hydrogen; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a dibenzothiophene group substituted or unsubstituted with deuterium; or a group represented by the above chemical formula 2.

[0169] In one embodiment of the present application, L3 and L4 may be the same as or different from each other, and may each independently be a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

[0170] In another embodiment, L3 and L4 are the same as or different from each other, and each independently may be a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0171] In another embodiment, L3 and L4 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0172] In another embodiment, L3 and L4 may be the same as or different from each other, and may each independently be a direct bond; a phenylene group substituted or unsubstituted with deuterium; or a biphenylene group substituted or unsubstituted with deuterium.

[0173] In one embodiment of the present application, R3 and R4 may be the same as or different from each other, and may each independently be a condensed ring group of a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring and a C3 to C40 aliphatic hydrocarbon ring group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0174] In another embodiment, R3 and R4 may be the same as or different from each other, and may each independently be a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring group, substituted or unsubstituted with at least one selected from the group consisting of deuterium, an alkyl group, and an aryl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0175] In another embodiment, R3 and R4 are the same or different from each other and are each independently ; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group, and R301 to R304 are the same as or different from each other, and each independently represent a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and R305 may be hydrogen or a substituted or unsubstituted alkyl group.

[0176] In another embodiment, R3 and R4 are the same or different from each other and are each independently ; 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 phenanthrene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group, and R301 to R304 are the same as or different from each other, and each independently represent an alkyl group; or an aryl group, and R305 may be hydrogen or an alkyl group.

[0177] In another embodiment, R3 and R4 are the same or different from each other and are each independently ; a phenyl group substituted or unsubstituted with a deuterium or substituted or unsubstituted branched alkyl group; a biphenyl group substituted or unsubstituted with a deuterium or substituted or unsubstituted branched alkyl group; a terphenyl group substituted or unsubstituted with a deuterium or substituted or unsubstituted branched alkyl group; a naphthyl group substituted or unsubstituted with a deuterium or substituted or unsubstituted branched alkyl group; a phenanthrene group substituted or unsubstituted with a deuterium or substituted or unsubstituted branched alkyl group; a dimethylfluorenyl group substituted or unsubstituted with a deuterium or substituted or unsubstituted branched alkyl group; a diphenylfluorenyl group substituted or unsubstituted with a deuterium or substituted or unsubstituted branched alkyl group; a spirobifluorenyl group substituted or unsubstituted with a deuterium or substituted or unsubstituted branched alkyl group; A dibenzofuran group substituted or unsubstituted with a deuterium atom or a substituted or unsubstituted branched alkyl group; or a dibenzothiophene group substituted or unsubstituted with a deuterium atom or a substituted or unsubstituted branched alkyl group.

[0178] In another embodiment, R3 and R4 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with a tert-butyl group substituted or unsubstituted with a deuterium or a tert-butyl group substituted or unsubstituted with a deuterium or a tert-butyl group substituted or unsubstituted with a deuterium or a deuterium; a biphenyl group unsubstituted or substituted with a tert-butyl group substituted or unsubstituted with a deuterium or a deuterium; a terphenyl group unsubstituted or substituted with a tert-butyl group substituted or unsubstituted with a deuterium or a deuterium; a naphthyl group unsubstituted or substituted with a tert-butyl group substituted or unsubstituted with a deuterium or a deuterium; a phenanthrene group unsubstituted or substituted with a tert-butyl group substituted or unsubstituted with a deuterium or a deuterium; A dimethylfluorenyl group unsubstituted or substituted with a tert-butyl group substituted or unsubstituted with a deuterium or deuterium substituted or unsubstituted tert-butyl group; a diphenylfluorenyl group unsubstituted or substituted with a tert-butyl group substituted or unsubstituted with a deuterium or deuterium substituted or unsubstituted tert-butyl group; a spirobifluorenyl group unsubstituted or substituted with a tert-butyl group substituted or unsubstituted with a deuterium or deuterium substituted or unsubstituted tert-butyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group substituted or unsubstituted with a deuterium or deuterium substituted or unsubstituted tert-butyl group; Or a dibenzothiophene group substituted or unsubstituted with a tert-butyl group substituted or unsubstituted with deuterium or a tert-butyl group substituted or unsubstituted with deuterium or a tert-butyl group substituted or unsubstituted with deuterium, R301 to R304 are the same as or different from each other, and can each independently be a methyl group, and R305 can be hydrogen or a tert-butyl group.

[0179] In another embodiment, R3 and R4 are the same or different from each other and are each independently ; deuterium, tert-butyl group or A phenyl group substituted or unsubstituted with deuterium, tert-butyl group or A biphenyl group substituted or unsubstituted with; a deuterium, tert-butyl group or A terphenyl group substituted or unsubstituted with hydrogen; a naphthyl group substituted or unsubstituted with hydrogen; a deuterium, tert-butyl group or A phenanthrene group substituted or unsubstituted with deuterium, tert-butyl group or A dimethylfluorenyl group substituted or unsubstituted with deuterium, tert-butyl group or A diphenylfluorenyl group substituted or unsubstituted with; a deuterium, tert-butyl group or A spirobifluorenyl group substituted or unsubstituted with R; a dibenzofuran group substituted or unsubstituted with deuterium; or a dibenzothiophene group substituted or unsubstituted with deuterium, and R305 may be hydrogen or a tert-butyl group.

[0180] In one embodiment of the present application, one of R1 and R2 may be represented by the chemical formula 2, and the other one of R1 and R2 and at least one of R3 and R4 may be substituted with two or more tert-butyl groups.

[0181] In another embodiment, either one of R1 and R2 may be represented by the chemical formula 2, and at least one of R3 and R4 may be substituted with two or more tert-butyl groups.

[0182] In another embodiment, one of R1 and R2 may be represented by the chemical formula 2, the other of R1 and R2 may be a substituted or unsubstituted branched alkyl group, and at least one of R3 and R4 may be substituted with two or more tert-butyl groups.

[0183] In another embodiment, one of R1 and R2 is represented by the chemical formula 2, and the other one of R1 and R2, and at least one of R3 and R4 are two or more. It may be replaced by .

[0184] In another embodiment, one of R1 and R2 is represented by the chemical formula 2, and the other one of R1 and R2; R3; and R4 is substituted with two or more tert-butyl groups, and the other one is substituted with two or more It may be replaced by .

[0185] In one embodiment of the present application, Ra, Rb and Rc may be the same as or different from each other, and may each independently be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0186] In another embodiment, Ra, Rb and Rc may be the same as or different from each other, and may each independently be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0187] In another embodiment, Ra, Rb and Rc may be the same as or different from each other, and may each independently be hydrogen; deuterium; a halogen group; a cyano group; a C1 to C20 alkyl group; a C6 to C20 aryl group; or a C2 to C20 heteroaryl group.

[0188] In another embodiment, Ra, Rb and Rc may be the same as or different from each other, and may each independently be hydrogen; deuterium; a halogen group; a cyano group; a methyl group; a propyl group; a butyl group; a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a dibenzofuran group; or a dibenzothiophene group.

[0189] In another embodiment, Ra, Rb and Rc are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0190] In one embodiment of the present application, p is an integer from 0 to 3, and when p is 2 or more, the substituents in parentheses may be the same or different from each other.

[0191] In another embodiment, p is an integer from 0 to 2, and when p is 2, the substituents in the parentheses may be the same or different from each other.

[0192] In another embodiment, p can be 0 or 1.

[0193] In another embodiment, p may be 1.

[0194] In another embodiment, p may be 0.

[0195] In one embodiment of the present application, q may be 0 or 1.

[0196] In another embodiment, q may be 1.

[0197] In another embodiment, q may be 0.

[0198] In one embodiment of the present application, r is an integer from 0 to 3, and when r is 2 or more, the substituents in parentheses may be the same or different from each other.

[0199] In another embodiment, r is an integer from 0 to 2, and when r is 2, the substituents in the parentheses may be the same or different from each other.

[0200] In another embodiment, r can be 0 or 1.

[0201] In another embodiment, r may be 1.

[0202] In another embodiment, r may be 0.

[0203] In one embodiment of the present application, the chemical formula 1 may be represented by any one of the following compounds.

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230] In one embodiment of the present application, the compound is an example and is not limited thereto, and may include other compounds included in the chemical formula 1 that include additional substituents. In addition, the substitution position of deuterium in the compound may exclude a specific position during the deuterium substitution and synthesis process, and hydrogen and deuterium may exist in a mixed state.

[0231] In addition, by introducing various substituents into the structure of the above chemical formula 1, compounds having the unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials used in the manufacture of organic light-emitting devices into the core structure, a material satisfying the conditions required for each organic layer can be synthesized.

[0232] In addition, by introducing various substituents into the structure of the above chemical formula 1 or changing the bonding position, the band gap can be finely controlled, and on the other hand, the properties at the interface between organic layers can be improved.

[0233] In addition, the compound of the above chemical formula 1 has excellent thermal stability, and this thermal stability provides operating stability to the organic light-emitting device and improves the life characteristics.

[0234] In one embodiment of the present application, an organic light-emitting device is provided, comprising: a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers includes a heterocyclic compound represented by the chemical formula 1.

[0235] In another embodiment, an organic light-emitting device is provided, comprising: a first electrode; a second electrode provided opposite the first electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers includes one type of heterocyclic compound represented by the chemical formula 1.

[0236] In another embodiment, an organic light-emitting device is provided, comprising: a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers includes two or more heterocyclic compounds represented by the chemical formula 1.

[0237] In another embodiment, the heterocyclic compound represented by the above chemical formula 1 can be used as a light-emitting material of a light-emitting layer of an organic light-emitting device.

[0238] In another embodiment, the heterocyclic compound represented by the above chemical formula 1 can be used as a host material of a light-emitting layer of an organic light-emitting device.

[0239] In one embodiment of the present application, the first electrode may be an anode, and the second electrode may be a cathode.

[0240] In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0241] In one embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound according to the chemical formula 1 may be used as a material of the blue organic light-emitting device.

[0242] In one embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material of the green organic light-emitting device.

[0243] In one embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material of the red organic light-emitting device.

[0244] In one embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound according to the chemical formula 1 may be used as a light-emitting layer material of the blue organic light-emitting device.

[0245] In one embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a light-emitting layer material of the green organic light-emitting device.

[0246] In one embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a light-emitting layer material of the red organic light-emitting device.

[0247] In one embodiment of the present application, the specific details of the heterocyclic compound represented by the chemical formula 1 are the same as those described above.

[0248] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the aforementioned heterocyclic compound.

[0249] The above heterocyclic compound can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0250] The organic layer of the organic light-emitting device of the present invention may be formed as a single-layer structure, but may also be formed as a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0251] In one embodiment of the present application, Ir(ppy)3, a green phosphorescent dopant, may be used as an iridium-based dopant.

[0252] In one embodiment of the present application, a red phosphorescent dopant, (piq)2(Ir)(acac), may be used as the iridium-based dopant.

[0253] In one embodiment of the present application, a pyrene-based dopant may be used as a blue phosphorescent dopant.

[0254] In one embodiment of the present application, an organic light-emitting device is provided, wherein the organic material layer of the organic light-emitting device includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound.

[0255] In one embodiment of the present application, an organic light-emitting device is provided, wherein the organic material layer of the organic light-emitting device includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes the heterocyclic compound.

[0256] In the organic light-emitting device of the present invention, the organic layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include the heterocyclic compound.

[0257] In another organic light-emitting device, the organic layer includes a hole-blocking layer, and the hole-blocking layer may include the heterocyclic compound.

[0258] In another organic light-emitting device, the organic layer includes an electron blocking layer, and the electron blocking layer may include the heterocyclic compound.

[0259] In another organic light-emitting device, the organic layer includes a hole transport layer, an emission layer, or an electron blocking layer, and the hole transport layer, the emission layer, or the electron blocking layer may include the heterocyclic compound.

[0260] In another organic light-emitting device, 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 heterocyclic compound.

[0261] In another organic light-emitting device, the organic layer includes a hole transport layer, and the hole transport layer may include the heterocyclic compound.

[0262] In the organic light-emitting device of the present application, materials having a relatively large work function can be used as the anode material, and transparent conductive oxides, metals, or conductive polymers can be used. 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 SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

[0263] Materials with relatively low work functions can be used as cathode materials, and metals, metal oxides, or conductive polymers can be used. Specific examples of the cathode materials 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; multilayered materials such as LiF / Al or LiO2 / Al.

[0264] As the hole injection material, a known hole injection material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a starburst amine derivative 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), a soluble conductive polymer such as polyaniline / dodecylbenzenesulfonic acid, or Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrene-sulfonate) can be used.

[0265] Pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used as hole transport materials, and low molecular weight or high molecular weight materials can also be used.

[0266] As the electron transport material, metal complexes of oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinoline and derivatives thereof, etc. can be used, and not only low molecular weight substances but also high molecular weight substances can be used.

[0267] For example, LiF is a representative material used in the art, but the present application is not limited thereto.

[0268] Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. At this time, two or more light-emitting materials may be deposited and used as individual sources, or may be premixed and deposited and used as a single source. In addition, a fluorescent material may be used as the light-emitting material, but it may also be used as a phosphorescent material. A material that emits light by combining holes and electrons injected from the anode and cathode, respectively, may be used as the light-emitting material, but materials in which both the host material and the dopant material participate in light emission may also be used.

[0269] When using a mixture of hosts for light-emitting materials, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, two or more types of materials, either n-type host materials or p-type host materials, may be selected and used as the host materials for the light-emitting layer.

[0270] An organic light-emitting device according to one embodiment of the present application may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

[0271] The heterocyclic compound according to one embodiment of the present application can function in organic electronic devices, including organic solar cells, organic photoconductors, organic transistors, etc., using a principle similar to that applied to organic light-emitting devices.

[0272] The organic light-emitting device of the present invention may further include one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0273] The organic light-emitting device of the present invention may further include one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0274] The stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present application is exemplified in Figures 1 to 4. However, the scope of the present application is not intended to be limited by these drawings, and the structure of an organic light-emitting device known in the art may also be applied to the present application.

[0275] According to FIG. 1, an organic light-emitting device is illustrated in which an anode (200), an organic layer (300), and a cathode (400) are sequentially laminated 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 layer, and an anode are sequentially laminated on a substrate, as shown in FIG. 2, may also be implemented.

[0276] Figures 3 and 4 illustrate a case where the organic layer is multilayer.

[0277] The organic light-emitting device according to FIG. 3 includes a hole injection layer (301), a hole transport layer (302), a light-emitting layer (303), a hole blocking layer (307), an electron transport layer (304), and an electron injection layer (305).

[0278] The organic light-emitting device according to FIG. 4 includes a hole injection layer (301), a hole transport layer (302), an electron blocking layer (306), a light-emitting layer (303), an electron transport layer (304), and an electron injection layer (305).

[0279] However, the scope of the present application is not limited by such a laminated structure, and layers other than the light-emitting layer may be omitted as needed, and other necessary functional layers may be added.

[0280] The organic layer containing the above chemical formula 1 may additionally contain other substances as needed.

[0281] Hereinafter, the present specification will be described in more detail through examples, but these are only intended to illustrate the present application and are not intended to limit the scope of the present application.

[0282] <Manufacturing Example>

[0283] [Manufacturing Example 1] Preparation of Compound 002

[0284]

[0285] 1) Preparation of compound 002-P3

[0286] 4-bromonaphthalen-2-ol (40 g, 179.32 mmol), phenyl boronic acid (24.54 g, 197.25 mmol), K2CO3 (49.56 g, 358.63 mmol), and Pd(PPh3)4 (10.36 g, 8.97 mmol) were added to 800 mL of toluene, 200 mL of ethanol, and 200 mL of H2O, and stirred under reflux for 6 hours. After completion of the reaction, the reaction solution was extracted with dichloromethane and distilled water, and the organic layer was dried over anhydrous MgSO4 and the solvent was removed using a rotary evaporator. Then, the mixture was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 002-P3 (30 g, 76%).

[0287] 2) Preparation of compound 002-P2

[0288] 4-phenylnaphthalen-2-ol (30 g, 136.2 mmol), 1,3-dichloro-2-fluoro-benzene (26.97 g, 163.44 mmol), and K2CO3 (37.64 g, 272.39 mmol) were added to 150 mL of NMP and 160 o The mixture was refluxed and stirred for 12 hours at C. After adding water to stop the reaction, the reaction solution was extracted with dichloromethane and distilled water, the organic layer was dried over anhydrous MgSO4, the solvent was removed using a rotary evaporator, and the mixture was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 002-P2 (21 g, 42%).

[0289] 3) Preparation of compound 002-P1

[0290] Add 210 mL of dimethylacetamide (DMA) to compound 002-P2 (21 g, 57.49 mmol), K2CO3 (11.92 g, 86.24 mmol), Pd(OAc)2 (0.65 g, 2.87 mmol), and PCy3HBF4 (2.12 g, 5.75 mmol) and 140 o The mixture was stirred at C for 12 hours. After adding water to stop the reaction, the reaction solution was extracted with dichloromethane and distilled water, the organic layer was dried over anhydrous MgSO4, the solvent was removed using a rotary evaporator, and the mixture was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 002-P1 (12 g, 63%).

[0291] 4) Preparation of compound 002

[0292] Compound 002-P1 (12 g, 36.5 mmol) and 3,5-ditert-butyl-N-(4-phenylphenyl)aniline (13.05 g, 36.5 mmol) were dissolved in 120 ml of toluene, and then Pd2(dba)3 (0.67 g, 0.73 mmol), xphos (0.7 g, 1.46 mmol), NaOtBu (7.01 g, 72.99 mmol) was added and stirred under reflux for 3 hours. After completion of the reaction, the reaction solution was extracted with dichloromethane and distilled water, the organic layer was dried over anhydrous MgSO4, the solvent was removed using a rotary evaporator, and the mixture was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 002 (16 g, 67%).

[0293] The target compound was synthesized using the same method as in Manufacturing Example 1 except that Compound A of Table 1 was used instead of 4-bromonaphthalen-2-ol, Compound B of Table 1 was used instead of phenyl boronic acid, Compound C of Table 1 was used instead of 1,3-dichloro-2-fluoro-benzene, and Compound D of Table 1 was used instead of 3,5-ditert-butyl-N-(4-phenylphenyl)aniline.

[0294] [Table 1]

[0295]

[0296]

[0297]

[0298]

[0299] [Manufacturing Example 2] Preparation of Compound 056

[0300]

[0301] In Manufacturing Example 2, the synthesis was performed in the same manner as in Manufacturing Example 1, except for the synthesis of compound 056-P3.

[0302] 1) Preparation of compound 056-P3

[0303] 3-iodonaphthalen-2-ol (30 g, 111.8 mmol), (3-bromo-6-chloro-2-fluoro-phenyl)boronic acid (29.54 g, 116.64 mmol), K2CO3 (30.7 g, 222.16 mmol), and Pd(PPh3)4 (6.42 g, 5.55 mmol) were added to 600 mL of toluene, 150 mL of ethanol, and 150 mL of H2O, and stirred under reflux for 6 hours. After completion of the reaction, the reaction solution was extracted with dichloromethane and distilled water, and the organic layer was dried over anhydrous MgSO4 and the solvent was removed using a rotary evaporator. Then, the mixture was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 056-P3 (30 g, 76%).

[0304] The target compound was synthesized using the same method as in Manufacturing Example 2, except that Compound A of Table 2 below was used instead of (3-bromo-6-chloro-2-fluoro-phenyl)boronic acid, Compound B of Table 2 below was used instead of phenylboronic acid, and Compound C of Table 2 below was used instead of 6,8-di-tert-butyl-9,9-dimethyl-N-phenyl-9H-fluoren-2-amine.

[0305] [Table 2]

[0306]

[0307]

[0308]

[0309]

[0310] [Manufacturing Example 3] Preparation of Compound 207

[0311]

[0312] Except for the synthesis of compound 207-P2 in Manufacturing Example 3, it was synthesized in the same manner as Manufacturing Examples 1 and 2.

[0313] 1) Preparation of compound 207-P2

[0314] Compound 207-P3 (22 g, 87.06 mmol) was dissolved in 300 mL of DMF and stirred for 3 hours at 60 o It was stirred at C. Distilled water was added to the mixture after the reaction was completed to precipitate a solid, which was then filtered and washed with distilled water and methanol to obtain compound 207-P2 (23.8 g, 82%).

[0315] The target compound was synthesized using the same method as in Manufacturing Example 3 above, except that Compound A of Table 3 below was used instead of 1-bromo-3-chloro-2-fluorobenzene, Compound B of Table 3 below was used instead of phenylboronic acid, and Compound C of Table 3 below was used instead of N-(3',5'-di-tert-butyl-[1,1'-biphenyl]-3-yl)-9,9-dimethyl-9H-fluoren-2-amine.

[0316] [Table 3]

[0317]

[0318]

[0319]

[0320] [Manufacturing Example 4] Preparation of Compound 321

[0321]

[0322] 1) Preparation of compound 321

[0323] Compound 008 (10 g, 12.56 mmol), Trifluoromethanesulfonic acid (9.43 g, 62.81 mmol), and 50 mL of D6-benzene were placed in a reaction flask and stirred under reflux for 5 hours. After the reaction was completed, distilled water was added to stop the reaction, and the mixture was extracted with dichloromethane and distilled water. The organic layer was dried over anhydrous MgSO4 and the solvent was removed using a rotary evaporator. The mixture was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 321 (9 g, 85%).

[0324] The target compound was synthesized by the same method as in Manufacturing Example 4, except that the reaction temperature and reaction time in Manufacturing Example 4 were performed at the reaction temperature and reaction time described in Table 4 below.

[0325] [Table 4]

[0326]

[0327] [Manufacturing Example 5] Preparation of Compound 323

[0328]

[0329] The synthesis of all compounds in Manufacturing Example 5 was carried out using the same method as in Manufacturing Examples 1 and 4.

[0330] The target compound was synthesized by the same method as in Manufacturing Example 5, except that the reaction temperature and reaction time in Table 5 were used instead of the reaction temperature and reaction time described in Compound 323-P1 of Manufacturing Example 5.

[0331] [Table 5]

[0332]

[0333] [Manufacturing Example 6] Preparation of Compound 466

[0334]

[0335] In the above Manufacturing Example 6, all syntheses were carried out using the same method as Manufacturing Examples 1 and 2.

[0336] [Table 6]

[0337]

[0338] The compound synthesized in the above manufacturing example was confirmed through 1H-NMR and FD-mass spectrometry. Table 7 1 The values ​​are measured by H NMR (DMSO, 300 MHz), and Table 8 is measured by FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0339] [Table 7]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345] [Table 8]

[0346]

[0347]

[0348] [Experimental Example]

[0349] Experimental Example 1

[0350] (1) Fabrication of organic light-emitting devices

[0351] A glass substrate coated with a 1,500 Å thick ITO film was ultrasonically cleaned in 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 for 5 minutes in a UV cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), where it was plasma-treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.

[0352]

[0353] Then the vacuum level inside the chamber is 10 -6 After evacuating to reach 10 torr, a current was applied to the cell to evaporate 2-TNATA and deposit a 600 Å thick hole injection layer on an ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was added to another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate it and deposit a 1000 Å thick hole transport layer on the hole injection layer.

[0354]

[0355] On top of that, the light-emitting layer was thermally vacuum-deposited as follows. The light-emitting layer was deposited with 400Å of a compound of 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-3,3'-Bi-9H-carbazole as a host, and the green phosphorescent dopant was deposited by doping with 7% Ir(ppy)3. After that, 60Å of BCP was deposited as a hole-blocking layer, and 300Å of E1 was deposited as an electron-transporting layer thereon.

[0356]

[0357] Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode, thereby manufacturing an organic electroluminescent device.

[0358] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -8 ~10 -6 It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0359] Except that the compounds shown in Table 8 below were used instead of the compound NPB used in forming the hole transport layer in Experimental Example 1, the driving voltage and luminous efficiency of the organic electroluminescent device according to Experimental Example 1 were as follows.

[0360] At this time, the hole transport compounds of the comparative examples excluding NPB are as follows.

[0361]

[0362] (2) Driving voltage and luminous efficiency of organic light-emitting devices

[0363] The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured using M7000 from MaxScience, and the standard luminance was determined to be 20,000 cd / m using the life measurement equipment (M6000) manufactured by MaxScience based on the measurement results. 2 When, T 95 was measured.

[0364] The characteristics of the organic electroluminescent device of the present invention are as shown in Table 9 below.

[0365] [Table 9]

[0366]

[0367]

[0368] As can be seen from the results in Table 9 above, Examples 1 to 45, which are organic light-emitting devices using the compound represented by Chemical Formula 1 of the present invention as a hole transport layer material, have lower operating voltages and significantly improved luminous efficiency and lifespans compared to Comparative Examples 1 to 12, which are organic light-emitting devices not using the compound represented by Chemical Formula 1 of the present invention as a hole transport layer material.

[0369] Compounds M2 to M12 used in Comparative Examples 2 to 12 have a naphthobenzofuran or naphthobenzothiophene skeleton and the introduced substituents are similar to those of the compound of the present invention, but they differ from the compound of the present invention in that they use two substituents of an arylamine group and a tert-butyl group, the positions of the introduced substituents, whether or not a linker is used, and at least two or more tert-butyl groups are not bonded in the meta position. The compound of the present invention has the characteristics of fast hole mobility by introducing two or more tert-butyl groups and arylamine substituents with electron donating characteristics as two substitutions, and has the properties of an appropriate HOMO level, thereby delocalizing the energy level and stabilizing the HOMO energy, while effectively preventing electrons from flowing over from the opposite side of the electron transport layer. In addition, M2, M3, and M6 used in comparative examples used carbazole, two or more amine groups, and 1 substitution. In this case, the hole mobility becomes too fast or too slow, making it difficult to have an appropriate energy level. For this reason, when the compound of the present invention was used as a hole transport layer, it was confirmed that hole transport to the light-emitting layer was easier than M2 to M12 used in comparative examples 2 to 12, resulting in a lower driving voltage and improved efficiency and lifespan.

[0370] Experimental Example 2

[0371] (1) Fabrication of organic light-emitting devices

[0372] A transparent electrode ITO thin film obtained from OLED glass (manufactured by Samsung Corning) was ultrasonically cleaned sequentially using trichloroethylene, acetone, ethanol, and distilled water for 5 minutes each, and then stored in isopropanol before use. Next, the ITO substrate was installed in the substrate folder of the vacuum deposition equipment, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine (4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was added to the cell in the vacuum deposition equipment.

[0373]

[0374] Then the vacuum level inside the chamber is 10 -6 After evacuating to reach 10 torr, a current was applied to the cell to evaporate 2-TNATA and deposit a 600 Å thick hole injection layer on an ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was added to another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate it and deposit a 1000 Å thick hole transport layer on the hole injection layer.

[0375]

[0376] Next, a compound of the structural formula M2 was deposited as an electron blocking layer with a thickness of 100 Å.

[0377]

[0378] On top of that, a blue light-emitting material having the following structure was deposited as a light-emitting layer. Specifically, a blue light-emitting host material, H1, was vacuum-deposited to a thickness of 300Å in one cell within a vacuum deposition device, and a blue light-emitting dopant material, D1, was vacuum-deposited thereon at a thickness of 5% relative to the host material.

[0379]

[0380] Next, a compound of the following structural formula E1 was deposited as an electron transport layer with a thickness of 300 Å.

[0381]

[0382] An OLED device was fabricated by depositing lithium fluoride (LiF) as an electron injection layer with a thickness of 10 Å and using an Al cathode with a thickness of 1,000 Å. Meanwhile, all organic compounds required for fabricating an OLED device were each 10 Å thick. -8 ~10 -6 It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0383] (2) Driving voltage and luminous efficiency of organic light-emitting devices

[0384] The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured using M7000 from MaxScience, and the standard luminance was determined to be 20,000 cd / m using the life measurement equipment (M6000) manufactured by MaxScience based on the measurement results. 2 At that time, T95 was measured.

[0385] Except that the compound shown in Table 10 below was used instead of the compound M1 used in forming the electron blocking layer in Experimental Example 2, the driving voltage and luminous efficiency of the organic electroluminescent device according to Experimental Example 2 are as shown in Table 10 below.

[0386] [Table 10]

[0387]

[0388]

[0389] As can be seen from the results in Table 10 above, Examples 45 to 89, which are organic light-emitting devices using the compound represented by Chemical Formula 1 of the present invention as an electron-blocking layer material, have lower driving voltages and significantly improved luminous efficiency and lifespans compared to Comparative Examples 13 to 24, which are organic light-emitting devices using M2 to M12 and NPB compounds as electron-blocking layer materials. In addition, the compound of the present invention introduces two or more tert-butyl groups with electron donating properties, so that the number of electrons increases, the repulsive energy increases, and the overall activation energy increases, resulting in a high LUMO level.

[0390] In general, when electrons are not combined in the emitting layer but pass through the hole transport layer to the anode, the efficiency and lifespan of the organic light-emitting device decrease. In this case, if a compound with a high LUMO (Lowest Unoccupied Molecular Orbital) level is used as an electron blocking layer, electrons trying to pass through the emitting layer to the anode are blocked by the energy barrier of the electron blocking layer, so that the phenomenon of decrease in the efficiency and lifespan of the organic light-emitting device can be prevented. In other words, if a compound with a high LUMO (Lowest Unoccupied Molecular Orbital) level is used as an electron blocking layer, the probability that holes and electrons form excitons increases, and the probability that they are emitted as light from the emitting layer increases.

[0391] Therefore, since the compound of the present invention has a higher LUMO Level than the compounds of Comparative Examples 13 to 24, when the compound of the present invention is used as an electron blocking layer of an organic light-emitting device, the electron blocking ability is further improved, and holes and electrons achieve charge balance, resulting in significant improvement in all aspects of operation, efficiency, and lifespan.

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X is O or S, L1 and L2 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted C6 to C60 arylene group, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or are represented by the following chemical formula 2, One of the above R1 and R2 is represented by the following chemical formula 2, and the others are a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, Ra, Rb and Rc are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, p is an integer from 0 to 4, and when p is 2 or greater, the substituents in the parentheses are the same or different from each other, q is an integer from 0 to 2, and when q is 2, the substituents in the parentheses are the same or different, r is an integer from 0 to 4, and when r is 2 or greater, the substituents in the parentheses are the same or different from each other, [Chemical formula 2] In the above chemical formula 2, L3 and L4 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted C6 to C60 arylene group, R3 and R4 are the same or different, and each independently represents a condensed ring group of a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring and a C3 to C60 aliphatic hydrocarbon ring group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, One of the above R1 and R2 is represented by the above chemical formula 2, and the other one of R1 and R2 and at least one of R3 and R4 is substituted with two or more substituted or unsubstituted C1 to C60 branched-chain alkyl groups.

2. In claim 1, A heterocyclic compound wherein one of the above R1 and R2 is represented by the above chemical formula 2, and the other one of R1 and R2, and at least one of R3 and R4 are substituted with two or more substituted or unsubstituted C1 to C60 branched-chain alkyl groups at the meta position to each other.

3. In claim 1, the chemical formula 1 is a heterocyclic compound represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In the above chemical formulas 1-1 to 1-4, The definitions of L1, L2, R1, R2, Ra, Rb, Rc, p, q and r are the same as those in the chemical formula 1 described above.

4. In claim 1, The above chemical formula 2 is a heterocyclic compound represented by the following chemical formula A or B: [Chemical Formula A] [Chemical Formula B] In the above chemical formulas A and B, The definitions of R4, L3 and L4 are the same as those in the chemical formula 1 described above, R5 to R13 are the same or different and are each independently hydrogen; deuterium; or a substituted or unsubstituted C1 to C60 branched-chain alkyl group, R14 and R15 are the same as or different from each other, and each independently represents a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group, or combine with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, Rd is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, s is an integer from 0 to 3, and when s is 2 or greater, the substituents in the parentheses are the same or different from each other, At least two of R5 to R9 are a substituted or unsubstituted C1 to C60 branched-chain alkyl group, and at least two of R10 to R13 are a substituted or unsubstituted C1 to C60 branched-chain alkyl group.

5. In claim 4, Among R5 to R9, R6 and R8 are substituted or unsubstituted C1 to C60 branched-chain alkyl groups, and the rest are hydrogen; or deuterium, A heterocyclic compound wherein among R10 to R13, R10 and R12 are substituted or unsubstituted C1 to C60 branched alkyl groups and the remainder are hydrogen; or deuterium, or among R10 to R13, R11 and R13 are substituted or unsubstituted C1 to C60 branched alkyl groups and the remainder are hydrogen; or deuterium.

6. In claim 1, The above R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; or a heterocyclic compound represented by the above chemical formula 2.

7. In claim 1, A heterocyclic compound wherein the above R3 and R4 are the same or different, and each independently represents a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

8. In claim 1, The above chemical formula 1 is a heterocyclic compound represented by any one of the following compounds: .

9. An organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a heterocyclic compound according to any one of claims 1 to 8.

10. An organic light-emitting device according to claim 9, wherein the organic layer includes a hole transport layer, and the hole transport layer includes the heterocyclic compound.

11. An organic light-emitting device according to claim 9, wherein the organic layer includes an electron-blocking layer, and the electron-blocking layer includes the heterocyclic compound.

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