Heterocyclic compound, organic light emitting device comprising the same, and composition for organic material layer of organic light emitting device

Abstract

To provide a heterocyclic compound, an organic light emitting device comprising the same, and a composition for an organic material layer of the organic light emitting device.SOLUTION: The invention provides a heterocyclic compound of Chemical Formula 1, an organic light emitting device comprising the same, and a composition for an organic material layer of the organic light emitting device. (In the formula, X is O or S.)SELECTED DRAWING: Figure 1

Description

Technical Field

[0001] This specification relates to a heterocyclic compound, an organic light-emitting device including the same, and a composition for an organic layer of an organic light-emitting device.

[0002] This application claims the benefit of the filing date of Korean Patent Application No. 10-2023-0171543, filed with the Korean Intellectual Property Office on November 30, 2023, and all of its contents are incorporated herein by reference.

Background Art

[0003] An electroluminescent device is a type of self-luminous display device, and has advantages such as a wide viewing angle, excellent contrast, and a fast response speed. An organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an organic light-emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then emit light while disappearing. The organic thin film can be composed of a single layer or multiple layers as needed.

[0004] The material of the organic thin film can have a light-emitting function as needed. For example, as the material of the organic thin film, a compound that can form a light-emitting layer by itself may be used, or a compound that can serve as a host or a dopant in a host-dopant type light-emitting layer may be used. In addition, as the material of the organic thin film, a compound that can serve as a hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, or the like may be used. In order to improve the performance, lifespan, or efficiency of an organic light-emitting device, the development of materials for organic thin films has been continuously demanded.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] This specification aims to provide a heterocyclic compound, an organic light-emitting device containing the same, and a composition for an organic layer of an organic light-emitting device.

Means for Solving the Problems

[0007] One embodiment of this specification provides a heterocyclic compound represented by the following Chemical Formula 1.

Chem.

[0008] Another embodiment of the present specification is an organic light-emitting device including a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain one or more of the heterocyclic compounds, and an organic light-emitting device is provided.

[0009] Another embodiment of the present specification provides a composition for an organic layer of an organic light-emitting device containing the heterocyclic compound.

Effects of the Invention

[0010] When the heterocyclic compound described in the present specification is used in an organic light-emitting device, it can lower the driving voltage of the device, improve the luminous efficiency, and improve the lifetime characteristics of the device. Specifically, the heterocyclic compound of the present invention has the 6-positions of two identical naphthobenzofuran groups / naphthobenzothiophene groups bonded to triazine as shown in Chemical Formula 1, and when used as a light-emitting layer material, it can effectively improve the performance of the device. By having triazine bonded to specific positions of two identical naphthobenzofuran groups / naphthobenzothiophene groups to have a symmetric structure in this way, the conjugation of the molecule is extended, and it has a suitable band gap and homo level. As a result, charge transfer becomes smooth, and there is an effect of increasing the luminous efficiency.

Brief Description of the Drawings

[0011]

Figure 1

Figure 2

Figure 3

Modes for Carrying Out the Invention

[0012] Hereinafter, the present specification will be described in more detail. As used herein, when a part "includes" a certain component, it means that, unless otherwise specified to the contrary, it does not exclude other components but may further include other components.

[0013] As used herein, "N to N'" means N or more and N' or less. In this specification, for the chemical formula

Chemical formula

[0014] The term "substituted" means that a hydrogen atom bonded to a carbon atom or a nitrogen atom of a compound is replaced by another substituent, and the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted. When two or more substitutions occur, the two or more substituents may be the same or different from each other.

[0015] As used herein, "substituted or unsubstituted" means deuterium; a halogen group; -CN; a C1 - C60 alkyl group; a C2 - C60 alkenyl group; a C2 - C60 alkynyl group; a C1 - C60 haloalkyl group; a C1 - C60 alkoxy group; a C6 - C60 aryloxy group; a C1 - C60 alkylthioxy group; a C6 - C60 arylthioxy group; a C1 - C60 alkylsulfinyl group; a C6 - C60 arylsulfinyl group; a C3 - C60 cycloalkyl group; a C2 - C60 heterocycloalkyl group; a C6 - C60 aryl group; a C2 - C60 heteroaryl group; a silyl group; a phosphine oxide group; and an amine group, one or more substituents selected from the group consisting of these, or substituted with a substituent formed by linking two or more substituents selected from among the above substituents, or unsubstituted.

[0016] As used herein, Cn1 - Cn2 (n1 and n2 are integers of 1 or more) means the range of the number of carbon atoms. For example, a C1 - C60 alkyl group means an alkyl group having 1 to 60 carbon atoms.

[0017] In this specification, "when no substituent is shown in the chemical formula or the structure of the compound" means that a hydrogen atom is bonded to the carbon atom. However, since deuterium ( 2 H, Deuterium) is an isotope of hydrogen, some of the hydrogen atoms may be deuterium.

[0018] In one embodiment of the present application, "when no substituent is shown in the chemical formula or the structure of the compound" may mean that all positions that can be substituents are hydrogen or deuterium. That is, in the case of deuterium, which is an isotope of hydrogen, some of the hydrogen atoms may be deuterium, which is an isotope. At this time, the deuterium content may be 0% to 100%, and the deuterium content may be expressed as the deuterium substitution rate.

[0019] In one embodiment of the present application, in the case of "when no substituent is shown in the chemical formula or the structure of the compound", when deuterium is not explicitly excluded, such as "the deuterium content is 0% and the hydrogen content is 100%", "all substituents are hydrogen", hydrogen and deuterium may be mixed and used in the compound. In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, and is an element having a deuteron composed of one proton and one neutron as its nucleus, and may be represented as hydrogen-2, and the element symbol may be D or 2 H.

[0020] In one embodiment of the present application, isotopes, which mean atoms having the same atomic number (Z) but different mass numbers (A), can also be interpreted as elements having the same number of protons but different numbers of neutrons.

[0021] In one embodiment of the present application, the meaning of the substitution rate T% of a specific substituent can be defined as follows. When the total number of substituents that the base compound can have is defined as T1, and the number of the specific substituent among them is defined as T2, then T2 / T1×100 = T%.

[0022] That is, in one example,

Chemical formula

Chemical formula

[0023] Also, in one embodiment of the present application, in the case of "a phenyl group with a deuterium substitution rate of 0%", it can mean a phenyl group that does not contain a deuterium atom as a substituent, that is, a phenyl group having 5 hydrogen atoms.

[0024] In this specification, examples of the halogen include fluorine, chlorine, bromine, or iodine.

[0025] In this specification, the alkyl group includes a straight-chain or branched-chain having 1 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, an n-heptyl group, a 1-methylhexyl group, an octyl group, an n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentyl group, an n-nonyl group, a 2,2-dimethylheptyl group, a 1-ethyl-propyl group, a 1,1-dimethyl-propyl group, an isohexyl group, a 2-methylpentyl group, a 4-methylhexyl group, a 5-methylhexyl group, etc., but are not limited thereto.

[0026] In this specification, the alkenyl group includes a straight-chain or branched-chain having 2 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples include a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, a styrenyl group, etc., but are not limited thereto.

[0027] In this specification, the alkynyl group includes a straight-chain or branched-chain having 2 to 60 carbon atoms and may be further substituted with other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0028] In this specification, the haloalkyl group means an alkyl group substituted with a halogen group. Specific examples include, but are not limited to, -CF 3 、-CF 2 CF 3 and the like.

[0029] In this specification, the alkoxy group is represented by -O(R101), and the examples of the alkyl group described above may be applicable to R101.

[0030] In this specification, the aryloxy group is represented by -O(R102), and the examples of the aryl group described above may be applicable to R102.

[0031] In this specification, the alkylthioxy group is represented by -S(R103), and the examples of the alkyl group described above may be applicable to R103.

[0032] In this specification, the arylthioxy group is represented by -S(R104), and the examples of the aryl group described above may be applicable to R104.

[0033] In this specification, the alkylsulfinyl group is represented by -S(=O) 2 (R105), and the examples of the alkyl group described above may be applicable to R105.

[0034] In this specification, the arylsulfinyl group is represented by -S(=O) 2 (R106), and the examples of the aryl group described above may be applicable to R106.

[0035] In this specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic group means a group in which the cycloalkyl group is directly linked 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, a heteroaryl group, etc. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc. may be mentioned, but are not limited thereto.

[0036] In this specification, the heterocycloalkyl group contains O, S, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic group means a group in which the heterocycloalkyl group is directly linked 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, a heteroaryl group, etc. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0037] In this specification, the aryl group includes a monocyclic or polycyclic group having 6 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic group means a group in which the aryl group is directly linked 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, a heteroaryl group, etc. The aryl group includes a spiro group. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group include 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, etc., but are not limited thereto.

[0038] In this specification, the terphenyl group may be selected from the following structures.

Chemical formula

[0039] In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0040] When the fluorenyl group is substituted, it may have the following structures, but is not limited thereto.

Chemical formula

[0041] In this specification, the heteroaryl group contains S, O, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic ring means a group in which the heteroaryl group is directly linked or condensed with another cyclic group. Here, the other cyclic group may be a heteroaryl group, but may also be other types of cyclic groups, for example, a cycloalkyl group, a heterocycloalkyl group, an aryl group, and the like. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25.Specific examples of the heteroaryl group include, but are not limited to, 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 dioxine group, a triazine group, a tetrazine group, a quinoline group, an isoquinoline group, a quinazoline group, an isoquinazoline group, a quinoxaline 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, a benzoxazole group, a benzimidazole group, a benzothiophene group, a benzofuran group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a benzocarbazole group, a dibenzocarbazole group, a phenazine group, a dibenzosilole group, spirobi(dibenzosilole), a dihydrophenazine group, a phenoxazine group, a phenanthridine group, a thienyl group, an indolo[2,3-a]carbazole group, an indolo[2,3-b]carbazole group, an indoline group, a 10,11-dihydro-dibenzo[b,f]azepine group, a 9,10-dihydroacridine group, a phenanthradine group, a phenothiazine group, a phthalazine group, a phenanthroline group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzo[c][1,2,5]thiadiazole group, a 2,3-dihydrobenzothiophene 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, a 5,11-dihydroindenol[1,2-b]carbazole group, and the like.

[0042] In the present specification, the benzocarbazole group may be any one of the following structures.

Chemical formula

[0043] In this specification, the dibenzocarbazole group may be any one of the following structures.

Chemical formula

[0044] In this specification, when the substituent is a carbazole group, a benzocarbazole group, or a dibenzocarbazole group, it means bonding to the nitrogen or carbon of the carbazole group, benzocarbazole group, or dibenzocarbazole group.

[0045] In this specification, when the carbazole group, benzocarbazole group, or dibenzocarbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole group, benzocarbazole group, or dibenzocarbazole group.

[0046] In this specification, the naphthobenzofuran group may be any one of the following structures.

Chemical formula

[0047] In this specification, the naphthobenzothiophene group may be any one of the following structures.

Chemical formula

[0048] In this specification, the silyl group contains Si and is a substituent in which the Si atom is directly linked as a radical, represented by -Si(R107)(R108)(R109), and R107 to R109 may be the same as or different from each other and are each independently 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.

[0049] Depending on the substituents bonded to the Si element, the silyl group may include an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, an alkylarylsilyl group, an arylheteroarylsilyl group, etc. The alkylsilyl group, arylsilyl group, or heteroarylsilyl group means that the Si element of the silyl group is substituted with an alkyl group, an aryl group, or a heteroaryl group, respectively. The alkylarylsilyl group means that the Si element of the silyl group is substituted with an alkyl group and an aryl group, and the arylheteroarylsilyl group means that the Si element of the silyl group is substituted with an aryl group and a heteroaryl group.

[0050] Specific examples of the silyl group include, but are not limited to, the following structures.

Chemical formula

[0051] In this specification, the phosphine oxide group is represented by -P(=O)(R110)(R111), where R110 and R111 may be the same as or different from each other and are each independently 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. Specifically, it may be substituted with an alkyl group or an aryl group, and the above-mentioned examples may be applicable to the alkyl group and the aryl group. For example, examples of the phosphine oxide group include, but are not limited to, the dimethylphosphine oxide group, the diphenylphosphine oxide group, dinaphthylphosphine oxide, etc.

[0052] In this specification, the amine group is represented by -N(R112)(R113), where R112 and R113 may be the same as or different from each other, and each independently may be a substituent consisting of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. The amine group may be -NH 2 ; 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 amine group include 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, a biphenyltriphenylenylamine group, etc., but are not limited thereto.

[0053] In this specification, the arylene group may be subject to the description of the aforementioned aryl group, except that it is a divalent group.

[0054] In this specification, the heteroarylene group may be subject to the description of the aforementioned heteroaryl group, except that it is a divalent group.

[0055] One embodiment of this specification provides a heterocyclic compound of the following Chemical Formula 1.

Chemical formula

[0056] The heterocyclic compound according to one embodiment of the present specification has two identical naphthobenzofuran groups / naphthobenzothiophene groups as substituents of the triazine group, and the structures and substitution positions of the naphthobenzofuran groups / naphthobenzothiophene groups are specified. By having such a structure, when used as a material for an organic light-emitting device, it is helpful for improving the performance of the organic light-emitting device.

[0057] That is, in the chemical formula 1, the two

Chemical formula

Chemical formula

Chemical formula

[0058] In one embodiment of the present specification, the X may be O.

[0059] In one embodiment of the present specification, the X may be S.

[0060] In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 1-O or 1-S.

Chemical formula

[0061] In one embodiment of the present specification, the L may be a direct bond; a substituted or unsubstituted C6-C30 arylene group; or a substituted or unsubstituted C2-C30 heteroarylene group.

[0062] In one embodiment of the present specification, the L may be a direct bond; a substituted or unsubstituted C6-C20 arylene group; or a substituted or unsubstituted C2-C20 heteroarylene group.

[0063] In one embodiment of the present specification, the L may be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted divalent dibenzofuran group; a substituted or unsubstituted divalent dibenzothiophene group; or a substituted or unsubstituted divalent carbazole group.

[0064] In one embodiment of the present specification, the L may be a direct bond; a C6-C60 arylene group substituted or unsubstituted with deuterium; or a C2-C60 heteroarylene group substituted or unsubstituted with deuterium.

[0065] In one embodiment of the present specification, L may be a direct bond; an arylene group having 6 to 30 carbon atoms which is substituted or unsubstituted with deuterium; or a heteroarylene group having 2 to 30 carbon atoms which is substituted or unsubstituted with deuterium.

[0066] In one embodiment of the present specification, L may be a direct bond; an arylene group having 6 to 20 carbon atoms which is substituted or unsubstituted with deuterium; or a heteroarylene group having 2 to 20 carbon atoms which is substituted or unsubstituted with deuterium.

[0067] In one embodiment of the present specification, L may be a direct bond; a phenylene group which is substituted or unsubstituted with deuterium; a naphthylene group which is substituted or unsubstituted with deuterium; a divalent dibenzofuran group which is substituted or unsubstituted with deuterium; a divalent dibenzothiophene group which is substituted or unsubstituted with deuterium; or a divalent carbazole group which is substituted or unsubstituted with deuterium.

[0068] In one embodiment of the present specification, L may be a direct bond or selected from the following structures.

Chemical formula

Chemical formula

[0069] In one embodiment of the present specification, Ar may be an alkyl group having 1 to 30 carbon atoms which is substituted or unsubstituted; a cycloalkyl group having 3 to 30 carbon atoms which is substituted or unsubstituted; a heterocycloalkyl group having 2 to 30 carbon atoms which is substituted or unsubstituted; an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted; or a heteroaryl group having 2 to 30 carbon atoms which is substituted or unsubstituted.

[0070] In one embodiment of the present specification, Ar may be a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

[0071] In one embodiment of the present specification, Ar may be a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0072] In one embodiment of the present specification, Ar may 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 phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted fluoranthenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted naphthobenzofuran group; or a substituted or unsubstituted naphthobenzothiophene group.

[0073] In one embodiment of the present specification, Ar may be a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a phenanthrenyl group; a triphenylenyl group; a fluoranthenyl group; a fluorenyl group; a dibenzofuran group; a dibenzothiophene group; a carbazole group; a naphthobenzofuran group; or a naphthobenzothiophene group, and Ar may be further substituted with one or more substituents or two or more linking groups selected from deuterium, a halogen group, an alkyl group, an aryl group, and a heteroaryl group.

[0074] In one embodiment of the present specification, the Ar is an optionally substituted C6-C60 aryl group with one or more substituents or two or more linking groups selected from deuterium, a halogen group, an alkyl group, an aryl group, and a heteroaryl group; or an optionally substituted C2-C60 heteroaryl group with one or more substituents or two or more linking groups selected from deuterium, a halogen group, an alkyl group, an aryl group, and a heteroaryl group.

[0075] In one embodiment of the present specification, the Ar is an optionally substituted C6-C30 aryl group with one or more substituents or two or more linking groups selected from deuterium, a halogen group, an alkyl group, an aryl group, and a heteroaryl group; or an optionally substituted C2-C30 heteroaryl group with one or more substituents or two or more linking groups selected from deuterium, a halogen group, an alkyl group, an aryl group, and a heteroaryl group.

[0076] In one embodiment of the present specification, the Ar is an optionally substituted C6-C60 aryl group with one or more substituents or two or more linking groups selected from deuterium, a halogen group, an alkyl group, an aryl group, and a heteroaryl group; or an optionally substituted C2-C60 heteroaryl group with one or more substituents or two or more linking groups selected from deuterium and an aryl group.

[0077] In one embodiment of the present specification, the Ar is an optionally substituted C6-C30 aryl group with one or more substituents or two or more linking groups selected from deuterium, a halogen group, an alkyl group, an aryl group, and a heteroaryl group; or an optionally substituted C2-C30 heteroaryl group with one or more substituents or two or more linking groups selected from deuterium and an aryl group.

[0078] The linking group means a substituent formed by linking two or more substituents. For example, the linking group of a halogen group and an aryl group may include an aryl group substituted with a halogen group, and the linking group of deuterium, a halogen group, and an aryl group may include an aryl group substituted with deuterium and a halogen group.

[0079] In one embodiment of the present specification, the R may be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C40 alkyl group; a substituted or unsubstituted C1-C40 haloalkyl group; a substituted or unsubstituted C3-C40 cycloalkyl group; a substituted or unsubstituted C2-C40 heterocycloalkyl group; a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0080] In one embodiment of the present specification, the R may be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1-C60 haloalkyl group; or a substituted or unsubstituted C6-C60 aryl group.

[0081] In one embodiment of the present specification, the R may be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1-C30 haloalkyl group; or a substituted or unsubstituted C6-C30 aryl group.

[0082] In one embodiment of the present specification, the R may be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1-C10 haloalkyl group; or a substituted or unsubstituted C6-C20 aryl group.

[0083] In one embodiment of the present specification, the R may be hydrogen; deuterium; a halogen group; -CF 3 ; or a substituted or unsubstituted phenyl group.

[0084] In one embodiment of the present specification, the R may be hydrogen; deuterium; a halogen group; a C1-C60 haloalkyl group; or a C6-C60 aryl group substituted or unsubstituted with deuterium.

[0085] In one embodiment of the present specification, the R may be hydrogen; deuterium; a halogen group; a C1-C30 haloalkyl group; or a C6-C30 aryl group which is substituted or unsubstituted with deuterium.

[0086] In one embodiment of the present specification, the R may be hydrogen; deuterium; a halogen group; a C1-C10 haloalkyl group; or a C6-C20 aryl group which is substituted or unsubstituted with deuterium.

[0087] In one embodiment of the present specification, the R is hydrogen; deuterium; a halogen group; -CF 3 ; or a phenyl group which is substituted or unsubstituted with deuterium.

[0088] In one embodiment of the present specification, the Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-4. [Chemical Formula] TIFF2025088772000021.tif73161 In the Chemical Formulas 1-1 to 1-4, the definitions of L, Ar, and X are the same as those in the Chemical Formula 1, H1 is hydrogen; or deuterium, Q1 is a halogen group; a substituted or unsubstituted C1-C60 haloalkyl group; or a substituted or unsubstituted C6-C60 aryl group, n is an integer from 1 to 9, and when it is 2 or more, the substituents in the parentheses are the same as or different from each other, o is an integer from 1 to 8, and when it is 2 or more, the substituents in the parentheses are the same as or different from each other.

[0089] In one embodiment of the present specification, the Q1 may be a halogen group; a substituted or unsubstituted C1-C30 haloalkyl group; or a substituted or unsubstituted C6-C30 aryl group.

[0090] In one embodiment of the present specification, Q1 may be a halogen group; a substituted or unsubstituted C1-C10 haloalkyl group; or a substituted or unsubstituted C6-C20 aryl group.

[0091] In one embodiment of the present specification, Q1 may be a halogen group; a C1-C30 haloalkyl group; or a C6-C30 aryl group substituted or unsubstituted with deuterium.

[0092] In one embodiment of the present specification, Q1 may be a halogen group; a C1-C10 haloalkyl group; or a C6-C20 aryl group substituted or unsubstituted with deuterium.

[0093] In one embodiment of the present specification, Q1 is a halogen group; -CF 3 ; or a phenyl group substituted or unsubstituted with deuterium.

[0094] For two of the chemical formula 1-3

Chemical formula

[0095] For two of the chemical formula 1-4

Chemical formula

[0096] In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 1-1-1.

Chemical formula

[0097] In one embodiment of the present specification, P1 to P9 may each independently be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1-C30 haloalkyl group; or a substituted or unsubstituted C6-C30 aryl group.

[0098] In one embodiment of the present specification, P1 to P9 may each independently be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1-C10 haloalkyl group; or a substituted or unsubstituted C6-C20 aryl group.

[0099] In one embodiment of the present specification, P1 to P9 may each independently be hydrogen; deuterium; a halogen group; a C1-C30 haloalkyl group; or a C6-C30 aryl group substituted or unsubstituted with deuterium.

[0100] In one embodiment of the present specification, P1 to P9 may each independently be hydrogen; deuterium; a halogen group; a C1-C10 haloalkyl group; or a C6-C20 aryl group substituted or unsubstituted with deuterium.

[0101] In one embodiment of the present specification, P1 to P9 are each independently hydrogen; deuterium; a halogen group; -CF 3 ; or a phenyl group substituted or unsubstituted with deuterium.

[0102] In one embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 may be 0% to 100%.

[0103] In one embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 is 0% or may be 5% to 100%.

[0104] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 0% or 10% - 100%.

[0105] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 0% or 20% - 100%.

[0106] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 0% or 30% - 100%.

[0107] In the present specification, the deuterium substitution rate of the chemical formula 1 means the substitution rate of deuterium with respect to the total number of hydrogen and deuterium contained in the chemical formula 1. For example, when there are 20 hydrogens and 20 deuteriums in the chemical formula 1, the substitution rate of 20 deuteriums with respect to the total 40 of hydrogen and deuterium is 50%.

[0108] In one embodiment of the present specification, when the deuterium substitution rate of the heterocyclic compound of the chemical formula 1 satisfies the above range, the photochemical characteristics of the compound containing no deuterium and the compound containing deuterium are almost similar. However, when deposited on a thin film, the substance containing deuterium tends to be packed with a narrower intermolecular distance.

[0109] Thereby, when an EOD (Electron Only Device) and an HOD (Hole Only Device) are fabricated and the current density by voltage is confirmed, it can be confirmed that among the heterocyclic compounds of the chemical formula 1 of the present invention, the compound containing deuterium exhibits a much more balanced charge transport characteristic compared to the compound containing no deuterium.

[0110] Also, when looking at the surface of the thin film with an atomic force microscope (AFM, Atomic Force Microscope), it can be confirmed that the thin film made from the compound containing deuterium has no aggregated areas and is deposited on a more uniform surface.

[0111] Furthermore, since the bond dissociation energy of the single bond between carbon and deuterium is higher than that of the single bond between carbon and hydrogen, among the heterocyclic compounds of Chemical Formula 1 of the present invention, in the case of the compounds containing deuterium, the stability of the whole molecule is increased, and there is an effect that the device lifetime is improved.

[0112] In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following compounds.

Chemical formula

[0113] Also, by introducing various substituents into the structure of Chemical Formula 1, compounds having the unique properties of the introduced substituents can be synthesized. For example, by introducing the substituents mainly used for the hole injection layer material, hole transport layer material, light emitting layer material, electron transport layer material, and charge generation layer material used in the manufacture of the organic light emitting device into the core structure, substances that satisfy the conditions required for each organic layer can be synthesized.

[0114] In addition, by introducing various substituents into the structure of the chemical formula 1, the energy band gap can be finely adjusted, while improving the characteristics at the interface between organic substances, and diversifying the uses of the substances. Another embodiment of the present specification provides an organic light-emitting device including a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain one or more heterocyclic compounds of the chemical formula 1.

[0115] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may contain one or more of the heterocyclic compounds.

[0116] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may contain one of the heterocyclic compounds.

[0117] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer contains a host, and the host may contain one or more of the heterocyclic compounds.

[0118] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer contains a host, and the host may contain one of the heterocyclic compounds.

[0119] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer contains a host, the host contains a green host, and the green host may contain one or more of the heterocyclic compounds.

[0120] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer contains a host, the host contains a red host, and the red host may contain one or more of the heterocyclic compounds.

[0121] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, the host includes a blue host, and the blue host may include one or more of the heterocyclic compounds.

[0122] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include the heterocyclic compound as an N-type host.

[0123] In one embodiment of the present specification, the organic layer containing the heterocyclic compound may further include a compound of the following Chemical Formula 2. [Chemical Formula] In Chemical Formula 2, L1 to L3 are each independently a direct bond; a substituted or unsubstituted C6 - C60 arylene group; or a substituted or unsubstituted C2 - C60 heteroarylene group, Ar1 and Ar2 are each independently a substituted or unsubstituted C6 - C60 aryl group; or a substituted or unsubstituted C2 - C60 heteroaryl group, R11 and R12 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 - C60 alkyl group; a substituted or unsubstituted C2 - C60 alkenyl group; a substituted or unsubstituted C2 - C60 alkynyl group; a substituted or unsubstituted C1 - C60 alkoxy group; a substituted or unsubstituted C3 - C60 cycloalkyl group; a substituted or unsubstituted C2 - C60 heterocycloalkyl group; a substituted or unsubstituted C6 - C60 aryl group; or a substituted or unsubstituted C2 - C60 heteroaryl group, or adjacent groups are bonded to form a substituted or unsubstituted C6 - C60 aromatic ring, or a substituted or unsubstituted C2 - C60 heterocyclic ring, q is an integer from 1 to 3, r is an integer from 1 to 4, When q and r are each 2 or more, the substituents in parentheses are the same as or different from each other.

[0124] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may further include the compound of Chemical Formula 2.

[0125] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, and the host may further include the compound of Chemical Formula 2.

[0126] In one embodiment of the present specification, the light-emitting layer may further include the compound of Chemical Formula 2 as a P-type host.

[0127] In one embodiment of the present specification, each of L1 to L3 may independently be a direct bond; or a substituted or unsubstituted C6 to C60 arylene group.

[0128] In one embodiment of the present specification, each of L1 to L3 may independently be a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

[0129] In one embodiment of the present specification, each of L1 to L3 may independently be a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0130] In one embodiment of the present specification, each of L1 to L3 may independently be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0131] In one embodiment of the present specification, each of L1 to L3 may independently be a direct bond; or a substituted or unsubstituted C6 to C60 arylene group substituted with deuterium.

[0132] In one embodiment of the present specification, each of L1 to L3 may independently be a direct bond; or a substituted or unsubstituted C6 to C40 arylene group substituted with deuterium.

[0133] In one embodiment of the present specification, L1 to L3 may each independently be a direct bond; or an arylene group of C6 to C20 which is substituted or unsubstituted with deuterium.

[0134] In one embodiment of the present specification, L1 to L3 may each independently be a direct bond; a phenylene group which is substituted or unsubstituted with deuterium; or a biphenylene group which is substituted or unsubstituted with deuterium.

[0135] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group of C6 to C40; or a substituted or unsubstituted heteroaryl group of C2 to C40.

[0136] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group of C6 to C30; or a substituted or unsubstituted heteroaryl group of C2 to C30.

[0137] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group of C6 to C30; or a substituted or unsubstituted heteroaryl group of C2 to C30 which contains O or S.

[0138] In one embodiment of the present specification, Ar1 and Ar2 may 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 phenanthrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0139] In one embodiment of the present specification, Ar1 and Ar2 are each independently an aryl group having 6 to 60 carbon atoms which is substituted or unsubstituted with one or more substituents selected from deuterium and alkyl groups; or a heteroaryl group having 2 to 60 carbon atoms which is substituted or unsubstituted with deuterium.

[0140] In one embodiment of the present specification, Ar1 and Ar2 are each independently an aryl group having 6 to 40 carbon atoms which is substituted or unsubstituted with one or more substituents selected from deuterium and alkyl groups; or a heteroaryl group having 2 to 40 carbon atoms which is substituted or unsubstituted with deuterium.

[0141] In one embodiment of the present specification, Ar1 and Ar2 are each independently an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with one or more substituents selected from deuterium and alkyl groups; or a heteroaryl group having 2 to 30 carbon atoms which is substituted or unsubstituted with deuterium.

[0142] In one embodiment of the present specification, Ar1 and Ar2 are each independently an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with one or more substituents selected from deuterium and alkyl groups; or a heteroaryl group having 2 to 30 carbon atoms which is substituted or unsubstituted with deuterium and contains O or S.

[0143] In one embodiment of the present specification, Ar1 and Ar2 are each independently a phenyl group which is substituted or unsubstituted with deuterium; a biphenyl group which is substituted or unsubstituted with deuterium; a terphenyl group which is substituted or unsubstituted with deuterium; a naphthyl group which is substituted or unsubstituted with deuterium; a phenanthrenyl group which is substituted or unsubstituted with deuterium; a dimethylfluorenyl group which is substituted or unsubstituted with deuterium; a dibenzofuran group which is substituted or unsubstituted with deuterium; or a dibenzothiophene group which is substituted or unsubstituted with deuterium.

[0144] In one embodiment of the present specification, each of the R11 and R12 is independently hydrogen; deuterium; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, or adjacent groups may combine to form a substituted or unsubstituted C6-C60 aromatic ring or a substituted or unsubstituted C2-C60 heterocyclic ring.

[0145] In one embodiment of the present specification, each of the R11 and R12 is independently hydrogen; deuterium; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, or adjacent groups may combine to form a substituted or unsubstituted C6-C60 aromatic ring.

[0146] In one embodiment of the present specification, each of the R11 and R12 is independently hydrogen; deuterium; a substituted or unsubstituted C1-C40 alkyl group; a substituted or unsubstituted C3-C40 cycloalkyl group; a substituted or unsubstituted C2-C40 heterocycloalkyl group; a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group, or adjacent groups may combine to form a substituted or unsubstituted C6-C40 aromatic ring or a substituted or unsubstituted C2-C40 heterocyclic ring.

[0147] In one embodiment of the present specification, each of R11 and R12 is independently hydrogen; deuterium; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C2-C20 heterocycloalkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group, or adjacent groups may combine to form a substituted or unsubstituted C6-C20 aromatic ring or a substituted or unsubstituted C2-C20 heterocyclic ring.

[0148] In one embodiment of the present specification, each of R11 and R12 is independently hydrogen; deuterium; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C2-C20 heterocycloalkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group, or adjacent groups may combine to form a substituted or unsubstituted C6-C20 aromatic ring.

[0149] In one embodiment of the present specification, each of R11 and R12 is independently hydrogen; deuterium; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, or adjacent groups may combine to form a substituted or unsubstituted C6-C60 aromatic ring or a substituted or unsubstituted C2-C60 heterocyclic ring.

[0150] In one embodiment of the present specification, each of R11 and R12 is independently hydrogen; deuterium; a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group, or adjacent groups may combine to form a substituted or unsubstituted C6-C40 aromatic ring or a substituted or unsubstituted C2-C40 heterocyclic ring.

[0151] In one embodiment of the present specification, each of the R11 and R12 is independently hydrogen; deuterium; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group, or adjacent groups may be bonded to form a substituted or unsubstituted C6-C20 aromatic ring or a substituted or unsubstituted C2-C20 heterocyclic ring.

[0152] In one embodiment of the present specification, each of the R11 and R12 is independently hydrogen; deuterium; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group, or adjacent groups may be bonded to form a substituted or unsubstituted C6-C20 aromatic ring.

[0153] In one embodiment of the present specification, each of the R11 and R12 is independently hydrogen; deuterium; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group, or adjacent groups may be bonded to form a substituted or unsubstituted benzene ring.

[0154] In one embodiment of the present specification, each of the R11 and R12 is independently hydrogen; deuterium; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group containing N, or adjacent groups may be bonded to form a substituted or unsubstituted C6-C20 aromatic ring.

[0155] In one embodiment of the present specification, each of the R11 and R12 is independently hydrogen; deuterium; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group containing N, or adjacent groups may be bonded to form a substituted or unsubstituted benzene ring.

[0156] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted carbazole group, or adjacent groups may combine to form a substituted or unsubstituted benzene ring.

[0157] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; a C6-C20 aryl group substituted or unsubstituted with deuterium or an aryl group; or a C2-C20 heteroaryl group substituted or unsubstituted with deuterium or an aryl group and containing N, or adjacent groups may combine to form a benzene ring substituted or unsubstituted with deuterium.

[0158] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; or a substituted or unsubstituted C6-C60 aryl group, or adjacent groups may combine to form a substituted or unsubstituted C6-C60 aromatic ring.

[0159] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; or a substituted or unsubstituted C6-C40 aryl group, or adjacent groups may combine to form a substituted or unsubstituted C6-C40 aromatic ring.

[0160] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; or a substituted or unsubstituted C6-C20 aryl group, or adjacent groups may combine to form a substituted or unsubstituted C6-C20 aromatic ring.

[0161] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; or a substituted or unsubstituted C6-C20 aryl group, or adjacent groups may combine to form a substituted or unsubstituted benzene ring.

[0162] In one embodiment of the present specification, each of R11 and R12 is independently hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group, or adjacent groups may be bonded to form a substituted or unsubstituted benzene ring.

[0163] In one embodiment of the present specification, the chemical formula 2 may be represented by any one of the following chemical formulas 2-1 to 2-4.

Chemical formula

[0164] In one embodiment of the present specification, Ar11 may be a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0165] In one embodiment of the present specification, Ar11 may be a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0166] In one embodiment of the present specification, Ar11 may be a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group containing N.

[0167] In one embodiment of the present specification, Ar11 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted carbazole group.

[0168] In one embodiment of the present specification, Ar11 may be a C6-C30 aryl group substituted or unsubstituted with deuterium or an aryl group; or a C2-C30 heteroaryl group substituted or unsubstituted with deuterium or an aryl group.

[0169] In one embodiment of the present specification, Ar11 may be a C6-C20 aryl group substituted or unsubstituted with deuterium or an aryl group; or a C2-C20 heteroaryl group substituted or unsubstituted with deuterium or an aryl group.

[0170] In one embodiment of the present specification, Ar11 may be a C6-C20 aryl group substituted or unsubstituted with deuterium or an aryl group; or a C2-C20 heteroaryl group substituted or unsubstituted with deuterium or an aryl group and containing N.

[0171] In one embodiment of the present specification, Ar11 may be a phenyl group substituted or unsubstituted with deuterium or an aryl group; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium or an aryl group; or a carbazole group substituted or unsubstituted with deuterium or an aryl group.

[0172] In one embodiment of the present specification, Ar11 may be a substituted or unsubstituted C6-C30 aryl group.

[0173] In one embodiment of the present specification, Ar11 may be a substituted or unsubstituted C6-C20 aryl group.

[0174] In one embodiment of the present specification, Ar11 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0175] In one embodiment of the present specification, Ar11 may be a C6-C30 aryl group substituted or unsubstituted with deuterium or an aryl group.

[0176] In one embodiment of the present specification, Ar11 may be a C6-C20 aryl group substituted or unsubstituted with deuterium or an aryl group.

[0177] In one embodiment of the present specification, Ar11 may be a phenyl group substituted or unsubstituted with deuterium or an aryl group; a biphenyl group substituted or unsubstituted with deuterium; or a naphthyl group substituted or unsubstituted with deuterium or an aryl group.

[0178] In one embodiment of the present specification, R21 and R22 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

[0179] In one embodiment of the present specification, R21 and R22 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; or a substituted or unsubstituted C6-C60 aryl group.

[0180] In one embodiment of the present specification, R21 and R22 may each independently be hydrogen; or deuterium.

[0181] In one embodiment of the present specification, Chemical Formula 2 may be selected from the following compounds.

Chemical formula

[0182] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and may further include a smaller number of organic layers.

[0183] In one embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

[0184] In another embodiment of the present specification, the first electrode may be a cathode, and the second electrode may be an anode.

[0185] The organic light-emitting device according to one embodiment of the present specification may be manufactured by the manufacturing methods and materials of ordinary organic light-emitting devices, except that one or more organic layers are formed using the heterocyclic compound of Chemical Formula 1 described above.

[0186] The heterocyclic compound of Chemical Formula 1 may be formed in the organic layer not only by a vacuum deposition method but also by a solution coating method during the manufacture of the organic light-emitting device. Here, the solution coating method means, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating, and the like.

[0187] In one embodiment of the present specification, 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. For example, the heterocyclic compound of Chemical Formula 1 may be included in the light-emitting layer of the blue organic light-emitting device.

[0188] In another embodiment of the present specification, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound of Chemical Formula 1 may be used as a material for the green organic light-emitting device. For example, the heterocyclic compound of Chemical Formula 1 may be included in the light-emitting layer of the green organic light-emitting device.

[0189] In another embodiment of the present specification, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound of Chemical Formula 1 may be used as a material for the red organic light-emitting device. For example, the heterocyclic compound of Chemical Formula 1 may be included in the light-emitting layer of the red organic light-emitting device.

[0190] The organic light-emitting device of the present invention may further include one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0191] The lamination order of the electrodes and the organic layers of the organic light-emitting device according to one embodiment of the present specification is illustrated in FIGS. 1 to 3. However, the scope of the present application is not limited by these drawings, and the structures of organic light-emitting devices well-known in the art may be applied to the present application.

[0192] According to FIG. 1, 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 is shown. However, it is not limited to such a structure only. As shown in FIG. 2, an organic light-emitting device in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate may be realized.

[0193] FIG. 3 illustrates a case where the organic layer is multilayered. 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 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of this application is not limited by such a stacked structure. If necessary, the layers other than the light-emitting layer may be omitted, and other necessary functional layers may be further added.

[0194] The organic layer containing the heterocyclic compound of Chemical Formula 1 may further contain other substances if necessary.

[0195] In the organic light-emitting device according to an embodiment of the present specification, materials other than the heterocyclic compound of Chemical Formula 1 are exemplified below. However, these are merely for illustration and not for limiting the scope of this application, and may be replaced by materials known in the art.

[0196] As the anode material, a material with a relatively large work function may be used, or a transparent conductive oxide, a metal, or a conductive polymer may be used. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0197] As the cathode material, a material with a relatively low work function may be used, such as a metal, a metal oxide, or a conductive polymer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; substances with a multilayer structure such as LiF / Al or LiO 2 / Al, etc., but are not limited thereto.

[0198] As the hole injection material, a known hole injection material may be used. For example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or starburst-type amine derivatives described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazolyl-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), polyaniline / dodecylbenzenesulfonic acid, which is a soluble conductive polymer, or poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrenesulfonate) may also be used.

[0199] As the hole transport material, pyrazoline derivatives, arylamine-based derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. may be used, and low-molecular or high-molecular materials may also be used.

[0200] As the electron transport material, an oxadiazole derivative, 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, metal complexes of 8-hydroxyquinoline and its derivatives, etc. may be used, and not only low molecular substances but also high molecular substances may be used.

[0201] As the electron injection material, for example, LiF is typically used in the art, but the present application is not limited thereto.

[0202] As the light-emitting material, a red, green, or blue light-emitting material may be used, 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 vapor-deposited and used as individual supply sources, or may be pre-mixed and vapor-deposited and used as one supply source. Also, as the light-emitting material, a fluorescent material may be used, but a phosphorescent material may also be used. As the light-emitting material, a material that alone combines holes and electrons injected from the anode and the cathode respectively to emit light may be used, or a material in which both the host material and the dopant material are involved in light emission may be used.

[0203] When mixing and using the hosts of the light-emitting material, hosts of the same system may be mixed and used, or hosts of different systems may be mixed and used. For example, any two or more materials of the N-type host material or the P-type host material may be selected and used as the host material of the light-emitting layer.

[0204] The organic light-emitting device according to an embodiment of the present specification may be a top emission type, a bottom emission type, or a double-sided emission type depending on the materials used.

[0205] According to one embodiment of the present specification, the heterocyclic compound can act on the same principle as that applied to the organic light-emitting device also in organic electronic devices such as organic solar cells, organic photoreceptors, and organic transistors.

[0206] In addition, by introducing various substituents into the structure of Chemical Formula 1, while the energy band gap can be finely adjusted, the characteristics at the interface between organic substances can be improved, and the uses of the substances can be diversified.

[0207] Another embodiment of the present specification provides a composition for an organic layer containing the heterocyclic compound.

[0208] In one embodiment of the present specification, the composition for the organic layer may further contain the compound of Chemical Formula 2.

[0209] In one embodiment of the present specification, the composition for the organic layer may contain the heterocyclic compound and the compound of Chemical Formula 2 in a weight ratio of 1:10 to 10:1.

[0210] In one embodiment of the present specification, the composition for the organic layer may contain the heterocyclic compound and the compound of Chemical Formula 2 in a weight ratio of 1:8 to 8:1, 1:5 to 5:1, or 1:3 to 3:1.

[0211] In one embodiment of the present specification, the composition for the organic layer may contain the heterocyclic compound and the compound of Chemical Formula 2 in a weight ratio of 1:1 to 5:1, or 1:1 to 3:1.

[0212] Another embodiment of the present specification provides a method for manufacturing an organic light-emitting device, including the steps of preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer, wherein the step of forming the organic layer includes the step of forming one or more organic layers using the composition for the organic layer described above.

[0213] In one embodiment of the present specification, the step of forming the organic layer may include a step of pre-mixing a composition for the organic layer of the organic light-emitting device and vapor-depositing it as one supply source.

[0214] The pre-mixing means that, before vapor-depositing the heterocyclic compound of Chemical Formula 1 and the compound of Chemical Formula 2 on the organic layer, the materials are first mixed and put into one supply source for mixing. When pre-mixing, instead of using two or more vapor-deposition sources, one vapor-deposition source is used, which has the advantage of simplifying the process.

[0215] When pre-mixing the composition for the organic layer, when vapor-depositing the pre-mixed substance, it can greatly affect vapor-deposition conditions such as the vapor-deposition rate according to the thermal properties inherent to the substance. Therefore, the thermal properties inherent to each substance to be pre-mixed must be confirmed. If the thermal properties between substances are not similar, the repeatability and reproducibility in the vapor-deposition process cannot be maintained, and a uniform OLED device cannot be fabricated.

[0216] To overcome this, by utilizing suitable combinations of the basic structures and substituents of each substance, the electrical properties of the substance can be adjusted, and the thermal properties can also be adjusted according to the form of the molecular structure. By adjusting the thermal properties of each substance, the diversity of various pre-mixed vapor-deposition processes between hosts can be ensured. Thereby, not only the diversity of pre-mixed vapor-deposition processes utilizing two types of compounds as hosts but also the diversity of pre-mixed vapor-deposition processes utilizing three or more host substances can be ensured.

[0217] In one embodiment of the present specification, the composition for the organic layer may include other hosts in addition to the compound of Chemical Formula 2.

[0218] In one embodiment of the present specification, the composition for the organic layer includes the compound of Chemical Formula 2 and may further include other hosts.

Example

[0219] Hereinafter, the present specification will be described in more detail by way of examples. However, these are merely for illustrating the present application and not for limiting the scope of the present application.

[0220] <Production Example> <Production Example 1: Production of Compound D-1>

Chemical Formula

[0221] 2) Synthesis of Compound D-1 Compound C-1 (37.9 g, 150 mmol), PdCl 2 (dppf) ([1,1’-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)) (8.6 g, 11.75 mmol), and KOAc (potassium acetate) (44 g, 450 mmol) were placed in a 1000 mL round-bottom flask. After creating a nitrogen atmosphere, 1,4-dioxane (350 mL) was added, and the mixture was stirred at 100 °C for 6 hours. After lowering the reaction temperature to room temperature, water (100 mL) was added to terminate the reaction, and then extraction was performed with MC (methylene chloride). The extracted organic solvent was dried over Mg 2 SO 4After drying, it was concentrated. It was recrystallized using a silica-gel column and methanol to obtain white solid Compound D-1 (48 g, 140 mmol, 93%).

[0222] <Production Example 2> Production of Compound D-3

Chemical formula

[0223] 2) Synthesis of Compound C-3 Compound B-1 (50 g, 150 mmol), Phenylboronic acid (X) (222 g, 200 mmol), Pd(PPh 3 ) 4 (Tetrakis(triphenylphosphine)palladium(0)) (18.5 g, 7 mmol), and K 2 CO 3 (41 g, 300 mmol) were placed in a 1000 mL round-bottom flask, dioxane (300 mL) / H 2 O (60 mL) was added, and the mixture was stirred at 120 °C for 6 hours. After completion of the reaction, the reaction temperature was lowered to room temperature, washed with water, and then extracted with MC. The extracted organic solvent was dried over Mg 2 SO 4 and then concentrated. It was purified by silica-gel column and recrystallized to obtain white solid Compound C-3 (47 g, 143 mmol, 96%).

[0224] 2) Synthesis of Compound D-3 Compound C-3 (47 g, 143 mmol), PdCl 2(dppf) (5.23 g, 7.15 mmol), and KOAc (28.06 g, 286 mmol) were placed in a 1000 mL round-bottom flask. After creating a nitrogen atmosphere, 1,4-dioxane (500 mL) was added, and the mixture was stirred at 100 °C for 3 hours. After lowering the reaction temperature to room temperature, water (100 mL) was added to terminate the reaction, and then extraction was performed with MC. The extracted organic solvent was dried over Mg 2 SO 4 and then concentrated. Recrystallization was performed using a silica-gel column and methanol to obtain a white solid compound D-3 (54 g, 129 mmol, 90%).

[0225] <Production Example 3> Production of Compound C-2

Chemical formula

[0226] <Production Example 4> Production of Compounds in Table 1 In the method of Production Example 1 or 2, compound A in Table 1 below was used instead of compound A-1 or A-2. In the case of Production Example 2, compound X was used instead of Phenylboronic acid. When the core structure contains deuterium, the method of Production Example 3 was further performed in the stage before the production of compound D (+3 indicates), and compounds B to D in Table 1 below were synthesized.

[0227]

Table 1

[0228] <Production Example 5> Production of Compound F-1

Chemical formula

[0229]

Table 2

[0230] <Production Example 6> Preparation of Compound G-15

Chemical Formula

[0231] In the above Production Example 6, Compound G was synthesized in the same manner as in Production Example 6, except that Compound H and Compound I in Table 3 below were used instead of Compound (H) and Compound (I).

[0232]

Table 3

[0233] The compounds synthesized according to the above Production Examples 1 to 6 were confirmed to have synthesized the target compound by FD-mass spectrometer and 1 1H-NMR. The measured values of the FD-mass spectrometer (FD-Mass: Field desorption mass spectrometry) are shown in Table 4 below, 1 and the measured values of 1H NMR (CDCl 3 , 200 MHz) are shown in Table 5 below.

[0234]

Table 4

[0235]

Table 5

[0236] <Experimental Example> <Experimental Example 1> (1) Fabrication of Organic Light-Emitting Device A glass substrate with a 1,500 Å-thick indium tin oxide (ITO) thin film coating was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol and dried, and then subjected to UVO (Ultraviolet Ozone) treatment using UV for 5 minutes by a UV (Ultraviolet) cleaner. Then, after transferring the substrate to a plasma cleaner (PT), plasma treatment was performed in a vacuum state for the work function of ITO and removal of the residual film, and it was transferred to a thermal evaporation apparatus for organic vapor deposition.

[0237] On the ITO transparent electrode (anode), as a common layer, a hole injection layer of 2-TNATA (4,4’,4’’-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer of NPB (N,N’-Di(1-naphthyl)-N,N’-diphenyl-(1,1’-biphenyl)-4,4’-diamine) were formed. On top of that, the light-emitting layer was thermally vacuum-evaporated as follows. The light-emitting layer used one compound described in Table 6 below as a red host and (piq) 2 (Ir)(acac) as a red phosphorescent dopant, and (piq) 2 (Ir)(acac) was doped at 3% and evaporated at 500 Å. Then, BCP was evaporated at 60 Å as a hole blocking layer, and on top of that, Alq 3 was evaporated at 200 Å as an electron transport layer. Then, BCP was evaporated at 60 Å as a hole blocking layer, and on top of that, Alq 3 was evaporated at 200 Å as an electron transport layer. Finally, lithium fluoride (LiF) was evaporated to a thickness of 10 Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was evaporated to a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby manufacturing an organic electroluminescent device.

[0238] The compounds X1 to X15 used in Table 6 below are as follows.

Chemical formula

[0239] (2) Measurement of driving voltage, luminous efficiency, and lifetime of the organic light-emitting element For the organic electroluminescent element fabricated as described above, the electroluminescence (EL) characteristics were measured via M7000 manufactured by Mac Science Co., Ltd. Using the measurement results, the lifetime measurement device (M6000) manufactured by Mac Science Co., Ltd. was used to measure T when the reference luminance was 6,000 cd / m 2 . 90 The T 90 means the lifetime (unit: h, hour) which is the time to reach 90% of the initial luminance. The characteristics of the organic electroluminescent element manufactured above are as shown in Table 6 below.

[0240]

Table 6

[0241] The heterocyclic compound of Chemical Formula 1 of the present invention has high thermal stability and suitable molecular weight and band gap. Such a suitable band gap of the light-emitting layer prevents the loss of electrons and holes and helps to form an effective recombination zone.

[0242] As can be seen from the results in Table 6 above, it was confirmed that the organic light-emitting device using the heterocyclic compound of Chemical Formula 1 of the present invention exhibited improved performance compared to the organic light-emitting devices using Compounds X1 to X15 of the comparative examples. Specifically, compared with Comparative Examples 1 to 9, 14, and 15, the example groups of the present invention showed particularly excellent results in terms of luminous efficiency and lifetime. This is judged to be the result that when a substituent is substituted at the 6-position of the naphtho[1,2-b]benzofuran core as in Chemical Formula 1 of the present invention, it has a higher hole mobility due to a deeper HOMO value than the compounds substituted at other positions. In addition, in the case of Comparative Examples 10 to 13, they have an asymmetric structure, which is judged to reduce the conjugation region of the molecule, lower the electron mobility, and show lower efficiency than the chemical formula of the present invention.

[0243] <Experimental Example 2> (1) Fabrication of Organic Light-Emitting Device In the above Experimental Example 1, an organic light-emitting device was fabricated in the same manner except that two compounds described in Table 7 below were used instead of one compound described in Table 6 as the red host of the light-emitting layer.

[0244] (2) Measurement of Driving Voltage, Luminous Efficiency, and Lifetime of Organic Light-Emitting Device For the organic electroluminescent device fabricated as described above, the electroluminescence (EL) characteristics were measured via M7000 manufactured by Mac Science Co., Ltd. Using the measurement results, via the lifetime measurement device (M6000) manufactured by Mac Science Co., Ltd., when the reference luminance is 6,000 cd / m 2 T 90 was measured. The T 90 means the lifetime (unit: h, hour) which is the time when it becomes 90% of the initial luminance. The characteristics of the organic electroluminescent device manufactured above are as shown in Table 7 below.

[0245]

Table 7

[0246] As can be seen from the results of Tables 6 and 7 above, when the heterocyclic compound of the present invention and the compound of Chemical Formula 2 are combined and used in the light-emitting layer of an organic light-emitting device, improved driving voltage, efficiency, and lifetime characteristics are shown as compared with the case of using a single compound. This is because when the heterocyclic compound of Chemical Formula 1 of the present invention and the compound of Chemical Formula 2 of the present invention are simultaneously used in the light-emitting layer of an organic light-emitting device, an acceptor (n-host) with good electron-transporting ability and a donor (p-host) with good hole-transporting ability are used as the host of the light-emitting layer, so that the driving voltage at which electrons and holes are injected can be lowered, leading to the result of improving efficiency and lifetime by forming an effective recombination zone.

Explanation of Reference Numerals

[0247] 100 ··· Substrate 200 ··· Anode 300 ··· Organic Layer 301 ··· Hole Injection Layer 302 ··· Hole Transport Layer 303 ··· Light-Emitting Layer 304 ··· Hole Blocking Layer 305 ··· Electron Transport Layer 306 ··· Electron Injection Layer 400 ··· Cathode

Claims

1. A heterocyclic compound represented by the following formula 1: 【Chemistry 1】 In the above Chemical Formula 1, X is O or S; L is a direct bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group; Ar is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; R is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C1-C60 haloalkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; m is an integer from 1 to 9, and when it is 2 or more, the substituents within the brackets are the same or different.

2. The heterocyclic compound according to claim 1, wherein the formula 1 is represented by the following formula 1-O or 1-S: 【Chemistry 2】 In the above Chemical Formulas 1-O and 1-S, The definition of each substituent is the same as that in Chemical Formula 1 above.

3. The heterocyclic compound according to claim 1, wherein Ar is a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

4. 2. The heterocyclic compound according to claim 1, wherein R is hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C30 haloalkyl group; or a substituted or unsubstituted C6 to C30 aryl group.

5. The heterocyclic compound according to claim 1, wherein the deuterium substitution rate of the compound of Formula 1 is 0% or 5% to 100%.

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

7. An organic light-emitting device including a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, 7. An organic light-emitting device, wherein at least one of the organic layers contains at least one heterocyclic compound according to claim 1.

8. The organic light-emitting element according to claim 7 , wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes one or more kinds of the heterocyclic compound.

9. The organic light-emitting device according to claim 8 , wherein the light-emitting layer comprises a host, and the host comprises one or more of the heterocyclic compounds.

10. The organic light-emitting device according to claim 7, wherein the organic material layer containing a heterocyclic compound further contains a compound represented by the following Chemical Formula 2: 【Chemistry 4】 In the above Chemical Formula 2, L1 to L3 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; Ar1 and Ar2 are each independently a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; R11 and R12 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C2-C60 alkenyl group; a substituted or unsubstituted C2-C60 alkynyl group; a substituted or unsubstituted C1-C60 alkoxy group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, or adjacent groups are joined to form a substituted or unsubstituted C6-C60 aromatic ring or a substituted or unsubstituted C2-C60 heterocycle; q is an integer from 1 to 3; r is an integer from 1 to 4; When q and r are each 2 or greater, the substituents within the brackets are the same or different from each other.

11. The organic light-emitting device according to claim 10, wherein the compound represented by Chemical Formula 2 is selected from the following compounds: 【Chemistry 5】 【change】 【change】

12. A composition for an organic layer of an organic light-emitting device, comprising the heterocyclic compound according to any one of claims 1 to 6.

13. The composition for an organic layer of an organic light-emitting device according to claim 12, further comprising a compound represented by the following Formula 2: 【Chemistry 6】 In the above Chemical Formula 2, L1 to L3 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; Ar1 and Ar2 are each independently a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; R11 and R12 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C2-C60 alkenyl group; a substituted or unsubstituted C2-C60 alkynyl group; a substituted or unsubstituted C1-C60 alkoxy group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, or adjacent groups are joined to form a substituted or unsubstituted C6-C60 aromatic ring or a substituted or unsubstituted C2-C60 heterocycle; q is an integer from 1 to 3; r is an integer from 1 to 4; When q and r are each 2 or greater, the substituents within the brackets are the same or different from each other.

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