Heterocyclic compound, organic light-emitting device containing the same, and composition for forming organic layer

Abstract

The present specification relates to a heterocyclic compound represented by Chemical Formula 1, an organic light-emitting device including the heterocyclic compound, and a composition for forming an organic layer. JPEG2025507687000121.jpg42170

Description

[Technical field]

[0001] The present specification relates to a heterocyclic compound, an organic light-emitting device containing the same, and a composition for forming an organic layer. This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0025928, filed with the Korean Intellectual Property Office on February 28, 2022, the entire contents of which are incorporated herein by reference. [Background technology]

[0002] An electroluminescent device is a type of self-luminous display device, and has the advantages of a wide viewing angle, excellent contrast, and fast response speed.

[0003] 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 pairs, and then disappear, emitting light. The organic thin film may be configured as a single layer or multiple layers as necessary.

[0004] The material of the organic thin film may have a light-emitting function as necessary. For example, the material of the organic thin film may be a compound that can form a light-emitting layer by itself, or a compound that can play the role of a host or dopant in a host-dopant type light-emitting layer. In addition, the material of the organic thin film may be a compound that can play the role of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, etc.

[0005] There is a continuing need to develop materials for organic thin films to improve the performance, lifetime, or efficiency of organic light-emitting devices. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] U.S. Patent No. 4,356,429 Summary of the Invention [Problem to be solved by the invention]

[0007] An object of the present specification is to provide a heterocyclic compound, an organic light-emitting device containing the same, and a composition for forming an organic layer. [Means for solving the problem]

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

[0009] [ka]

[0010] In the above Chemical Formula 1, X is O or S; L1 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; Y1 to Y3 each independently represent N or CR, and at least one is N; Het is a substituted or unsubstituted C2-C60 fused polycyclic heteroaryl group; R, R1, Ar1, and Ar2 are each independently hydrogen; deuterium; a halogen group; a cyano group; 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; R2 is hydrogen; or deuterium; l1 is an integer from 0 to 3; r1 is an integer from 0 to 6; r2 is an integer from 0 to 4; When l1, r1, and r2 are each 2 or greater, the substituents within the brackets are the same or different from each other.

[0011] In another embodiment of the present specification, there is provided an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains one or more of the heterocyclic compounds.

[0012] In another embodiment of the present specification, there is provided a composition for forming an organic layer, comprising the heterocyclic compound. Effect of the Invention

[0013] When the heterocyclic compound described in this specification is used in an organic light-emitting device, it can reduce the driving voltage of the device, improve the light-emitting efficiency, and improve the life characteristics of the device. Specifically, the heterocyclic compound of the present invention is characterized in that an azine group is substituted at a specific position of a core structure of dibenzofuran or dibenzothiophene, a phenylene group is included as a linker between the core structure and the substituent Het, and the core structure and the substituent Het are bonded at the ortho position with respect to the phenylene group. In particular, the substituent Het is bonded to the core structure at the ortho position of the phenylene group, so that the dihedral angle is increased compared to the meta or para position. The increase in the dihedral angle suppresses the extension of conjugation with respect to the phenylene group, so that the ortho position has a higher T than the meta or para position. 1 (Triplet energy level). 1 (Triplet energy level) is suitable for maximizing the luminescence properties of phosphorescent dopants. 1When a phosphorescent host material having a triplet energy level is used, a back energy transfer occurs in which the triplet state electron of the dopant is transferred back to the host, degrading the light-emitting properties of the dopant and degrading device performance. In the present invention, the core structure and the substituent Het are bonded to the ortho position based on the phenylene group as in Chemical Formula 1, thereby achieving a high T 1 By using a compound having a triplet energy level, back energy transfer is prevented, luminescence characteristics of the dopant are maximized, and device performance is improved.

[0014] In addition, when the azine group present in the core structure is bonded to the 3-position of dibenzofuran or dibenzothiophene, it has a higher glass transition temperature than other positions. If the glass transition temperature is low, the material loses its original properties and has completely different properties, which reduces the lifespan. The present invention has the effect of improving the lifespan by substituting an azine group at the 3-position of dibenzofuran or dibenzothiophene, which has a high glass transition temperature. [Brief description of the drawings]

[0015] [Figure 1] 1 is a diagram illustrating an example of a layered structure of an organic light-emitting device according to an embodiment of the present specification. [Diagram 2] 1 is a diagram illustrating an example of a layered structure of an organic light-emitting device according to an embodiment of the present specification. [Diagram 3] 1 is a diagram illustrating an example of a layered structure of an organic light-emitting device according to an embodiment of the present specification. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0016] This specification will be explained in more detail below.

[0017] In this specification, when a part "comprises" a certain component, it does not mean excluding other components, and means that the part may further include other components, unless otherwise specified to the contrary.

[0018] In this specification, the chemical formula [ka] means the binding position.

[0019] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different.

[0020] In this specification, "substituted or unsubstituted" means deuterium; a halogen group; -CN; an alkyl group of C1 to C60; an alkenyl group of C2 to C60; an alkynyl group of C2 to C60; a haloalkyl group of C1 to C60; an alkoxy group of C1 to C60; an aryloxy group of C6 to C60; an alkylthioxy group of C1 to C60; an arylthioxy group of C6 to C60; an alkylsulfoxy group of C1 to C60; an arylsulfoxy group of C6 to C60; a cycloalkyl group of C3 to C60; a heterocycloalkyl group of C2 to C60; an arylsulfoxy group of C6 to C60; and -NRR', or a substituent in which two or more substituents selected from the above-listed substituents are linked, and R, R', and R'' 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.

[0021] In this specification, when "no substituent is shown in the chemical formula or compound structure," it means that a hydrogen atom is bonded to the carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0022] In one embodiment of the present application, "when no substituent is shown in the chemical formula or compound structure", it may mean that all positions where a substituent can be substituted 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, and in this case, the content of deuterium may be 0% to 100%.

[0023] In one embodiment of the present application, in the case where "substituents are not shown in the chemical formula or compound structure", when deuterium is not explicitly excluded, such as when the deuterium content is 0%, the hydrogen content is 100%, or all substituents are hydrogen, hydrogen and deuterium may be used together in the compound.

[0024] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, and is an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, and may be represented as hydrogen-2, and the atomic symbol is D or 2 It may also be written as H.

[0025] In one embodiment of the present application, isotopes, meaning atoms with the same atomic number (Z) but different mass numbers (A), can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0026] In one embodiment of the present application, the content T% of a specific substituent can be defined as T2 / T1×100=T%, where T1 is the total number of substituents that the base compound may have and T2 is the number of specific substituents among the total number of substituents.

[0027] That is, in one example, [ka] In a phenyl group represented by the formula, the deuterium content is 20% when the total number of substituents that the phenyl group may have is 5 (T1 in the formula), of which the number of deuterium is 1 (T2 in the formula). In other words, a phenyl group with a deuterium content of 20% may be represented by the following structural formula. [ka] In addition, in one embodiment of the present application, a "phenyl group having a deuterium content of 0%" may mean a phenyl group that does not contain a deuterium atom, that is, a phenyl group that has five hydrogen atoms.

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

[0029] In this specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-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, and a 3,3-dimethylbutyl group. , 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

[0030] In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms 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, and a styrenyl group, but are not limited thereto.

[0031] In this specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkynyl group may be 2 to 60, specifically 2 to 40, more specifically 2 to 20.

[0032] In the present specification, a haloalkyl group means an alkyl group substituted with a halogen group, and a specific example is -CF 3 , -CF 2 CF 3 These include, but are not limited to:

[0033] In this specification, an alkoxy group is represented by -O(R101), and R101 may be any of the alkyl groups exemplified above.

[0034] In this specification, the aryloxy group is represented by -O(R102), and R102 may be any of the examples of the aryl group mentioned above.

[0035] In this specification, an alkylthio group is represented by -S(R103), and R103 may be any of the alkyl groups exemplified above.

[0036] In this specification, an arylthioxy group is represented by -S(R104), and R104 may be any of the examples of aryl groups mentioned above.

[0037] As used herein, an alkylsulfoxy group is defined as -S(=O) 2 (R105), where R105 may be any of the alkyl groups exemplified above.

[0038] As used herein, an arylsulfoxy group is defined as -S(=O) 2 (R106), where R106 may be any of the examples of the aryl group mentioned above.

[0039] In the present 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, or a heteroaryl group. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples of the cycloalkyl group include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0040] In the present specification, the heterocycloalkyl group includes 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, or a heteroaryl group. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 20.

[0041] In this specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, which may be further substituted with other substituents. Here, the polycyclic ring 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, or a heteroaryl group. 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, 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.

[0042] As used herein, the terphenyl group may be selected from the following structures: [ka]

[0043] In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0044] When the fluorenyl group is substituted, it may have the following structure, but is not limited to these. [ka]

[0045] In the present specification, the heteroaryl group includes 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, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 25.Specific examples of the heteroaryl group include a 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 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, 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, 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, phenothiazine group, phthalazine group, phenanthroline group, naphthobenzofuran group, naphthobenzo Examples of such groups include, but are not limited to, a thiophene group, a benzo[c][1,2,5]thiadiazole group, a 2,3-dihydrobenzo[b]thiophene group, a 2,3-dihydrobenzofuran group, a 5,10-dihydrodibenzo[b,e][1,4]azasiline group, a pyrazolo[1,5-c]quinazoline group, a pyrido[1,2-b]indazole group, a pyrido[1,2-a]imidazo[1,2-e]indoline group, and a 5,11-dihydroindeno[1,2-b]carbazole group.

[0046] As used herein, a benzocarbazole group may have any one of the following structures: [ka]

[0047] As used herein, a dibenzocarbazole group may have any one of the following structures: [ka]

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

[0049] As used herein, when a carbazole, benzocarbazole, or dibenzocarbazole group is substituted, the carbazole, benzocarbazole, or dibenzocarbazole group may be substituted with additional substituents on a nitrogen or a carbon.

[0050] As used herein, a naphthobenzofuran group may have any one of the following structures: [ka]

[0051] As used herein, a naphthobenzothiophene group may have any one of the following structures: [ka]

[0052] In this specification, a silyl group is a substituent that contains Si and is directly linked to the Si atom as a radical, and is represented by -Si(R107)(R108)(R109), where R107 to R109 may be the same or different and each independently represent at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group.

[0053] Specific examples of the silyl group include, but are not limited to, the following structures. [ka]

[0054] In the present specification, the phosphine oxide group is represented by -P(=O)(R110)(R111), where R110 and R111 are the same or different and each may be 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 of the alkyl group and the aryl group may be applied. For example, the phosphine oxide group may include, but is not limited to, a dimethylphosphine oxide group, a diphenylphosphine oxide group, and a dinaphthylphosphine oxide group.

[0055] In the present specification, the amine group is represented by -N(R112)(R113), where R112 and R113 may be the same or different and each independently may be a substituent consisting of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, and a heteroaryl group. The amine group is represented by -NH 2The amine group may be selected from the group consisting of 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, and a biphenyltriphenylenylamine group, but are not limited thereto.

[0056] In this specification, the arylene group may be the same as the aryl group described above, except that the arylene group is a divalent group.

[0057] In this specification, the heteroarylene group may be the same as the heteroaryl group described above, except that the heteroarylene group is a divalent group.

[0058] One embodiment of the present specification provides a heterocyclic compound represented by Chemical Formula 1.

[0059] In one embodiment of the present specification, R1 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0060] In one embodiment of the present specification, R1 is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0061] In one embodiment of the present specification, R1 may be hydrogen; deuterium; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0062] In one embodiment of the present invention, R1 may be hydrogen; or deuterium.

[0063] In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following chemical formulae 1-1 to 1-4. [ka] [ka]

[0064] In the above chemical formulas 1-1 to 1-4, the definitions of the respective substituents are the same as those in chemical formula 1.

[0065] In one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0066] In one embodiment of the present specification, L1 may be a direct bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0067] In one embodiment of the present specification, L1 may be a direct bond; or a substituted or unsubstituted C6 to C30 arylene group.

[0068] In one embodiment of the present invention, L1 may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0069] In one embodiment of the present specification, L1 may be a direct bond; or a deuterium-substituted or unsubstituted C6-C30 arylene group.

[0070] In one embodiment of the present invention, L1 may be a direct bond; a deuterium-substituted or unsubstituted phenylene group; or a deuterium-substituted or unsubstituted biphenylene group.

[0071] In one embodiment of the present specification, Y1 to Y3 are each independently N or CR, and at least one is N.

[0072] In one embodiment of the present specification, Y1 to Y3 are each independently N or CR, and at least two are N.

[0073] In one embodiment of the present specification, Y1 to Y3 may be N.

[0074] In one embodiment of the present specification, the above-mentioned Chemical Formula 1 may be represented by the following Chemical Formula 1-A. [ka]

[0075] In Chemical Formula 1-A, the definitions of each substituent are the same as those in Chemical Formula 1.

[0076] In one embodiment of the present specification, Ar1 and Ar2 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0077] In one embodiment of the present specification, Ar1 and Ar2 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0078] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0079] In one embodiment of the present invention, Ar1 and Ar2 may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted dibenzofuran group.

[0080] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a deuterium-substituted or unsubstituted C6 to C30 aryl group; or a deuterium-substituted or unsubstituted C2 to C30 heteroaryl group.

[0081] In one embodiment of the present invention, Ar1 and Ar2 may each independently be a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; or a deuterium-substituted or unsubstituted dibenzofuran group.

[0082] In one embodiment of the present specification, Het is a substituted or unsubstituted C2 to C60 fused polycyclic heteroaryl group.

[0083] In one embodiment of the present specification, Het may be a substituted or unsubstituted C2 to C30 fused polycyclic heteroaryl group.

[0084] In one embodiment of the present specification, Het may be a substituted or unsubstituted, O-, S- or N-containing C2-C30 fused polycyclic heteroaryl group.

[0085] In one embodiment herein, Het may be a substituted or unsubstituted carbazole group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0086] In one embodiment of the present specification, Het may be represented by the following formula H-1 or H-2. [ka]

[0087] In the above chemical formulas H-1 and H-2, Z is O; S; or NR'; R', R11, and R12 are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group; r11 is an integer from 0 to 7, r12 is an integer from 0 to 8, When r11 and r12 are each 2 or greater, the substituents in brackets are the same or different from each other.

[0088] In one embodiment herein, Z may be O.

[0089] In one embodiment herein, Z may be S.

[0090] In one embodiment of the present specification, Z is NR', where R' may be a substituted or unsubstituted C6 to C30 aryl group.

[0091] In one embodiment herein, R' may be a substituted or unsubstituted phenyl group.

[0092] In one embodiment of the present specification, R' may be a deuterium-substituted or unsubstituted C6 to C30 aryl group.

[0093] In one embodiment herein, R' can be a deuterium substituted or unsubstituted phenyl group.

[0094] In one embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C30 aryl group.

[0095] In one embodiment of the present invention, R11 and R12 may each independently be hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0096] In one embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; or a C6 to C30 aryl group unsubstituted or substituted with deuterium.

[0097] In one embodiment of the present invention, R11 and R12 may each independently be hydrogen; deuterium; or a phenyl group unsubstituted or substituted with deuterium.

[0098] In one embodiment of the present specification, the deuterium content of the compound of Chemical Formula 1 may be 0% to 100%.

[0099] In one embodiment of the present specification, the deuterium content of the above-mentioned Chemical Formula 1 may be 0%.

[0100] In one embodiment of the present specification, the deuterium content of the compound of Chemical Formula 1 may be 20% to 100%.

[0101] In one embodiment of the present specification, the deuterium content of the compound of Chemical Formula 1 may be 30% to 100%.

[0102] In one embodiment of the present specification, the deuterium content of the compound of Chemical Formula 1 may be 50% to 100%.

[0103] In one embodiment of the present specification, the deuterium content of the compound of Chemical Formula 1 may be 70% to 100%.

[0104] In one embodiment of the present specification, the deuterium content of the above-mentioned Formula 1 may be 100%.

[0105] In one embodiment of the present specification, the heterocyclic compound of Chemical Formula 1 has a deuterium content within the above range, and the photochemical characteristics of the compound containing deuterium and the compound not containing deuterium are almost similar, but when deposited as a thin film, the material containing deuterium tends to have closer intermolecular packing.

[0106] As a result, by preparing an EOD (Electron Only Device) and a HOD (Hole Only Device) and examining the current density as a function of voltage, it can be confirmed that, among the heterocyclic compounds of Chemical Formula 1 of the present invention, compounds containing deuterium exhibit far more balanced charge transport properties than compounds not containing deuterium.

[0107] In addition, when the thin film surface was examined with an atomic force microscope (AFM), it was confirmed that the thin film made using the compound containing deuterium was deposited on a more uniform surface without any aggregates.

[0108] Furthermore, since the bond dissociation energy of a single bond between carbon and deuterium is higher than the bond dissociation energy of a single bond between carbon and hydrogen, when the heterocyclic compound of Chemical Formula 1 of the present invention has a deuterium content within the above range, the stability of the entire molecule is increased, and the life of the device is improved.

[0109] In one embodiment of the present specification, the deuterium content of the above-mentioned Chemical Formula 1 may be 0% or may be 20% to 100%.

[0110] In one embodiment of the present specification, the deuterium content of the above-mentioned Chemical Formula 1 may be 0% or 30% to 100%.

[0111] In one embodiment of the present specification, the deuterium content of the above-mentioned Chemical Formula 1 may be 0% or 50% to 100%.

[0112] In one embodiment of the present specification, the deuterium content of the above-mentioned Chemical Formula 1 may be 0%, or may be 70% to 100%.

[0113] In one embodiment of the present specification, the deuterium content of the above-mentioned Chemical Formula 1 may be 0% or 100%.

[0114] In one embodiment of the present specification, the above-mentioned Chemical Formula 1 may be represented by any one of the following compounds:

[0115] [ka]

[0116] [ka]

[0117] [ka]

[0118]

change

[0119]

change

[0120]

change

[0121]

change

[0122]

change

[0123]

change

[0124]

change

[0125]

change

[0126]

change

[0127]

change

[0128]

change

[0129]

change

[0130]

change

[0131]

change

[0132]

change

[0133]

change

[0134]

change

[0135]

change

[0136]

change

[0137]

change

[0138]

change

[0139] [ka]

[0140] [ka]

[0141] [ka]

[0142] [ka]

[0143] [ka]

[0144] [ka]

[0145] [ka]

[0146] In addition, it is possible to synthesize compounds having properties specific to the introduced substituents by introducing various substituents into the structure of Chemical Formula 1. For example, it is possible to synthesize materials that satisfy the requirements for each organic layer by introducing into the core structure substituents that are mainly used in hole injection layer materials, hole transport layer materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light emitting devices.

[0147] In addition, by introducing various substituents into the structure of Formula 1, the energy band gap can be finely adjusted, and the properties at the interface between organic materials can be improved, thereby diversifying the uses of the material.

[0148] In another embodiment of the present specification, there is provided an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, at least one of the organic layers comprising one or more heterocyclic compounds represented by Chemical Formula 1.

[0149] In one embodiment of the present specification, the organic layer may include a light-emitting layer, and the light-emitting layer may include one or more of the heterocyclic compounds.

[0150] In one embodiment of the present specification, the organic layer may include a light-emitting layer, and the light-emitting layer may include one type of the heterocyclic compound.

[0151] In one embodiment of the present specification, the organic layer includes an emitting layer, the emitting layer includes a host, and the host may include one or more of the heterocyclic compounds.

[0152] In one embodiment of the present specification, the organic layer includes an emitting layer, the emitting layer includes a host, and the host may include one type of the heterocyclic compound.

[0153] In one embodiment of the present specification, the organic layer includes an emitting layer, the emitting layer includes a host, the host includes a green host, and the green host may include one or more of the heterocyclic compounds.

[0154] In one embodiment of the present specification, the organic layer includes an emitting layer, the emitting layer includes a host, the host includes a red host, and the red host may include one or more of the heterocyclic compounds.

[0155] In one embodiment of the present specification, the organic layer includes an emitting layer, the emitting layer includes a host, the host includes a blue host, and the blue host may include one or more of the heterocyclic compounds.

[0156] In one embodiment of the present specification, the organic layer may include an emitting layer, and the emitting layer may include the heterocyclic compound as an N-type host.

[0157] In one embodiment of the present specification, the organic layer containing a heterocyclic compound may further contain a compound represented by the following Chemical Formula 2. [ka]

[0158] In the above Chemical Formula 2, Ar21 and Ar22 are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; R21 and R22 are each independently hydrogen; deuterium; a halogen group; a cyano group; 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; Each of r21 and r22 is an integer of 0 to 7, and when each of r21 and r22 is 2 or greater, the substituents in the parentheses are the same or different.

[0159] In one embodiment of the present specification, the organic layer including the heterocyclic compound may further include the compound of Chemical Formula 2 as a P-type host.

[0160] In one embodiment of the present specification, Ar21 and Ar22 are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0161] In one embodiment of the present specification, Ar21 and Ar22 may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0162] In one embodiment of the present specification, Ar21 and Ar22 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 triphenylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0163] In one embodiment of the present specification, Ar21 and Ar22 may each independently be a C6 to C30 aryl group substituted or unsubstituted with one or more substituents selected from deuterium and an alkyl group; or a C2 to C30 heteroaryl group substituted or unsubstituted with deuterium.

[0164] In one embodiment of the present specification, Ar21 and Ar22 may each independently be a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; a deuterium-substituted or unsubstituted terphenyl group; a deuterium-substituted or unsubstituted triphenylene group; a fluorenyl group substituted or unsubstituted with one or more substituents selected from deuterium and an alkyl group; a deuterium-substituted or unsubstituted dibenzofuran group; or a deuterium-substituted or unsubstituted dibenzothiophene group.

[0165] In one embodiment of the present specification, R21 and R22 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0166] In one embodiment of the present specification, R21 and R22 may each independently be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0167] In one embodiment of the present specification, R21 and R22 may each independently be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0168] In one embodiment of the present specification, R21 and R22 may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0169] In one embodiment of the present invention, R21 and R22 may each independently be hydrogen; or deuterium.

[0170] In one embodiment of the present specification, the deuterium content of the above-mentioned Chemical Formula 2 may be 0% to 100%.

[0171] In one embodiment of the present specification, the deuterium content of the above-mentioned Chemical Formula 2 may be 0%.

[0172] In one embodiment of the present specification, the deuterium content of the above-mentioned Chemical Formula 2 may be 20% to 100%.

[0173] In one embodiment of the present specification, the deuterium content of the compound of Chemical Formula 2 may be 30% to 100%.

[0174] In one embodiment of the present specification, the deuterium content of the compound of Chemical Formula 2 may be 50% to 100%.

[0175] In one embodiment of the present specification, the deuterium content of the above-mentioned Formula 2 may be 100%.

[0176] In one embodiment of the present specification, the deuterium content of the above-mentioned Chemical Formula 2 may be 0% or may be 20% to 100%.

[0177] In one embodiment of the present specification, the deuterium content of the above-mentioned Chemical Formula 2 may be 0% or 30% to 100%.

[0178] In one embodiment of the present specification, the deuterium content of the above-mentioned Chemical Formula 2 may be 0% or 50% to 100%.

[0179] In one embodiment of the present specification, the compound of formula 2 has a deuterium content within the above range, and when a compound containing deuterium is deposited as a thin film, the molecular distance tends to be closer to each other and the compound is deposited on a more uniform surface without agglomeration, compared to a compound not containing deuterium. In addition, when a compound containing deuterium is contained, the compound exhibits much more balanced charge transport characteristics than a compound not containing deuterium, and the high single bond dissociation energy of carbon and deuterium increases the stability of the entire molecule, improving the life of the device.

[0180] In one embodiment of the present specification, the formula 2 may be represented by any one of the following compounds:

[0181] [ka]

[0182] [ka]

[0183] [ka]

[0184] [ka]

[0185] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have 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 layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0186] In one embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

[0187] In another embodiment of the present specification, the first electrode may be a cathode, and the second electrode may be an anode.

[0188] The organic light emitting device according to an embodiment of the present specification may 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 heterocyclic compound of Chemical Formula 1 described above.

[0189] In manufacturing an organic light emitting device, the heterocyclic compound of Formula 1 may be formed in an organic layer by a solution coating method as well as a vacuum deposition method, where the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0190] 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 of the blue organic light-emitting device. For example, the heterocyclic compound of Chemical Formula 1 may be included in an emission layer of the blue organic light-emitting device.

[0191] 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 of the green organic light-emitting device. For example, the heterocyclic compound of Chemical Formula 1 may be included in an emission layer of the green organic light-emitting device.

[0192] 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 of the red organic light-emitting device. For example, the heterocyclic compound of Chemical Formula 1 may be included in an emission layer of the red organic light-emitting device.

[0193] 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.

[0194] 1 to 3 show examples of the stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present specification. However, these drawings do not limit the scope of the present application, and structures of organic light-emitting devices known in the technical field may be applied to the present application.

[0195] 1 shows an organic light-emitting element in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, the present invention is not limited to such a structure, and an organic light-emitting element in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate as shown in FIG.

[0196] Fig. 3 illustrates an example in which the organic layer is multi-layered. 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, such a laminated structure does not limit the scope of the present application, and the remaining layers except for the light-emitting layer may be omitted as necessary, and other necessary functional layers may be further added.

[0197] The organic layer containing the heterocyclic compound of Chemical Formula 1 may further contain other materials, if necessary.

[0198] In an 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, but these are merely examples and are not intended to limit the scope of the present application, and may be replaced with materials known in the art.

[0199] The anode material may be a material with a relatively large work function, such as a transparent conductive oxide, a metal, or a conductive polymer. Specific examples of the anode material include 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); ZnO:Al, or SnO 2 These include, but are not limited to: a combination of a metal and an oxide, such as Sb; and conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0200] The cathode material may be a material with a relatively low work function, such as a metal, a metal oxide, or a conductive polymer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; LiF / Al or LiO 2Examples of the material include, but are not limited to, multi-layered materials such as / Al.

[0201] The hole injection material may be a known hole injection material, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429, or a starburst type amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], for example, 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, polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic acid), etc. Alternatively, poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / Camphor sulfonic acid, or polyaniline / Poly(4-styrenesulfonate) may be used.

[0202] As the hole transport material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, or the like may be used, and a low molecular weight or high molecular weight material may also be used.

[0203] As the electron transport material, oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc. may be used, and not only low molecular weight substances but also polymeric substances may be used.

[0204] As the electron injection material, for example, LiF is typically used in the industry, but the present application is not limited thereto.

[0205] The light-emitting material may be a red, green, or blue light-emitting material, or may be a mixture of two or more light-emitting materials, if necessary. In this case, the two or more light-emitting materials may be evaporated as individual supply sources, or may be premixed and evaporated as one supply source. The light-emitting material may be a fluorescent material or a phosphorescent material. The light-emitting material may be a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, or a material in which both the host material and the dopant material are involved in light emission may be used.

[0206] When the hosts of the light-emitting materials are mixed, the hosts may be of the same type or different types. For example, two or more of N-type host materials or P-type host materials may be selected and used as the host material of the light-emitting layer.

[0207] The organic light emitting device according to an embodiment of the present specification may be a top-emitting type, a bottom-emitting type, or a dual-sided emitting type, depending on the materials used.

[0208] The heterocyclic compound according to an embodiment of the present specification can also function in organic electronic devices such as organic solar cells, organic photoreceptors, and organic transistors based on the same principle as that applied to organic light-emitting devices.

[0209] In addition, by introducing various substituents into the structure of Formula 1, the energy band gap can be finely adjusted, and the properties at the interface between organic materials can be improved, thereby diversifying the uses of the material.

[0210] In one embodiment of the present specification, there is provided a composition for forming an organic layer, comprising the heterocyclic compound.

[0211] In one embodiment of the present specification, the composition for forming an organic layer may further include a compound of Chemical Formula 2.

[0212] In one embodiment of the present specification, the composition for forming an organic layer may contain the heterocyclic compound and the compound of Chemical Formula 2 in a weight ratio of 1:10 to 10:1.

[0213] In one embodiment of the present specification, there is provided a method for manufacturing an organic light-emitting element, comprising the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layers, wherein the step of forming the organic material layers comprises forming one or more organic material layers using a composition for forming an organic material layer that contains the heterocyclic compound.

[0214] In one embodiment of the present specification, there is provided a method for manufacturing an organic light-emitting device, comprising 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 layers, wherein the step of forming the organic layers comprises forming one or more organic layers using a composition for forming an organic layer, the composition including the heterocyclic compound and the compound of Chemical Formula 2 or 3.

[0215] In one embodiment of the present specification, there is provided a method for manufacturing an organic light-emitting device, wherein the step of forming the organic material layer comprises pre-mixing the heterocyclic compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 and forming the organic material layer using a thermal vacuum deposition method.

[0216] The term "pre-mixed" means that the heterocyclic compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 are mixed in one source before being deposited on an organic layer.

[0217] The premixed materials can be referred to as an organic layer forming composition according to one embodiment of the present specification.

[0218] The present specification will be described in more detail below with reference to examples. However, these are merely for illustrating the present application and are not intended to limit the scope of the present application. EXAMPLES

[0219] <Production Example> <Production Example 1> Production of Compound 3 [ka]

[0220] 1) Preparation of compound 3-P4 Compound 3-P5 (1-bromo-7-chlorodibenzo[b,d]furan) 20 g (71.04 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 27.06 g (106.56 mmol) were dissolved in 200 mL of 1,4-dioxane, and then Pd(dppf)Cl 22.89g (3.55mmol) of ([1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)) and 20.92g (213.12mmol) of potassium acetate were added and stirred under reflux for 16 hours. After the reaction was completed, ethyl acetate was added to the reaction solution to dissolve it, and the solution was extracted with distilled water. The organic layer was then washed with anhydrous MgSO 4 After drying at 40°C, the solvent was removed using a rotary evaporator. The mixture was then purified by column chromatography using dichloromethane and hexane as developing solvents to obtain 18.5 g (yield 79%) of compound 3-P4.

[0221] 2) Preparation of Compound 3-P3 Compound 3-P4 (18.5 g, 56.30 mmol) and 1-bromo-2-iodobenzene (15 g, 56.30 mmol) were dissolved in 1,4-dioxane (200 mL) and distilled water (40 mL), and then Pd(PPh 3 ) 4 (Tetrakis(triphenylphosphine)palladium(0)) 3.25g (2.81mmol) and K 2 CO 3 After adding 19.45 g (140.75 mmol) of ethyl acetate, the mixture was stirred under reflux for 16 hours. After the reaction was completed, ethyl acetate was added to the reaction solution to dissolve it, and the solution was extracted with distilled water. The organic layer was then washed with anhydrous MgSO 4 After drying at 40° C., 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 16.1 g (yield 80%) of compound 3-P3.

[0222] 3) Preparation of Compound 3-P2 16.1 g (49.00 mmol) of compound 3-P3 and 10.39 g (49.00 mmol) of dibenzo[b,d]furan-3-ylboronic acid (compound A) were dissolved in 175 mL of 1,4-dioxane and 35 mL of distilled water, and then Pd(PPh 3 ) 43.25g (2.45mmol) and K 2 CO 3 After adding 16.93 g (122.49 mmol) of the reaction mixture, the mixture was stirred under reflux for 16 hours. After the reaction was completed, ethyl acetate was added to the reaction mixture to dissolve it, and the mixture was extracted with distilled water. The organic layer was then washed with anhydrous MgSO 4 After drying at 40° C., 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 14.5 g (yield 66%) of compound 3-P2.

[0223] 4) Preparation of Compound 3-P1 Compound 3-P2 (14.5 g, 32.59 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (12.41 g, 48.89 mmol) were dissolved in 150 mL of 1,4-dioxane, and then Pd 2 (dba) 3 1.49 g (1.63 mmol) of (tris(dibenzylideneacetone)dipalladium(0)), 9.6 g (97.77 mmol) of potassium acetate, and 1.55 g (3.26 mmol) of Xphos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) were added and stirred under reflux for 16 hours. After the reaction was completed, ethyl acetate was added to the reaction solution to dissolve it, and the solution was extracted with distilled water. The organic layer was then washed with anhydrous MgSO 4 After drying at 40° C., 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 13.1 g (yield 75%) of compound 3-P1.

[0224] 5) Preparation of Compound 3 13.1 g (24.42 mmol) of compound 3-P1 and 6.54 g (24.42 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine (compound B) were dissolved in 150 mL of 1,4-dioxane and 30 mL of distilled water, and then Pd(PPh 3 ) 4 1.41g (1.22mmol) and K 2CO 3 After adding 8.44 g (61.05 mmol) of the reaction mixture, the mixture was stirred under reflux for 16 hours. After the reaction was completed, ethyl acetate was added to the reaction mixture to dissolve it, and the mixture was extracted with distilled water. The organic layer was then washed with anhydrous MgSO 4 After drying at 40° C., 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 11.45 g of compound 3 (yield 73%).

[0225] The target compound in Table 1 was synthesized in the same manner as in Preparation Example 1, except that compound P5' in Table 1 below was used instead of compound 3-P5, compound A' in Table 1 below was used instead of compound A, and compound B' in Table 1 below was used instead of compound B.

[0226] [Table 1-1]

[0227] [Table 1-2]

[0228] [Table 1-3]

[0229] [Table 1-4]

[0230] [Table 1-5]

[0231] [Table 1-6]

[0232] [Table 1-7]

[0233] <Production Example 2> Production of Compound 49 [ka]

[0234] 1) Preparation of compound 49-P4 Compound 49-P5 (1-bromo-7-chlorodibenzo[b,d]furan) 20 g (71.04 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 27.06 g (106.56 mmol) were dissolved in 200 mL of 1,4-dioxane, and then Pd(dppf)Cl 2 2.89g (3.55mmol) of potassium acetate and 20.92g (213.12mmol) of potassium acetate were added and stirred under reflux for 16 hours. After the reaction was completed, ethyl acetate was added to the reaction solution to dissolve it, and the solution was extracted with distilled water. The organic layer was then washed with anhydrous MgSO 4 After drying at 40°C, 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 18.5 g (yield 79%) of compound 49-P4.

[0235] 2) Preparation of compound 49-P3 Compound 49-P4 (18.5 g, 56.30 mmol) and 1-bromo-2-fluorobenzene (9.85 g, 56.30 mmol) were dissolved in 1,4-dioxane (200 mL) and distilled water (40 mL), and then Pd(PPh 3 ) 4 3.25g (2.81mmol) and K 2 CO 3 After adding 19.45 g (140.75 mmol) of ethyl acetate, the mixture was stirred under reflux for 16 hours. After the reaction was completed, ethyl acetate was added to the reaction solution to dissolve it, and the solution was extracted with distilled water. The organic layer was then washed with anhydrous MgSO 4After drying at 40°C, 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 12.7 g (yield 76%) of compound 49-P3.

[0236] 3) Preparation of compound 49-P2 12.7 g (42.80 mmol) of compound 49-P3 and 7.16 g (42.80 mmol) of 9H-carbazole (compound C) were dissolved in 200 mL of N,N-dimethylacetamide, and then the solution was diluted with Cs 2 CO 3 After adding 41.84 g (128.40 mmol) of the reaction mixture, the mixture was refluxed and stirred for 24 hours. After the reaction was completed, ethyl acetate was added to the reaction mixture to dissolve it, and the mixture was extracted with distilled water. The organic layer was then washed with anhydrous MgSO 4 After drying at 40°C, 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 13.5 g (yield 71%) of compound 49-P2.

[0237] 4) Preparation of compound 49-P1 Compound 49-P2 (13.5 g, 30.41 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.58 g, 45.62 mmol) were dissolved in 135 mL of 1,4-dioxane, and then Pd 2 (dba) 3 The mixture was stirred under reflux for 16 hours after addition of 1.39g (1.52mmol), potassium acetate 8.95g (91.23mmol), and Xphos 1.45g (3.04mmol). After completion of the reaction, ethyl acetate was added to the reaction solution to dissolve it, and the solution was extracted with distilled water. The organic layer was then washed with anhydrous MgSO 4 After drying at 40°C, 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 12.4 g (yield 76%) of compound 49-P1.

[0238] 5) Preparation of Compound 49 12.4 g (23.16 mmol) of compound 49-P1 and 6.20 g (23.16 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine (compound D) were dissolved in 150 mL of 1,4-dioxane and 30 mL of distilled water, and then Pd(PPh 3 ) 4 1.34g (1.16mmol) and K 2 CO 3 After adding 8.00 g (57.90 mmol) of the reaction mixture, the mixture was stirred under reflux for 16 hours. After the reaction was completed, ethyl acetate was added to the reaction mixture to dissolve it, and the mixture was extracted with distilled water. The organic layer was then washed with anhydrous MgSO 4 After drying at 40°C, 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 11.2 g of compound 49 (yield 75%).

[0239] The target compound in Table 2 was synthesized in the same manner as in Preparation Example 2, except that compound P5″ in Table 2 below was used instead of compound 49-P5, compound C′ in Table 2 below was used instead of compound C, and compound D′ in Table 2 below was used instead of compound D.

[0240] [Table 2-1]

[0241] [Table 2-2]

[0242] <Production Example 3> Production of Compound 2-79 [ka]

[0243] 1) Preparation of compound 2-79-1 In a one-neck round-bottom flask, 9H,9'H-3,3'-bicarbazole (10 g, 0.030 mol), 4-bromo-1,1'-biphenyl- (compound E) (7.26 g, 0.030 mol), CuI (0.57 g, 0.003 mol), trans-1,2-diaminocyclohexane (0.34 g, 0.003 mol), and K 3 PO 4 (12.74 g, 0.06 mol) was dissolved in 100 mL of 1,4-dioxane and refluxed at 125 °C for 8 hours. After the reaction was completed, distilled water and dichloromethane were added at room temperature for extraction, and the organic layer was diluted with MgSO 4 After drying at 40° C., the solvent was removed by a rotary evaporator. The reaction product was purified by column chromatography (dichloromethane:hexane=1:3) and recrystallized from methanol to obtain compound 2-79-1 (13.92 g, yield 94%).

[0244] 2) Preparation of Compound 2-79 In a one-neck round-bottom flask, compound 2-79-1 (13.92 g, 0.028 mol), 3-bromo-1,1'-biphenyl (compound E') (6.83 g, 0.028 mol), CuI (0.53 g, 0.0028 mol), trans-1,2-diaminocyclohexane (0.32 g, 0.0028 mol), and K 3 PO 4 (11.89 g, 0.056 mol) was dissolved in 140 mL of 1,4-dioxane and refluxed at 125 °C for 8 hours. After the reaction was completed, distilled water and dichloromethane were added at room temperature for extraction, and the organic layer was diluted with MgSO 4 After drying at 40° C., the solvent was removed by a rotary evaporator. The reaction product was purified by column chromatography (dichloromethane:hexane=1:3) and recrystallized from methanol to obtain the target compound 2-79 (16.14 g, yield 88%).

[0245] In the case where Compound E and Compound E' are the same in Preparation Example 3, the target compound can be directly synthesized by adding 2 equivalents of Compound E in 1) of Preparation Example 3. That is, when Compound E and Compound E' are the same, 2) of Preparation Example 3 can be omitted.

[0246] The target compound in Table 3 was synthesized in the same manner as in Preparation Example 3, except that compound E1 in Table 3 below was used instead of compound E, and compound E'1 in Table 3 below was used instead of compound E'.

[0247] [Table 3]

[0248] <Production Example 4> Production of Compound 2-57 [ka]

[0249] 1) Preparation of Compound 2-57 In a one-neck round-bottom flask, compound 2-79 (12.17 g, 0.017 mol) prepared in Preparation Example 3, 51.5 g of triflic acid, and D 6 -Benzene (D 6 -benzene) (608.5 mL) was added and stirred at 50°C for 1 hour. 2 Na in O 2 CO 3 After quenching, the mixture was dissolved in dichloromethane, and the organic layer was separated and washed with anhydrous MgSO 4 After drying at 40° C., the solvent was removed using a rotary evaporator, and the product was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain the target compound 2-57 (8.01 g, 70% yield).

[0250] The target compound in Table 4 was synthesized in the same manner as in Preparation Example 4, except that Compound E3 in Table 4 was used instead of Compound 2-79. [Table 4]

[0251] The remaining compounds other than those described in Preparation Examples 1 to 4 and Tables 1 to 4 were also prepared in the same manner as described in the above Preparation Examples, and the synthesis results are shown in Tables 5 and 6 below. 1 H NMR (CDCl 3 The values ​​are measured by FT-MS (Field desorption mass spectrometry), and Table 6 below shows the values ​​measured by FD-MS (Field desorption mass spectrometry).

[0252] [Table 5-1]

[0253] [Table 5-2]

[0254] [Table 5-3]

[0255] [Table 5-4]

[0256] [Table 6-1]

[0257] [Table 6-2]

[0258] <Experimental Example 1> 1) Preparation of organic light-emitting devices A glass substrate coated with a thin ITO film to a thickness of 1,500 Å was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then UVO treatment was performed for 5 minutes using UV in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treatment was performed in a vacuum state to determine the work function of the ITO and remove residual film, and then transferred to a thermal evaporation device for organic deposition.

[0259] On the ITO transparent electrode (anode), a hole injection layer 2-TNATA (4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) were formed as a common layer.

[0260] An emitting layer was formed thereon by thermal vacuum deposition as follows: The emitting layer used the compound in Table 7 below as a host and Ir(ppy) as a green phosphorescent dopant. 3 (tris(2-phenylpyridine)iridium) was used as the host, and Ir(ppy) 3 Then, BCP was evaporated to a thickness of 60 Å as a hole blocking layer, and Alq was evaporated on top of it as an electron transport layer. 3 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.

[0261] The compounds of the Examples and Comparative Examples were used as green hosts, except for those separately indicated as red hosts in Table 7 below. In the Examples used as red hosts, Ir(piq) was used as a red phosphorescent dopant. 2 (acac) was used.

[0262] On the other hand, all the organic compounds required for the production of OLED elements are about 10 -8 ~10 -6 The resulting material was purified by vacuum sublimation under torr and used to fabricate OLEDs. [ka]

[0263] 2) Driving voltage and luminous efficiency of organic electroluminescent devices The electroluminescence (EL) characteristics of the organic electroluminescent device prepared as described above were measured using a Mac Science M7000. Using the measurement results, a reference luminance of 6,000 cd / m was measured using a Mac Science M6000 lifespan measurement device. 2 When T 90 was measured.

[0264] The driving voltage, luminous efficiency, color coordinate (CIE), and life span of the organic light emitting device manufactured according to the present invention were measured, and the results are shown in Table 7 below.

[0265] [Table 7-1]

[0266] [Table 7-2]

[0267] [Table 7-3]

[0268] From the results of Table 7, it can be seen that the organic light emitting device including the heterocyclic compound of Chemical Formula 1 of the present invention is superior in terms of driving voltage, luminous efficiency, and life span compared to the comparative examples. The compounds used in Example 1 and Comparative Examples 5 and 6, Example 6 and Comparative Example 1, and Example 16 and Comparative Example 3 are identical in structure except for the substitution position of the azine group, and it can be seen that the driving voltage of the examples is lower, the luminous efficiency is higher, and the life span is longer than that of the respective comparative examples. That is, it can be seen that the substitution of the azine group at a specific position of the core structure as in Chemical Formula 1 of the present invention provides better performance when used as a material for an organic light emitting device than compounds substituted at other positions.

[0269] In addition, the compounds used in Example 3 and Comparative Examples 7 and 8, and Example 19 and Comparative Example 4 have the same structure except for the bond structure of the core structure-phenylene-substituent Het. It can be confirmed that the examples in which the core structure-phenylene-substituent Het is bonded to the ortho position have superior results in terms of driving voltage, luminous efficiency, and lifetime compared to the comparative examples in which the core structure-phenylene-substituent Het is bonded to the meta or para position.

[0270] In the compound of the present invention represented by Chemical Formula 1, the substituent Het is bonded to the core structure at the ortho position of the phenylene group, which increases the dihedral angle compared to the meta or para positions. The increased dihedral angle suppresses the extension of the conjugation based on the phenylene group, so that the triplet energy level T is higher at the ortho position than at the meta or para position. 1 (Triplet energy level). 1 (Triplet energy level) is suitable for maximizing the luminescence properties of phosphorescent dopants. 1When a phosphorescent host material having a triplet energy level is used, a back energy transfer occurs in which the triplet state electron of the dopant is transferred back to the host, degrading the luminescence characteristics of the dopant and degrading device performance. The present invention relates to a phosphorescent compound having a high T 1 It is believed that by using a compound having a triplet energy level, back energy transfer is prevented, the luminescence characteristics of the dopant are maximized, and device performance is improved.

[0271] In other words, when the heterocyclic compound of the present invention represented by Chemical Formula 1 is used as a host in the light-emitting layer, it is confirmed that the driving voltage, light-emitting efficiency, and life span are remarkably excellent.

[0272] <Experimental Example 2> 1) Preparation of organic light-emitting devices A glass substrate coated with a thin ITO film to a thickness of 1,500 Å was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then UVO treatment was performed for 5 minutes using UV in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treatment was performed in a vacuum state to determine the work function of the ITO and remove residual film, and then transferred to a thermal evaporation device for organic deposition.

[0273] On the ITO transparent electrode (anode), a hole injection layer 2-TNATA (4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) were formed as a common layer.

[0274] The light-emitting layer was then deposited thereon by thermal vacuum deposition as follows: The light-emitting layer was formed by premixing two compounds (N-host and P-host) shown in Table 8 below as hosts in the weight ratio shown in Table 8 below, and then depositing the compounds to a thickness of 360 Å from a single source. The green phosphorescent dopant was Ir(ppy). 3 Then, BCP was deposited at 60 Å as a hole blocking layer, and Alq was deposited on it as an electron transport layer. 3 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.

[0275] The compounds of the Examples and Comparative Examples were used as green hosts, except for those separately indicated as red hosts in Table 8 below. In the Examples used as red hosts, Ir(piq) was used as a red phosphorescent dopant. 2 (acac) was used.

[0276] On the other hand, all the organic compounds required for the production of OLED elements are about 10 -8 ~10 -6 The resulting material was purified by vacuum sublimation under torr and used to fabricate OLEDs.

[0277] The electroluminescence (EL) characteristics of the organic electroluminescent device prepared as described above were measured using a Mac Science M7000. Using the measurement results, a reference luminance of 6,000 cd / m was measured using a Mac Science M6000 lifespan measurement device. 2 When T 90 was measured.

[0278] The driving voltage, luminous efficiency, color coordinate (CIE), and life span of the organic light emitting device manufactured according to the present invention were measured, and the results are shown in Table 8 below.

[0279] [Table 8-1]

[0280] [Table 8-2]

[0281] [Table 8-3]

[0282] Comparing the results of Table 7 with those of Table 8, it can be seen that when the heterocyclic compound of Chemical Formula 1 and the compound of Chemical Formula 2 are used simultaneously as hosts in the emission layer, more specifically, when the heterocyclic compound of Chemical Formula 1 is used as an N-type host and the compound of Chemical Formula 2 is used as a P-type host, all of the driving voltage, luminous efficiency, and lifetime are improved.

[0283] From these results, it can be predicted that an exciplex phenomenon will occur when the two compounds are contained simultaneously.

[0284] The exciplex phenomenon is a phenomenon in which energy of the magnitude of the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host) is released by electron exchange between two molecules. When the exciplex phenomenon between two molecules occurs, reverse intersystem crossing (RISC) occurs, and the internal quantum efficiency of the fluorescence can be increased to 100%. When a donor (p-host) with good hole transporting ability and an acceptor (n-host) with good electron transporting ability are used as a host of the light-emitting layer, holes are injected into the p-host and electrons are injected into the n-host, so that the driving voltage can be reduced, which can help improve the lifespan. In the present invention, it was confirmed that the heterocyclic compound of Chemical Formula 1 plays the role of an acceptor and the compound of Chemical Formula 2 plays the role of a donor, and thus excellent device characteristics can be obtained when used together as a host of the light-emitting layer.

[0285] In particular, it can be confirmed that the compound of Chemical Formula 2 has excellent life characteristics when it contains deuterium. In Examples 59 to 142 in Table 8, 14 compounds of Chemical Formula 1 were used in combination with two compounds that have the same structure but differ only in whether they contain deuterium as a P-type host. From the results in Table 8, it can be seen that the life is significantly improved when the heterocyclic compound of Chemical Formula 1 is used in combination with the compound of Chemical Formula 2 containing deuterium. This is because the compound containing deuterium in the same structure shows much more balanced charge transport characteristics than the compound not containing deuterium, and the stability of the entire molecule is increased due to the high single bond dissociation energy between carbon and deuterium, leading to an increased life.

[0286] In contrast, when a compound not included in the scope of the present invention is used in combination with the compound of Chemical Formula 2 (Comparative Examples 13 to 24), the driving voltage, luminous efficiency, and lifespan are lower than those of the present invention.

[0287] That is, when the heterocyclic compound of Chemical Formula 1 and the compound of Chemical Formula 2 are used simultaneously as hosts in the light-emitting layer, it is confirmed that the driving voltage, light-emitting efficiency, and life span are remarkably excellent. [Explanation of symbols]

[0288] 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; L1 is a direct bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group; Y1 to Y3 each independently represent N or CR, and at least one is N; Het is a substituted or unsubstituted C2-C60 fused polycyclic heteroaryl group; R, R1, Ar1, and Ar2 are each independently hydrogen; deuterium; a halogen group; a cyano group; 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; R2 is hydrogen; or deuterium; l1 is an integer from 0 to 3; r1 is an integer from 0 to 6; r2 is an integer from 0 to 4; When l1, r1, and r2 are each 2 or more, the substituents in brackets are the same or different from each other.

2. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4: 【Chemistry 2】 【Chemistry 3】 In the above Chemical Formulas 1-1 to 1-4, the definitions of the respective substituents are the same as those in Chemical Formula 1.

3. The heterocyclic compound according to claim 1, wherein the Het is a substituted or unsubstituted C2-C30 fused polycyclic heteroaryl group.

4. The heterocyclic compound according to claim 1, wherein Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

5. 2. The heterocyclic compound according to claim 1, wherein the deuterium content of the formula (1) is 0% or 20% to 100%.

6. The heterocyclic compound according to claim 1 , wherein the formula 1 is represented by any one of the following formulas: 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemical 29】 【Chemistry 30】 【Chemistry 31】 【Chemistry 32】 【Chemical 33】 【Chemical 34】 。

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

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 35】 In the above Chemical Formula 2, Ar21 and Ar22 are each independently a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; R21 and R22 are each independently hydrogen; deuterium; a halogen group; a cyano group; 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; Each of r21 and r22 is an integer of 0 to 7, and when each of r21 and r22 is 2 or more, the substituents in the brackets are the same or different.

11. The organic light emitting device according to claim 10, wherein the deuterium content of the compound of Formula 2 is 0% or in the range of 20% to 100%.

12. The organic light-emitting device according to claim 10, wherein the formula 2 is represented by any one of the following formulas: 【Chemical 36】 【Chemical 37】 【Chemical Formula 38】 【Chemical 39】 。

13. A composition for forming an organic layer, comprising the heterocyclic compound according to claim 1 .

14. The composition for forming an organic layer according to claim 13, further comprising a compound represented by the following formula 2: 【Chemistry 40】 In the above Chemical Formula 2, Ar21 and Ar22 are each independently a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; R21 and R22 are each independently hydrogen; deuterium; a halogen group; a cyano group; 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; Each of r21 and r22 is an integer of 0 to 7, and when each of r21 and r22 is 2 or more, the substituents in the brackets are the same or different.

15. The composition for forming an organic layer according to claim 14, wherein a weight ratio of the heterocyclic compound to the compound of Chemical Formula 2 is 1:10 to 10:1.

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