Heterocyclic compound, organic light-emitting element comprising same, and composition for organic layer of organic light-emitting element

Abstract

The present specification relates to a heterocyclic compound of chemical formula 1, an organic light-emitting element comprising same, and a composition for an organic layer of the organic light-emitting element.

Description

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

[0001] The present 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 Korean Patent Application No. 10-2023-0171539, filed with the Korean Intellectual Property Office on November 30, 2023, the entire contents of which are incorporated herein by reference.

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

[0004] Organic light-emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting device of this structure, electrons and holes injected from the two electrodes combine in the organic thin film, forming pairs and then disappearing, emitting light. The organic thin film may be composed of a single layer or multiple layers, as needed.

[0005] The material of the organic thin film may have a light-emitting function as needed. For example, the organic thin film material may be a compound that can form a light-emitting layer on its own, or a compound that can act as a host or dopant in a host-dopant light-emitting layer. In addition, the material of the organic thin film may be a compound that can perform roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection.

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

[0007] [Prior Art Literature]

[0008] (Patent Document 1) U.S. Patent No. 4,356,429

[0009] The present specification provides a heterocyclic compound, an organic light-emitting device including the same, and a composition for an organic layer of the organic light-emitting device.

[0010] In one embodiment of the present specification, a heterocyclic compound of the following chemical formula 1 is provided.

[0011] [Chemical Formula 1]

[0012]

[0013] In the above chemical formula 1,

[0014] Ar is an aryl group having 6 to 60 carbon atoms, substituted or unsubstituted with deuterium; or a heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted with deuterium,

[0015] Het1 and Het2 are identical and are represented by the following chemical formula H,

[0016] [Chemical formula H]

[0017]

[0018] In the above chemical formula H,

[0019] Any one of H1 to H3 is combined with the above chemical formula 1,

[0020] The remainder of H1 to H3 and R are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; or a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms.

[0021] a is an integer from 1 to 7, and if it is 2 or greater, R is equal or different.

[0022] In another embodiment of the present specification, an organic light-emitting device is provided, comprising: a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers includes at least one type of the heterocyclic compound.

[0023] In another embodiment of the present specification, a composition for an organic layer of an organic light-emitting device comprising the heterocyclic compound is provided.

[0024] The heterocyclic compound described herein, when used in an organic light-emitting device, can lower the driving voltage of the device, improve the luminous efficiency, and enhance the lifespan characteristics of the device.

[0025] Specifically, the heterocyclic compound of chemical formula 1 of the present invention has two identical naphthobenzofuran groups bonded to the triazine at the same position as a substituent of the triazine group, and the substitution position of the naphthobenzofuran group is specified, so that when used as a light-emitting layer material, the performance of the device can be effectively improved. By including two identical naphthobenzofuran groups in this way, the hole characteristics are superior to when substituted with an aryl group. In addition, it is believed that the triazine group forms an appropriate band gap by bonding to a specific position of the naphthobenzofuran group, thereby preventing loss of electrons and holes in the light-emitting layer and contributing to building an effective recombination region.

[0026] In particular, when the compound of the chemical formula 2 of the present invention is used together with the heterocyclic compound of the chemical formula 1, each has high electronic and hole characteristics, thereby improving the charge balance compared to when each is used alone, thereby improving the efficiency and lifespan of the organic light-emitting device.

[0027] Figures 1 to 3 are diagrams each exemplifying a laminated structure of an organic light-emitting device according to one embodiment of the present specification.

[0028] [Explanation of symbols]

[0029] 100: Substrate

[0030] 200: Bipolar

[0031] 300: Organic layer

[0032] 301: Hole injection layer

[0033] 302: Hole transport layer

[0034] 303: Emissive layer

[0035] 304: Hole blocking layer

[0036] 305: Electron transport layer

[0037] 306: Electron injection layer

[0038] 400: Cathode

[0039] Hereinafter, the present specification will be described in more detail.

[0040] In this specification, when a part is said to "include" a component, this does not mean that it excludes other components, but rather that it may include other components, unless specifically stated otherwise.

[0041] In this specification, “N to N'” means N or more and N' or less.

[0042] In this specification, the chemical formula means the position where it is combined.

[0043] The term "substitution" above means that a hydrogen atom bonded to a carbon atom or nitrogen atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where a hydrogen atom is replaced, i.e. a position where a substituent can be replaced, and when two or more are replaced, the two or more substituents may be the same or different from each other.

[0044] In this specification, "substituted or unsubstituted" means deuterium; halogen group; -CN; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C1 to C60 haloalkyl group; C1 to C60 alkoxy group; C6 to C60 aryloxy group; C1 to C60 alkylthioxy group; C6 to C60 arylthioxy group; C1 to C60 alkylsulfoxy group; C6 to C60 arylsulfoxy group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; C6 to C60 aryl group; C2 to C60 heteroaryl group; silyl group; phosphine oxide group; And it means that it is substituted with one or more substituents selected from the group consisting of amine groups, or two or more substituents selected from the above substituents are connected to a substituent, or is unsubstituted.

[0045] In this specification, Cn1 to Cn2 (n1 and n2 are integers greater than or equal to 1) refer to a range of carbon atoms. For example, an alkyl group of C1 to C60 refers to an alkyl group having 1 to 60 carbon atoms.

[0046] In this specification, "when no substituent is indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0047] In one embodiment of the present application, "when no substituent is indicated in the chemical formula or compound structure" may mean that all positions that can be substituted are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, in which case the deuterium content may be 0% to 100%, and the deuterium content may also be expressed as a deuterium substitution ratio.

[0048] In one embodiment of the present application, in the case where “no substituent is indicated in the chemical formula or compound structure,” if deuterium is not explicitly excluded, such as “the deuterium content is 0%, the hydrogen content is 100%,” or “all substituents are hydrogen,” hydrogen and deuterium may be used in combination in the compound.

[0049] In one embodiment of the present application, deuterium is an element having a deuteron, which is one of the isotopes of hydrogen and is composed of one proton and one neutron, as its nucleus, and can be expressed as hydrogen-2, and its element symbol is D or 2 It can also be written as H.

[0050] In one embodiment of the present application, an isotope means an atom having the same atomic number (Z) but a different mass number (A). An isotope can also be interpreted as an element having the same number of protons but a different number of neutrons.

[0051] In one embodiment of the present application, the meaning of the substitution rate T% of a specific substituent can be defined as T2 / T1Х100 = T%, where the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2.

[0052] That is, in one example, In the phenyl group represented by , a deuterium substitution rate of 20% means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and if the number of deuteriums among them is 1 (T2 in the formula), it can be expressed as 20%. In other words, a deuterium substitution rate of 20% in the phenyl group can be expressed by the structural formula below.

[0053]

[0054] Additionally, in one embodiment of the present application, the term "phenyl group having a deuterium substitution rate of 0%" may mean a phenyl group that does not contain a deuterium atom as a substituent, i.e., has 5 hydrogen atoms.

[0055] In this specification, halogen may be fluorine, chlorine, bromine or iodine.

[0056] In the present specification, an alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The alkyl group may have 1 to 60 carbon atoms, specifically 1 to 40 carbon atoms, and more specifically 1 to 20 carbon atoms. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, Examples include, but are not limited to, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, and 5-methylhexyl group.

[0057] In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms. Specific examples include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group.

[0058] In the present specification, an alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkynyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms.

[0059] In this specification, a haloalkyl group means an alkyl group substituted with a halogen group, and specific examples include, but are not limited to, -CF3, -CF2CF3, etc.

[0060] In this specification, an alkoxy group is represented as -O(R101), and examples of the alkyl group described above can be applied to R101.

[0061] In this specification, the aryloxy group is represented as -O(R102), and R102 can be applied to the examples of the aryl group described above.

[0062] In this specification, the alkylthioxy group is represented as -S(R103), and examples of the alkyl group described above can be applied to R103.

[0063] In this specification, the arylthioxy group is represented as -S(R104), and R104 can be applied to the examples of the aryl group described above.

[0064] In this specification, an alkylsulfoxy group is represented as -S(=0)2(R105), and examples of the alkyl group described above can be applied to R105.

[0065] In this specification, an arylsulfoxy group is represented as -S(=0)2(R106), and examples of the aryl group described above can be applied to R106.

[0066] In the present specification, a cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The cycloalkyl group may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, and more specifically 5 to 20 carbon atoms. Specifically, there are, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc.

[0067] In the present specification, a heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, etc. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

[0068] In the present specification, an aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, etc. The aryl group includes a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 25 carbon atoms. Specific examples of the above aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and condensed ring groups thereof.

[0069] In this specification, the terphenyl group may be selected from the following structures.

[0070]

[0071] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0072] When the above fluorenyl group is substituted, the structures below can be formed, but are not limited thereto.

[0073]

[0074] In the present specification, a heteroaryl group includes S, O, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic ring means a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms.Specific examples of the above heteroaryl group include a pyridine group, a pyrrole group, a pyrimidine group, a pyridazine group, a furan group, a thiophene group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, a triazole group, a furazan group, an oxadiazole group, a thiadiazole group, a dithiazole group, a tetrazolyl group, a pyran group, a thiopyran group, a diazine group, an oxazine group, a thiazine group, a dioxin group, a triazine group, a tetrazine group, a quinoline group, an isoquinoline group, a quinazoline group, an isoquinazoline group, a quinozoline group, a naphthyridine group, an acridine group, a phenanthridine group, an imidazopyridine group, a diazanaphthalene group, a triazaindene group, an indole group, an indolizine group, a benzothiazole group, Benzoxazole group, benzimidazole group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazole group, benzocarbazole group, dibenzocarbazole group, phenazine group, dibenzosilole group, spirobi(dibenzosilole), dihydrophenazine group, phenoxazine group, phenanthridine group, thienyl group, indolo[2,3-a]carbazole group, indolo[2,3-b]carbazole group, indoline group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridine group, phenanthrazine group, phenothiathiazine group, phthalazine group, phenanthroline group, naphthobenzofuran group, naphthobenzothiophene group, benzo[c][1,2,5]thiadiazole group, Examples thereof include, but are not limited to, 2,3-dihydrobenzo[b]thiophene group, 2,3-dihydrobenzofuran group, 5,10-dihydrodibenzo[b,e][1,4]azacillin group, pyrazolo[1,5-c]quinazoline group, pyrido[1,2-b]indazole group, pyrido[1,2-a]imidazo[1,2-e]indolin group, and 5,11-dihydroindeno[1,2-b]carbazole group.

[0075] In the present specification, the benzocarbazole group may have any of the following structures.

[0076]

[0077] In the present specification, the dibenzocarbazole group may have any of the following structures.

[0078]

[0079] In the present specification, when the substituent is a carbazole group, a benzocarbazole group, or a dibenzocarbazole group, it means that it is bonded to the nitrogen or carbon of the carbazole group, the benzocarbazole group, or the dibenzocarbazole group.

[0080] In the present specification, when a carbazole group, a benzocarbazole group, or a dibenzocarbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole group, the benzocarbazole group, or the dibenzocarbazole group.

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

[0082]

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

[0084]

[0085] In the present specification, a silyl group is a substituent that contains Si and is directly connected to the Si atom as a radical, and is represented by -Si(R107)(R108)(R109), and R107 to R109 are the same as or different from each other, and may each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group.

[0086] The above silyl group may include an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, an alkylarylsilyl group, an arylheteroarylsilyl group, etc., depending on the substituent bonded to the Si element. An alkylsilyl group, an arylsilyl group, or a heteroarylsilyl group means that the Si element of a silyl group is substituted with an alkyl group, an aryl group, or a heteroaryl group, respectively, an alkylarylsilyl group means that the Si element of a silyl group is substituted with an alkyl group and an aryl group, and an arylheteroarylsilyl group means that the Si element of a silyl group is substituted with an aryl group and a heteroaryl group.

[0087] Specific examples of silyl groups include, but are not limited to, the following structures.

[0088] (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group)

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

[0090] In the present specification, an amine group is represented by -N(R112)(R113), and R112 and R113 are the same as or different from each other, and can each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. The amine group can be selected from the group consisting of -NH2; a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; a dialkylamine group; a diarylamine group; a diheteroarylamine group; an alkylarylamine group; an alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the above amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group.

[0091] In this specification, the description of the aryl group described above may be applied, except that the arylene group is divalent.

[0092] In this specification, the description of the heteroaryl group described above may be applied, except that the heteroarylene group is divalent.

[0093] One embodiment of the present specification provides a heterocyclic compound of the following chemical formula 1.

[0094] [Chemical Formula 1]

[0095]

[0096] In the above chemical formula 1,

[0097] Ar is an aryl group having 6 to 60 carbon atoms, substituted or unsubstituted with deuterium; or a heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted with deuterium,

[0098] Het1 and Het2 are identical and are represented by the following chemical formula H,

[0099] [Chemical formula H]

[0100]

[0101] In the above chemical formula H,

[0102] Any one of H1 to H3 is combined with the above chemical formula 1,

[0103] The remainder of H1 to H3 and R are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; or a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms.

[0104] a is an integer from 1 to 7, and if it is 2 or greater, R is equal or different.

[0105] A heterocyclic compound according to one embodiment of the present disclosure has two identical naphthobenzofuran groups as substituents for a triazine group, and is substituted at a specific position of the naphthobenzofuran group. By having this structure, when used as a material for an organic light-emitting device, it helps improve the performance of the organic light-emitting device.

[0106] Specifically, in the case of a specific substitution position of a specific structure not included in the scope of the present invention, there is a problem that an imbalance of the band gap occurs within the light-emitting layer, resulting in loss of electrons and holes, which in turn reduces the efficiency and lifespan of the device.

[0107] In one embodiment of the present specification, the chemical formula H may be represented by the following chemical formula A or B.

[0108] [Chemical Formula A]

[0109]

[0110] [Chemical Formula B]

[0111]

[0112] In the above chemical formulas A and B,

[0113] The definition of R is the same as that in the above chemical formula H,

[0114] Any one of A1 to A3 and any one of B1 to B3 are combined with the above chemical formula 1,

[0115] The remainder of A1 to A3 and the remainder of B1 to B3 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; or a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms,

[0116] m and n are each an integer from 1 to 7, and when they are 2 or greater, the substituents in the parentheses are the same or different.

[0117] In one embodiment of the present specification, any one of A1 to A3 and any one of B1 to B3 may be combined with the chemical formula 1, and the remainder of A1 to A3 and the remainder of B1 to B3 may be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms; or a substituted or unsubstituted heterocycloalkyl group having 2 to 40 carbon atoms.

[0118] In one embodiment of the present specification, any one of A1 to A3 and any one of B1 to B3 may be combined with the chemical formula 1, and the remainder of A1 to A3 and the remainder of B1 to B3 may be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; or a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms.

[0119] In one embodiment of the present specification, any one of A1 to A3 and any one of B1 to B3 are combined with the chemical formula 1, and the remaining ones of A1 to A3 and the remaining ones of B1 to B3 may each independently be hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms.

[0120] In one embodiment of the present specification, any one of A1 to A3 and any one of B1 to B3 are combined with the chemical formula 1, and the remaining ones of A1 to A3 and the remaining ones of B1 to B3 may each independently be hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms.

[0121] In one embodiment of the present specification, any one of A1 to A3 and any one of B1 to B3 are combined with the chemical formula 1, and the remaining ones of A1 to A3 and the remaining ones of B1 to B3 may each independently be hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms.

[0122] In one embodiment of the present specification, any one of A1 to A3 and any one of B1 to B3 are combined with the chemical formula 1, and the remaining ones of A1 to A3 and the remaining ones of B1 to B3 may each independently be hydrogen or deuterium.

[0123] When the heterocyclic compound of chemical formula 1 according to the present invention includes substituents of chemical formulae A and B, it forms an appropriate band gap to prevent loss of electrons and holes from the light-emitting layer and build an effective recombination region, which consequently plays a role in improving light-emitting efficiency.

[0124] On the other hand, when chemical formula 1 is bonded to carbon 7, which is not A1 to A3 of chemical formula A, or when chemical formula 1 is bonded to carbon 11, which is not B1 to B3 of chemical formula B, a node is generated due to steric influence between the triazine and naphthobenzofuran groups, which significantly lowers the hole injection characteristics, thereby lowering the efficiency and lifespan.

[0125] In one embodiment of the present specification, the chemical formula H can be represented by the following chemical formula C.

[0126] [Chemical Formula C]

[0127]

[0128] In the above chemical formula C,

[0129] The definition of R is the same as that in the above chemical formula H,

[0130] C1 is combined with the above chemical formula 1,

[0131] o is an integer from 1 to 9, and if it is 2 or greater, R is equal to or different from o.

[0132] When the heterocyclic compound of chemical formula 1 according to the present invention includes a substituent of chemical formula C, it forms an appropriate band gap to prevent loss of electrons and holes from the light-emitting layer and build an effective recombination region, which consequently plays a role in improving the lifespan.

[0133] On the other hand, when the 1st carbon, not C1 of the chemical formula C, is combined with the chemical formula 1, a node is generated due to the steric effect between the triazine and the naphthobenzofuran group, which significantly reduces the hole injection characteristics, resulting in lower efficiency and lifetime, and when combined with the 2nd or 3rd carbon of the chemical formula C, the HOMO-LUMO band gap becomes smaller due to the substitution position characteristics of the naphthobenzofuran group having a linear structure, resulting in lower efficiency.

[0134] 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 1-7.

[0135] [Chemical Formula 1-1]

[0136]

[0137] [Chemical Formula 1-2]

[0138]

[0139] [Chemical Formula 1-3]

[0140]

[0141] [Chemical Formula 1-4]

[0142]

[0143] [Chemical Formula 1-5]

[0144]

[0145] [Chemical Formula 1-6]

[0146]

[0147] [Chemical Formula 1-7]

[0148]

[0149] In the above chemical formulas 1-1 to 1-7,

[0150] The definitions of Ar and R are the same as those in the above chemical formula 1 and H, respectively,

[0151] m1, n1 and o1 are each integers from 1 to 9, and when each is 2 or greater, the substituents in parentheses are the same or different.

[0152] 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 1-6.

[0153] In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 1-7.

[0154] In one embodiment of the present specification, R may be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms; or a substituted or unsubstituted heterocycloalkyl group having 2 to 40 carbon atoms.

[0155] In one embodiment of the present specification, R may be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; or a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms.

[0156] In one embodiment of the present specification, R may be hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms.

[0157] In one embodiment of the present specification, R may be hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms.

[0158] In one embodiment of the present specification, R may be hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms.

[0159] In one embodiment of the present specification, R may be hydrogen or deuterium.

[0160] In one embodiment of the present specification, Ar may be an aryl group having 6 to 40 carbon atoms, substituted or unsubstituted with deuterium; or a heteroaryl group having 2 to 40 carbon atoms, substituted or unsubstituted with deuterium.

[0161] In one embodiment of the present specification, Ar may be an aryl group having 6 to 20 carbon atoms, substituted or unsubstituted with deuterium; or a heteroaryl group having 2 to 20 carbon atoms, substituted or unsubstituted with deuterium.

[0162] In one embodiment of the present specification, Ar may be an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; or a heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with deuterium and containing O or S.

[0163] In one embodiment of the present specification, Ar may be a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; or a dibenzothiophene group substituted or unsubstituted with deuterium.

[0164] In one embodiment of the present specification, Ar may be an aryl group having 6 to 20 carbon atoms, substituted or unsubstituted with deuterium; or a heteroaryl group having 2 to 20 carbon atoms, substituted or unsubstituted with deuterium and containing O.

[0165] In one embodiment of the present specification, Ar may be a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; or a dibenzofuran group substituted or unsubstituted with deuterium.

[0166] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 0% to 100%. That is, the chemical formula 1 may not contain deuterium or may contain 1 or more deuterium.

[0167] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 0%, or 5% to 100%.

[0168] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 0% or 10% to 100%.

[0169] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 0% or 20% to 100%.

[0170] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 0% or 30% to 100%.

[0171] In this specification, the deuterium substitution rate of the chemical formula 1 refers to the substitution rate of deuterium with respect to the total number of hydrogens and deuteriums contained in the chemical formula 1. For example, if there are 20 hydrogens and 20 deuteriums contained in the chemical formula 1, the substitution rate of 20 deuteriums with respect to the total of 40 hydrogens and deuteriums is 50%.

[0172] In one embodiment of the present specification, the deuterium substitution rate of Ar means the substitution rate of deuterium with respect to the total number of hydrogen and deuterium contained in Ar, and may be 0% to 100%.

[0173] In one embodiment of the present specification, the deuterium substitution rate of Het1 and Het2 means the substitution rate of deuterium with respect to the total number of hydrogens and deuteriums contained in Het1 and Het2, respectively, and the deuterium substitution rates of Het1 and Het2 are the same and may be 0% to 100%.

[0174] In one embodiment of the present specification, the deuterium substitution rate of Ar, Het1 and Het2 may be 0%, or the deuterium substitution rate of at least one of Ar, Het1 and Het2 may be greater than 0% and less than or equal to 100%.

[0175] 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 not containing deuterium and the compound containing deuterium are almost similar, but when deposited on a thin film, the material containing deuterium tends to be packed with a narrower intermolecular distance.

[0176] Accordingly, by manufacturing an EOD (Electron Only Device) and a HOD (Hole Only Device) and checking the current density according to the voltage, it can be confirmed that the compound containing deuterium among the heterocyclic compounds of chemical formula 1 of the present invention exhibits much more balanced charge transport characteristics than the compound not containing deuterium.

[0177] Additionally, when looking at the surface of the thin film with an atomic force microscope (AFM), it can be confirmed that the thin film made of a compound containing deuterium is deposited with a more uniform surface without any aggregated areas.

[0178] Additionally, since the single bond dissociation energy of carbon and deuterium is higher than the single bond dissociation energy of carbon and hydrogen, in the case of a compound containing deuterium among the heterocyclic compounds of chemical formula 1 of the present invention, the stability of the entire molecule increases, thereby improving the lifespan of the device.

[0179] In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following compounds.

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188] In the structures of the above compounds, hydrogen is indicated separately only in substituents containing deuterium, and substituents without hydrogen or deuterium notation are those in which only hydrogen is substituted.

[0189] In addition, by introducing various substituents into the structure of the above chemical formula 1, compounds having the unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection 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 into the core structure, a material satisfying the conditions required for each organic layer can be synthesized.

[0190] In addition, by introducing various substituents into the structure of the above chemical formula 1, it is possible to finely control the energy band gap, while improving the properties at the interface between organic substances and diversifying the uses of the material.

[0191] In another embodiment of the present specification, an organic light-emitting device is provided, comprising: a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one layer of the organic layer comprises at least one heterocyclic compound of the chemical formula 1.

[0192] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include one or more types of the heterocyclic compound.

[0193] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include one type of the heterocyclic compound.

[0194] 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 include one or more of the heterocyclic compounds.

[0195] 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 include one type of the heterocyclic compound.

[0196] 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 green host, and the green host may include one or more of the heterocyclic compounds.

[0197] 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 red host, and the red host may include one or more of the heterocyclic compounds.

[0198] 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.

[0199] 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.

[0200] In one embodiment of the present specification, the organic layer including the heterocyclic compound may further include a compound of the following chemical formula 2.

[0201] [Chemical Formula 2]

[0202]

[0203] In the above chemical formula 2,

[0204] L, L1 and L2 are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

[0205] Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0206] R11 and R12 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or adjacent groups combine to form a substituted or unsubstituted aromatic ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms,

[0207] q is an integer from 1 to 3,

[0208] r is an integer from 1 to 4,

[0209] When q and r are each 2 or more, the substituents in parentheses are the same or different.

[0210] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may further include a compound of the chemical formula 2.

[0211] 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 a compound of the chemical formula 2.

[0212] In one embodiment of the present specification, the light-emitting layer may further include a compound of the above chemical formula 2 as a P-type host.

[0213] In one embodiment of the present specification, L, L1 and L2 may each independently be a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

[0214] In one embodiment of the present specification, L, L1 and L2 may each independently be a direct bond; or a substituted or unsubstituted arylene group having 6 to 40 carbon atoms.

[0215] In one embodiment of the present specification, L, L1 and L2 may each independently be a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0216] In one embodiment of the present specification, L, L1 and L2 may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0217] In one embodiment of the present specification, L, L1 and L2 may each independently be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0218] In one embodiment of the present specification, L, L1 and L2 may each independently be a direct bond; or an arylene group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium.

[0219] In one embodiment of the present specification, L, L1 and L2 may each independently be a direct bond; or an arylene group having 6 to 40 carbon atoms substituted or unsubstituted with deuterium.

[0220] In one embodiment of the present specification, L, L1 and L2 may each independently be a direct bond; or an arylene group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0221] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0222] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0223] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms and containing O or S.

[0224] 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.

[0225] In one embodiment of the present specification, Ar1 and Ar2 may each independently be an aryl group having 6 to 60 carbon atoms, unsubstituted or substituted with one or more substituents among deuterium and alkyl groups; or a heteroaryl group having 2 to 60 carbon atoms, unsubstituted or substituted with deuterium.

[0226] In one embodiment of the present specification, Ar1 and Ar2 may each independently be an aryl group having 6 to 40 carbon atoms, unsubstituted or substituted with one or more substituents selected from deuterium and alkyl groups; or a heteroaryl group having 2 to 40 carbon atoms, unsubstituted or substituted with deuterium.

[0227] In one embodiment of the present specification, Ar1 and Ar2 may each independently be an aryl group having 6 to 30 carbon atoms, unsubstituted or substituted with one or more substituents selected from deuterium and alkyl groups; or a heteroaryl group having 2 to 30 carbon atoms, unsubstituted or substituted with deuterium.

[0228] In one embodiment of the present specification, Ar1 and Ar2 may each independently be an aryl group having 6 to 30 carbon atoms, unsubstituted or substituted with one or more substituents selected from deuterium and alkyl groups; or a heteroaryl group having 2 to 30 carbon atoms, unsubstituted or substituted with deuterium and containing O or S.

[0229] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrenyl group substituted or unsubstituted with deuterium; a dimethyl fluorenyl group substituted or unsubstituted with deuterium; a spirobifluorenyl group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; or a dibenzothiophene group substituted or unsubstituted with deuterium.

[0230] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or adjacent groups may combine to form a substituted or unsubstituted aromatic ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms.

[0231] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or adjacent groups may combine to form a substituted or unsubstituted aromatic ring having 6 to 60 carbon atoms.

[0232] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 40 carbon atoms; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or adjacent groups may combine to form a substituted or unsubstituted aromatic ring having 6 to 40 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 40 carbon atoms.

[0233] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or adjacent groups may combine to form a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 20 carbon atoms.

[0234] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or adjacent groups may combine to form a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms.

[0235] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or adjacent groups may combine to form a substituted or unsubstituted aromatic ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms.

[0236] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or adjacent groups may combine to form a substituted or unsubstituted aromatic ring having 6 to 40 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 40 carbon atoms.

[0237] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or adjacent groups may combine to form a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 20 carbon atoms.

[0238] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or adjacent groups may combine to form a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms.

[0239] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or adjacent groups may combine to form a substituted or unsubstituted benzene ring.

[0240] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or adjacent groups may combine to form a substituted or unsubstituted aromatic ring having 6 to 60 carbon atoms.

[0241] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or adjacent groups may combine to form a substituted or unsubstituted aromatic ring having 6 to 40 carbon atoms.

[0242] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or adjacent groups may combine to form a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms.

[0243] In one embodiment of the present specification, R11 and R12 are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or adjacent groups may combine to form a substituted or unsubstituted benzene ring.

[0244] 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 phenanthrenyl group, or adjacent groups may combine to form a substituted or unsubstituted benzene ring.

[0245] 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 2-5.

[0246] [Chemical Formula 2-1]

[0247]

[0248] [Chemical Formula 2-2]

[0249]

[0250] [Chemical Formula 2-3]

[0251]

[0252] [Chemical Formula 2-4]

[0253]

[0254] [Chemical Formula 2-5]

[0255]

[0256] In the above chemical formulas 2-1 to 2-5,

[0257] The definitions of L, L1, L2, Ar1, Ar2 and q are the same as those in the above chemical formula 2,

[0258] Ar11 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms,

[0259] R21 and R22 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0260] s is an integer from 1 to 5,

[0261] t is 1 or 2,

[0262] u is an integer from 1 to 6,

[0263] When t is 2 and s and u are each 2 or greater, the substituents in parentheses are the same or different.

[0264] In one embodiment of the present specification, Ar11 may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0265] In one embodiment of the present specification, Ar11 may be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0266] 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 phenanthrenyl group.

[0267] In one embodiment of the present specification, Ar11 may be an aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with deuterium or an aryl group.

[0268] In one embodiment of the present specification, Ar11 may be an aryl group having 6 to 20 carbon atoms, which is substituted or unsubstituted with deuterium or an aryl group.

[0269] In one embodiment of the present specification, Ar11 may be a phenyl group unsubstituted or substituted with deuterium or an aryl group; a biphenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium or an aryl group; or a phenanthrenyl group unsubstituted or substituted with deuterium.

[0270] In one embodiment of the present specification, R21 and R22 may each independently be hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0271] In one embodiment of the present specification, R21 and R22 may each independently be hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0272] In one embodiment of the present specification, R21 and R22 may each independently be hydrogen or deuterium.

[0273] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 2 may be 0% to 100%. That is, the chemical formula 2 may not contain deuterium or may contain 1 or more deuterium.

[0274] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 2 may be 0% or 5% to 100%.

[0275] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 2 may be 0% or 10% to 100%.

[0276] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 2 may be 0% or 20% to 100%.

[0277] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 2 may be 0% or 30% to 100%.

[0278] In this specification, the deuterium substitution rate of the chemical formula 2 refers to the substitution rate of deuterium with respect to the total number of hydrogens and deuteriums contained in the chemical formula 2. For example, if there are 20 hydrogens and 20 deuteriums contained in the chemical formula 2, the substitution rate of 20 deuteriums with respect to the total of 40 hydrogens and deuteriums is 50%.

[0279] The description of the compound containing deuterium among the compounds of the above chemical formula 2 is the same as that described in the above chemical formula 1.

[0280] In one embodiment of the present specification, the chemical formula 2 may be selected from the following compounds.

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288] In the structures of the above compounds, hydrogen is indicated separately only in substituents containing deuterium, and substituents without hydrogen or deuterium notation are those in which only hydrogen is substituted.

[0289] The organic layer of the organic light-emitting device of the present invention may be formed as a single-layer structure, but may also be formed as a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0290] In one embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

[0291] In another embodiment of the present specification, the first electrode may be a cathode and the second electrode may be an anode.

[0292] An organic light-emitting device according to one embodiment of the present specification can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the heterocyclic compound of the above-described chemical formula 1.

[0293] The heterocyclic compound of the above chemical formula 1 can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0294] 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 the chemical formula 1 may be used as a material of the blue organic light-emitting device. For example, the heterocyclic compound of the chemical formula 1 may be included in a light-emitting layer of the blue organic light-emitting device.

[0295] 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 the chemical formula 1 may be used as a material of the green organic light-emitting device. For example, the heterocyclic compound of the chemical formula 1 may be included in a light-emitting layer of the green organic light-emitting device.

[0296] 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 the chemical formula 1 may be used as a material of the red organic light-emitting device. For example, the heterocyclic compound of the chemical formula 1 may be included in a light-emitting layer of the red organic light-emitting device.

[0297] 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.

[0298] The stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present disclosure is exemplified in Figures 1 to 3. However, the scope of the present application is not intended to be limited by these drawings, and the structure of an organic light-emitting device known in the art may also be applied to the present application.

[0299] According to FIG. 1, an organic light-emitting device is illustrated in which an anode (200), an organic layer (300), and a cathode (400) are sequentially laminated on a substrate (100). However, the present invention is not limited to this structure, and an organic light-emitting device in which a cathode, an organic layer, and an anode are sequentially laminated on a substrate, as shown in FIG. 2, may also be implemented.

[0300] 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 the present application is not limited by such a laminated structure, and, if necessary, the remaining layers except for the light-emitting layer may be omitted, and other necessary functional layers may be further added.

[0301] The organic layer containing the heterocyclic compound of the above chemical formula 1 may additionally contain other substances as needed.

[0302] In an organic light-emitting device according to one embodiment of the present specification, materials other than the heterocyclic compound of the above chemical formula 1 are exemplified below, but these are only for exemplification and are not intended to limit the scope of the present application, and may be replaced with materials known in the art.

[0303] Materials having a relatively large work function can be used as the anode material, and transparent conductive oxides, metals, or conductive polymers can be used. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0304] Materials with relatively low work functions can be used as cathode materials, and metals, metal oxides, or conductive polymers can be used. Specific examples of the cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0305] As the hole injection material, a known hole injection material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a starburst amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), a soluble conductive polymer such as polyaniline / dodecylbenzenesulfonic acid, or Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrenesulfonate) can be used.

[0306] Pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used as hole transport materials, and low molecular weight or high molecular weight materials can also be used.

[0307] As the electron transport material, metal complexes of oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinoline and derivatives thereof, etc. can be used, and not only low molecular weight substances but also high molecular weight substances can be used.

[0308] For example, LiF is a representative material used in the art, but the present application is not limited thereto.

[0309] Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. At this time, two or more light-emitting materials may be deposited and used as individual sources, or may be premixed and deposited and used as a single source. In addition, a fluorescent material may be used as the light-emitting material, but it may also be used as a phosphorescent material. A material that emits light by combining holes and electrons injected from the anode and cathode, respectively, may be used as the light-emitting material, but materials in which both the host material and the dopant material participate in light emission may also be used.

[0310] When using a mixture of hosts for light-emitting materials, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, two or more types of materials, either N-type host materials or P-type host materials, may be selected and used as the host materials for the light-emitting layer.

[0311] An organic light-emitting device according to one embodiment of the present specification may be a front-emitting, back-emitting, or double-sided emitting device depending on the material used.

[0312] The heterocyclic compound according to one embodiment of the present specification can function in organic electronic devices, including organic solar cells, organic photoconductors, organic transistors, etc., by a similar principle to that applied to organic light-emitting devices.

[0313] In addition, by introducing various substituents into the structure of the above chemical formula 1, it is possible to finely control the energy band gap, while improving the properties at the interface between organic substances and diversifying the uses of the material.

[0314] Another embodiment of the present specification provides a composition for an organic layer comprising the heterocyclic compound.

[0315] In one embodiment of the present specification, the composition for the organic layer may further include a compound of the chemical formula 2.

[0316] In one embodiment of the present specification, the composition for the organic layer may include the heterocyclic compound and the compound of the chemical formula 2 in a weight ratio of 1:10 to 10:1.

[0317] In one embodiment of the present specification, the composition for the organic layer may include the heterocyclic compound and the compound of the chemical formula 2 in a weight ratio of 1:8 to 8:1, 1:5 to 5:1, or 1:3 to 3:1.

[0318] In one embodiment of the present specification, the composition for the organic layer may include the heterocyclic compound and the compound of the chemical formula 2 in a weight ratio of 1:1 to 5:1, or 1:1 to 3:1.

[0319] In one embodiment of the present specification, the composition for the organic layer of the organic light-emitting device may include the heterocyclic compound of the chemical formula 1 and the compound of the chemical formula 2 in a weight ratio of 1:1 to 1:5, 1:1.1 to 1:3, or 1:1.1 to 1:2.

[0320] Another embodiment of the present specification provides 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 layer, wherein the step of forming the organic layer includes the step of forming one or more organic layers using the organic layer composition described above.

[0321] In one embodiment of the present specification, the step of forming the organic layer may include a step of premixing a composition for the organic layer of the organic light-emitting device and depositing it using one source.

[0322] The above pre-mixing means that the heterocyclic compound of the above chemical formula 1 and the compound of the above chemical formula 2 are mixed in one container before being deposited on the organic layer. In the case of pre-mixing, there is an advantage in that the process is simpler because one deposition source is used instead of two or more deposition sources.

[0323] When premixing the composition for the above organic layer, the inherent thermal properties of each material can significantly affect deposition conditions, such as the deposition rate, when depositing the premixed material. Therefore, the inherent thermal properties of each material to be premixed must be confirmed. If the thermal properties of the materials are not similar, repeatability and reproducibility in the deposition process cannot be maintained, and uniform OLED devices cannot be manufactured.

[0324] To overcome this, the electrical properties of each material can be tuned by appropriately combining the basic structure and substituents of each material, while thermal properties can also be controlled based on the morphology of the molecular structure. By manipulating the thermal properties of each material, a variety of host-to-host premixed deposition processes can be secured. This allows for the creation of diverse premixed deposition processes utilizing not only two compounds as hosts, but also three or more host materials.

[0325] In one embodiment of the present specification, the composition for the organic layer may include a host other than the compound of the chemical formula 2.

[0326] In one embodiment of the present specification, the composition for the organic layer includes the compound of the chemical formula 2 and may further include another host.

[0327] Hereinafter, the present specification will be described in more detail through examples, but these are only intended to illustrate the present application and are not intended to limit the scope of the present application.

[0328] <Manufacturing Example>

[0329] <Manufacturing Example 1> Preparation of compound A001 and compounds of Table 1

[0330]

[0331] In a 1 L two-neck flask, 7.0 g (30.97 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine (A), 22.38 g (65.03 mmol) of 4,4,5,5-tetramethyl-2-(naphtho[1,2-b]benzofuran-8-yl)-1,3,2-dioxaborolane (B), 1.8 g (1.55 mmol) of Pd(pph3)4(Tetrakis(triphenylphosphine)palladium(0)), and 12.8 g (92.90 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O (200 ml / 40 ml) and refluxed for 1 hour. The reactant was purified by recrystallization from methanol, and 12.84 g (yield 91%) of compound A001 was obtained.

[0332] Compounds in Table 1 below were synthesized in the same manner as in Manufacturing Example 1 above, except that compounds A and B in Table 1 below were used instead of compounds (A) and (B) in Manufacturing Example 1 above.

[0333]

[0334]

[0335]

[0336] The compound synthesized in the above manufacturing example 1 was analyzed by FD-mass spectrometry and 1The synthesis of the desired compound was confirmed through H-NMR. The measured values ​​of FD-mass spectrometry (FD-MS: Field desorption mass spectrometry) are shown in Table 2 below. 1 The measured values ​​of H NMR (CDCl3, 400 MHz) are listed in Table 3 below.

[0337] Compound number FD-MS Compound number FD-MSA001 m / z = 589.18 (C 41 H 23 N3O2, 589.64)A045m / z= 593.20 (C 41 H 19 D4N3O2, 593.66)A002m / z= 639.19 (C 45 H 25 N3O2, 639.70)A088m / z= 644.23 (C 45 H 20 D5N3O2, 644.73)A008m / z= 665.21 (C 47 H 27 N3O2, 665.74)A098m / z= 683.21 (C 47 H 21 D4N3O3, 683.74)A009m / z= 665.21 (C 47 H 27 N3O2, 665.74)A103m / z= 593.20 (C 41 H 19 D4N3O2, 593.66)A010m / z= 589.18 (C 41 H 23 N3O2, 589.64)A107m / z= 679.30 (C 47 H 13 D 14 N3O2, 679.82)A017m / z= 679.19 (C 47 H 25 N3O3, 679.72)A123m / z= 679.30 (C 14 H 13 D 14 N3O2, 679.82)A022m / z= 639.19 (C 45 H 25<h2 style=";text-align:left;direction:ltr">N3O2, 639.70)A132m / z= 679.45 (C<h2 style=";text-align:left;direction:ltr"> 47 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 13 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 14 <h2 style=";text-align:left;direction:ltr"> N3O2, 679.82)A028m / z= 679.19 (C<h2 style=";text-align:left;direction:ltr"> 47 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 25 <h2 style=";text-align:left;direction:ltr"> N3O3, 679.72)A133m / z= 603.27 (C<h2 style=";text-align:left;direction:ltr"> 41 <h2 style=";text-align:left;direction:ltr"> H9D<h2 style=";text-align:left;direction:ltr"> 14 <h2 style=";text-align:left;direction:ltr"> N3O2,603.73)A034m / z= 665.21 (C<h2 style=";text-align:left;direction:ltr"> 47 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> N3O2, 665.74)A149m / z= 698.31 (C<h2 style=";text-align:left;direction:ltr"> 47 <h2 style=";text-align:left;direction:ltr"> H6D<h2 style=";text-align:left;direction:ltr"> 19 <h2 style=";text-align:left;direction:ltr"> N3O3, 698.84)A037m / z= 679.19 (C)<h2 style=";text-align:left;direction:ltr"> 47 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 25 <h2 style=";text-align:left;direction:ltr"> N3O3, 679.72)A157m / z= 609.30 (C<h2 style=";text-align:left;direction:ltr"> 41 <h2 style=";text-align:left;direction:ltr"> H3D<h2 style=";text-align:left;direction:ltr"> 20 <h2 style=";text-align:left;direction:ltr"> N3O2, 609.76)A044m / z= 589.18 (C<h2 style=";text-align:left;direction:ltr"> 41 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 23 <h2 style=";text-align:left;direction:ltr"> N3O2, 589.64)A173m / z= 687.35 (C<h2 style=";text-align:left;direction:ltr"> 47 <h2 style=";text-align:left;direction:ltr"> H5D<h2 style=";text-align:left;direction:ltr"> 22 <h2 style=";text-align:left;direction:ltr"> N3O2, 687.87)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0338] <h2 style=";text-align:left;direction:ltr"> 화합물번호<h2 style=";text-align:left;direction:ltr"> 1<h2 style=";text-align:left;direction:ltr">H NMR(CDCl3, 400MHz)A001δ = 8.28 (2H, s), 8.16 (4H, d), 7.89 (2H, d), 7.81 (2H, d), 7.72 (2H, d), 7.71 (2H, d), 7.67 (4H, d), 7.53 (2H, d), 7.51 (2H, d), 7.41 (1H, dd)A002δ = 9.09 (1H, s), 8.49 (1H, d), 8.16 (4H, d), 8 (2H, d), 7.92 (1H, d), 7.89 (2H, d), 7.81 (2H, d), 7.72 (2H, d), 7.71 (2H, d), 7.67 (4H, dd), 7.53 (2H, d)A008δ = 8.16 (4H, s), 7.95 (2H, d), 7.89 (2H, d), 7.85 (2H, d), 7.75 (2H, d), 7.67 (4H, d), 7.64 (2H, d), 7.53 (2H, d), 7.52 (2H, d), 7.25 (2H, dd)A009δ = 8.16 (4H, s), 7.95 (2H, d), 7.89 (2H, d), 7.85 (2H, d), 7.79 (2H, d), 7.75 (2H, d), 7.67 (4H, d), 7.64 (2H, d), 7.53 (2H, d), 7.47 (2H, dd)A010δ = 8.28 (2H, s), 8.16 (4H, d), 7.89 (2H, d), 7.85 (2H, d), 7.81 (2H, d), 7.67 (4H, d), 7.53 (2H, d), 7.51 (2H, d), 7.41 (1H, d), 7.38 (2H, dd)A017δ = 8.16 (4H, s), 7.89 (3H, d), 7.85 (2H, d), 7.81 (2H, d), 7.75 (1H, d), 7.67 (4H, d), 7.66 (1H, d), 7.62 (1H, d), 7.53 (2H, d), 7.44 (1H, dd), 7.38 (3H, d), 7.32 (1H, d)A022δ = 9.09 (1H, s), 8.49 (1H, d), 8.<h2 style=";text-align:left;direction:ltr">16 (4H, d), 8 (2H, d), 7.92 (1H, d), 7.85 (2H, d), 7.81 (2H, d), 7.67 (4H, d), 7.49 (2H, d), 7.42 (2H, dd), 7.38 (2H, d), A028δ = 8.16 (4H, s), 7.89 (1H, d), 7.85 (2H, d), 7.81 (3H, d), 7.72 (1H, d), 7.71 (1H, d), 7.67 (4H, d), 7.66 (1H, d), 7.49 (2H, d), 7.42 (2H, dd), 7.38 (3H, d), 7.32 (1H, d)A034δ = 8.54 (2H, s), 8.16 (2H, d), 7.85 (2H, d), 7.81 (2H, d), 7.72 (2H, d), 7.71 (2H, d), 7.67 (4H, d), 7.66 (2H, d), 7.59 (2H, d), 7.52 (2H, dd), 7.25 (2H, d)A037δ = 8.54 (2H, s), 8.16 (2H, d), 7.89 (1H, d), 7.81 (3H, d), 7.72 (3H, d), 7.71 (3H, d), 7.67 (4H, d), 7.66 (3H, d), 7.59 (2H, d), 7.38 (1H, dd), 7.32 (1H, d)A044δ = 8.54 (2H, s), 8.28 (2H, d), 8.16 (2H, d), 7.85 (2H, d), 7.81 (2H, d), 7.67 (4H, d), 7.66 (2H, d), 7.59 (2H, d), 7.51 (2H, d), 7.41 (1H, dd), 7.38 (2H, d)A045δ = 8.16 (4H, s), 7.89 (2H, d), 7.81 (2H, d), 7.72 (2H, d), 7.71 (2H, d), 7.67 (4H, d), 7.53 (2H, d), 7.5 (1H, d)A088δ = 8.16 (4H, s), 7.95 (2H, d), 7.85 (2H, d), 7.81 (2H, d), 7.67 (4H, d), 7.49 (2H, d), 7.42 (2H, d), 7.38 (2H, d)A098δ = 8.54 (2H, s), 8.16 (2H, d), 7.89 (1H, d), 7.81 (2H, d), 7.72 (2H, d), 7.71 (2H, d), 7.6 (2H, d), 7.6 (7.6H, d), d (7.6H, d). 7.66 (2H, d), 7.59 (2H, dd), 7.44 (1H, d)A103δ = 8.54 (2H, s), 8.16 (2H, d), 7.95 (2H, d), 7.75 (2H, d), 7.67 (4H, d), 7.6 (2H, d), 7.6 (2H, d), d 7.59 (2H, d), 7.4 (1H, d)A107δ = 7.85 (2H, s), 7.79 (2H, d), 7.52 (2H, d), 7.51 (2H, d), 7.44 (2H, d), 7.41 (1H, d), 7.2 (1H, d) = 7.25 (2H, d). (1H, s), 7.89 (1H, d), 7.75 (1H, d), 7.66 (1H, d), 7.64 (1H, d), 7.5 (2H, d), 7.38 (1H, d), 7.32 (1H, d)A132δ = 7.95 (2H, d), 7.58 (2H, d), (7.5H, d). (2H, d), 7.51 (2H, d), 7.5 (2H, d), 7.41 (1H, d), 7.25 (2H, d)A1338.28 (2H, s), 7.95 (2H, d), 7.51 (2H, d), 7.5 (2H, d), 7.51 (2H, d), 7.5 (2H, d), 7.51 (2H, d) = 14.99δ (2H, s), 7.8 (1H, d), 7.76 (2H, d), 7.69 (1H, d)A157δ = 7.95 (2H, s), 7.4 (1H, s)A173δ = 7.95 (2H, s), 7.79 (2H, s), 7.5 (1H, s).

[0339] <제조예 2> 화합물 B26 및 표 4의 화합물의 제조

[0340]

[0341] 1) 중간체 B26-1의 제조

[0342] In a 1 L two-neck flask, 30.0 g (90.5 mmol) of 5-bromo-9-chloronaphtho[1,2-b]benzofuran (A), 12.1 g (99.6 mmol) of phenylboronic acid (B), 45.2 g (4.5 mmol) of Pd(pph3), and 25.0 g (181.0 mmol) of K2CO3 were dissolved in 1,4-dioxane / H2O (300 ml / 60 ml) and refluxed for 1 hour. The reactant was purified by recrystallization from methanol, and 24.8 g (yield 83.3%) of intermediate B26-1 was obtained.

[0343] 2) Preparation of compound B26

[0344] In a 500 ml two-neck flask, 10.0 g (30.4 mmol) of intermediate B26-1, 11.3 g (30.4 mmol) of di([1,1'-biphenyl]-4-yl)amine(C), 1.4 g (1.5 mmol) of Pd2dba3(Tris(dibenzylideneacetone)dipalladium(0)), 1.4 g (3.0 mmol) of Xphos(2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl), and 5.8 g (60.8 mmol) of NaOtBu(Sodium tert-butoxide) were added, dissolved in toluene (150 ml), and refluxed for 1 hour. The reactant was purified by recrystallization from methanol, and 17.6 g (yield 87.2%) of the target compound B26 was obtained.

[0345] Compounds in Table 4 below were synthesized in the same manner as in Manufacturing Example 2, except that compounds A, B and C in Table 4 below were used instead of compounds (A), (B) and (C) in Manufacturing Example 2 above.

[0346]

[0347]

[0348] <Manufacturing Example 3> Preparation of compound B20 and compounds in Table 5

[0349]

[0350] 1) Preparation of intermediate B20-1

[0351] In a 1 L two-neck flask, 30.0 g (90.5 mmol) of 5-bromo-7-chloronaphtho[1,2-b]benzofuran (A), 12.1 g (99.6 mmol) of phenylboronic acid (B), 45.2 g (4.5 mmol) of Pd(pph3), and 25.0 g (181.0 mmol) of K2CO3 were dissolved in 1,4-dioxane / H2O (300 ml / 60 ml) and refluxed for 1 hour. The reactant was purified by recrystallization from methanol, and 24.8 g (yield 83.3%) of intermediate B20-1 was obtained.

[0352] 2) Preparation of compound B20

[0353] In a 250 ml two-neck flask, 10.0 g (30.4 mmol) of intermediate B20-1, 13.4 g (30.4 mmol) of (4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid(C), 1.4 g (1.5 mmol) of Pd2dba, 1.4 g (3.0 mmol) of Xphos, and 8.4 g (60.8 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O (100 ml / 20 ml) and refluxed for 1 hour. The reactant was purified by recrystallization from methanol, and 15.1 g (yield 80.9%) of the target compound B20 was obtained.

[0354] Compounds in Table 5 below were synthesized in the same manner as in Manufacturing Example 3, except that compounds A, B, and C in Table 5 below were used instead of compounds (A), (B), and (C) in Manufacturing Example 3 above.

[0355]

[0356]

[0357] <Manufacturing Example 4> Preparation of compound B88 and compounds in Table 6

[0358]

[0359] 1) Preparation of intermediate B88-1

[0360] In a 500 ml two-neck flask, 10.0 g (30.31 mmol) of compounds 5-bromo-9-chloronaphtho[2,1-b]benzofuran (A), 11.3 g (30.31 mmol) of N-(4-(naphthalen-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (B), 30.34 g (1.5 mmol) of Pd2dba, 1.4 g (60.62 mmol) of Xphos, and 5.8 g (60.62 mmol) of NaOtBu were added, dissolved in toluene (150 ml), and refluxed for 1 hour. The reactant was purified by recrystallization from methanol, and 16.57 g (yield 88%) of intermediate B88-1 was obtained.

[0361] 2) Preparation of compound B88

[0362] In a 1 L two-neck flask, 16.57 g (26.67 mmol) of compound B88-1, 4.88 g (40.01 mmol) of phenylboronic acid(C), 41.54 g (1.33 mmol) of Pd(pph3), and 11.06 g (80.02 mmol) of K2CO3 were dissolved in 1,4-dioxane / H2O (300 ml / 60 ml) and refluxed for 1 hour. The reactant was purified by recrystallization from methanol, and 15.22 g (yield 86%) of the target compound B88 was obtained.

[0363] Compounds in Table 6 below were synthesized in the same manner as in Manufacturing Example 4, except that compounds A, B, and C in Table 6 below were used instead of compounds (A), (B), and (C) in Manufacturing Example 4 above.

[0364]

[0365] The compounds synthesized in the above manufacturing examples 2 to 4 were analyzed using an FD-mass spectrometer and 1 The synthesis of the desired compound was confirmed through H NMR. The measured values ​​of FD-mass spectrometry (FD-MS: Field desorption mass spectrometry) are shown in Table 7 below. 1 The measured values ​​of H NMR (CDCl3, 400 MHz) are listed in Table 8 below.

[0366] Compound number FD-MS Compound number FD-MSB1 m / z = 613.24 (C 46 H 31 NO, 613.74)B62m / z= 587.22 (C 44 H 29 NO, 587.71)B3m / z= 637.24 (C 48 H 31 NO, 637.77)B63m / z= 689.27 (C 52 H 35 NO, 689.84)B4m / z= 689.27 (C 52 H 35 NO, 689.84)B64m / z= 689.27 (C 52 H 35 NO, 689.84)B7m / z= 703.25 (C 52 H 33 NO2, 703.82)B66m / z= 613.24 (C 46 H 31 NO, 613.74)B11m / z= 587.22 (C 44 H 29 NO, 587.71)B69m / z= 587.22 (C 44 H 29 NO, 587.71)B12m / z= 689.27 (C 52 H 35 NO, 689.84)B74m / z= 613.24 (C 46 H 31 NO, 613.74)B13m / z= 739.29 (C 56 H 37 NO, 739.90)B78m / z= 613.24 (C 46 H31 NO, 613.74)B16m / z= 663.26 (C 50 H 33 NO, 663.80)B84m / z= 637.24 (C 48 H 31 NO, 637.77)B17m / z= 765.30 (C 58 H 39 NO, 765.94)B88m / z= 663.26 (C 50 H 33 NO, 663.80)B20m / z= 689.27 (C 52 H 35 NO, 689.84)B91m / z= 637.24 (C 48 H 31 NO, 637.77)B21m / z= 713.27 (C 54 H 35 NO, 713.86)B93m / z= 703.25 (C 52 H 33 NO2, 703.82)B24m / z= 703.25 (C 52 H 33 NO2, 703.82)B98m / z= 634.37 (C 46 H 10 D 21 NO, 634.87)B25m / z= 689.27 (C 52 H 35 NO, 689.84)B101m / z= 613.24 (C 46 H 31 NO, 613.74)B26m / z= 613.24 (C 46 H 31 NO, 613.74)B106m / z= 613.24 (C 46 H 31 NO, 613.74)B29m / z= 637.24 (C 48 H 31 NO, 637.77)B110m / z= 663.26 (C 50 H 33 NO, 663.80)B31m / z= 653.27 (C 49 H 35 NO, 653.81)B116m / z= 663.26 (C50 H 33 NO, 663.80)B37m / z= 639.40 (C 46 H5D 26 NO, 639.90)B118m / z= 613.24 (C 46 H 31 NO, 613.74)B41m / z= 613.24 (C 46 H 31 NO, 613.74)B119m / z= 613.24 (C 46 H 31 NO, 613.74)B58m / z= 613.24 (C 46 H 31 NO, 613.74)B136m / z= 663.26 (C 50 H 33 NO, 663.80)

[0367] 화합물번호 1H NMR(CDCl3, 400MHz)B1δ = 8.55 (1H, s), 8.18 (1H, d), 7.79 (2H, d), 7.71 (1H, d), 7.65 (1H, d), 7.55 (2H, d), 7.54 (4H, d), 7.52 (4H, d), 7.51 (6H, d), 7.41 (4H, dd), 6.69 (4H, d), 6.39 (1H, d)B3δ = 8.93 (1H, s), 8.68 (1H, d), 8.55 (1H, d), 8.18 (1H, d), 8.12 (1H, d), 7.88 (1H, d), 7.82 (1H, d), 7.79 (2H, d), 7.71 (3H, d), 7.65 (1H, dd), 7.55 (2H, d), 7.54 (2H, d), 7.52 (2H, dd), 7.51 (4H, dd), 7.41 (3H, s), 7.32 (1H, t), 7.08 (1H, t), 6.69 (2H, dd), 6.39 (1H, dd)B4δ = 8.55 (1H, s), 8.18 (1H, d), 7.81 (1H, d), 7.79 (2H, d), 7.72 (1H, d), 7.71 (2H, d), 7.55 (2H, d), 7.54 (6H, d), 7.52 (4H, d), 7.51 (6H, dd), 7.41 (3H, d), 6.69 (6H, d)B7δ = 8.55 (1H, s), 8.18 (1H, d), 7.89 (1H, d), 7.81 (1H, d), 7.79 (2H, d), 7.72 (1H, d), 7.71 (2H, d), 7.66 (1H, d), 7.64 (1H, d), 7.55 (2H, dd), 7.54 (4H, d), 7.52 (2H, d), 7.51 (4H, dd), 7.43 (1H, dd), 7.41 (2H, s), 7.38 (1H, t), 7.32 (1H, t), 6.69 (4H, dd), 6.33 (1H, dd)B11δ =8.55 (1H, s), 8.18 (1H, d), 7.88 (1H, d), 7.84 (1H, d), 7.79 (2H, d), 7.77 (1H, d), 7.74 (1H, d), 7.71 (1H, d), 7.55 (2H, d), 7.54 (2H, dd), 7.52 (2H, d), 7.51 (4H, d), 7.5 (1H, dd), 7.49 (1H, dd), 7.41 (2H, s), 7.36 (1H, t), 7.25 (1H, t), 7.07 (1H, dd), 6.69 (2H, dd), 6.39 (1H, t)B12δ =8.55 (1H, s), 8.18 (1H, d), 7.85 (1H, d), 7.81 (1H, d), 7.79 (2H, d), 7.71 (1H, d), 7.55 (2H, d), 7.54 (5H, d), 7.52 (2H, d), 7.51 (6H, dd), 7.41 (3H, d), 7.38 (1H, d), 7.16 (1H, dd), 7.08 (2H, dd), 6.87 (1H, s), 6.69 (5H, t)B13δ = 8.55 (1H, s), 8.18 (1H, d), 8 (2H, d), 7.95 (1H, d), 7.92 (1H, d), 7.75 (1H, d), 7.73 (1H, d), 7.71 (1H, d), 7.64 (1H, d), 7.59 (2H, dd), 7.58 (1H, d), 7.55 (2H, d), 7.54 (5H, dd), 7.52 (2H, dd), 7.51 (4H, s), 7.41 (2H, t), 7.16 (1H, t), 7.08 (2H, dd), 6.87 (1H, dd), 6.69 (5H, t)B16δ = 8.55 (1H, s), 8.18 (1H, d), 7.88 (1H, d), 7.84 (1H, d), 7.79 (2H, d), 7.77 (1H, d), 7.74 (1H, d), 7.71 (1H, d), 7.55 (2H, d), 7.54 (2H, dd), 7.52 (2H, d), 7.51 (4H, d), 7.5 (1H, dd), 7.49 (1H, dd), 7.41 (2H, s), 7.36 (1H, t), 7.25 (4H, t), 7.13 (1H, dd), 7.02 (1H, dd), 6.69 (2H, t), 6.33 (1H, d)B17δ = 8.55 (1H, s), 8.18 (1H, d), 7.79 (2H, d), 7.75 (1H, d), 7.71 (1H, d), 7.62 (1H, d), 7.55 (2H, d), 7.54 (4H, d), 7.52 (4H, d), 7.51 (6H, dd), 7.44 (2H, d), 7.41 (3H, d), 7.25 (4H, dd), 6.89 (1H, dd), 6.88 (1H, s), 6.69 (4H, t), 6.59 (1H, t)B20δ = 8.55 (1H, s), 8.18 (1H, d), 7.79 (2H, d), 7.75 (1H, d), 7.71 (1H, d), 7.62 (1H, d), 7.55 (2H, d), 7.54 (6H, d), 7.52 (4H, d), 7.51 (6H, dd), 7.44 (1H, d), 7.41 (3H, d), 6.69 (6H, dd)B21δ = 8.93 (2H, s), 8.55 (1H, d), 8.18 (1H, d), 8.12 (2H, d), 7.93 (1H, d), 7.88 (2H, d), 7.82 (2H, d), 7.79 (2H, d), 7.71 (1H, d), 7.55 (2H, dd), 7.54 (4H, d), 7.52 (2H, d), 7.51 (4H, dd), 7.41 (2H, dd), 7.13 (1H, s), 7.02 (1H, t), 6.69 (4H, t), 6.33 (1H, dd)B24δ = 8.55 (1H, s), 8.18 (1H, d), 7.89 (1H, d), 7.79 (2H, d), 7.75 (1H, d), 7.71 (1H, d), 7.66 (1H, d), 7.64 (1H, d), 7.62 (1H, d), 7.55 (2H, dd), 7.54 (4H, d), 7.52 (2H, d), 7.51 (4H, dd), 7.44 (1H, dd), 7.43 (1H, s), 7.41 (2H, t), 7.38 (1H, t), 7.32 (1H, dd), 6.69 (4H, dd), 6.33 (1H, t)B25δ = 8.55 (1H, s), 8.18 (1H, d), 7.95 (1H, d), 7.79 (2H, d), 7.75 (1H, d), 7.71 (1H, d), 7.64 (1H, d), 7.55 (2H, d), 7.54 (6H, d), 7.52 (4H, dd), 7.51 (6H, d), 7.41 (3H, d), 6.69 (6H, dd)B26δ = 8.55 (1H, s), 8.18 (1H, d), 7.79 (2H, d), 7.71 (1H, d), 7.64 (1H, d), 7.55 (2H, d), 7.54 (4H, d), 7.52 (4H, d), 7.51 (6H, d), 7.43 (1H, dd), 7.41 (3H, d), 6.69 (4H, d), 6.33 (1H, dd)B29δ = 8.93 (2H, s), 8.55 (1H, d), 8.18 (1H, d), 8.12 (2H, d), 7.93 (1H, d), 7.88 (2H, d), 7.82 (2H, d), 7.79 (2H, d), 7.71 (1H, d), 7.64 (1H, dd), 7.55 (2H, d), 7.54 (2H, d), 7.51 (2H, dd), 7.43 (1H, dd), 7.41 (1H, s), 7.2 (2H, t), 6.81 (1H, t), 6.69 (2H, dd), 6.63 (2H, dd), 6.33 (1H, t)B31δ = 8.55 (1H, s), 8.18 (1H, d), 7.87 (1H, d), 7.79 (2H, d), 7.71 (1H, d), 7.64 (1H, d), 7.62 (1H, d), 7.55 (3H, d), 7.54 (2H, d), 7.52 (2H, dd), 7.51 (4H, d), 7.43 (1H, d), 7.41 (2H, dd), 7.38 (1H, dd), 7.28 (1H, s), 6.75 (1H, t), 6.69 (2H, t), 6.58 (1H, dd), 6.33 (1H, dd), 1.72 (2H, t)B37δ = 7.52 (2H, d), 7.51 (2H, d), 7.41 (1H, d)B41δ = 8.55 (2H, s), 7.79 (2H, d), 7.64 (2H, d), 7.55 (2H, d), 7.54 (4H, d), 7.52 (2H, d), 7.54 (4H, d), 7.52 (2H, d), 6.5, d). 7.43 (1H, d), 7.41 (3H, d), 6.69 (4H, dd), 6.33 (1H, d)B58δ = 8.55 (2H, s), 7.95 (1H, d), 7.79 (2H, d), 7.75 (1H, d), 7.41 (2H, d). 7.54 (2H, d), 7.52 (2H, d), 7.51 (4H, d), 7.44 (1H, dd), 7.41 (2H, d), 7.2 (2H, d), 6.89 (1H, dd), 6.88 (1H, dd), 6.81 (1H, s), (6.6H, 6.9), t (2H, t), 6.59 (1H, dd)B62δ = 8.55 (4H, s), 8 (4H, d), 7.92 (2H, d), 7.73 (2H, d), 7.64 (4H, d), 7.59 (4H, d), 7.58 (2H, dd), 7.59 (4H, d), 7.58 (4, 4H, d). d), 7.52 (4H, dd), 7.51 (4H, d), 7.43 (2H, d), 7.41 (2H, dd), 7.2 (4H, dd), 6.81 (2H, s), 6.69 (4H, t), 6.63 (4H, t), 6.33 (2H, dd) = 8.55. (2H, s), 7.64 (2H, d), 7.55 (2H, d), 7.54 (3H, d), 7.52 (4H, d), 7.51 (6H, d), 7.43 (1H, d), 7.41 (3H, d), 7.25 (4H, d), 7.11 (6H, d), (2H, d.), (2H, d. 6.87 (1H, d), 6.69 (3H, dd), 6.33 (1H, dd)B64δ = 8.55 (4H, s), 7.64 (2H, d), 7.55 (4H, d), 7.54 (6H, d), 7.52 (12H, d),51 (12H, d), 7.43 (1H, d), 7.41 (6H, d), 7.25 (7H, d), 6.69 (6H, dd), 6.33 (1H, d)B66δ = 8.55 (2H, s), 7.79 (2H, d), 7.43 (1H, d), 7.5 (2H, d). 7.54 (2H, d), 7.52 (2H, d), 7.51 (4H, d), 7.41 (2H, d), 7.25 (5H, d), 7.2 (2H, dd), 7.07 (1H, d), 6.81 (1H, d), 6.69 (2H, d), (2H, dd), 6.69 (6H, d). (1H, s)B69δ =8.55 (2H, s), 7.88 (1H, d), 7.84 (1H, d), 7.79 (2H, d), 7.77 (1H, d), 7.74 (1H, d), 7.65 (1H, d), 7.64 (1H, d), 7.65 (1H, d), 7.64 (1H, d), 7.5, d, 7.5). (2H, dd), 7.52 (2H, d), 7.51 (4H, d), 7.5 (1H, dd), 7.49 (1H, dd), 7.41 (3H, s), 7.36 (1H, t), 6.69 (2H, t), 6.39 (1H, dd), 6.39 (1H, dd) (2H, 5.5 s), 7.79 (2H, d), 7.64 (1H, d), 7.55 (2H, d), 7.54 (2H, d), 7.52 (2H, d), 7.51 (4H, d), 7.41 (2H, d), 7.25 (4H, d), 7.2 (2H, d), 7.25 (4H, d), 7.2 (2H, d), 7.01, d. (1H, d), 6.81 (1H, dd), 6.69 (2H, dd), 6.63 (2H, s), 6.33 (1H, t)B78δ = 8.55 (2H, s), 7.81 (1H, d), 7.79 (2H, d). (1H, d), 7.55 (2H, d), 7.54 (4H, d), 7.52 (2H, d), 7.51 (4H, dd), 7.41 (2H, d), 7.2 (2H, d), 6.81 (1H, dd), 6.69 (4H, dd),63 (2H, s)B84δ = 8.93 (2H, s), 8.55 (1H, d), 8.12 (2H, d), 8.08 (1H, d), 7.93 (1H, d), 7.88 (2H, d), 7.85 (1H, d), 7.82 (2H, d), 7.81 (1H, d), 7.55 (2H, dd), 7.54 (2H, d), 7.52 (2H, d), 7.51 (2H, dd), 7.46 (1H, dd), 7.41 (1H, s), 7.38 (1H, t), 7.2 (2H, t), 6.81 (1H, dd), 6.69 (2H, dd), 6.63 (2H, t)B88δ = 8.55 (1H, s), 8.08 (1H, d), 8 (2H, d), 7.95 (1H, d), 7.92 (1H, d), 7.75 (1H, d), 7.73 (1H, d), 7.64 (1H, d), 7.59 (2H, d), 7.58 (1H, dd), 7.55 (2H, d), 7.54 (4H, d), 7.52 (4H, dd), 7.51 (4H, dd), 7.46 (1H, s), 7.41 (2H, t), 6.69 (4H, t)B91δ = 8.93 (2H, s), 8.55 (1H, d), 8.12 (2H, d), 8.08 (1H, d), 7.93 (1H, d), 7.88 (2H, d), 7.82 (2H, d), 7.81 (1H, d), 7.72 (1H, d), 7.71 (1H, dd), 7.55 (2H, d), 7.54 (2H, d), 7.52 (2H, dd), 7.51 (2H, dd), 7.46 (1H, s), 7.41 (1H, t), 7.2 (2H, t), 6.81 (1H, dd), 6.69 (2H, dd), 6.63 (2H, t)B93δ = 8.55 (1H, s), 8.08 (1H, d), 7.89 (1H, d), 7.75 (1H, d), 7.66 (1H, d), 7.64 (1H, d), 7.62 (1H, d), 7.55 (2H, d), 7.54 (2H, d), 7.52 (4H, dd), 7.51 (4H, d), 7.<h2 style=";text-align:left;direction:ltr">46 (1H, d), 7.44 (1H, dd), 7.43 (1H, dd), 7.41 (2H, s), 7.38 (1H, t), 7.32 (1H, t), 7.25 (4H, dd), 6.69 (2H, dd), 6.33 (1H, t)B98δ = 7.95 (1H, s), 7.79 (2H, d), 7.64 (1H, d), 7.51 (2H, d), 7.5 (1H, d), 7.41 (2H, d), 6.8 (1H, d)B101δ = 8.16 (2H, s), 7.79 (2H, d), 7.67 (2H, d), 7.54 (4H, d), 7.52 (4H, d), 7.51 (7H, d), 7.49 (1H, d), 7.42 (1H, d), 7.41 (3H, d), 7.39 (1H, dd), 6.69 (4H, d)B106δ = 8.16 (2H, s), 7.79 (2H, d), 7.67 (2H, d), 7.6 (1H, d), 7.57 (1H, d), 7.54 (4H, d), 7.52 (2H, d), 7.51 (4H, d), 7.49 (1H, d), 7.42 (1H, dd), 7.41 (2H, d), 7.2 (2H, d), 6.81 (1H, dd), 6.69 (4H, dd), 6.63 (2H, s)B110δ = 8.16 (2H, s), 8 (2H, d), 7.92 (1H, d), 7.73 (1H, d), 7.67 (2H, d), 7.59 (2H, d), 7.58 (1H, d), 7.54 (4H, d), 7.52 (4H, d), 7.51 (5H, dd), 7.49 (1H, d), 7.42 (1H, d), 7.41 (2H, dd), 7.39 (1H, dd), 6.69 (4H, s)B116δ = 8.16 (2H, s), 8 (2H, d), 7.92 (1H, d), 7.73 (1H, d), 7.67 (2H, d), 7.59 (2H, d), 7.58 (1H, d), 7.54 (2H, d), 7.52 (2H, d), 7.51 (3H, dd), 7.49 (1H, d), 7.42 (1H, d), 7.41 (1H, dd), 7.39 (1H, dd), 7.25 (4H, s), 7.2 (2H, t), 6.81 (1H, t), 6.69 (2H, dd), 6.63 (2H, dd)B118δ = 8.16 (2H, s), 7.6 (H, 4, dd). d), 7.52 (4H, d), 7.51 (6H, d), 7.49 (2H, d), 7.46 (1H, d), 7.42 (1H, d), 7.41 (3H, d), 7.08 (2H, dd), 6.69 (4H, d) d), 7.6 (1H, d), 7.54 (2H, d), 7.52 (4H, d), 7.51 (4H, d), 7.49 (1H, d), 7.42 (1H, d), 7.41 (2H, d), 7.25 (4H, dd), 7.2 (2H, d), 6.6H, d. (2H, dd), 6.63 (2H, dd), 6.39 (1H, s)B136δ = 8.16 (2H, s), 8 (2H, d), 7.92 (1H, d), 7.79 (2H, d), 7.73 (1H, d), 7.67 (2H, d), 7.73 (1H, d), 7.67 (2H, d), 7.85, d. (1H, d), 7.54 (4H, d), 7.52 (2H, dd), 7.51 (5H, d), 7.49 (1H, d), 7.42 (1H, dd), 7.41 (2H, dd), 7.39 (1H, s), 6.69 (4H, t).

[0368] <실험예>

[0369] <실험예 1>

[0370] (1) 유기 발광 소자의 제작 (호스트 1종 사용)

[0371] A glass substrate coated with a 1,500 Å thick indium tin oxide (ITO) film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) for 5 minutes using UV (Ultraviolet) in a UV (Ultraviolet) cleaner. After that, the substrate was transferred to a plasma cleaner (PT), and plasma treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic vapor deposition.

[0372] A common layer, 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 on the ITO transparent electrode (anode).

[0373] On top of that, a light-emitting layer was thermally vacuum deposited as follows. The light-emitting layer was deposited to a thickness of 500 Å by using the compounds described in Table 9 below as a red host and doping the host with 3% of (piq)2(Ir)(acac) as a red phosphorescent dopant.

[0374] Afterwards, BCP was deposited as a hole blocking layer with a thickness of 60Å, and Alq3 was deposited as an electron transport layer with a thickness of 200Å thereon. Afterwards, BCP was deposited as a hole blocking layer with a thickness of 60Å, and Alq3 was deposited as an electron transport layer with a thickness of 200Å thereon. Finally, lithium fluoride (LiF) was deposited on the electron transport layer with a thickness of 10Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer with a thickness of 1,200Å to form a cathode, thereby manufacturing an organic light-emitting device.

[0375] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -8 ~10 -6 It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0376] The comparative compounds used in Comparative Examples 1 to 17 are as follows.

[0377]

[0378]

[0379] (2) Measurement of driving voltage and luminous efficiency of organic light-emitting devices

[0380] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using MacScience's M7000, and the results are shown in Table 9 below.

[0381] Compound threshold voltage (V) on ) Driving voltage (V) op)Efficiency (cd / A)Color coordinate (x, y)Example 1A12.273.5350.24(0.684, 0.316)Example 2A22.243.4751.24(0.685, 0.314)Example 3A82.233.4556.24(0.684, 0.315)Example 4A92.253.4955.24(0.684, 0.316)Example 5A102.263.5149.24(0.684, 0.316)Example 6A172.233.4550.24(0.684, 0.316)Example 7A222.073.1332.24(0.684, 0.316)Example 8A282.023.0334.24(0.684, 0.315)Example 9A342.133.2542.24(0.683, 0.317)Example 10A372.123.2344.24(0.684, 0.316)Example 11A442.193.3740.24(0.683, 0.318)Example 12A452.273.5350.24(0.685, 0.314)Example 13A882.073.1332.24(0.684, 0.315) Example 14A982.123.2345.24(0.685, 0.315) Example 15A1032.143.2144.76(0.685, 0.314) Example 16A1072.233.4552.24(0.683, 0.318) Example 17A1232.213.4151.24(0.684, 0.315) Example 18A1322.143.2741.24(0.683, 0.318) Example 19A1332.133.2245.25(0.685, 0.314) Example 20A1492.233.4550.24(0.680, 0.319)Example 21A1572.083.1531.24(0.684, 0.316)Example 22A1732.193.3743.24(0.685, 0.315)Comparative Example 1J2.263.4829.84(0.684, 0.316)Comparative Example 2K2.233.3328.73(0.684, 0.316)Comparative Example 3L2.193.2827.46(0.683, 0.317)Comparative Example 4M2.183.2711.87(0.684, 0.316)Comparative Example 5N2.133.1224.52(0.684, 0.316) Comparative example 6O2.083.0824.89(0.683, 0.317) Comparative example 7P1.843.122.14(0.684, 0.316) Comparative example 8Q2.183.2711.87(0.684, 0.316) Comparative example 9R2.353.5818.44(0.684, 0.316) Comparative example 10S2.413.6717.98(0.684, 0.316) Comparative example 11T2.553.7715.34(0.683, 0.317) Comparative example 12U2.473.8326.43(0.684, 0.316) Comparative example 13V2.273.4312.24(0.684, 0.316) Comparative example 14W2.333.5522.24(0.683, 0.317)Comparative example 15X2.173.4220.24(0.684, 0.316)Comparative example 16Y1.973.022.24(0.684, 0.316)Comparative example 17Z2.033.1412.24(0.683, 0.317).

[0382]

[0383] (3) Measurement of the lifespan of organic light-emitting devices

[0384] Based on the measurement results of the above driving voltage and luminous efficiency, the standard luminance was measured to be 6,000 cd / m using the life measurement equipment (M6000) manufactured by Max Science. 2 When, T 90 was measured, and the results are shown in Table 10 below. The above T 90 refers to the lifespan (unit: h, hours), which is the time it takes for the initial brightness to drop to 90%.

[0385] Compound lifetime (T 90 ) Compound lifetime (T 90) Example 1A161 Example 21A15798 Example 2A260 Example 22A17387 Example 3A855 Comparative Example 1J28 Example 4A956 Comparative Example 2K27 Example 5A1062 Comparative Example 3L31 Example 6A1761 Comparative Example 4M20 Example 7A2277 Comparative Example 5N32 Example 8A2875 Comparative Example 6O40 Example 9A3468 Comparative Example 7P30 Example 10A3766 Comparative Example 8Q20 Example 11A4470 Comparative Example 9R30 Example 12A4573 Comparative Example 10S33 Example 13A8889 Comparative Example 11T23 Example 14A9877 Comparative Example 12U29 Example 15A10375 Comparative Example 13V45 Example 16A10774 Comparative Example 14W38 Example 17A12376 Comparative Example 15X14 Example 18A13285 Comparative Example 16Y34 Example 19A13388 Comparative Example 17Z23 Example 20A14977

[0386] As can be seen from the results in Tables 9 and 10 above, it was confirmed that when the organic material layer (light-emitting layer) of the organic light-emitting device was manufactured using the heterocyclic compound according to the present application, the efficiency or lifespan of the organic light-emitting device was improved.

[0387] In particular, looking at the luminescence efficiency measurement results in Table 9, it can be seen that among the heterocyclic compounds of the present invention, the luminescence efficiency is high in the case of including the chemical formula A as Het1 and Het2. This is because the structure has relatively slow hole characteristics, so it meets with electrons accumulated in the luminescent layer and provides the best performance in terms of efficiency.

[0388] On the other hand, examining the lifetime measurement results in Table 10, when the group represented by the chemical formula C is included, it exhibits relatively fast hole transport characteristics compared to other structures due to the structural characteristics of the long naphthobenzofuran ring. Therefore, it was confirmed that charge balance was better achieved within the light-emitting layer, resulting in an excellent lifetime.

[0389] In the case of chemical formula B, it is judged to have properties that are intermediate between chemical formulas A and C, and to exhibit efficiency and lifespan at the average level of chemical formulas A and C.

[0390] That is, in terms of luminous efficiency, the structure of chemical formula A is the highest, in terms of lifespan, the structure of chemical formula C is the highest, and the structure of chemical formula B has an intermediate performance in both luminous efficiency and lifespan.

[0391] Compounds J to O have different substitution positions of naphthobenzofuran compared to the heterocyclic compound of the present invention. When compounds J to O are used instead of the heterocyclic compound of the present invention, the compound has fast hole characteristics due to the heterocyclic compound, but it is judged that an imbalance of the band gap occurs within the light-emitting layer, resulting in loss of electrons and holes, which reduces efficiency and lifespan.

[0392] For compounds P and Q, although the electronic properties are superior to those of the heterocyclic compound of the present invention, it is believed that the efficiency and lifespan of the device are reduced due to compound deterioration when deposited on the device due to thermal stability issues caused by high molecular weight.

[0393] Compound R is a compound in which two naphthobenzofurans are connected to a triazine through an arylene group as a linker, but has a problem in that the arylene group as a linker inhibits hole transport properties.

[0394] For compounds S and T, although two naphthobenzofurans are substituted, it was confirmed that the remaining substituent of the triazine, the aryl group, has an additional substituent, thereby inhibiting hole transport and electron transport properties.

[0395] Compounds U and V contain only one naphthobenzofuran, so their electronic properties are worse than those of the heterocyclic compound of chemical formula 1. Compounds X to Z contain three naphthobenzofurans, so their electronic properties are better than those of the heterocyclic compound of chemical formula 1. However, due to the thermal stability problem caused by the high molecular weight, it is judged that when deposited on a device, the efficiency and lifespan of the device are reduced due to compound deterioration.

[0396] That is, it was confirmed through comparative example compounds that the heterocyclic compound structure according to the present invention has excellent effects as a material for an organic light-emitting device.

[0397]

[0398] Experimental Example 2

[0399] (1) Fabrication of organic light-emitting devices (using a combination of two hosts)

[0400] A glass substrate coated with a 1,500 Å thick indium tin oxide (ITO) film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) for 5 minutes using UV (Ultraviolet) in a UV (Ultraviolet) cleaner. After that, the substrate was transferred to a plasma cleaner (PT), and plasma treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic vapor deposition.

[0401] A common layer, 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 on the ITO transparent electrode (anode).

[0402] On top of that, a light-emitting layer was thermally vacuum-deposited as follows. The light-emitting layer was prepared by mixing two compounds described in Table 11 below as a red host and using them as a single source, and using (piq)2(Ir)(acac) as a red phosphorescent dopant, the host was doped with 3% of (piq)2(Ir)(acac) and deposited to a thickness of 500 Å.

[0403] Afterwards, BCP was deposited as a hole blocking layer with a thickness of 60Å, and Alq3 was deposited as an electron transport layer with a thickness of 200Å thereon. Afterwards, BCP was deposited as a hole blocking layer with a thickness of 60Å, and Alq3 was deposited as an electron transport layer with a thickness of 200Å thereon. Finally, lithium fluoride (LiF) was deposited on the electron transport layer with a thickness of 10Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer with a thickness of 1,200Å to form a cathode, thereby manufacturing an organic light-emitting device.

[0404] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -8 ~10 -6 It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0405]

[0406] (2) Measurement of driving voltage and luminous efficiency of organic light-emitting devices

[0407] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using MacScience's M7000, and the results are shown in Table 11 below.

[0408] First host (P) Second host (N) Ratio (P:N) Threshold voltage (V) on ) Driving voltage (V) op) Luminous efficacy (cd / A) Color coordinates (x, y) Example 23B1A0011: 12.314.1385.65 (0.683, 0.318) Example 24B20A0011: 12.735.0688.44 (0.684, 0.316) Example 25B11A0021: 12.374.3985.72 (0.685, 0.315) Example 26B17A0021: 12.685.0789.75 (0.684, 0.316) Example 27B17A0021.5: 12.655.0187.96 (0.680, 0.319) Example 28B17A0021:1.52.715.1391.55(0.684, 0.316) Example 29B17A0021:22.745.1990.65(0.684, 0.315) Example 30B17A0021:32.775.2588.86(0.683, 0.318) Example 31B13A0081:12.444.3590.73(0.683, 0.318) Example 32B13A0081.5:12.414.2988.92(0.683, 0.317) Example 33B13A0081:1.52.474.4192.55(0.685, 0.315) Example 34B13A0081:22.504.4791.64(0.683, 0.318) Example 35B13A0081:32.534.5389.83(0.684, 0.316) Example 36B16A0081:12.534.8693.51(0.685, 0.314) Example 37B16A0081.5:12.504.8091.64(0.683, 0.318) Example 38B16A0081:1.52.564.9295.38(0.684, 0.316) Example 39B16A0081:22.594.9894.45(0.684, 0.315) Example 40B16A0081:32.625.0492.58(0.683, 0.318) Example 41B29A0091:12.214.1590.96(0.683, 0.317) Example 42B29A0091.5:12.184.0989.15(0.685, 0.315) Example 43B29A0091:1.52.244.2192.78(0.683, 0.318) Example 44B29A0091:22.274.2791.87(0.684, 0.316) Example 45B29A0091:32.304.3390.06(0.684, 0.315) Example 46B13A0091:12.464.3889.73(0.684, 0.316) Example 47B41A0101:12.324.4180.38(0.683, 0.318) Example 48B74A0171:12.363.7084.06(0.684, 0.316) Example 49B3A0221:12.144.0867.34(0.684, 0.316) Example 50B58A0221:12.113.265.39(0.680, 0.319) Example 51B118A0221:12.124.7462.71(0.680, 0.319) Example 52B101A0221:12.034.7862.38(0.685, 0.314) Example 53B25A0281:12.173.4171.20(0.684, 0.316) Example 54B93A0281:12.214.5768.40(0.684, 0.316) Example 55B4A0341:12.283.2878.58(0.684, 0.316) Example 56B91A0341:12.23.7475.06(0.685, 0.314) Example 57B98A0371:12.154.2075.72(0.684, 0.316) Example 58B11A0441:12.324.3274.72(0.685, 0.314) Example 59B74A0441:12.323.6474.06(0.684, 0.315) Example 60B66A0451:12.223.6683.73(0.685, 0.315) Example 61B12A0881:12.254.1367.03(0.680, 0.319) Example 62B66A0881:12.023.3865.73(0.683, 0.318) Example 63B66A0881.5:11.993.3264.42(0.684, 0.316) Example 64B66A0881:1.52.053.4467.05(0.684, 0.315) Example 65B66A0881:22.083.5066.39(0.683, 0.318) Example 66B66A0881:32.113.5665.08(0.684, 0.316) Example 67B106A0881:12.034.8362.05(0.684, 0.316) Example 68B66A0981:12.073.4578.73(0.684, 0.316) Example 69B66A1031:12.123.5279.21(0.685, 0.314) Example 70B69A1071:12.354.0784.39(0.683, 0.318) Example 71B101A1231:12.174.9781.38(0.684, 0.315) Example 72B17A1321:12.584.9379.75(0.684, 0.315) Example 73B119A1321:12.214.7972.05(0.684, 0.315) Example 74B101A1321:12.104.8871.38(0.680, 0.319) Example 75B101A1331:12.184.9280.97(0.680, 0.319) Example 76B101A1491:12.195.0080.38(0.683, 0.318) Example 77B16A1571:12.384.6568.51(0.685, 0.314) Example 78B16A1571.5:12.354.5967.14(0.683, 0.318) Example 79B16A1571:1.52.414.7169.88(0.684, 0.316) Example 80B16A1571:22.444.7769.2(0.684, 0.315) Example 81B16A1571:32.474.8367.83(0.683, 0.318) Example 82B78A1571:12.263.9163.72(0.680, 0.319) Example 83B78A1571.5:12.233.8562.45(0.683, 0.318) Example 84B78A1571:1.52.293.9765.00(0.684, 0.316) Example 85B78A1571:22.324.0364.36(0.684, 0.315) Example 86B78A1571:32.354.0963.09(0.683, 0.318) Example 87B106A1571:12.044.8461.05(0.684, 0.315) Example 88B106A1571.5:12.014.7859.83(0.683, 0.318) Example 89B106A1571:1.52.074.9062.28(0.684, 0.316)Example 90B106A1571:22.104.9661.67(0.684, 0.315)Example 91B106A1571:32.135.0260.44(0.683, 0.318) Example 92B37A1731:12.323.5579.89(0.684, 0.315) Comparative Example 18B1J1:12.404.0246.26(0.684, 0.315) Comparative Example 19B69J1:12.484.0243.00(0.684, 0.315) Comparative Example 20B11K1:12.464.3044.22(0.683, 0.318) Comparative Example 21B74K1:12.463.3443.56(0.683, 0.318) Comparative Example 22B41L1: 12.244.0537.04(0.683, 0.318) Comparative example 23B13M1: 12.414.1241.81(0.684, 0.316) Comparative example 24B101M1: 12.165.0537.46(0.684, 0.316) Comparative example 25B3N1: 12.013.9918.25(0.680, 0.319) Comparative example 26B16N1: 12.244.7920.42(0.684, 0.316) Comparative example 27B58N1: 11.982.7316.30(0.683, 0.318) Comparative example 28B69N1:12.063.6615.30(0.683, 0.318)Comparative example 29B106N1:11.905.0612.96(0.680, 0.319)Comparative example 30B66O1:12.243.1541.96(0.684, 0.316)Comparative example 31B29P1:12.193.7341.25(0.680, 0.319)Comparative example 32B12Q1:12.464.2127.67(0.683, 0.318)Comparative example 33B37Q1:12.413.1429.53(0.684, 0.315)Comparative example 34B66Q1: 12.233.1426.37(0.684, 0.315)Comparative example 35B78Q1: 12.463.8825.36(0.684, 0.316)Comparative example 36B41R1: 12.514.5530.59(0.683, 0.318)Comparative example 37B29R1: 12.414.1935.17(0.683, 0.318)Comparative example 38B69R1: 12.574.1231.60(0.683, 0.318)Comparative example 39B11S1: 12.644.6433.47(0.684, 0.316)Comparative example 40B41S1:12.574.6430.13(0.684, 0.316) Comparative example 41B88S1: 12.464.5430.80(0.684, 0.316) Comparative example 42B17T1: 13.095.7134.86(0.684, 0.315) Comparative example 43B66T1: 12.603.6429.84(0.680, 0.319) Comparative example 44B118T1: 12.705.5826.82(0.684, 0.315) Comparative example 45B1U1: 12.614.3746.65(0.684, 0.315) Comparative example 46B29U1: 12.534.4446.96(0.680, 0.319) Comparative example 47B69U1: 12.694.3743.39(0.684, 0.315) Comparative example 48B11V1: 12.504.4027.72(0.683, 0.318) Comparative example 49B41V1: 12.434.4024.38(0.683, 0.318) Comparative example 50B74V1: 12.53.4427.06(0.683, 0.318) Comparative example 51B13W1: 12.644.4937.73(0.684, 0.316) Comparative example 52B66W1: 12.383.4236.73(0.684, 0.316) Comparative example 53B101W1: 12.395.4233.38(0.684, 0.316) Comparative example 54B3X1: 12.344.2936.34(0.680, 0.319) Comparative example 55B25X1: 12.423.4338.20(0.684, 0.315) Comparative example 56B78X1: 12.454.0333.72(0.680, 0.319) Comparative example 57B12Y1: 12.253.9618.03(0.683, 0.318) Comparative example 58B58Y1: 12.112.6316.39(0.683, 0.318) Comparative example 59B93Y1:12.264.6917.40(0.684, 0.316) Comparative example 60B16Z1:12.434.8130.51(0.684, 0.316) Comparative example 61B66Z1:12.083.0126.73(0.684, 0.316) Comparative example 62B118Z1:12.184.9523.71(0.685, 0.314).

[0409]

[0410] (3) Measurement of the lifespan of organic light-emitting devices

[0411] Based on the measurement results of the above driving voltage and luminous efficiency, the standard luminance was measured to be 6,000 cd / m using the life measurement equipment (M6000) manufactured by Max Science. 2 When, T 90 was measured, and the results are shown in Table 12 below. The above T 90 refers to the lifespan (unit: h, hours), which is the time it takes for the initial brightness to drop to 90%.

[0412] First host (P) Second host (N) Ratio (P:N) Lifespan (T) 90)Embodiment 23B1A0011:1116Embodiment 24B20A0011:1115Embodiment 25B11A0021:1116Embodiment 26B17A0021:1114Embodiment 27B17A0021.5:1115Embodiment 28B17A0021:1.5118Embodiment 29B17A0021:2119Embodiment 30B17A0021:3113Embodiment 31B13A0081:1110Embodiment 32B13A0081.5:1112Embodiment 33B13A0081:1.5114Embodiment 34B13A0081:2115Embodiment 35B13A0081:3109 embodiment 36B16A0081:1109 embodiment 37B16A0081.5:1111 embodiment 38B16A0081:1.5113 embodiment 39B16A0081:2114 embodiment 40B16A0081:3108 embodiment 41B29A0091:1111 embodiment 42B29A0091.5:1112 embodiment 43B29A0091:1.5114 embodiment 44B29A0091:2115 embodiment 45B29A0091:3109 embodiment 46B13A0091:1112 embodiment 47B41A0101:1125 Embodiment 48B74A0171:1120 Embodiment 49B3A0221:1138 Embodiment 50B58A0221:1142 Embodiment 51B118A0221:1140 Embodiment 52B101A0221:1139 Embodiment 53B25A0281:1135 Embodiment 54B93A0281:1139 Embodiment 55B4A0341:1126 Embodiment 56B91A0341:1132 Embodiment 57B98A0371:1131 Embodiment 58B11A0441:1129 Embodiment 59B74A0441:1132 Example 60B66A0451:1136 Example 61B12A0881:1153 Example 62B66A0881:1157 Example 63B66A0881.5:1159 Example 64B66A0881:1.5162 Embodiment 65B66A0881:2163 Embodiment 66B66A0881:3155 Embodiment 67B106A0881:1154 Embodiment 68B66A0981:1142 Embodiment 69B66A1031:1140 Embodiment 70B69A1071:1141 Embodiment 71B101A1231:1137 Embodiment 72B17A1321:1146 Embodiment 73B119A1321:1150 Embodiment 74B101A1321:1149 Embodiment 75B101A1331:1132 Embodiment 76B101A1491:1138 Embodiment 77B16A1571:1163 Example 78B16A1571.5:1165 Example 79B16A1571:1.5168 Example 80B16A1571:2170 Example 81B16A1571:3162 Example 82B78A1571:1169 Example 83B78A1571.5:1171 Example 84B78A1571:1.5174 Example 85B78A1571:2176 Example 86B78A1571:3167 Example 87B106A1571:1165 Example 88B106A1571.5:1167 Example 89B106A1571:1.5170 Example 90B106A1571:2172 Example 91B106A1571:3164 Example 92B37A1731:1149 Comparative Example 18B1J1:138 Comparative Example 19B69J1:145 Comparative Example 20B11K1:138 Comparative Example 21B74K1:141 Comparative Example 22B41L1:158 Comparative Example 23B13M1:147 Comparative Example 24B101M1:148 Comparative Example 25B3N1:141 Comparative Example 26B16N1:140 Comparative Example 27B58N1:145 Comparative Example 28B69N1:147 Comparative Example 29B106N1:142 Comparative example 30B66O1:146 Comparative example 31B29P1:142 Comparative example 32B12Q1:131 Comparative example 33B37Q1:130 Comparative example 34B66Q1:135 Comparative example 35B78Q1:136 Comparative example 36B41R1:148 Comparative example 37B29R1:140 Comparative example 38B69R1:147 Comparative example 39B11S1:144 Comparative example 40B41S1:151 Comparative example 41B88S1:150 Comparative example 42B17T1:132 Comparative example 43B66T1:138 Comparative example 44B118T1:136 Comparative example 45B1U1:138Comparative example 46B29U1:138Comparative example 47B69U1:145Comparative example 48B11V1:160Comparative example 49B41V1:167Comparative example 50B74V1:163Comparative example 51B13W1:149Comparative example 52B66W1:153Comparative example 53B101W1:150Comparative example 54B3X1:124Comparative example 55B25X1:123Comparative example 56B78X1:129Comparative example 57B12Y1:145Comparative example 58B58Y1:149Comparative example 59B93Y1:148Comparative example 60B16Z1:133Comparative example 61B66Z1:138Comparative example 62B118Z1:136.

[0413] Comparing the results of Tables 9 and 10 with the results of Tables 11 and 12, it was confirmed that when the heterocyclic compound according to the present application is used in combination with the compound of Chemical Formula 2 as a material for the organic layer (light-emitting layer) of an organic light-emitting device, the efficiency or lifespan of the organic light-emitting device is more efficiently improved.

[0414] Specifically, the heterocyclic compound of the above chemical formula 1 is characterized by a low threshold voltage, a low operating voltage, high efficiency, and a long lifespan. Comparatively, when the compound of the above chemical formula 2 is used alone, it exhibits low efficiency and a short lifespan, but when used in combination with the heterocyclic compound of the above chemical formula 1, charge balance is achieved, and higher efficiency and a longer lifespan are exhibited than when the heterocyclic compound of the above chemical formula 1 is used alone. This is because the compound of the above chemical formula 2 has a fast hole supply, and when used together with the heterocyclic compound of the above chemical formula 1, it plays a role in maintaining charge balance within the device, thereby improving the lifespan and efficiency.

[0415] On the other hand, it was confirmed that the comparative compounds did not show a significant improvement in luminescence efficiency or lifespan even when used in combination with the compound of Chemical Formula 2, and provided performance at or below the level of the heterocyclic compound of the present invention used alone.

[0416] In particular, since compounds R to V have different electronic or hole characteristics from the heterocyclic compound of the present invention, it is judged that when combined with the compound of chemical formula 2, a charge imbalance occurs, resulting in a decrease in efficiency and a decrease in lifespan.

[0417] In addition, for compounds X to Z, it is judged that although the charge balance is excellent when combined with the compound of chemical formula 2, the efficiency and lifespan of the device are reduced due to deterioration of the compound due to high molecular weight.

[0418] That is, it was found that the heterocyclic compound of chemical formula 1 of the present invention has high electronic properties and, when combined with the compound of chemical formula 2, has excellent charge balance, and thus, when used in combination, effectively improves the performance of the organic light-emitting device. In particular, when the ratio of the compound of chemical formula 2 is high, the charge balance occurs well, resulting in high efficiency and long lifespan. Specifically, it was found that when the weight ratio of the heterocyclic compound of chemical formula 1 and the compound of chemical formula 2 is 1:2 or 1:1.5, excellent luminous efficiency and lifespan are exhibited.

Claims

1. A heterocyclic compound of the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, Ar is an aryl group having 6 to 60 carbon atoms, substituted or unsubstituted with deuterium; or a heteroaryl group having 2 to 60 carbon atoms, substituted or unsubstituted with deuterium, Het1 and Het2 are identical and are represented by the following chemical formula H: [chemical formula H] In the above chemical formula H, Any one of H1 to H3 is combined with the chemical formula 1, The remainder of H1 to H3 and R are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; or a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms, a is an integer from 1 to 7, and if it is 2 or greater, R is equal or different.

2. In claim 1, the chemical formula H is a heterocyclic compound represented by the following chemical formula A or B: [Chemical Formula A] [Chemical Formula B] In the above chemical formulas A and B, The definition of R is the same as that in the chemical formula H above, Any one of A1 to A3 and any one of B1 to B3 are combined with the chemical formula 1, The remainder of A1 to A3 and the remainder of B1 to B3 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; or a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms, m and n are each an integer from 1 to 7, and when they are 2 or greater, the substituents in the parentheses are the same or different.

3. In claim 1, the chemical formula H is a heterocyclic compound represented by the following chemical formula C: [Chemical formula C] In the above chemical formula C, The definition of R is the same as that in the chemical formula H above, C1 is combined with the above chemical formula 1, o is an integer from 1 to 9, and if it is 2 or greater, R is equal or different.

4. In claim 1, the chemical formula 1 is a heterocyclic compound represented by any one of the following chemical formulas 1-1 to 1-7: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] In the above chemical formulas 1-1 to 1-7, The definitions of Ar and R are the same as those in the chemical formula 1 and H, respectively. m1, n1, and o1 are each integers from 1 to 9, and when each is 2 or greater, the substituents in parentheses are the same or different.

5. A heterocyclic compound according to claim 1, wherein Ar is an aryl group having 6 to 20 carbon atoms, which is unsubstituted or substituted with deuterium; or a heteroaryl group having 2 to 20 carbon atoms, which is unsubstituted or substituted with deuterium and contains O or S.

6. A heterocyclic compound according to claim 1, wherein R is hydrogen or deuterium.

7. A heterocyclic compound according to claim 1, wherein the deuterium substitution rate of the chemical formula 1 is 0% or 10% to 100%.

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

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

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

11. An organic light-emitting device according to claim 10, wherein the light-emitting layer comprises a host, and the host comprises at least one heterocyclic compound.

12. In claim 9, an organic light-emitting device wherein the organic layer including the heterocyclic compound further includes a compound of the following chemical formula 2: [Chemical formula 2] In the above chemical formula 2, L, L1 and L2 are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, R11 and R12 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or adjacent groups are combined to form a substituted or unsubstituted aromatic ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms, 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 or different.

13. In claim 12, an organic light-emitting device wherein the chemical formula 2 is selected from the following compounds:

14. A composition for an organic layer of an organic light-emitting device comprising a heterocyclic compound according to any one of claims 1 to 8.

15. In claim 14, A composition for an organic layer of an organic light-emitting device further comprising a compound of the following chemical formula 2: [Chemical formula 2] In the above chemical formula 2, L, L1 and L2 are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, R11 and R12 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or adjacent groups are combined to form a substituted or unsubstituted aromatic ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms, 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 or different.

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