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

Abstract

The present invention relates to a heterocyclic compound represented by chemical formula 1, an organic light-emitting device comprising same, and a composition for an organic layer.

Description

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

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

[0002]

[0003] Organic light-emitting diodes are a type of self-luminous display device that have the advantages of a wide viewing angle, excellent contrast, and 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]

[0008] [Previous literature]

[0009] [Patent Document]

[0010] (Patent Document 1) U.S. Patent No. 4,356,429

[0011]

[0012] The present invention provides a heterocyclic compound, an organic light-emitting device including the same, and a composition for an organic layer.

[0013]

[0014] To achieve the above purpose,

[0015] The present invention provides a heterocyclic compound represented by the following chemical formula 1.

[0016] [Chemical Formula 1]

[0017]

[0018] In the above chemical formula 1,

[0019] The above X1 and X2 are the same or different from each other, and are each independently O; or S,

[0020] wherein R1 to R9 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; And -NR101R102, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0021] The above a, e and g are the same as or different from each other, and are each independently an integer from 0 to 4, and when a is 2 or more, R1 is the same as or different from each other, when e is 2 or more, R7 is the same as or different from each other, and when g is 2 or more, R9 is the same as or different from each other,

[0022] The above b and c are equal to or different from each other, and are each independently an integer from 0 to 5, and when the above b is 2 or more, R4 are equal to or different from each other, and when the above c is 2 or more, R5 are equal to or different from each other,

[0023] The above d and f are the same as or different from each other, and are each independently an integer from 0 to 3. When the above d is 2 or more, R6 is the same as or different from each other, and when the above f is 2 or more, R8 is the same as or different from each other.

[0024]

[0025] In addition, the present invention comprises a first electrode;

[0026] A second electrode provided opposite to the first electrode; and

[0027] An organic light-emitting device comprising at least one organic layer provided between the first electrode and the second electrode,

[0028] An organic light-emitting device is provided, wherein at least one of the organic layers comprises a heterocyclic compound represented by the chemical formula 1.

[0029]

[0030] In addition, the present invention provides an organic light-emitting device in which the organic material layer further includes a heterocyclic compound represented by the following chemical formula 3.

[0031] [Chemical Formula 3]

[0032]

[0033] In the above chemical formula 3,

[0034] The above R21, R23 and R25 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; And -NR201R202, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R201, R202 and R203 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0035] The above j is an integer from 0 to 4, and when the above j is 2 or more, R21 are equal to or different from each other,

[0036] The above k is an integer from 0 to 3, and when the above k is 2 or more, R25 are equal to or different from each other,

[0037] The above R22 and R24 are different from each other and are represented by the following chemical formula 4 or chemical formula 5,

[0038] [Chemical Formula 4]

[0039]

[0040] [Chemical Formula 5]

[0041]

[0042] In the above chemical formulas 4 and 5,

[0043] The above L1 to L4 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0044] The above l is an integer from 0 to 5, and when the above l is 2 or more, L1 is equal to or different from each other,

[0045] The above m is an integer from 0 to 5, and when the above m is 2 or greater, L2 are equal to or different from each other,

[0046] The above n is an integer from 0 to 5, and when the above n is 2 or greater, L3 are equal to or different from each other,

[0047] The above o is an integer from 0 to 5, and when the above o is 2 or more, L4 are equal to or different from each other,

[0048] The above Ar1 to Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0049]

[0050] In addition, the present invention provides a composition for an organic layer comprising a heterocyclic compound represented by the above chemical formula 1 and a heterocyclic compound represented by the above chemical formula 3.

[0051]

[0052] The compound described herein can be used as an organic layer material of an organic light-emitting device. The compound can serve as a hole injection layer material, a hole transport layer material, a light-emitting layer material, an electron transport layer material, an electron injection layer material, etc. in the organic light-emitting device. In particular, the compound can be used as a light-emitting layer material of an organic light-emitting device, and the compound can be used alone as a light-emitting material, or can be used as a host material or dopant material of the light-emitting layer.

[0053] Specifically, the compound may be used alone as a light-emitting material, or as a host material or dopant material in a light-emitting layer. When the heterocyclic compound represented by the above chemical formula 1 is used in an organic layer, the driving voltage of the organic light-emitting device can be lowered, the light-emitting efficiency can be improved, and the lifespan characteristics can be improved.

[0054]

[0055] Figures 1 to 3 are schematic drawings each showing a laminated structure of an organic light-emitting device according to one embodiment of the present invention.

[0056]

[0057] Hereinafter, the present invention will be described in more detail.

[0058]

[0059] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where a hydrogen atom is 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.

[0060] In this specification, "substituted or unsubstituted" means deuterium; halogen; cyano group; straight or branched chain alkyl group having 1 to 60 carbon atoms; straight or branched chain alkenyl group having 2 to 60 carbon atoms; straight or branched chain alkynyl group having 2 to 60 carbon atoms; monocyclic or polycyclic cycloalkyl group having 3 to 60 carbon atoms; monocyclic or polycyclic heterocycloalkyl group having 2 to 60 carbon atoms; monocyclic or polycyclic aryl group having 6 to 60 carbon atoms; monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms; -SiRR'R"; -P(=O)RR'; means a group consisting of a C1 to C20 alkylamine group; a C6 to C60 monocyclic or polycyclic arylamine group; and a C2 to C60 monocyclic or polycyclic heteroarylamine group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of a C1 to C20 alkylamine group; a C6 to C60 monocyclic or polycyclic arylamine group; and a C2 to C60 monocyclic or polycyclic heteroarylamine group, or is unsubstituted or substituted with a substituent in which two or more substituents selected from the above-mentioned substituents are connected, and the R, R' or R" may be a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0061] In this specification, halogen may be fluorine, chlorine, bromine or iodine.

[0062] 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 a methyl group; an ethyl group; an n-propyl group; an isopropyl group; an n-butyl group; an isobutyl group; a tert-butyl group; a sec-butyl group; a 1-methyl-butyl group; a 1-ethyl-butyl group; an n-pentyl group; an isopentyl group; a neopentyl group; a tert-pentyl group; an n-hexyl group; a 1-methylpentyl group; a 2-methylpentyl group; a 4-methyl-2-pentyl group; a 3,3-dimethylbutyl group; a 2-ethylbutyl group; a n-heptyl group; a 1-methylhexyl group; a cyclopentylmethyl group; a cyclohexylmethyl group; n-octyl group; tert-octyl group; 1-methylheptyl group; 2-ethylhexyl group; 2-propylpentyl group; n-nonyl group; 2,2-dimethylheptyl group; 1-ethyl-propyl group; 1,1-dimethyl-propyl group; isohexyl group; 4-methylhexyl group; 5-methylhexyl group, etc., but are not limited thereto.

[0063] In the present specification, an 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 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; 2,2-bis(diphenyl-1-yl)vinyl-1-yl group; stilbenyl group; styrenyl group, etc., but are not limited thereto.

[0064] 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.

[0065] In the present specification, the alkoxy group may be linear, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, examples thereof include, but are not limited to, a methoxy group; an ethoxy group; an n-propoxy group; an isopropoxy group; an n-butoxy group; an isobutoxy group; a tert-butoxy group; a sec-butoxy group; an n-pentyloxy group; a neopentyloxy group; an isopentyloxy group; an n-hexyloxy group; a 3,3-dimethylbutyloxy group; a 2-ethylbutyloxy group; an n-octyloxy group; an n-nonyloxy group; an n-decyloxy group; a benzyloxy group; and a p-methylbenzyloxy group.

[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; for example, 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, 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; 4-tert-butylcyclohexyl group; cycloheptyl group; cyclooctyl group, etc., but are not limited thereto.

[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; for example, 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; for example, a cycloalkyl group; a heterocycloalkyl group; a heteroaryl group, etc. The aryl group may include a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 20 carbon atoms. Specific examples of the aryl group include a phenyl group; a biphenyl group; a triphenyl group; a naphthyl group; 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; Acenaphthylenyl group; benzofluorenyl group; spirobifluorenyl group; 2,3-dihydro-1H-indenyl group; and condensed ring groups thereof, but are not limited thereto.

[0069] In the present specification, the phosphine oxide group may be a substituent represented by -P(=O)R101R102, wherein R101 and R102 are the same as or different from each other, and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 monocyclic or polycyclic cycloalkyl group; a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl group; and a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heteroaryl group. Specifically, the phosphine oxide group may be substituted with a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl group, and the above-described examples may be applied to the aryl group. For example, the phosphine oxide group may be a diphenylphosphine oxide group; Examples include, but are not limited to, dinaphthylphosphine oxide groups.

[0070] In the present specification, a silyl group is a substituent containing Si and directly connecting the Si atom as a radical, and is represented by -SiR101R102R103, wherein R101 to R103 are the same as or different from each other, and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 monocyclic or polycyclic cycloalkyl group; a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl group; and a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heterocyclic group. Specific examples of the silyl group include a trimethylsilyl group; a triethylsilyl group; a t-butyldimethylsilyl group; a vinyldimethylsilyl group; Examples thereof include, but are not limited to, propyldimethylsilyl group; triphenylsilyl group; diphenylsilyl group; and phenylsilyl group.

[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, It can be, but is not limited to, the following.

[0073] In the present specification, a spiro group is a group including a spiro structure and may have 15 to 60 carbon atoms. For example, the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro-bonded to a fluorenyl group. Specifically, the following spiro group may include any one of the groups having the following structural formula.

[0074]

[0075] In the present specification, a heteroaryl group includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms and a heteroatom selected from S, O, Se, N or Si, 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, for example, 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 pyridyl group; a pyrrolyl group; a pyrimidyl group; a pyridazinyl group; a furanyl group; a thiophenyl group; an imidazolyl group; a pyrazolyl group; an oxazolyl group; an isoxazolyl group; a thiazolyl group; an isothiazolyl group; a triazolyl group; a furazanyl group; an oxadiazolyl group; a thiadiazolyl group; a dithiazolyl group; a tetrazolyl group; a pyranyl group; a thiopyranyl group; a diazinyl group; an oxazinyl group; a thiazinyl group; a dioxynyl group; a triazinyl group; a tetrazinyl group; a quinolyl group; an isoquinolyl group; a quinazolinyl group; an isoquinazolinyl group; a quinozolinyl group; a naphthyridyl group; an acridinyl group; a phenanthridinyl group; an imidazopyridinyl group; a diazanaphthalenyl group; Triazaindenyl group; 2-indolyl group; indolizinyl group; benzothiazolyl group; benzoxazolyl group; benzimidazolyl group; benzothiophenyl group; benzofuranyl group; dibenzothiophenyl group; dibenzofuranyl group; carbazolyl group; benzocarbazolyl group; dibenzocarbazolyl group; phenazinyl group; dibenzosilole group; spirobi(dibenzosilole) group; dihydrophenazinyl group; phenoxazinyl group; phenanthridyl group; thienyl group; indolo[2,3-a]carbazolyl group; indolo[2,3-b]carbazolyl group; indolinyl group; 10,11-dihydro-dibenzo[b,f]azepinyl group; 9,10-dihydroacridinyl group; phenanthrazinyl group; phenothiazinyl group; Examples thereof include, but are not limited to, a phthalazinyl group; a naphthyridinyl group; a phenanthrolinyl group; a benzo[c][1,2,5]thiadiazolyl group; a 5,10-dihydrodibenzo[b,e][1,4]azacylinyl group; a pyrazolo[1,5-c]quinazolinyl group; a pyrido[1,2-b]indazolyl group; a pyrido[1,2-a]imidazo[1,2-e]indolinyl group; and a 5,11-dihydroindeno[1,2-b]carbazolyl group.

[0076] In the present specification, the amine group may be selected from the group consisting of a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; -NH2; a dialkylamine group; a diarylamine group; a diheteroarylamine group; an alkylarylamine group; an alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group; a dimethylamine group; an ethylamine group; a diethylamine group; a phenylamine group; a naphthylamine group; a biphenylamine group; a dibiphenylamine group; 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; Biphenyltriphenylenylamine groups, etc. are included, but are not limited thereto.

[0077] In this specification, an arylene group means a group having two bonding positions to an aryl group, i.e., a divalent group. The description of the aryl group described above may be applied to these groups, except that each group is divalent. In addition, a heteroarylene group means a group having two bonding positions to a heteroaryl group, i.e., a divalent group. The description of the heteroaryl group described above may be applied to these groups, except that each group is divalent.

[0078] As used herein, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent sterically closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

[0079] In the present invention, "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 ( 2Since H, Deuterium (D)) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0080] In one embodiment of the present invention, "when no substituent is indicated in the chemical formula or compound structure" may mean that all positions that can be substituted are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the deuterium content may be 0% to 100%.

[0081] In one embodiment of the present invention, in cases where “no substituent is indicated in the chemical formula or compound structure,” hydrogen and deuterium may be used in combination in the compound, unless deuterium is explicitly excluded, such as “the content of deuterium is 0%,” “the content of hydrogen is 100%,” or “all substituents are hydrogen.”

[0082] In one embodiment of the present invention, 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. -2 It can be expressed as , and the element symbol is D or 2 It can also be written as H.

[0083] In one embodiment of the present invention, 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.

[0084] In one embodiment of the present invention, the meaning of the content 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.

[0085] That is, in one example, In the phenyl group represented by , the content of deuterium of 20% can mean that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and among them, the number of deuterium is 1 (T2 in the formula). That is, the content of deuterium of 20% in the phenyl group can be expressed by the structural formula below.

[0086]

[0087]

[0088] Additionally, in one embodiment of the present invention, the term “phenyl group having a deuterium content of 0%” may mean a phenyl group that does not contain deuterium atoms, i.e., has 5 hydrogen atoms.

[0089] In the present invention, the C6 to C60 aromatic hydrocarbon ring means a compound including an aromatic ring composed of C6 to C60 carbons and hydrogen, and examples thereof include, but are not limited to, phenyl, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, etc., and includes all aromatic hydrocarbon ring compounds known in the art that satisfy the above carbon number.

[0090]

[0091] The present invention provides a heterocyclic compound represented by the following chemical formula 1.

[0092] [Chemical Formula 1]

[0093]

[0094] In the above chemical formula 1,

[0095] The above X1 and X2 are the same or different from each other, and are each independently O; or S,

[0096] wherein R1 to R9 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; And -NR101R102, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0097] The above a, e and g are the same as or different from each other, and are each independently an integer from 0 to 4, and when a is 2 or more, R1 is the same as or different from each other, when e is 2 or more, R7 is the same as or different from each other, and when g is 2 or more, R9 is the same as or different from each other,

[0098] The above b and c are equal to or different from each other, and are each independently an integer from 0 to 5, and when the above b is 2 or more, R4 are equal to or different from each other, and when the above c is 2 or more, R5 are equal to or different from each other,

[0099] The above d and f are the same as or different from each other, and are each independently an integer from 0 to 3. When the above d is 2 or more, R6 is the same as or different from each other, and when the above f is 2 or more, R8 is the same as or different from each other.

[0100]

[0101] In one embodiment of the present invention, X1 may be O and X2 may be O.

[0102] In another embodiment of the present invention, X1 may be O and X2 may be S.

[0103] In another embodiment of the present invention, X1 may be S and X2 may be O.

[0104] In another embodiment of the present invention, X1 may be S and X2 may be S.

[0105]

[0106] In one embodiment of the present invention, R1 to R9 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; Or -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0107] In another embodiment of the present invention, R1 to R9 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; Or -NR101R102, or two or more adjacent groups combine with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0108] In another embodiment of the present invention, R1 to R9 may be the same as or different from each other, and each independently be hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0109] In another embodiment of the present invention, R1 to R9 may be the same as or different from each other, and each independently be hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C6 to C20 aryl group; or substituted or unsubstituted C2 to C20 heteroaryl group.

[0110] In another embodiment of the present invention, R1 to R9 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0111] In another embodiment of the present invention, at least one of R1 to R9 may contain deuterium, and at least one of R1 to R9 may contain non-deuterated hydrogen.

[0112] In another embodiment of the present invention, R1 to R9 may be hydrogen.

[0113] In another embodiment of the present invention, R1 to R9 may be deuterium.

[0114]

[0115] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1 may be represented by either the following chemical formula 1-1 or chemical formula 1-2.

[0116] [Chemical Formula 1-1]

[0117]

[0118] [Chemical Formula 1-2]

[0119]

[0120] In the above chemical formulas 1-1 and 1-2,

[0121] The above h is an integer from 0 to 2, and when the above h is 2 or greater, R6 are the same or different from each other,

[0122] The above i is an integer from 0 to 3, and when the above i is 2 or greater, R7 are equal to or different from each other,

[0123] The above X1, X2, R1 to R9 and a to g are the same as defined in the above chemical formula 1.

[0124]

[0125] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1-1 may be represented by either the following chemical formula 1-1a or chemical formula 1-1b.

[0126] [Chemical Formula 1-1a]

[0127]

[0128] [Chemical Formula 1-1b]

[0129]

[0130] In the above chemical formulas 1-1a and 1-1b,

[0131] The above X1, X2, R1 to R9, a to c, e, f and g are the same as the definitions in the above chemical formula 1,

[0132] The above h is the same as the definition in the above chemical formula 1-1.

[0133]

[0134] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1-2 may be represented by either the following chemical formula 1-2a or chemical formula 1-2b.

[0135] [Chemical Formula 1-2a]

[0136]

[0137] [Chemical Formula 1-2b]

[0138]

[0139] In the above chemical formulas 1-2a and 1-2b,

[0140] The above X1, X2, R1 to R9, a to d, f and g are the same as the definitions in the above chemical formula 1,

[0141] The above i is the same as the definition in the above chemical formula 1-2.

[0142]

[0143] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1-1 may be represented by either the following chemical formula 1-1-1 or chemical formula 1-1-2.

[0144] [Chemical Formula 1-1-1]

[0145]

[0146] [Chemical Formula 1-1-2]

[0147]

[0148] In the above chemical formulas 1-1-1 and 1-1-2,

[0149] The above R11 to R14 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; And -NR101R102, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0150] The above X1, X2, R1 to R5, R7 to R9, a to c and e to g are the same as defined in the above chemical formula 1.

[0151]

[0152] In one embodiment of the present invention, R11 to R14 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; Or -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0153] In another embodiment of the present invention, R11 to R14 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; Or -NR101R102, or two or more adjacent groups combine with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0154] In another embodiment of the present invention, R11 to R14 may be the same as or different from each other, and each independently be hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0155] In another embodiment of the present invention, R11 to R14 may be the same as or different from each other, and may each independently be hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C6 to C20 aryl group; or substituted or unsubstituted C2 to C20 heteroaryl group.

[0156] In another embodiment of the present invention, R11 to R14 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0157] In another embodiment of the present invention, one of R11 and R12 may contain deuterium, and the other of R11 and R12 may contain non-deuterated hydrogen.

[0158] In another embodiment of the present invention, R11 and R12 may be hydrogen.

[0159] In another embodiment of the present invention, R11 and R12 may be deuterium.

[0160] In another embodiment of the present invention, one of R13 and R14 may contain deuterium, and the other of R13 and R14 may contain non-deuterated hydrogen.

[0161] In another embodiment of the present invention, R13 and R14 may be hydrogen.

[0162] In another embodiment of the present invention, R13 and R14 may be deuterium.

[0163]

[0164] In one embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be, for example, more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0165] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0166] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0167] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0168] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0169]

[0170] In one embodiment of the present invention, the chemical formula 1 may be represented by any one of the following compounds.

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201] In addition, by introducing various substituents into the structure of the above chemical formula 1, compounds having 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, electron blocking 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.

[0202] 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.

[0203] Meanwhile, the heterocyclic compound exhibits excellent thermal stability due to its high glass transition temperature (Tg). This increased thermal stability is an important factor in providing operating stability to the device.

[0204] The heterocyclic compound according to one embodiment of the present invention can be prepared through a multi-step chemical reaction. Some intermediate compounds are prepared first, and then the compound of formula 1 can be prepared from these intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of the present invention can be prepared based on the preparation example described below.

[0205]

[0206] Another embodiment of the present invention provides an organic light-emitting device comprising a heterocyclic compound represented by the above chemical formula 1. The “organic light-emitting device” may be expressed by terms such as “organic light-emitting diode”, “OLED (Organic Light Emitting Diodes)”, “OLED device”, and “organic electroluminescent device”.

[0207]

[0208] In addition, the present invention

[0209] First electrode;

[0210] A second electrode provided opposite to the first electrode; and

[0211] An organic light-emitting device comprising at least one organic layer provided between the first electrode and the second electrode,

[0212] The present invention relates to an organic light-emitting device, wherein at least one of the organic layers comprises a heterocyclic compound represented by the chemical formula 1.

[0213]

[0214] In one embodiment of the present invention, the first electrode may be an anode, and the second electrode may be a cathode.

[0215] In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0216]

[0217] In one embodiment of the present invention, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material for the red organic light-emitting material.

[0218] In another embodiment of the present invention, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material for the blue organic light-emitting material.

[0219] In another embodiment of the present invention, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material for the green organic light-emitting material.

[0220]

[0221] In one embodiment of the present invention, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a light-emitting layer material of the red organic light-emitting device.

[0222] In another embodiment of the present invention, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a light-emitting layer material of the blue organic light-emitting device.

[0223] In another embodiment of the present invention, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a light-emitting layer material of the green organic light-emitting device.

[0224]

[0225] The specific details of the heterocyclic compound represented by the above chemical formula 1 are the same as described above.

[0226]

[0227] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described heterocyclic compound.

[0228] The above heterocyclic compound can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0229] 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 multilayer 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, an electron blocking layer, a hole transport layer, a light-emitting layer, an electron transport layer, a hole blocking 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.

[0230]

[0231] In the organic light-emitting device of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by the chemical formula 1. When the heterocyclic compound is used in the light-emitting layer, the HOMO (Highest Occupied Molecular Orbital) and the LUMO (Lowest Unoccupied Molecular Orbital) are spatially separated, thereby enabling strong charge transfer, and thus the operating efficiency and lifespan of the organic light-emitting device may be improved.

[0232]

[0233] In an organic light-emitting device according to one embodiment of the present invention, an organic material layer including a heterocyclic compound represented by the above chemical formula 1 further includes a heterocyclic compound represented by the following chemical formula 3.

[0234] [Chemical Formula 3]

[0235]

[0236] In the above chemical formula 3,

[0237] The above R21, R23 and R25 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; And -NR201R202, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R201, R202 and R203 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0238] The above j is an integer from 0 to 4, and when the above j is 2 or more, R21 are equal to or different from each other,

[0239] The above k is an integer from 0 to 3, and when the above k is 2 or more, R25 are equal to or different from each other,

[0240] The above R22 and R24 are different from each other and are represented by the following chemical formula 4 or chemical formula 5,

[0241] [Chemical Formula 4]

[0242]

[0243] [Chemical Formula 5]

[0244]

[0245] In the above chemical formulas 4 and 5,

[0246] The above L1 to L4 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0247] The above l is an integer from 0 to 5, and when the above l is 2 or more, L1 is equal to or different from each other,

[0248] The above m is an integer from 0 to 5, and when the above m is 2 or greater, L2 are equal to or different from each other,

[0249] The above n is an integer from 0 to 5, and when the above n is 2 or greater, L3 are equal to or different from each other,

[0250] The above o is an integer from 0 to 5, and when the above o is 2 or more, L4 are equal to or different from each other,

[0251] The above Ar1 to Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0252]

[0253] In one embodiment of the present invention, R21, R23 and R25 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R202R202; -SiR201R202R203; Or -NR201R202, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocycle, wherein R201, R202 and R203 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0254] In another embodiment of the present invention, R21, R23 and R25 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; Or -NR201R202, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 heterocycle, wherein R201, R202 and R203 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0255] In another embodiment of the present invention, R21, R23 and R25 may be the same as or different from each other, and each independently be hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0256] In another embodiment of the present invention, R21, R23 and R25 may be the same as or different from each other, and each independently be hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0257] In another embodiment of the present invention, R21, R23 and R25 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0258]

[0259] In one embodiment of the present invention, R22 may be the chemical formula 4, and R24 may be the chemical formula 5.

[0260] In another embodiment of the present invention, R22 may be the chemical formula 5, and R24 may be the chemical formula 4.

[0261]

[0262] In one embodiment of the present invention, L1 to L4 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0263] In another embodiment of the present invention, L1 to L4 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0264] In another embodiment of the present invention, L1 may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0265] In another embodiment of the present invention, L2 and L3 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0266] In another embodiment of the present invention, L4 may be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0267]

[0268] In one embodiment of the present invention, Ar1 to Ar3 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0269] In another embodiment of the present invention, Ar1 to Ar3 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0270] In another embodiment of the present invention, Ar1 and Ar2 may be the same as or different from each other, and 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 fluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0271] The substituent of the above substituted fluorenyl group may be a methyl group or a phenyl group.

[0272] In another embodiment of the present invention, Ar3 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted carbazolyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0273] The substituent of the above substituted fluorenyl group may be a methyl group, and the substituent of the above substituted carbazolyl group may be deuterium; or a phenyl group.

[0274]

[0275] In one embodiment of the present invention, R21 to R25, L1 to L4 and Ar1 to Ar3 may all include non-deuterated hydrogen (H).

[0276] In another embodiment of the present invention, at least one of R21 to R25, L1 to L4 and Ar1 to Ar3 may contain deuterium (D), and at least one of R21 to R25, L1 to L4 and Ar1 to Ar3 may contain non-deuterated hydrogen.

[0277] In another embodiment of the present invention, R21 to R25, L1 to L4 and Ar1 to Ar3 may all contain deuterium.

[0278]

[0279] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 3 may be represented by either the following chemical formula 3-1 or chemical formula 3-2.

[0280] [Chemical Formula 3-1]

[0281]

[0282] [Chemical Formula 3-2]

[0283]

[0284] In the above chemical formulas 3-1 and 3-2,

[0285] The above R21, R23, R25, j and k are the same as the definitions in the above chemical formula 3,

[0286] The above L1 to L3, Ar1, Ar2 and l to n are the same as the definitions in the above chemical formula 4,

[0287] The above L4, Ar3 and o are the same as defined in the above chemical formula 5.

[0288]

[0289] In one embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be, for example, more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0290] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0291] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0292] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0293] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0294]

[0295] When the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 are simultaneously included, superior efficiency and lifespan effects are exhibited. From this, it can be expected that an exciplex phenomenon will occur when the two compounds are simultaneously included.

[0296] The above exciplex phenomenon is a phenomenon in which energy of the size of the HOMO energy level of the donor (p-host) and the LUMO energy level of the acceptor (n-host) is released due to electron exchange between two molecules. When the exciplex phenomenon between two molecules occurs, reverse intersystem crossing (RISC) occurs, and this can increase the internal quantum efficiency of fluorescence up to 100%. When a donor (p-host) with a good hole transport ability and an acceptor (n-host) with a good electron transport ability are used as the host of the light-emitting layer, holes are injected into the p-host and electrons are injected into the n-host, so the driving voltage can be lowered, which can help improve the lifespan. That is, when the compound represented by the above chemical formula 3 is used as the donor and the compound represented by the above chemical formula 1 is used as the acceptor, excellent device characteristics are exhibited.

[0297]

[0298] In one embodiment of the present invention, when the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 are simultaneously included, at least one of the compounds may not include deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0299] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0300] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0301] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0302] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0303]

[0304] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 3 may be at least one selected from the following compounds.

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326] In addition, one embodiment of the present invention provides a composition for an organic layer comprising a heterocyclic compound represented by the above chemical formula 1 and a heterocyclic compound represented by the above chemical formula 3.

[0327] The specific details of the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 are the same as described above.

[0328]

[0329] In one embodiment of the present invention, the weight ratio of the heterocyclic compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 3 in the composition for the organic layer may be 1:9 to 9:1, 1:9 to 5:5, or 2:8 to 5:5, but is not limited thereto.

[0330]

[0331] The above composition for an organic layer can be used when forming an organic material of an organic light-emitting device, and in particular, can be more preferably used when forming a host for a light-emitting layer.

[0332]

[0333] In one embodiment of the present invention, the organic layer includes a heterocyclic compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 3, and can be used together with a phosphorescent dopant.

[0334] As the above phosphorescent dopant material, those known in the art can be used. For example, phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L2MX', and L3M can be used, but the scope of the present invention is not limited by these examples.

[0335] The above M can be iridium, platinum, osmium, etc.

[0336] The above L is sp 2An anionic two-dentate ligand coordinated to M by carbon and heteroatoms, and X can perform the function of trapping electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, phenylpyridine, benzothiophenylpyridine, 3-methoxy-2-phenylpyridine, thiophenylpyridine, tolylpyridine, etc. Non-limiting examples of X' and X" include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, etc.

[0337] Specific examples of the above phosphorescent dopants are shown below, but are not limited to these examples.

[0338]

[0339]

[0340] In one embodiment of the present invention, the organic layer includes a heterocyclic compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 3, and can be used together with an iridium-based dopant.

[0341]

[0342] In one embodiment of the present invention, the iridium-based dopant may be (piq)2(Ir)(acac) as a red phosphorescent dopant or Ir(ppy)3 as a green phosphorescent dopant.

[0343]

[0344] In one embodiment of the present invention, the content of the dopant may be 1% to 15%, preferably 2% to 10%, and more preferably 3% to 7% based on the total weight of the light-emitting layer.

[0345]

[0346] In an organic light-emitting device according to one embodiment of the present invention, the organic layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include a heterocyclic compound represented by the chemical formula 1.

[0347] In an organic light-emitting device according to another embodiment of the present invention, the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include a heterocyclic compound represented by the chemical formula 1.

[0348] In an organic light-emitting device according to another embodiment, the organic layer includes an electron transport layer, a light-emitting layer, or a hole blocking layer, and the electron transport layer, light-emitting layer, or hole blocking layer may include a heterocyclic compound represented by the chemical formula 1.

[0349] In an organic light-emitting device according to another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by the chemical formula 1.

[0350] In an organic light-emitting device according to another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 3.

[0351] In an organic light-emitting device according to another embodiment, the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material may include a heterocyclic compound represented by the chemical formula 1.

[0352] In an organic light-emitting device according to another embodiment, the light-emitting layer may include two or more host materials, at least one of the host materials may include a heterocyclic compound represented by the chemical formula 1, and the other may include a heterocyclic compound represented by the chemical formula 3.

[0353] In an organic light-emitting device according to another embodiment, the light-emitting layer may be used by pre-mixing two or more host materials, and at least one of the two or more host materials may include a heterocyclic compound represented by the chemical formula 1, and the other may include a heterocyclic compound represented by the chemical formula 3.

[0354] The above pre-mixed means that the light-emitting layer is mixed by first mixing the materials and storing them in one supply source before depositing two or more host materials on the organic layer.

[0355]

[0356] An organic light-emitting device according to one embodiment of the present invention may further include one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0357]

[0358] The stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present invention is illustrated in FIGS. 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.

[0359] 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.

[0360] 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.

[0361]

[0362] In one embodiment of the present invention,

[0363] Steps to prepare the substrate;

[0364] A step of forming a first electrode on the substrate;

[0365] A step of forming one or more organic layers on the first electrode; and

[0366] A method for manufacturing an organic light-emitting device, comprising: forming a second electrode on the organic layer of one or more layers; wherein the step of forming the organic layer of one or more layers includes forming the organic layer of one or more layers using a composition for an organic layer according to one embodiment of the present invention.

[0367]

[0368] In one embodiment of the present invention, the step of forming the organic layer may be to pre-mix the heterocyclic compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 3, and form the organic layer using a thermal vacuum deposition method.

[0369] The above pre-mixed means that the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 are mixed in one supply source before being deposited on the organic layer.

[0370] The pre-mixed material may be referred to as a composition for an organic layer according to one embodiment of the present application.

[0371] The organic layer including the heterocyclic compound represented by the above chemical formula 1 may additionally include other substances as needed.

[0372] The organic layer containing both the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 may additionally contain other substances as needed.

[0373]

[0374] In the organic light-emitting device according to one embodiment of the present invention, materials other than the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 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.

[0375]

[0376] 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.

[0377]

[0378] 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.

[0379]

[0380] As the hole injection layer material, a known hole injection layer 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"-tris[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.

[0381]

[0382] Pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used as hole transport layer materials, and low molecular weight or high molecular weight materials can also be used.

[0383]

[0384] As the electron transport layer 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.

[0385]

[0386] For example, LiF is typically used as an electron injection layer material in the art, but the present application is not limited thereto.

[0387]

[0388] Red, green, or blue light-emitting materials can be used as the light-emitting layer material, and if necessary, two or more light-emitting materials can be mixed and used. At this time, two or more light-emitting materials can be deposited and used as individual sources, or can be pre-mixed and deposited and used as a single source. In addition, a fluorescent material can be used as the light-emitting layer material, but a phosphorescent material can also be used. A material that emits light by combining holes and electrons injected from the anode and cathode, respectively, can be used as the light-emitting layer material, but materials in which both the host material and the dopant material participate in light emission can also be used.

[0389]

[0390] When using a mixture of host materials for the light-emitting layer, 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 material for the light-emitting layer.

[0391]

[0392] An organic light-emitting device according to one embodiment of the present invention may be a front-emitting, back-emitting, or double-sided emitting device depending on the material used.

[0393]

[0394] The heterocyclic compound according to one embodiment of the present invention can function in organic electronic devices, including organic solar cells, organic photoconductors, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.

[0395]

[0396] Hereinafter, preferred examples are presented to help understand the present invention, but the following examples are provided only to make it easier to understand the present invention and the present invention is not limited thereto.

[0397]

[0398] <Manufacturing Example>

[0399] Manufacturing Example 1. Preparation of Compound A

[0400]

[0401]

[0402] Manufacturing Example 1-1. Preparation of Compound 1-A

[0403] 50.0 g (177.6 mM) of 1-bromo-3-chlorodibenzo[b,d]furan, 67.6 g (266.4 mM) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 6.5 g (8.9 mM) of PdCl2(dppf), and 43.6 g (444.0 mM) of KOAc were dissolved in 500 mL of 1,4-dioxane, and the mixture was refluxed for 3 hours.

[0404] The reaction product was purified by column chromatography (dichloromethane:hexane = 1:1 (volume ratio)) to obtain 47.9 g (82.1%) of the target compound 1-A.

[0405]

[0406] Manufacturing Example 1-2. Preparation of Compound A

[0407] Compound 1-A 40.0 g (121.7 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine 32.6 g (121.7 mM), Pd(PPh3) 47.0 g (6.1 mM), and K2CO- 42.1 g (304.3 mM) were dissolved in 600 mL of 1,4-dioxane and 120 mL of distilled water (H2O), and stirred for 6 hours.

[0408] Afterwards, 47.5 g (90.0%) of target compound A was obtained by vacuum filtration.

[0409]

[0410] In the above Manufacturing Example 1, the target compound of Table 1 was synthesized by the same method as Manufacturing Example 1, except that Intermediate A of Table 1 below was used instead of the 1-bromo-3-chlorodibenzo[b,d]furan.

[0411]

[0412]

[0413]

[0414]

[0415] Manufacturing Example 2. Preparation of Compound 1-1

[0416]

[0417]

[0418] Manufacturing Example 2-1. Manufacturing of Compound 1-2-1

[0419] 30.0 g (106.6 mM) of 3-bromo-1-chlorodibenzo[b,d]furan, 22.6 g (106.6 mM) of dibenzo[b,d]furan-1-ylboronic acid, 46.1 g (5.3 mM) of Pd(PPh3), and 36.8 g (266.5 mM) of K2CO3 were dissolved in 300 mL of 1,4-dioxane and 60 mL of distilled water (H2O), and then stirred for 6 hours.

[0420] Afterwards, filtration under reduced pressure was performed to obtain 33.7 g (85.7%) of the target compound 1-2-1.

[0421]

[0422] Manufacturing Example 2-2. Preparation of Compound 1-1-1

[0423] Compound 1-2-1 33.0 g (89.5 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 34.1 g (134.3 mM), Pd2dba 34.1 g (4.5 mM), Xphos 4.3 g (9.0 mM), and KOAc 17.6 g (179.0 mM) were dissolved in 400 mL of 1,4-Dioxane and refluxed for 3 hours.

[0424] The reactant was purified by column chromatography (dichloromethane:hexane = 1:1 (volume ratio)) to obtain 26.5 g (82.1%) of the target compound 1-1-1.

[0425]

[0426] Manufacturing Example 2-3. Manufacturing of Compound 1-1

[0427] Compound 1-1-1 15.0 g (41.6 mM), compound A 18.0 g (41.6 mM) prepared in the above Preparation Example 1, Pd(dba) 21.2 g (2.1 mM), Xphos 2.0 g (4.2 mM), and NaOH 3.3 g (83.2 mM) were dissolved in 300 mL of 1,4-dioxane and 60 mL of distilled water (H2O), and stirred for 6 hours.

[0428] Afterwards, 25.5 g (83.7%) of target compound 1-1 was obtained by vacuum filtration.

[0429]

[0430] In the above Manufacturing Example 2, the target compound of Table 2 was synthesized in the same manner as Manufacturing Example 2, except that Intermediate B of Table 2 below was used instead of 1-bromo-3-chlorodibenzo[b,d]furan, Intermediate C of Table 2 below was used instead of dibenzo[b,d]furan-1-ylboronic acid, and Intermediate D of Table 2 below was used instead of compound A.

[0431]

[0432] [Correction pursuant to Rule 91, September 30, 2024]

[0433] [Correction pursuant to Rule 91, September 30, 2024]

[0434] [Correction pursuant to Rule 91, September 30, 2024]

[0435] [Correction pursuant to Rule 91, September 30, 2024]

[0436] [Correction pursuant to Rule 91, September 30, 2024]

[0437] [Correction pursuant to Rule 91, September 30, 2024]

[0438] [Correction pursuant to Rule 91, September 30, 2024]

[0439] [Correction pursuant to Rule 91, September 30, 2024]

[0440] [Correction pursuant to Rule 91, September 30, 2024]

[0441] [Correction pursuant to Rule 91, September 30, 2024]

[0442] [Correction pursuant to Rule 91, September 30, 2024]

[0443] [Correction pursuant to Rule 91, September 30, 2024]

[0444] [Correction pursuant to Rule 91, September 30, 2024]

[0445] [Correction pursuant to Rule 91, September 30, 2024]

[0446] [Correction pursuant to Rule 91, September 30, 2024]

[0447] [Correction pursuant to Rule 91, September 30, 2024]

[0448] [Correction pursuant to Rule 91, September 30, 2024]

[0449] [Correction pursuant to Rule 91, September 30, 2024]

[0450] [Correction pursuant to Rule 91, September 30, 2024]

[0451] [Correction pursuant to Rule 91, September 30, 2024]

[0452] [Correction pursuant to Rule 91, September 30, 2024]

[0453] [Correction pursuant to Rule 91, September 30, 2024]

[0454] [Correction pursuant to Rule 91, September 30, 2024]

[0455] [Correction pursuant to Rule 91, September 30, 2024]

[0456] [Correction pursuant to Rule 91, September 30, 2024]

[0457] [Correction pursuant to Rule 91, September 30, 2024]

[0458] [Correction pursuant to Rule 91, September 30, 2024]

[0459] [Correction pursuant to Rule 91, September 30, 2024]

[0460] [Correction pursuant to Rule 91, September 30, 2024]

[0461] [Correction pursuant to Rule 91, September 30, 2024]

[0462] [Correction pursuant to Rule 91, September 30, 2024]

[0463] [Correction pursuant to Rule 91, September 30, 2024]

[0464] [Correction pursuant to Rule 91, September 30, 2024]

[0465]

[0466] Manufacturing Example 3. Preparation of Compound E

[0467]

[0468] 30.0 g (121.4 mM) of 1-bromo-3-chlorodibenzo[b,d]furan was dissolved in 300 mL of d6-benzene, and 67.4 mL (724.9 mM) of triflic acid was slowly added, followed by refluxing for 1 hour.

[0469] After completion of the reaction, the product was purified by recrystallization from methanol, and 29.2 g (95.2%) of the target compound E was obtained.

[0470]

[0471] In the above Manufacturing Example 3, the target compound of Table 3 was synthesized by the same method as Manufacturing Example 3, except that Intermediate E of Table 3 below was used instead of the 1-bromo-3-chlorodibenzo[b,d]furan.

[0472]

[0473]

[0474]

[0475] Manufacturing Example 4. Preparation of Compound 1-493

[0476]

[0477] After dissolving 10.0 g (13.7 mM) of compound 1-1 in 100 mL of d6-benzene, 4.8 mL (54.8 mM) of triflic acid was slowly added and refluxed for 40 minutes.

[0478] After completion of the reaction, the product was purified by recrystallization from methanol, and 9.5 g (93.4%) of the target compound 1-493 was obtained.

[0479]

[0480] Manufacturing Example 5. Preparation of Compound 1-494

[0481]

[0482] After dissolving 10.0 g (13.7 mM) of compound 1-1 in 100 mL of d6-benzene, 6.4 mL (68.5 mM) of triflic acid was slowly added and the mixture was refluxed for 1 hour.

[0483] After completion of the reaction, the product was purified by recrystallization from methanol, and 9.7 g (94.2%) of the target compound 1-494 was obtained.

[0484]

[0485] In the above Manufacturing Examples 4 and 5, the target compound of Table 4 was synthesized by the same method as in Manufacturing Examples 4 and 5, except that the intermediate F of Table 4 below was used instead of the compound 1-1.

[0486]

[0487]

[0488]

[0489]

[0490]

[0491]

[0492]

[0493]

[0494]

[0495] Manufacturing Example 6. Preparation of Compound D

[0496]

[0497] Manufacturing Example 6-1. Preparation of Compound 1-D

[0498] 30.0 g (121.4 mM) of 1-bromodibenzo[b,d]furan was dissolved in 300 mL of d6-benzene, and 89.4 mL (961.5 mM) of triflic acid was slowly added, followed by refluxing for 1 hour.

[0499] After completion of the reaction, the product was purified by recrystallization from methanol, and 29.4 g (95.3%) of the target compound 1-D was obtained.

[0500]

[0501] Manufacturing Example 6-2. Preparation of Compound D

[0502] Compound 1-D 29.0 g (111.4 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 42.4 g (167.1 mM), PdCl2(dppf) 4.1 g (5.6 mM) and KOAc 27.3 g (278.5 mM) were dissolved in 300 mL of 1,4-dioxane and refluxed for 3 hours.

[0503] The reaction product was purified by column chromatography (dichloromethane:hexane = 1:1 (volume ratio)) to obtain 27.0 g (80.4%) of the target compound D.

[0504]

[0505] The results of the synthesis of the compounds described in Manufacturing Examples 2, 4 and 5 and Tables 2 and 4 are shown in Tables 5 and 6 below.

[0506] Table 5 below 1 The values ​​are measured by H NMR (CDCl3, 400 MHz), and Table 6 below is measured by FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0507]

[0508] Compound number 1H NMR(CDCl3, 400MHz)1-1δ = 8.71~8.70(d, 4H), 8.52~8.49(m, 3H), 7.88~7.84(m, 3H), 7.75~7.42(m, 16H), 7.32~7.27(m, 2H), 7.15~7.13(t, 1H)1-2δ = 8.71~8.70(d, 4H), 8.52~8.48(m, 3H), 7.88~7.85(m, 3H), 7.75~7.41(m, 16H), 7.32~7.27(m, 2H), 7.15~7.13(t, 1H)1-3δ = 8.71~8.70(d, 4H), 8.52~8.49(m, 3H), 7.88~7.84(m, 3H), 7.75~7.42(m, 16H), 7.32~7.27(m, 2H), 7.15~7.13(t, 1H)1-4δ = 8.71~8.70(d, 4H), 8.51~8.48(m, 3H), 7.88~7.83(m, 3H), 7.75~7.42(m, 16H), 7.32~7.27(m, 2H), 7.15~7.12(t, 1H)1-5δ = 8.71~8.70(d, 4H), 8.25~8.03(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.31~7.27(m, 2H), 7.15~7.13(t, 1H)1-6δ = 8.72~8.70(d, 4H), 8.25~8.09(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.31~7.27(m, 2H), 7.15~7.13(t, 1H)1-7δ = 8.72~8.70(d, 4H), 8.25~8.09(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.31~7.27(m, 2H), 7.15~7.13(t, 1H)1-8δ = 8.71~8.70(d, 4H), 8.25~8.00(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.31~7.27(m, 2H), 7.15~7.13(t, 1H)1-9δ = 8.71~8.70(d, 4H), 8.51~8.48(m, 3H), 7.92~7.90(m, 2H), 7.73~7.39(m, 17H), 7.32~7.27(m, 2H), 7.15~7.13(t, 1H)1-10δ = 8.71~8.70(d, 4H), 8.51~8.48(m, 3H), 7.92~7.90(m, 2H), 7.73~7.39(m, 17H), 7.32~7.27(m, 2H), 7.15~7.13(t, 1H)1-11δ = 8.71~8.70(d, 4H), 8.51~8.48(m, 3H), 7.92~7.90(m, 2H), 7.73~7.39(m, 17H), 7.32~7.27(m, 2H), 7.15~7.13(t, 1H)1-12δ = 8.71~8.70(d, 4H), 8.52~8.48(m, 3H), 7.88~7.85(m, 2H), 7.70~7.39(m, 17H), 7.32~7.27(m, 2H), 7.15~7.12 (t, 1H)1-13δ = 8.72~8.71(d, 4H), 8.46~8.42(m, 2H), 7.85~7.80(m, 2H), 7.78~7.76(d, 2H), 7.73~7.39(m, 16H), 7.32~7.27(m, 2H), 7.11~7.08(t, 1H)1-14δ = 8.71~8.70(d, 4H), 8.46~8.43(m, 2H), 7.84~7.80(m, 2H), 7.78~7.76(d, 2H), 7.73~7.39(m, 16H), 7.32~7.27(m, 2H), 7.11~7.08(t, 1H)1-15δ = 8.72~8.71(d, 4H), 8.46~8.43(m, 2H), 7.84~7.80(m, 2H), 7.78~7.76(d, 2H), 7.73~7.39(m, 16H), 7.32~7.27(m, 2H), 7.11~7.08(t, 1H)1-16δ = 8.72~8.71(d, 4H), 8.46~8.42(m, 2H), 7.85~7.80(m, 2H), 7.78~7.76(d, 2H), 7.73~7.39(m, 16H), 7.32~7.27(m, 2H), 7.08~7.05(t, 1H)1-17δ = 8.72~8.71(d, 4H), 8.47~8.42(m, 3H), 7.89~7.82(m, 3H), 7.78~7.75(m, 2H), 7.74~7.39(m, 14H), 7.32~7.28(m, 2H), 7.15~7.11(t, 1H)1-18δ = 8.71~8.70(d, 4H), 8.46~8.42(m, 3H), 7.89~7.82(m, 3H), 7.78~7.75(m, 2H), 7.74~7.39(m, 14H), 7.32~7.28(m, 2H), 7.15~7.11(t, 1H)1-19δ = 8.71~8.70(d, 4H), 8.47~8.42(m, 3H), 7.89~7.82(m, 3H), 7.78~7.75(m, 2H), 7.74~7.39(m, 14H), 7.32~7.28(m, 2H), 7.15~7.11(t, 1H)1-20δ = 8.72~8.71(d, 4H), 8.45~8.40(m, 3H), 7.89~7.82(m, 3H), 7.78~7.75(m, 2H), 7.74~7.39(m, 14H), 7.32~7.28(m, 2H), 7.15~7.11(t, 1H)1-21δ = 8.71~8.70(d, 4H), 8.42~8.38(m, 2H), 7.85~7.83(d, 2H), 7.75~7.40(m, 18H), 7.33~7.27(m, 2H), 7.17~7.14(t, 1H)1-22δ = 8.71~8.69(d, 4H), 8.43~8.40(m, 2H), 7.85~7.83(d, 2H), 7.75~7.40(m, 18H), 7.33~7.27(m, 2H), 7.16~7.13(t, 1H)1-23δ = 8.71~8.69(d, 4H), 8.43~8.40(m, 2H), 7.85~7.83(d, 2H), 7.75~7.40(m, 18H), 7.33~7.27(m, 2H), 7.16~7.13(t, 1H)1-24δ = 8.71~8.70(d, 4H), 8.42~8.38(m, 2H), 7.85~7.83(d, 2H), 7.75~7.40(m, 18H), 7.33~7.27(m, 2H), 7.17~7.14(t, 1H)1-25δ = 8.71~8.70(d, 4H), 8.45~8.40(m, 3H), 7.90~7.84(m, 3H), 7.72~7.39(m, 16H), 7.33~7.27(m, 2H), 7.16~7.13(t, 1H)1-26δ = 8.71~8.70(d, 4H), 8.45~8.40(m, 3H), 7.90~7.84(m, 3H), 7.72~7.39(m, 16H), 7.33~7.27(m, 2H), 7.16~7.13(t, 1H)1-29δ = 8.70~8.69(d, 4H), 8.44~8.37(m, 4H), 7.83~7.79(m, 2H), 7.71~7.42(m, 15H), 7.33~7.27(m, 3H), 7.16~7.13(t, 1H)1-30δ = 8.70~8.69(d, 4H), 8.44~8.36(m, 4H), 7.83~7.79(m, 2H), 7.72~7.42(m, 15H), 7.33~7.27(m, 3H), 7.16~7.13(t, 1H)1-33δ = 8.71~8.69(d, 4H), 8.45~8.40 (m, 4H), 7.82~7.42(m, 17H), 7.33~7.27(m, 3H), 7.13~7.10(t, 1H)1-34δ = 8.70~8.69(d, 4H), 8.45~8.40 (m, 4H), 7.82~7.42(m, 17H), 7.33~7.27(m, 3H), 7.12~7.09(t, 1H)1-37δ = 8.70~8.69(d, 4H), 8.49~8.47(d, 2H), 8.40~8.38(m, 2H), 7.82~7.42(m, 17H), 7.33~7.27(m, 3H), 7.12~7.09(t, 1H)1-38δ = 8.70~8.69(d, 4H), 8.49~8.47(d, 2H), 8.40~8.37(m, 2H), 7.83~7.41(m, 17H), 7.33~7.27(m, 3H), 7.12~7.09(t, 1H)1-41δ = 8.70~8.69(d, 4H), 8.49~8.47(d, 2H), 8.38~8.35(d, 2H), 7.82~7.41(m, 17H), 7.32~7.27(m, 3H), 7.13~7.10(t, 1H)1-42δ = 8.70~8.69(d, 4H), 8.49~8.47(d, 2H), 8.38~8.35(d, 2H), 7.82~7.41(m, 17H), 7.32~7.27(m, 3H), 7.14~7.10(t, 1H)1-45δ = 8.70~8.69(d, 4H), 8.50~8.48(m, 2H), 7.88~7.85(m, 2H), 7.77~7.74(m, 2H), 7.70~7.41(m, 16H), 7.31~7.27(m, 2H), 7.15~7.12(t, 1H)1-46δ = 8.70~8.69(d, 4H), 8.50~8.47(m, 2H), 7.88~7.85(m, 2H), 7.78~7.75(m, 2H), 7.70~7.41(m, 16H), 7.31~7.27(m, 2H), 7.15~7.12(t, 1H)1-49δ = 8.70~8.69(d, 4H), 8.50~8.48(m, 2H), 7.88~7.76(m, 4H), 7.71~7.42(m, 16H), 7.31~7.27(m, 2H), 7.15~7.12(t, 1H)1-50δ = 8.70~8.69(d, 4H), 8.50~8.47(m, 2H), 7.87~7.77(m, 4H), 7.70~7.42(m, 16H), 7.31~7.27(m, 2H), 7.15~7.11(t, 1H)1-53δ = 8.71~8.70(d, 4H), 8.50~8.47(m, 2H), 7.82~7.42(m, 20H), 7.30~7.27(m, 2H), 7.15~7.11(t, 1H)1-54δ = 8.71~8.70(d, 4H), 8.50~8.47(m, 2H), 7.82~7.42(m, 20H), 7.30~7.27(m, 2H), 7.14~7.11(t, 1H)1-57δ = 8.71~8.70(d, 4H), 8.48~8.46(m, 2H), 7.81~7.42(m, 20H), 7.31~7.27(m, 2H), 7.16~7.14(t, 1H)1-58δ = 8.71~8.70(d, 4H), 8.48~8.46(m, 2H), 7.81~7.42(m, 20H), 7.30~7.27(m, 2H), 7.16~7.13(t, 1H)1-61δ = 8.71~8.70(d, 4H), 8.48~8.45(m, 2H), 7.85~7.83(m, 2H), 7.77~7.73(m, 2H), 7.71~7.40(m, 16H), 7.31~7.27(m, 2H), 7.18~7.15(t, 1H)1-62δ = 8.71~8.70(d, 4H), 8.48~8.45(m, 3H), 7.85~7.83(m, 2H), 7.77~7.73(m, 3H), 7.71~7.40(m, 14H), 7.31~7.27(m, 2H), 7.18~7.15(t, 1H)1-65δ = 8.71~8.70(d, 4H), 8.50~8.45(m, 3H), 7.86~7.83(d, 2H), 7.77~7.73(m, 3H), 7.71~7.40(m, 14H), 7.33~7.27(m, 2H), 7.18~7.15(t, 1H)1-66δ = 8.71~8.70(d, 4H), 8.51~8.48(m, 3H), 7.85~7.83(d, 2H), 7.77~7.73(m, 3H), 7.71~7.40(m, 14H), 7.33~7.27(m, 2H), 7.18~7.15(t, 1H)1-69δ = 8.71~8.70(d, 4H), 8.50~8.49(m, 2H), 7.86~7.83(d, 2H), 7.74~7.73(m, 2H), 7.71~7.40(m, 16H), 7.33~7.27(m, 2H), 7.17~7.13(t, 1H)1-70δ = 8.71~8.70(d, 4H), 8.50~8.49(m, 2H), 7.86~7.85(m, 2H), 7.74~7.40(m, 18H), 7.33~7.27(m, 2H), 7.17~7.13(t, 1H)1-73δ = 8.71~8.70(d, 4H), 8.48~8.47(m, 2H), 7.86~7.40(m, 20H), 7.33~7.27(m, 2H), 7.15~7.13(t, 1H)1-74δ = 8.71~8.70(d, 4H), 8.48~8.47(m, 2H), 7.86~7.40(m, 20H), 7.33~7.27(m, 2H), 7.15~7.13(t, 1H)1-77δ = 8.71~8.70(d, 4H), 8.50~8.47(m, 2H), 7.87~7.42(m, 20H), 7.31~7.25(m, 2H), 7.15~7.13(t, 1H)1-78δ = 8.71~8.70(d, 4H), 8.50~8.47(m, 2H), 7.87~7.42(m, 20H), 7.31~7.25(m, 2H), 7.15~7.13(t, 1H)1-81δ = 8.71~8.70(d, 4H), 8.49~8.47(m, 2H), 7.82~7.80(m, 2H), 7.74~7.40(m, 18H), 7.33~7.27(m, 2H), 7.17~7.15(t, 1H)1-82δ = 8.71~8.70(d, 4H), 8.49~8.47(m, 2H), 7.82~7.80(m, 2H), 7.74~7.40(m, 18H), 7.33~7.27(m, 2H), 7.17~7.14(t, 1H)1-85δ = 8.71~8.70(d, 4H), 8.45~8.43(m, 2H), 7.83~7.80(m, 2H), 7.75~7.41(m, 18H), 7.33~7.27(m, 2H), 7.16~7.14(t, 1H)1-86δ = 8.71~8.70(d, 4H), 8.45~8.42(m, 2H), 7.83~7.80(m, 2H), 7.75~7.41(m, 18H), 7.33~7.27(m, 2H), 7.16~7.13(t, 1H)1-89δ = 8.71~8.70(d, 4H), 8.44~8.42(m, 3H), 7.84~7.80(m, 3H), 7.73~7.39(m, 16H), 7.33~7.27(m, 2H), 7.16~7.13(t, 1H)1-90δ = 8.71~8.69(d, 4H), 8.44~8.42(m, 3H), 7.84~7.80(m, 3H), 7.73~7.38(m, 16H), 7.33~7.29(m, 2H), 7.16~7.13(t, 1H)1-93δ = 8.71~8.70(d, 4H), 8.45~8.42(m, 3H), 7.83~7.79(m, 3H), 7.74~7.41(m, 16H), 7.34~7.29(m, 2H), 7.15~7.13(t, 1H)1-94δ = 8.71~8.70(d, 4H), 8.45~8.41(m, 3H), 7.83~7.79(m, 3H), 7.74~7.40(m, 16H), 7.34~7.29(m, 2H), 7.15~7.13(t, 1H)1-97δ = 8.71~8.70(d, 4H), 8.47~8.45(m, 2H), 7.83~7.41(m, 20H), 7.34~7.30 (m, 2H), 7.17~7.15(t, 1H)1-98δ = 8.71~8.70(d, 4H), 8.48~8.45(m, 2H), 7.82~7.40(m, 20), 7.34~7.30 (m, 2H), 7.17~7.14(t, 1H)1-101δ = 8.71~8.70(d, 4H), 8.44~8.39(m, 3H), 7.83~7.41(m, 19H), 7.33~7.29(m, 2H), 7.15~7.12(t, 1H)1-102δ = 8.71~8.70(d, 4H), 8.44~8.39(m, 3H), 7.83~7.41(m, 19H), 7.33~7.29(m, 2H), 7.15~7.11(t, 1H)1-105δ = 8.71~8.70(d, 4H), 8.42~8.40(m, 2H), 7.99~7.97(d, 2H), 7.88~7.86(m, 2H), 7.83~7.41(m, 15H), 7.33~7.29(m, 2H), 7.15~7.11(m, 2H)1-106δ = 8.71~8.70(d, 4H), 8.42~8.40(m, 2H), 7.99~7.97(d, 2H), 7.88~7.86(m, 2H), 7.83~7.41(m, 15H), 7.33~7.29(m, 2H), 7.15~7.11(m, 2H)1-109δ = 8.71~8.70(d, 4H), 8.44~8.41(m, 3H), 7.92~7.86(m, 3H), 7.83~7.41(m, 14H), 7.33~7.28(m, 3H), 7.15~7.11(m, 2H)1-110δ = 8.71~8.70(d, 4H), 8.44~8.41(m, 3H), 7.92~7.86(m, 3H), 7.81~7.41(m, 14H), 7.32~7.28(m, 3H), 7.15~7.11(m, 2H)1-113δ = 8.71~8.70(d, 4H), 8.43~8.40(m, 3H), 7.88~7.86(m, 2H), 7.83~7.40(m, 17H), 7.32~7.28(m, 2H), 7.15~7.11(m, 1H)1-114δ = 8.71~8.70(d, 4H), 8.43~8.40(m, 3H), 7.88~7.86(m, 2H), 7.82~7.40(m, 17H), 7.32~7.28(m, 2H), 7.15~7.12(m, 1H)1-117δ = 8.71~8.70(d, 4H), 8.45~8.41(m, 3H), 7.89~7.86(m, 2H), 7.82~7.40(m, 15H), 7.33~7.27(m, 3H), 7.15~7.12(m, 2H)1-118δ = 8.71~8.70(d, 4H), 8.45~8.41(m, 3H), 7.89~7.86(m, 2H), 7.81~7.40(m, 15H), 7.32~7.27(m, 3H), 7.14~7.10(m, 2H)1-121δ = 8.71~8.70(d, 4H), 8.44~8.41(m, 2H), 7.85~7.41(m, 19H), 7.33~7.27(m, 3H), 7.15~7.12(t, 1H)1-122δ = 8.71~8.70(d, 4H), 8.44~8.41(m, 2H), 7.85~7.41(m, 19H), 7.33~7.27(m, 3H), 7.15~7.12(t, 1H)1-125δ = 8.71~8.70(d, 4H), 8.46~8.44(m, 2H), 7.83~7.39(m, 19H), 7.32~7.27(m, 3H), 7.15~7.12(t, 1H)1-126δ = 8.71~8.70(d, 4H), 8.47~8.44(m, 2H), 7.83~7.39(m, 19H), 7.31~7.27(m, 3H), 7.16~7.13(t, 1H)1-129δ = 8.71~8.70(d, 4H), 8.46~8.43(m, 3H), 7.88~7.84(m, 3H), 7.79~7.39(m, 14H), 7.31~7.27(m, 3H), 7.16~7.12(t, 2H)1-130δ = 8.71~8.70(d, 4H), 8.46~8.42(m, 3H), 7.88~7.84(m, 3H), 7.80~7.39(m, 14H), 7.32~7.27(m, 3H), 7.16~7.12(t, 2H)1-133δ = 8.71~8.70(d, 4H), 8.45~8.43(m, 2H), 7.89~7.86(m, 2H), 7.81~7.40(m, 18H), 7.31~7.27(m, 2H), 7.16~7.13(t, 1H)1-134δ = 8.71~8.70(d, 4H), 8.45~8.43(m, 2H), 7.89~7.86(m, 2H), 7.81~7.40(m, 18H), 7.31~7.27(m, 2H), 7.15~7.12(t, 1H)1-137δ = 8.71~8.70(d, 4H), 8.42~8.40(m, 2H), 7.85~7.40(m, 20H), 7.32~7.27(m, 2H), 7.15~7.13(t, 1H)1-138δ = 8.71~8.70(d, 4H), 8.42~8.39(m, 2H), 7.85~7.41(m, 20H), 7.32~7.27(m, 2H), 7.15~7.13(t, 1H)1-141δ = 8.71~8.70(d, 4H), 8.43~8.40(m, 2H), 7.89~7.86(m, 3H), 7.81~7.39(m, 17H), 7.31~7.26(m 2H), 7.14~7.11(t, 1H)1-142δ = 8.71~8.70(d, 4H), 8.43~8.40(m, 2H), 7.89~7.85(m, 3H), 7.81~7.39(m, 17H), 7.31~7.26(m 2H), 7.14~7.11(t, 1H)1-145δ = 8.71~8.70(d, 4H), 8.42~8.39(m, 2H), 7.91~7.89(d, 2H), 7.87~7.85(m, 2H), 7.79~7.39(m, 16H), 7.32~7.27(m 2H), 7.14~7.11(t, 1H)1-146δ = 8.71~8.70(d, 4H), 8.42~8.39(m, 2H), 7.90~7.88(d, 2H), 7.84~7.81(m, 2H), 7.77~7.39(m, 16H), 7.32~7.27(m 2H), 7.15~7.12(t, 1H)1-149δ = 8.71~8.70(d, 4H), 8.44~8.39(m, 3H), 7.85~7.40(m, 17H), 7.32~7.26(m, 3H), 7.15~7.10(m, 2H)1-150δ = 8.71~8.70(d, 4H), 8.44~8.39(m, 3H), 7.85~7.40(m, 17H), 7.32~7.26(m, 3H), 7.15~7.10(m, 2H)1-153δ = 8.71~8.70(d, 4H), 8.43~8.39(m, 3H), 7.83~7.40(m, 17H), 7.33~7.27(m, 3H), 7.15~7.10(m, 2H)1-154δ = 8.71~8.70(d, 4H), 8.43~8.40(m, 3H), 7.83~7.40(m, 17H), 7.33~7.27(m, 3H), 7.15~7.10(m, 2H)1-157δ = 8.71~8.70(d, 4H), 8.45~8.42(m, 2H), 7.92~7.89(m 2H), 7.87~7.85(m, 2H), 7.78~7.39(m, 16H), 7.32~7.27(m 2H), 7.13~7.10(t, 1H)1-158δ = 8.71~8.70(d, 4H), 8.45~8.42(m, 2H), 7.92~7.89(m 2H), 7.87~7.85(m, 2H), 7.78~7.39(m, 16H), 7.32~7.27(m 2H), 7.11~7.08(t, 1H)1-161δ = 8.71~8.70(d, 4H), 8.44~8.41(m, 2H), 7.89~7.85(m, 4H), 7.79~7.39(m, 16H), 7.32~7.28(m 2H), 7.12~7.09(t, 1H)1-162δ = 8.71~8.70(d, 4H), 8.45~8.42(m, 2H), 7.89~7.86(m, 4H), 7.79~7.39(m, 16H), 7.32~7.28(m 2H), 7.11~7.08(t, 1H)1-165δ = 8.71~8.70(d, 4H), 8.46~8.43(m, 2H), 7.86~7.41(m, 19H), 7.31~7.27(m, 3H), 7.12~7.10(t, 1H)1-166δ = 8.71~8.70(d, 4H), 8.46~8.43(m, 2H), 7.86~7.41(m, 19H), 7.31~7.27(m, 3H), 7.12~7.09(t, 1H)1-169δ = 8.71~8.70(d, 4H), 8.42~8.39(m, 3H), 7.84~7.40(m, 18H), 7.33~7.29(m, 3H), 7.15~7.12(t, 1H)1-170δ = 8.71~8.70(d, 4H), 8.42~8.39(m, 3H), 7.84~7.40(m, 18H), 7.33~7.29(m, 3H), 7.14~7.12(t, 1H)1-173δ = 8.72~8.71(d, 4H), 8.52~8.49(m, 3H), 7.88~7.84(m, 3H), 7.75~7.42(m, 16H), 7.32~7.27(m, 2H), 7.20~7.17(t, 1H)1-174δ = 8.72~8.71(d, 4H), 8.52~8.48(m, 3H), 7.88~7.85(m, 3H), 7.75~7.41(m, 16H), 7.32~7.27(m, 2H), 7.20~7.17(t, 1H)1-175δ = 8.72~8.71(d, 4H), 8.52~8.49(m, 3H), 7.88~7.84(m, 3H), 7.75~7.42(m, 16H), 7.32~7.27(m, 2H), 7.20~7.17(t, 1H)1-176δ = 8.71~8.70(d, 4H), 8.51~8.48(m, 3H), 7.88~7.83(m, 3H), 7.75~7.42(m, 16H), 7.32~7.27(m, 2H), 7.15~7.12(t, 1H)1-177δ = 8.72~8.71(d, 4H), 8.25~8.03(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.31~7.27(m, 2H), 7.17~7.15(t, 1H)1-178δ = 8.72~8.71(d, 4H), 8.25~8.09(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.31~7.27(m, 2H), 7.20~7.17(t, 1H)1-179δ = 8.72~8.71(d, 4H), 8.25~8.09(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.31~7.27(m, 2H), 7.20~7.17(t, 1H)1-180δ = 8.71~8.70(d, 4H), 8.25~8.00(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.31~7.27(m, 2H), 7.15~7.13(t, 1H)1-181δ = 8.74~8.72(d, 4H), 8.46~8.42(m, 2H), 7.85~7.80(m, 2H), 7.78~7.76(d, 2H), 7.73~7.39(m, 16H), 7.32~7.27(m, 2H), 7.17~7.14(t, 1H)1-182δ = 8.74~8.72(d, 4H), 8.46~8.43(m, 2H), 7.84~7.80(m, 2H), 7.78~7.76(d, 2H), 7.73~7.39(m, 16H), 7.32~7.27(m, 2H), 7.17~7.14(t, 1H)1-185δ = 8.74~8.73(d, 4H), 8.47~8.42(m, 3H), 7.89~7.82(m, 3H), 7.78~7.75(m, 2H), 7.74~7.39(m, 14H), 7.32~7.28(m, 2H), 7.17~7.15(t, 1H)1-186δ = 8.74~8.73(d, 4H), 8.46~8.42(m, 3H), 7.89~7.82(m, 3H), 7.78~7.75(m, 2H), 7.74~7.39(m, 14H), 7.32~7.28(m, 2H), 7.17~7.15(t, 1H)1-189δ = 8.74~8.72(d, 4H), 8.42~8.38(m, 2H), 7.85~7.83(d, 2H), 7.75~7.40(m, 18H), 7.33~7.27(m, 2H), 7.18~7.15(t, 1H)1-190δ = 8.74~8.72(d, 4H), 8.43~8.40(m, 2H), 7.85~7.83(d, 2H), 7.75~7.40(m, 18H), 7.33~7.27(m, 2H), 7.18~7.15(t, 1H)1-193δ = 8.74~8.73(d, 4H), 8.45~8.40(m, 3H), 7.90~7.84(m, 3H), 7.72~7.39(m, 16H), 7.33~7.27(m, 2H), 7.20~7.16(t, 1H)1-194δ = 8.74~8.73(d, 4H), 8.45~8.40(m, 3H), 7.90~7.84(m, 3H), 7.72~7.39(m, 16H), 7.33~7.27(m, 2H), 7.20~7.16(t, 1H)1-197δ = 8.74~8.72(d, 4H), 8.45~8.40 (m, 4H), 7.82~7.42(m, 17H), 7.33~7.27(m, 3H), 7.17~7.14(t, 1H)1-198δ = 8.73~8.72(d, 4H), 8.45~8.40 (m, 4H), 7.82~7.42(m, 17H), 7.33~7.27(m, 3H), 7.17~7.14(t, 1H)1-201δ = 8.75~8.73(d, 4H), 8.49~8.47(d, 2H), 8.40~8.38(m, 2H), 7.82~7.42(m, 17H), 7.33~7.27(m, 3H), 7.20~7.17(t, 1H)1-202δ = 8.75~8.73(d, 4H), 8.49~8.47(d, 2H), 8.40~8.37(m, 2H), 7.83~7.41(m, 17H), 7.33~7.27(m, 3H), 7.20~7.17(t, 1H)1-205δ = 8.72~8.71(d, 4H), 8.49~8.47(d, 2H), 8.38~8.35(d, 2H), 7.82~7.41(m, 17H), 7.32~7.27(m, 3H), 7.15~7.12(t, 1H)1-206δ = 8.72~8.71(d, 4H), 8.49~8.47(d, 2H), 8.38~8.35(d, 2H), 7.82~7.41(m, 17H), 7.32~7.27(m, 3H), 7.15~7.12(t, 1H)1-209δ = 8.74~8.73(d, 4H), 8.50~8.48(m, 2H), 7.88~7.76(m, 4H), 7.71~7.42(m, 16H), 7.31~7.27(m, 2H), 7.17~7.15(t, 1H)1-210δ = 8.74~8.72(d, 4H), 8.50~8.47(m, 2H), 7.87~7.77(m, 4H), 7.70~7.42(m, 16H), 7.31~7.27(m, 2H), 7.17~7.15(t, 1H)1-213δ = 8.74~8.72(d, 4H), 8.50~8.47(m, 2H), 7.82~7.42(m, 20H), 7.30~7.27(m, 2H), 7.15~7.11(t, 1H)1-214δ = 8.74~8.72(d, 4H), 8.50~8.47(m, 2H), 7.82~7.42(m, 20H), 7.30~7.27(m, 2H), 7.14~7.11(t, 1H)1-217δ = 8.72~8.71(d, 4H), 8.48~8.45(m, 2H), 7.85~7.83(m, 2H), 7.77~7.73(m, 2H), 7.71~7.40(m, 16H), 7.31~7.27(m, 2H), 7.18~7.15(t, 1H)1-218δ = 8.72~8.71(d, 4H), 8.48~8.45(m, 3H), 7.85~7.83(m, 2H), 7.77~7.73(m, 3H), 7.71~7.40(m, 14H), 7.31~7.27(m, 2H), 7.18~7.15(t, 1H)1-277δ = 8.72~8.71(d, 4H), 8.52~8.49(m, 3H), 7.88~7.84(m, 3H), 7.75~7.42(m, 16H), 7.35~7.30(m, 2H), 7.20~7.17(t, 1H)1-278δ = 8.72~8.71(d, 4H), 8.52~8.48(m, 3H), 7.88~7.85(m, 3H), 7.75~7.41(m, 16H), 7.35~7.31(m, 2H), 7.21~7.18(t, 1H)1-279δ = 8.73~8.71(d, 4H), 8.52~8.49(m, 3H), 7.88~7.84(m, 3H), 7.75~7.42(m, 16H), 7.35~7.31(m, 2H), 7.21~7.18(t, 1H)1-280δ = 8.73~8.71(d, 4H), 8.51~8.48(m, 3H), 7.88~7.83(m, 3H), 7.75~7.42(m, 16H), 7.35~7.30(m, 2H), 7.21~7.18(t, 1H)1-281δ = 8.74~8.73(d, 4H), 8.25~8.03(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.35~7.31(m, 2H), 7.20~7.17(t, 1H)1-282δ = 8.74~8.72(d, 4H), 8.25~8.09(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.35~7.31(m, 2H), 7.20~7.17(t, 1H)1-283δ = 8.74~8.73(d, 4H), 8.25~8.09(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.35~7.31(m, 2H), 7.21~7.18(t, 1H)1-284δ = 8.73~8.71(d, 4H), 8.25~8.00(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.34~7.30(m, 2H), 7.18~7.15(t, 1H)1-285δ = 8.73~8.72(d, 4H), 8.46~8.42(m, 2H), 7.85~7.80(m, 2H), 7.78~7.76(d, 2H), 7.73~7.39(m, 16H), 7.35~7.31(m, 2H), 7.18~7.15(t, 1H)1-286δ = 8.74~8.73(d, 4H), 8.46~8.43(m, 2H), 7.84~7.80(m, 2H), 7.78~7.76(d, 2H), 7.73~7.39(m, 16H), 7.35~7.31(m, 2H), 7.18~7.15(t, 1H)1-289δ = 8.73~8.72(d, 4H), 8.47~8.42(m, 3H), 7.89~7.82(m, 3H), 7.78~7.75(m, 2H), 7.74~7.39(m, 14H), 7.34~7.30(m, 2H), 7.19~7.15(t, 1H)1-290δ = 8.73~8.71(d, 4H), 8.46~8.42(m, 3H), 7.89~7.82(m, 3H), 7.78~7.75(m, 2H), 7.74~7.39(m, 14H), 7.34~7.30(m, 2H), 7.19~7.15(t, 1H)1-293δ = 8.73~8.72(d, 4H), 8.42~8.38(m, 2H), 7.85~7.83(d, 2H), 7.75~7.40(m, 18H), 7.34~7.30(m, 2H), 7.20~7.17(t, 1H)1-294δ = 8.72~8.71(d, 4H), 8.43~8.40(m, 2H), 7.85~7.83(d, 2H), 7.75~7.40(m, 18H), 7.33~7.27(m, 2H), 7.20~7.18(t, 1H)1-297δ = 8.72~8.71(d, 4H), 8.45~8.40(m, 3H), 7.90~7.84(m, 3H), 7.72~7.39(m, 16H), 7.33~7.27(m, 2H), 7.16~7.13(t, 1H)1-298δ = 8.72~8.71(d, 4H), 8.45~8.40(m, 3H), 7.90~7.84(m, 3H), 7.72~7.39(m, 16H), 7.33~7.27(m, 2H), 7.16~7.13(t, 1H)1-301δ = 8.72~8.70(d, 4H), 8.45~8.40 (m, 4H), 7.82~7.42(m, 17H), 7.34~7.30(m, 3H), 7.15~7.12(t, 1H)1-302δ = 8.72~8.70(d, 4H), 8.45~8.40 (m, 4H), 7.82~7.42(m, 17H), 7.34~7.29(m, 3H), 7.15~7.12(t, 1H)1-305δ = 8.71~8.70(d, 4H), 8.49~8.47(d, 2H), 8.40~8.38(m, 2H), 7.82~7.42(m, 17H), 7.35~7.31(m, 3H), 7.14~7.11(t, 1H)1-306δ = 8.71~8.70(d, 4H), 8.49~8.47(d, 2H), 8.40~8.37(m, 2H), 7.83~7.41(m, 17H), 7.35~7.30(m, 3H), 7.14~7.11(t, 1H)1-385δ = 8.76~8.75(d, 4H), 8.53~8.49(m, 3H), 7.88~7.84(m, 3H), 7.75~7.42(m, 16H), 7.32~7.27(m, 2H), 7.17~7.14(t, 1H)1-386δ = 8.76~8.74(d, 4H), 8.56~8.53(m, 3H), 7.88~7.85(m, 3H), 7.75~7.41(m, 16H), 7.32~7.27(m, 2H), 7.17~7.14(t, 1H)1-387δ = 8.75~8.74(d, 4H), 8.54~8.50(m, 3H), 7.88~7.84(m, 3H), 7.75~7.42(m, 16H), 7.32~7.27(m, 2H), 7.17~7.14(t, 1H)1-388δ = 8.76~8.74(d, 4H), 8.54~8.50(m, 3H), 7.88~7.83(m, 3H), 7.75~7.42(m, 16H), 7.32~7.27(m, 2H), 7.17~7.15(t, 1H)1-389δ = 8.73~8.71(d, 4H), 8.25~8.03(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.31~7.27(m, 2H), 7.16~7.13(t, 1H)1-390δ = 8.73~8.71(d, 4H), 8.25~8.09(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.31~7.27(m, 2H), 7.16~7.13(t, 1H)1-391δ = 8.73~8.71(d, 4H), 8.25~8.09(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.31~7.27(m, 2H), 7.16~7.14(t, 1H)1-392δ = 8.73~8.72(d, 4H), 8.25~8.00(m, 5H), 7.89~7.85(m, 2H), 7.74~7.41(m, 15H), 7.31~7.27(m, 2H), 7.16~7.13(t, 1H)1-393δ = 8.76~8.75(d, 4H), 8.50~8.48(m, 2H), 7.85~7.80(m, 2H), 7.78~7.76(d, 2H), 7.73~7.39(m, 16H), 7.32~7.27(m, 2H), 7.16~7.14(t, 1H)1-394δ = 8.76~8.75(d, 4H), 8.51~8.48(m, 2H), 7.84~7.80(m, 2H), 7.78~7.76(d, 2H), 7.73~7.39(m, 16H), 7.32~7.27(m, 2H), 7.16~7.14(t, 1H)1-397δ = 8.75~8.73(d, 4H), 8.48~8.42(m, 3H), 7.89~7.82(m, 3H), 7.78~7.75(m, 2H), 7.74~7.39(m, 14H), 7.32~7.28(m, 2H), 7.16~7.14(t, 1H)1-398δ = 8.75~8.73(d, 4H), 8.46~8.42(m, 3H), 7.89~7.82(m, 3H), 7.78~7.75(m, 2H), 7.74~7.39(m, 14H), 7.32~7.28(m, 2H), 7.16~7.15(t, 1H)1-401δ = 8.75~8.73(d, 4H), 8.48~8.45(m, 2H), 7.85~7.83(d, 2H), 7.75~7.40(m, 18H), 7.33~7.27(m, 2H), 7.17~7.14(t, 1H)1-402δ = 8.75~8.73(d, 4H), 8.48~8.45(m, 2H), 7.85~7.83(d, 2H), 7.75~7.40(m, 18H), 7.33~7.27(m, 2H), 7.17~7.14(t, 1H)1-405δ = 8.75~8.74(d, 4H), 8.45~8.40(m, 3H), 7.90~7.84(m, 3H), 7.72~7.39(m, 16H), 7.33~7.27(m, 2H), 7.18~7.15(t, 1H)1-406δ = 8.75~8.75(d, 4H), 8.45~8.40(m, 3H), 7.90~7.84(m, 3H), 7.72~7.39(m, 16H), 7.33~7.27(m, 2H), 7.18~7.16(t, 1H)1-409δ = 8.75~8.73(d, 4H), 8.45~8.40 (m, 4H), 7.82~7.42(m, 17H), 7.33~7.27(m, 3H), 7.17~7.14(t, 1H)1-410δ = 8.75~8.73(d, 4H), 8.45~8.40 (m, 4H), 7.82~7.42(m, 17H), 7.33~7.27(m, 3H), 7.16~7.14(t, 1H)1-413δ = 8.75~8.74(d, 4H), 8.51~8.48(d, 2H), 8.40~8.38(m, 2H), 7.82~7.42(m, 17H), 7.33~7.27(m, 3H), 7.15~7.13(t, 1H)1-414δ = 8.75~8.74(d, 4H), 8.52~8.50(d, 2H), 8.40~8.37(m, 2H), 7.83~7.41(m, 17H), 7.33~7.27(m, 3H), 7.15~7.12(t, 1H)1-417δ = 8.75~8.73(d, 4H), 8.51~8.49(d, 2H), 8.38~8.35(d, 2H), 7.82~7.41(m, 17H), 7.32~7.27(m, 3H), 7.15~7.12(t, 1H)1-418δ = 8.75~8.74(d, 4H), 8.50~8.48(d, 2H), 8.38~8.35(d, 2H), 7.82~7.41(m, 17H), 7.32~7.27(m, 3H), 7.15~7.13(t, 1H)1-493δ = 7.88~7.86(d, 1H), 7.75~7.42(m, 12H), 7.32~7.27(m, 2H), 7.15~7.13(t, 1H)1-494δ = 7.88~7.86(d, 1H), 7.64~7.42(m, 6H), 7.32~7.27(m, 2H), 7.15~7.13(t, 1H)1-496δ = 8.71~8.70(d, 4H), 8.52~8.49(m, 2H), 7.88~7.85(m, 2H), 7.75~7.42(m, 13H), 7.32~7.30(m, 1H), 7.15~7.13(t, 1H)1-497δ = 8.71~8.70(d, 4H), 8.52~8.49(m, 3H), 7.88~7.84(m, 2H), 7.75~7.42(m, 12H), 7.30~7.27(m, 1H),1-498δ = 8.71~8.70(d, 4H), 8.52~8.50(m, 1H), 7.88~7.84(m, 2H), 7.75~7.42(m, 13H), 7.32~7.27(m, 2H), 7.15~7.<h2 style=";text-align:left;direction:ltr">13(t, 1H).<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0509] <h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0510] <h2 style=";text-align:left;direction:ltr"> 화합물FD-Mass화합물FD-Mass1-1m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-2m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-3m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-4m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-5m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-6m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-7m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-8m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-9m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-10m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-11 m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-12m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-13m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-14m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-15m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29<h2 style=";text-align:left;direction:ltr">N3O3, 731.2209)1-16m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-17m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-18 m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-19m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-20m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-21m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-22m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-23m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-24m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-25m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-26m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-29m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-30m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-33m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-34m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-37m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29<h2 style=";text-align:left;direction:ltr">N3O3, 731.2209)1-38m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-41 m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-42m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-45 m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-46m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-49m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-50 m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-53m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-54 m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-57m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-58m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-61 m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-62m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-65m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-66m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-69m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29<h2 style=";text-align:left;direction:ltr">N3O3, 731.2209)1-70m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-73m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-74m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-77m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-78m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-81 m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-82m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-85m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-86m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-89 m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-90m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-93m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-94m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-97m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-98m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O3, 731.2209)1-101 m / z= 731.8110 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29N3O3, 731.2209)1-102m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-105m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-106m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-109m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-110m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-113m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-114m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-117m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-118m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-121m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-122m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-125m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-126m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-129m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-130m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-133m / z= 731.8110 (C 51 H29 N3O3, 731.2209)1-134m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-137m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-138m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-141m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-142m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-145m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-146m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-149m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-150m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-153m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-154m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-157m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-158m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-161m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-162m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-165m / z= 731.8110 (C51 H 29 N3O3, 731.2209)1-166m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-169m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-170m / z= 731.8110 (C 51 H 29 N3O3, 731.2209)1-173m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-174m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-175m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-176m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-177m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-178m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-179m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-180m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-181m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-182m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-185m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-186m / z= 747.8720 (C 51 H 29N3O2S, 747.1980)1-189m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-190m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-193m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-194m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-197m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-198m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-201m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-202m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-205m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-206m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-209m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-210m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-213m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-214m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-217m / z= 747.8720 (C 51 H 29 N3O2S, 747.1980)1-218m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-277m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-278m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-279m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-280m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-281m / z= 747.8720 (C)<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-282m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-283m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-284m / z= 747.8720 (C)<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-285m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-286m / z= 747.8720 (C)<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-289m / z= 747.8720 (C)<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-290m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-293m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-294m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-297m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29<h2 style=";text-align:left;direction:ltr">N3O2S, 747.1980)1-298m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-301m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-302m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-305m / z= 747.8720 (C)<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-306m / z= 747.8720 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2S, 747.1980)1-385m / z= 763.9330 (C)<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3OS2, 763.1752)1-386m / z= 763.9330 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3OS2, 763.1752)1-387m / z= 763.9330 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3OS2, 763.1752)1-388 m / z= 763.9330 (C)<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3OS2, 763.1752)1-389m / z= 763.9330 (C)<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3OS2, 763.1752)1-390m / z= 763.9330 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3OS2, 763.1752)1-391m / z= 763.9330 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3OS2, 763.1752)1-392m / z= 763.9330 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3OS2, 763.1752)1-393m / z= 763.9330 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3OS2, 763.1752)1-394m / z= 763.9330 (C<h2 style=";text-align:left;direction:ltr"> 51 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3OS2, 763.1752)1-397m / z= 763.9330 (C51 H 29 N3OS2, 763.1752)1-398m / z= 763.9330 (C 51 H 29 N3OS2, 763.1752)1-401m / z= 763.9330 (C 51 H 29 N3OS2, 763.1752)1-402m / z= 763.9330 (C 51 H 29 N3OS2, 763.1752)1-405m / z= 763.9330 (C 51 H 29 N3OS2, 763.1752)1-406m / z= 763.9330 (C 51 H 29 N3OS2, 763.1752)1-409m / z= 763.9330 (C 51 H 29 N3OS2, 763.1752)1-410m / z= 763.9330 (C 51 H 29 N3OS2, 763.1752)1-413m / z= 763.9330 (C 51 H 29 N3OS2, 763.1752)1-414m / z= 763.9330 (C 51 H 29 N3OS2, 763.1752)1-417m / z= 763.9330 (C 51 H 29 N3OS2, 763.1752)1-418m / z= 763.9330 (C 51 H 29 N3OS2, 763.1752)1-493m / z= 744.8903 (C 51 H 16 D 13 N3O3, 744.3025)1-494m / z= 750.9269 (C 51 H 10 D 19 N3O3, 750.3401)1-495m / z= 760.9880 (C 51 D 29 N3O3, 760.4029)1-496m / z= 737.8476 (C 51 H23 D6N3O3, 737.2586)1-497m / z= 738.8537 (C 51 H 22 D7N3O3, 738.2648)1-498m / z= 737.8476 (C 51 H 23 D6N3O3, 737.2586)1-499m / z= 760.9880 (C 51 D 29 N3O3, 760.4029)1-500m / z= 760.9880 (C 51 D 29 N3O3, 760.4029)1-501m / z= 760.9880 (C 51 D 29 N3O3, 760.4029)1-502m / z= 760.9880 (C 51 D 29 N3O3, 760.4029)1-503m / z= 760.9880 (C 51 D 29 N3O3, 760.4029)1-504m / z= 760.9880 (C 51 D 29 N3O3, 760.4029)1-505m / z= 760.9880 (C 51 D 29 N3O3, 760.4029)1-506m / z= 760.9880 (C 51 D 29 N3O3, 760.4029)1-507m / z= 760.9880 (C 51 D 29 N3O3, 760.4029)1-508m / z= 760.9880 (C 51 D 29 N3O3, 760.4029)1-509m / z= 760.9880 (C 51 D 29 N3O3, 760.4029)1-510m / z= 760.9880 (C 51 D 29 N3O3, 760.4029)1-511m / z= 760.9880 (C 51 D 29 N3O3, 760.4029)1-512m / z= 760.9880 (C51 D 29 N3O3, 760.4029)1-513m / z= 777.0490 (C 51 D 29 N3O2S, 776.3801)1-514m / z= 777.0490 (C 51 D 29 N3O2S, 776.3801)1-515m / z= 777.0490 (C 51 D 29 N3O2S, 776.3801)1-516m / z= 777.0490 (C 51 D 29 N3O2S, 776.3801)1-529m / z= 777.0490 (C 51 D 29 N3O2S, 776.3801)1-530m / z= 777.0490 (C 51 D 29 N3O2S, 776.3801)1-531m / z= 777.0490 (C 51 D 29 N3O2S, 776.3801)1-532m / z= 777.0490 (C 51 D 29 N3O2S, 776.3801)1-545m / z= 793.1100 (C 51 D 29 N3OS2, 792.3572)1-546m / z= 793.1100 (C 51 D 29 N3OS2, 792.3572)1-547m / z= 793.1100 (C 51 D 29 N3OS2, 792.3572)1-548m / z= 793.1100 (C 51 D 29 N3OS2, 792.3572)

[0511]

[0512] Manufacturing Example 7. Preparation of Compound 3-5

[0513]

[0514]

[0515] Manufacturing Example 7-1. Preparation of compound 3-2-5

[0516] 30.0 g (118.7 mM) of 8-chloronaphtho[1,2-b]benzofuran and 21.2 g (118.7 mM) of N-bromosuccinimide were dissolved in 300 mL of dimethylformamide (DMF) and refluxed.

[0517] After completion of the reaction, the product was purified by recrystallization from methanol, and 37.4 g (95.0%) of the target compound 3-2-5 was obtained.

[0518]

[0519] Manufacturing Example 7-2. Preparation of Compound 3-1-5

[0520] Compound 3-2-5 37.0 g (111.6 mM), phenylboronic acid 13.6 g (111.6 mM), Pd(PPh3) 46.4 g (5.6 mM), and K2CO3 30.8 g (223.2 mM) were dissolved in 400 mL of 1,4-dioxane and 80 mL of distilled water (H2O), and stirred for 3 hours.

[0521] After completion of the reaction, the product was purified by recrystallization from methanol, and 32.5 g (88.5%) of the target compound 3-1-5 was obtained.

[0522]

[0523] Manufacturing Example 7-3. Preparation of Compound 3-5

[0524] Compound 3-1-5 15.0 g (45.6 mM), di([1,1'-biphenyl]-4-yl)amine 14.7 g (45.6 mM), Pd(dba) 22.1 g (2.3 mM), Xphos 2.2 g (4.6 mM), and NaOtBu 8.8 g (91.2 mM) were dissolved in 200 mL of toluene and stirred for 3 hours.

[0525] The reactant was purified by column chromatography (dichloromethane:hexane = 1:1 (volume ratio)) to obtain 23.9 g (85.3%) of the target compound 3-5.

[0526]

[0527] In the above Manufacturing Example 7, the intermediate G of Table 7 below was used instead of the 8-chloronaphtho[1,2-b]benzofuran, the intermediate H of Table 7 below was used instead of phenylboronic acid, and the intermediate I of Table 7 below was used instead of di([1,1'-biphenyl]-4-yl)amine, and the target compound of Table 7 below was synthesized in the same manner as in Manufacturing Example 7.

[0528]

[0529] [Correction pursuant to Rule 91, September 30, 2024]

[0530] [Correction pursuant to Rule 91, September 30, 2024]

[0531]

[0532] Manufacturing Example 8. Preparation of Compound G

[0533]

[0534] 15.0 g (44.9 mM) of 7-chloro-5-(phenyl-d5)naphtho[1,2-b]benzofuran was dissolved in 150 mL of d6-benzene, and 16.7 mL (179.6 mM) of triflic acid was slowly added, followed by refluxing for 40 minutes.

[0535] After completion of the reaction, the product was purified by recrystallization from methanol, and 14.1 g (92.9%) of the target compound G was obtained.

[0536]

[0537] Manufacturing Example 9. Preparation of Compound H

[0538]

[0539] 15.0 g (44.9 mM) of 7-chloro-5-(phenyl-d5)naphtho[1,2-b]benzofuran was dissolved in 150 mL of d6-benzene, and 28.4 mL (305.3 mM) of triflic acid was slowly added, followed by refluxing for 1 hour.

[0540] After completion of the reaction, the product was purified by recrystallization from methanol, and 14.1 g (91.8%) of the target compound H was obtained.

[0541]

[0542] Manufacturing Example 10. Preparation of Compound 3-394

[0543]

[0544] Compound G 10.0 g (29.6 mM), N-(4-(naphthalen-2-yl)phenyl)-[1,1'-biphenyl]-4-amine 11.0 g (29.6 mM), Pd(dba) 21.4 g (1.5 mM), Xphos 1.4 g (3.0 mM), and NaOtBu 5.7 g (59.2 mM) were dissolved in 150 mL of toluene and stirred for 3 hours.

[0545] The reaction product was purified by column chromatography (dichloromethane:hexane = 1:1 (volume ratio)) to obtain 17.1 g (85.8%) of the target compound 3-394.

[0546]

[0547] In the above Manufacturing Example 10, the intermediate J of the following Table 8 was used instead of the compound G, and the intermediate K of the following Table 8 was used instead of N-(4-(naphthalen-2-yl)phenyl)-[1,1'-biphenyl]-4-amine, and the target compound of the following Table 8 was synthesized by the same method as in the above Manufacturing Example 10.

[0548]

[0549]

[0550]

[0551] The results of the synthesis of the compounds described in Manufacturing Examples 7 and 10 and Tables 7 and 8 are shown in Tables 9 and 10 below.

[0552] Table 9 below 1 The values ​​are measured by H NMR (CDCl3, 400 MHz), and Table 10 below is measured by FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0553]

[0554] Compound number 1H NMR(CDCl3, 400MHz)3-5δ =8.53~8.51(d, 1H), 8.00~7.98(m, 1H), 7.84~7.81(m, 2H), 7.69~7.39(m, 21H), 7.32~7.24(m, 6H)3-147δ =8.43~8.41(d, 1H), 7.98~7.96(d, 1H), 7.90(s, 1H), 7.86`7.84(d, 1H), 7.64~7.44(m, 21H), 7.35~7.25(m, 6H)3-234δ = 7.97~7.91(m, 3H), 7.80~7.77(m ,1H), 7.61~7.37(m, 21H), 7.33~7.29(m, 6H)3-352δ = 8.54~8.52(d, 1H), 7.93~7.82(m,5H), 7.63~7.49(m, 8H), 7.41~7.33(m, 7H), 7.30~7.10(m, 10H)3-354δ = 8.54~8.52(d, 1H), 7.98(s, 1H), 7.93~7.82(m, 4H), 7.63~7.49(m, 8H), 7.42~7.31(m, 8H), 7.30~7.10(m, 13H)3-381δ = 8.54~8.52(d, 1H), 7.98(s, 1H), 7.93~7.82(m, 4H), 7.63~7.49(m, 8H), 7.42~7.31(m, 8H), 7.30~7.10(m, 11H)3-390δ = 853~8.51(d, 1H), 8.14~8.12(d, 1H), 7.93~7.87(m, 2H), 7.62~7.59(t, 2H), 7.51~7.18(m, 31H), 6.92~6.90(d, 1H)3-393δ = 8.54~8.52(d, 1H), 7.98(s, 1H), 7.93~7.82(m, 4H), 7.63~7.49(m, 8H), 7.42~7.31(m, 6H), 7.30~7.10(m, 8H)3-394δ =7.98(s, 1H), 7.88~7.82(m, 2H), 7.63~7.49(m, 7H), 7.42~7.31(m, 6H), 7.30~7.10(m, 8H)3-395δ =7.58~7.49(m, 6H), 7.42~7.31(m, 6H), 7.30~7.10(m, 8H)。

[0555]

[0556] Compound FD-Mass Compound FD-Mass3-5 m / z = 613.7600 (C 46 H 31 NO, 613.2406)3-147m / z= 613.7600 (C 46 H 31 NO, 613.2406)3-234m / z= 613.7600 (C 46 H 31 NO, 613.2406)3-352m / z= 613.7600 (C 46 H 31 NO, 613.2406)3-354m / z= 689.8580 (C 52 H 35 NO, 689.2719)3-381m / z= 663.8200 (C 50 H 33 NO, 663.2562)3-390m / z= 778.9550 (C 58 H 38 N2O, 778.2984)3-393m / z= 668.8505 (C 50 H 28 D5NO, 668.2876)3-394m / z= 672.8749 (C 50 H 24 D9NO, 672.3127)3-395m / z= 676.8993 (C 50 H 20 D 13 NO, 676.3378)3-396m / z= 697.0214 (C 50 D 33 NO, 696.4633)

[0557]

[0558] Experimental Example 1.

[0559] Experimental Example 1-1. Fabrication of an Organic Light-Emitting Device

[0560] A glass substrate coated with a 1,500 Å thick ITO film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) for 5 minutes using UV (Ultraviolet) in a UV (Ultraviolet) cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), and plasma treated in a vacuum to increase the ITO work function and remove residual films, and then transferred to a thermal evaporation equipment for organic vapor deposition.

[0561] On the above ITO transparent electrode (anode), 4,4',4''-tris[2-naphthyl(phenyl)amino] triphenylamine (2-TNATA) was deposited as a hole injection layer and N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was deposited as a hole transport layer.

[0562]

[0563] On top of that, a light-emitting layer was thermally vacuum deposited as follows. The light-emitting layer was deposited with a compound described in Table 11 as a red host, and (piq)2(Ir)(acac) was used as a red phosphorescent dopant, and the host was doped with 3 wt% of (piq)2(Ir)(acac) to deposit a thickness of 400 Å.

[0564] Afterwards, BPhen was deposited with a thickness of 30 Å as a hole blocking layer, and Alq3 was deposited with a thickness of 250 Å as an electron transport layer thereon. Finally, lithium fluoride (LiF) was deposited with a thickness of 10 Å on the electron transport layer to form an electron injection layer, and then aluminum (Al) was deposited with a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby manufacturing an organic electroluminescent device.

[0565]

[0566]

[0567] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -6 ~10 -8 It was purified by vacuum sublimation under 10 torr and used in the production of OLED (Organic Light Emitting Device).

[0568]

[0569] Experimental Example 1-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Devices

[0570] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using M7000 from MaxScience, and the standard luminance was determined to be 6,000 cd / m using the lifespan measurement equipment (M6000) manufactured by MaxScience based on the measurement results. 2 When, T 90 The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention are shown in Table 11 below.

[0571] The above T 90 refers to the lifespan (unit: hours), which is the time it takes for the initial brightness to drop to 90%.

[0572]

[0573] Light-emitting layer Turn-on (V) Driving voltage (V) Efficiency (cd / A) Color coordinate (x, y) Lifespan (T 90) Comparative Example 1A4.256.8520.50(0.684, 0.316)5 Comparative Example 2B4.226.8120.78(0.684, 0.316)5 Comparative Example 3C4.096.6820.78(0.684. 0.316)7 Comparative Example 4D4.066.6521.00(0.685. 0.315)5 Comparative Example 5E4.276.8820.08(0.685, 0.315)5 Comparative Example 6F3.806.4118.50(0.685, 0.315)5 Comparative Example 7G3.706.3113.00(0.685, 0.315)5 Comparative Example 8H3.556.0815.58(0.685, 0.315)8Comparative example 9I3.305.8226.10(0.684. 0.316)8Comparative example 10J3.676.2022.11(0.684, 0.316)5Comparative example 11K3.656.1722.50(0.684. 0.316)5Comparative example 12L3.506.0025.15(0.685. 0.315)8Comparative example 13M3.556.0622.99(0.684. 0.316)5Comparative example 14N3.606.1124.80(0.684. 0.316)5Comparative example 153-1473.507.1114.00(0.684. 0.316)1Comparative Example 163-3543.356.9516.01(0.684, 0.316)1Example 11-12.625.0458.72(0.685. 0.315)40Example 21-22.594.9860.33(0.685, 0.315)33Example 31-32.574.9560.91(0.685, 0.315)27Example 41-42.805.2253.10(0.684. 0.316)20 Example 51-52.70 5.15 5.10 (0.684, 0.316)25 Example 61-62.67 5.07 5.623 (0.684, 0.316)22 Example 71-72.65 5.04 5.700 (0.684, 0.316)20 Example 81-82.88 5.29 5.05 (0.685, 0.315)20 Example 91-92.62 5.06 5.35 (0.685, 0.315)40 Example 101-102.60 5.03 5.43 (0.685, 0.315)32 Example 111-112.574.9955.42(0.685, 0.315)26Example 121-122.825.2650.10(0.684. 0.316)20Example 131-132.585.0157.00(0.685, 0.315)38Example 141-142.554.9858.65(0.684. 0.316)31Example 151-152.524.9460.25(0.685, 0.315)25Example 161-162.755.2052.22(0.684. 0.316)20Example 171-172.544.9758.91(0.685, 0.315)33Example 181-182.514.9360.51(0.684. 0.316)28Example 191-192.494.9061.05(0.685, 0.315)23Example 201-202.715.1453.35(0.684, 0.316)20Example 211-212.755.1950.65(0.684, 0.316)25Example 221-222.725.1651.33(0.684, 0.316)20Example 231-232.695.1252.21(0.684, 0.316)20Example 241-242.915.3246.89(0.685, 0.315)20Example 251-252.755.2052.10(0.684, 0.316)22 Example 261-262.735.1753.30(0.684, 0.316)20 Example 271-292.785.2749.12(0.684, 0.316)22 Example 281-302.775.2549.99(0.685, 0.315)20 Example 291-332.685.0953.55(0.685, 0.315)30 Example 301-342.655.0554.39(0.684, 0.316)26 Example 311-372.625.0255.32(0.685, 0.315)27Example 321-382.594.9956.28(0.684, 0.316)23Example 331-412.805.2348.60(0.684, 0.316)22Example 341-422.785.1849.28(0.684, 0.316)20Example 351-452.554.9458.99(0.685, 0.315)32Example 361-462.534.9161.35(0.684, 0.316)23Example 371-492.715.1353.95(0.684, 0.316)40 Example 381-502.685.1154.68(0.684, 0.316)35Example 391-532.605.0256.10(0.684, 0.316)32Example 401-542.524.9558.39(0.684, 0.316)27Example 411-572.514.9259.28(0.685, 0.315)27Example 421-582.444.8561.55(0.684, 0.316)23Example 431-612.755.1550.99(0.685, 0.315)20Example 441-622.735.1351.50(0.684, 0.316)20Example 451-652.524.9460.11(0.684, 0.316)30Example 461-662.504.9162.49(0.684, 0.316)20Example 471-692.554.9955.13(0.684, 0.316)35Example 481-702.514.9355.95(0.685, 0.315)31Example 491-732.494.9057.12(0.685, 0.315)20Example 501-742.454.8560.50(0.685, 0.315)20Example 511-772.444.8460.00(0.685, 0.315)25Example 521-782.404.8062.55(0.684, 0.316)20Example 531-812.625.0555.81(0.685, 0.315)20Example 541-822.595.0156.90(0.684, 0.316)20Example 551-852.835.2454.88(0.684, 0.316)26Example 561-862.805.2055.67(0.685. 0.315)23Example 571-892.885.3050.98(0.685, 0.315)20Example 581-902.875.2751.87(0.685, 0.315)20Example 591-932.785.2054.30(0.685, 0.315)25Example 601-942.755.1854.99(0.684, 0.316)20Example 611-972.755.1555.00(0.684, 0.316)23Example 621-982.715.1155.91(0.684, 0.316)20Example 631-1012.705.1155.85(0.684. 0.316)21 Example 641-1022.695.09.56.85(0.685. 0.315)20 Example 651-1052.855.2751.33(0.685, 0.315)20 Example 661-1062.845.2552.00(0.685, 0.315)20 Example 671-1092.705.1155.78(0.685, 0.315)25 Example 681-1102.665.0856.52(0.684. 0.316)21 Example 691-1132.805.2050.05(0.685, 0.315)30Example 701-1142.785.1850.65(0.684, 0.316)25Example 711-1172.695.1052.85(0.684. 0.316)27Example 721-1182.675.0753.50(0.685. 0.315)22Example 731-1212.615.0155.95(0.685, 0.315)22Example 741-1222.584.9856.71(0.685, 0.315)20Example 751-1252.855.2648.10(0.685, 0.315)20 Example 761-1262.835.2348.99(0.684. 0.316)20 Example 771-1292.685.0856.89(0.684, 0.316)26 Example 781-1302.655.0557.51(0.684, 0.316)22 Example 791-1332.755.1552.87(0.685, 0.315)27 Example 801-1342.715.1153.80(0.684, 0.316)24 Example 811-1372.675.0853.91(0.684. 0.316)24 Example 821-1382.655.0554.65(0.685. 0.315)21 Example 831-1412.605.0057.00(0.685, 0.315)22 Example 841-1422.574.9857.71(0.685, 0.315)20 Example 851-1452.805.2249.95(0.685, 0.315)20 Example 861-1462.785.1850.66(0.684. 0.316)20 Example 871-1493.005.4344.30(0.684. 0.316)20 Example 881-1502.975.3944.58(0.685. 0.315)20 Example 891-1532.935.3547.60(0.685, 0.315)21 Example 901-1542.915.3347.85(0.685, 0.315)20 Example 911-1572.925.3345.95(0.685, 0.315)22 Example 921-1582.905.3146.77(0.684, 0.316)20 Example 931-1612.885.3046.88(0.684, 0.316)20 Example 941-1622.855.2547.50(0.684, 0.316)20 Example 951-1652.855.2647.77(0.684. 0.316)20 Example 961-1662.825.2248.55(0.685. 0.315)20 Example 971-1692.975.3843.88(0.685, 0.315)20 Example 981-1702.955.3544.00(0.685, 0.315)20 Example 991-1732.424.8348.71(0.685, 0.315)60 Example 1001-1742.394.7950.32(0.685, 0.315)53Example 1011-1752.374.7750.93(0.685, 0.315)47Example 1021-1762.625.0342.95(0.684. 0.316)39Example 1031-1772.504.9345.10(0.684, 0.316)45Example 1041-1782.464.8656.35(0.684, 0.316)42Example 1051-1792.444.8547.12(0.684. 0.316)38Example 1061-1802.695.1240.02(0.685. 0.315)20Example 1071-1812.434.8543.60(0.685, 0.315)60Example 1081-1822.404.8144.35(0.685, 0.315)52Example 1091-1852.344.7548.92(0.684, 0.316)53Example 1101-1862.304.7150.00(0.684, 0.316)47Example 1111-1892.554.9740.65(0.684, 0.316)44Example 1121-1902.534.9541.35(0.685. 0.315)38 Example 1131-1932.554.9642.10(0.685, 0.315)40Example 1141-1942.534.9443.25(0.685, 0.315)37Example 1151-1972.484.9043.54(0.685, 0.315)50Example 1161-1982.464.8744.38(0.684, 0.316)46Example 1171-2012.424.8345.31(0.684, 0.316)47Example 1181-2022.394.8046.28(0.684, 0.316)43Example 1191-2052.605.0038.95(0.684. 0.316)40Example 1201-2062.584.9839.40(0.685. 0.315)37Example 1211-2092.514.9243.92(0.685, 0.315)60Example 1221-2102.484.8944.60(0.685, 0.315)54Example 1231-2132.414.8146.21(0.685, 0.315)62Example 1241-2142.324.7348.31(0.684. 0.316)57Example 1251-2172.554.9940.89(0.684, 0.316)30Example 1261-2182.524.9541.55(0.684, 0.316)20Example 1271-2772.524.9453.35(0.684, 0.316)50Example 1281-2782.494.9155.23(0.685, 0.315)43Example 1291-2792.474.8855.92(0.685, 0.315)38Example 1301-2802.705.1147.25(0.685, 0.315)25Example 1311-2812.615.0250.25(0.685, 0.315)35Example 1321-2822.584.9951.00(0.684, 0.316)31Example 1331-2832.554.9552.01(0.684, 0.316)28Example 1341-2842.785.2044.99(0.684, 0.316)25Example 1351-2852.484.9052.15(0.684, 0.316)48Example 1361-2862.454.8653.45(0.685, 0.315)41Example 1371-2892.444.8553.81(0.685, 0.315)41 Example 1381-2902.414.8155.15(0.685, 0.315)36 Example 1391-2932.655.0845.66(0.685, 0.315)35 Example 1401-2942.625.0346.33(0.684, 0.316)20 Example 1411-2972.655.0647.25(0.684, 0.316)25 Example 1421-2982.635.0548.30(0.684, 0.316)20 Example 1431-301 2.58 5.00 48.55 (0.684, 0.316) 40 Example 1441-302 2.55 4.97 49.38 (0.685, 0.315) 36 Example 1451-305 2.52 4.93 50.32 (0.685, 0.315) 37 Example 1461-306 2.49 4.90 51.25 (0.685, 0.315) 33 Example 1471-385 2.32 4.73 45.71 (0.685, 0.315) 70 Example 1481-386 2.29 4.70 47.32 (0.684, 0.316) 64 Example 1491-3872.284.6947.88(0.685, 0.315)57 Example 1501-3882.504.9540.10(0.685, 0.315)40 Example 1511-3892.404.8242.11(0.685, 0.315)55 Example 1521-3902.374.7843.23(0.684, 0.316)52 Example 1531-3912.354.7644.11(0.684, 0.316)48 Example 1541-3922.585.0037.18(0.684, 0.316)40 Example 1551-3932.284.7044.02(0.684. 0.316)68 Example 1561-3942.254.6545.25(0.685. 0.315)61 Example 1571-3972.244.6645.91(0.685, 0.315)63 Example 1581-3982.214.6247.10(0.685, 0.315)58 Example 1591-4012.454.8737.78(0.685, 0.315)55 Example 1601-4022.424.8538.91(0.684. 0.316)40 Example 1611-4052.354.7739.20(0.684, 0.316)52 Example 1621-4062.334.7440.32(0.684, 0.316)50 Example 1631-4092.384.7940.55(0.684. 0.316)60 Example 1641-4102.354.7641.38(0.685. 0.315)55 Example 1651-4132.324.7442.33(0.685, 0.315)57 Example 1661-4142.294.7043.28(0.685, 0.315)53 Example 1671-4172.504.9135.61(0.685, 0.315)52 Example 1681-4182.484.8936.30(0.685, 0.315)50 Example 1691-4932.635.0658.18(0.684, 0.316)43 Example 1701-4942.645.0757.80(0.685, 0.315)46 Example 1711-4952.655.0857.50(0.684, 0.316)48 Example 1721-4962.635.0558.45(0.684, 0.316)40 Example 1731-4972.625.0458.55(0.684, 0.316)40 Example 1741-4982.625.0458.56(0.684, 0.316)40 Example 1751-4992.625.0259.01(0.685, 0.315)40 Example 1761-5002.605.0159.60(0.685, 0.315)33 Example 1771-5012.835.2651.85(0.685, 0.315)23 Example 1781-5022.745.2053.79(0.685, 0.315)29 Example 1791-503 2.70 5.12 54.95 (0.684, 0.316) 25 Example 1801-504 2.68 5.09 55.68 (0.684, 0.316) 23 Example 1811-505 2.61 5.05 55.71 (0.684, 0.316) 45 Example 1821-506 2.58 5.02 57.20 (0.684, 0.316) 38 Example 1831-507 2.54 4.97 59.00 (0.685, 0.315) 29 Example 1841-508 2.79 5.25 50.85 (0.685, 0.315) 22 Example 1851-5092.575.0157.60(0.685, 0.315)40 Example 1861-5102.544.9759.10(0.685, 0.315)33 Example 1871-5112.524.9459.70(0.685, 0.315)27 Example 1881-5122.755.2052.00(0.685, 0.315)22 Example 1891-5132.454.9247.30(0.685, 0.315)73 Example 1901-5142.424.8349.30(0.684, 0.316)61 Example 1911-5152.404.8149.59(0.684, 0.316)57Example 1921-5162.665.0841.60(0.684, 0.316)45Example 1931-5292.554.9952.01(0.684, 0.316)60Example 1941-5302.524.9553.89(0.685, 0.315)51Example 1951-5312.504.9254.59(0.685, 0.315)45Example 1961-5322.745.1645.80(0.685, 0.315)28Example 1971-5452.354.7644.41(0.685, 0.315)85 Example 1981-5462.324.7346.00(0.684, 0.316)70 Example 1991-5472.314.7246.58(0.684, 0.316)61 Example 2001-5482.545.0038.85(0.684, 0.316)46.

[0574]

[0575] [Comparative example compound]

[0576]

[0577]

[0578] Experimental example 2.

[0579] Experimental Example 2-1. Fabrication of an Organic Light-Emitting Device

[0580] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the light-emitting layer was deposited from a single source after preliminarily mixing one type of first host (heterocyclic compound represented by Chemical Formula 1) and one type of second host (heterocyclic compound represented by Chemical Formula 3) described in Table 12 below.

[0581]

[0582] Experimental Example 2-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Devices

[0583] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using M7000 from MaxScience, and the standard luminance was determined to be 6,000 cd / m using the lifespan measurement equipment (M6000) manufactured by MaxScience based on the measurement results. 2 When, T 90 The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention are shown in Table 12 below.

[0584] The above T 90 refers to the lifespan (unit: hours), which is the time it takes for the initial brightness to drop to 90%.

[0585]

[0586] 1st host 2nd host ratio Turn-on driving voltage efficiency color coordinate lifespan (N) (P) (N:P) (V) (V) (cd / A) (x, y) (T 90) Comparative Example 17A3-3541: 13.906.4025.55(0.684. 0.316)7 Comparative Example 18I3-3541: 13.205.71.28.00(0.684, 0.316)10 Comparative Example 19K3-3541: 13.606.1123.55(0.684. 0.316)7 Comparative Example 20L3-3541: 13.445.9226.38(0.684. 0.316)10 Example 2011-13-3541: 82.654.8745.00(0.684. 0.316)70 Example 2021-13-3541: 62.504.7556.75(0.685, 0.315) 100 Example 2031-13-3541: 42.474.7059.95(0.685, 0.315) 200 Example 2041-13-3541: 22.434.6561.55(0.685, 0.315) 350 Example 2051-13-3541: 12.424.6362.72(0.685, 0.315) 400 Example 2061-13-3542: 12.414.6162.71(0.685, 0.315) 410 Example 2071-13-3544:12.424.6461.20(0.685, 0.315)380 Example 2081-13-3546:12.454.6759.05(0.684. 0.316)300 Example 2091-13-3548:12. 514.7358.77(0.684, 0.316)185 Example 2101-13-51:12.304.5059.35(0.684, 0.316)150 Example 2111-13-1471:12.354.5560.27(0.684, 0.316)285 Example 2121-11-2341:12.504.7361.00(0.685, 0.315)100 Example 2131-13-3521:12.444.6561.85(0.685, 0.315)335 Example 2141-13-3901:12.324.5262.65(0.685, 0.315)250 Example 2151-13-3811:12.424.6362.30(0.685, 0.315)380 Example 2161-13-3931:12.434.6462.27(0.684, 0.316)380 Example 2171-13-3941:12.444.6561.85(0.684. 0.316)420 Example 2181-13-3951:12.444.6561.80(0.685, 0.315)425 Example 2191-13-3961:12.464.6661.00(0.685, 0.315)500 Example 2201-23-3541:12.404.6063.85(0.685, 0.315)465 Example 2211-33-3541:12.394.6064.65(0.685, 0.315)420 Example 2221-43-3541:12.654.9355.15(0.684, 0.316)250 Example 2231-693-3541:12.354.5758.10(0.684. 0.316)300 Example 2241-773-3541:12.314.5268.88(0.685. 0.315)250 Example 2251-783-3541:12.304.5070.98(0.685, 0.315)215 Example 2261-1733-3541:12.234.4351.00(0.685, 0.315)700 Example 2271-1743-3541:12.224.4252.00(0.685, 0.315)630Example 2281-2773-3541:12.324.5255.35(0.684, 0.316)520Example 2291-2783-3541:12.314.5157.31(0.684. 0.316)445Example 2301-3853-3541:12.154.3348.00(0.685. 0.315)850.

[0587]

[0588] Comparative examples Compounds A to E are dibenzofuran substituted with a carbazolyl group. The HOMO level is higher than that of compounds substituted with an aryl group, dibenzofuranyl group, or dibenzothiophenyl group on dibenzofuran, and thus have an energy level that is not suitable for the light-emitting layer region. Since the energy level of the heterocyclic compound represented by Chemical Formula 1 of the present invention is suitable for use together with the heterocyclic compound represented by Chemical Formula 3 in the light-emitting layer, the organic light-emitting device can have low driving voltage, high efficiency, and lifespan characteristics.

[0589] In addition, comparative compounds F, G, H, J, K, L, and M are compounds in which one heteroaryl group is substituted on dibenzofuran or dibenzothiophene, or compounds in which an aryl group is substituted, excluding a triazine group. The heterocyclic compound represented by chemical formula 1 of the present invention has a more expanded conjugation than the comparative compound, so that charge conduction is faster and charges can be effectively injected into the light-emitting layer.

[0590] Comparative example compound I is one in which a heteroaryl group, dibenzofuran, is substituted at the 2nd position of dibenzofuran. Compared to the heterocyclic compound 1-61 represented by the chemical formula 1 of the present invention, the conjugation is distorted, charge conduction is slow, so that charges cannot be effectively injected into the light-emitting layer, driving is slow, and efficiency is reduced. Comparative example compound N is one in which a triazine group is substituted at the 1st position of dibenzofuran, and dibenzofuran-dibenzofuran is substituted at the 2nd position, so that the conjugation is distorted. Therefore, the charge conductivity is reduced, and accordingly, the driving voltage is high, and the lifetime characteristics and luminous efficiency are very low.

[0591]

[0592] As shown in the results in Table 11 above, the heterocyclic compound represented by Chemical Formula 1 of the present invention has expanded conjugation compared to the comparative example compound, and thus has high thermal stability while also having an appropriate molecular weight and band gap. The appropriate band gap of the light-emitting layer can improve the electron transport ability and help form an effective recombination zone within the light-emitting layer. Therefore, it can be seen that the example including the heterocyclic compound represented by Chemical Formula 1 of the present invention has a lower driving voltage and superior luminous efficiency and lifespan compared to the comparative example.

[0593] In addition, in the results in Table 12 above, when the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 3 were used together in the light-emitting layer, the driving voltage was lowered and the luminous efficiency and lifespan were increased compared to when the heterocyclic compound represented by Chemical Formula 1 was used alone. This shows that when an acceptor (n-host, Chemical Formula 1) with good electron transport ability and a donor (p-host, Chemical Formula 3) with good hole transport ability are used as co-hosts in the light-emitting layer, electrons and holes can be smoothly injected into the light-emitting layer, which can lower the driving voltage and form an effective recombination zone, thereby improving the luminous efficiency and lifespan characteristics.

[0594]

[0595] Experimental Example 3.

[0596] Experimental Example 3-1. Fabrication of an Organic Light-Emitting Device

[0597] A glass substrate coated with a 1,500 Å thick ITO film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) for 5 minutes using UV (Ultraviolet) in a UV (Ultraviolet) cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), and plasma treated in a vacuum to increase the ITO work function and remove residual films, and then transferred to a thermal evaporation equipment for organic vapor deposition.

[0598] On the above ITO transparent electrode (anode), 4,4',4''-tris[2-naphthyl(phenyl)amino] triphenylamine (2-TNATA) is used as a hole injection layer, N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) is used as a hole transport layer, and cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine] (TAPC) is used as an electron blocking layer or Tris(4-carbazoyl-9-ylphenyl)amine (Tris(4-carbazoyl-9-ylphenyl)amine) is used as an exciton blocking layer. TCTA) was deposited.

[0599]

[0600]

[0601] On top of that, a light-emitting layer was thermally vacuum deposited as follows. The light-emitting layer was deposited with a compound described in Table 13 as a red host, and (piq)2(Ir)(acac) was used as a red phosphorescent dopant, and the host was doped with 3 wt% of (piq)2(Ir)(acac) to deposit a thickness of 400 Å.

[0602] The above light-emitting layer was manufactured by depositing the compound described in Table 13 below as a host alone, or by preliminarily mixing one type of first host (heterocyclic compound represented by Chemical Formula 1) and one type of second host (heterocyclic compound represented by Chemical Formula 3) described in Table 13 below as hosts and then depositing them from one source.

[0603] Afterwards, BPhen was deposited as a hole blocking layer with a thickness of 30 Å, and TPBI was deposited as an electron transport layer with a thickness of 250 Å. Finally, lithium fluoride (LiF) was deposited on the electron transport layer with a thickness of 10 Å to form an electron injection layer, and then aluminum (Al) was deposited on the electron injection layer with a thickness of 1,200 Å to form a cathode, thereby manufacturing an organic electroluminescent device.

[0604]

[0605] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -6 ~10 -8 It was purified by vacuum sublimation under 10 torr and used in the production of OLED (Organic Light Emitting Device).

[0606]

[0607] Experimental Example 3-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Devices

[0608] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using M7000 from MaxScience, and the standard luminance was determined to be 6,000 cd / m using the lifespan measurement equipment (M6000) manufactured by MaxScience based on the measurement results. 2 When, T 90 The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention are shown in Table 13 below.

[0609] The above T 90 refers to the lifespan (unit: hours), which is the time it takes for the initial brightness to drop to 90%.

[0610]

[0611] 1st host 2nd host ratio Turn-on driving voltage efficiency color coordinate lifespan (N) (P) (N:P) (V) (V) (cd / A) (x, y) (T90 ) Comparative Example 21A--4.306.9021.60(0.684, 0.316)6 Comparative Example 22C--4.156.7121.15(0.684. 0.316)8 Comparative Example 23L--3.556.0725.35(0.685. 0.315)9 Comparative Example 24L3-3541:13.505.9726.50(0.685, 0.315)11 Example 2311-1--2.655.0760.00(0.685, 0.315)50 Example 2321-2--2.635.0161.71(0.685, 0.315)42 Example 2331-3--2.594.9762.10(0.684, 0.316)33 Example 2341-4--2.855.2855.00(0.684. 0.316)25 Example 2351-173--2.454.8850.33(0.685. 0.315)75 Example 2361-174--2.424.8251.71(0.685, 0.315)66 Example 2371-277--2.554.9555.00(0.685, 0.315)61 Example 2381-278--2.524.9656.91(0.685, 0.315)54 Example 2391-385--2.354.7747.15(0.684, 0.316)89 Example 2401-386--2.314.7449.11(0.684. 0.316)79 Example 2411-13-3541:12.454.6764.00(0.685. 0.315)540 Example 2421-23-3541:12.434.6365.15(0.685, 0.315)600 Example 2431-43-3541:12.684.9656.95(0.685, 0.315)270 Example 2441-1733-3541:12.264.4952.55(0.685, 0.315)810 Example 2451-2773-3541:12.354.5857.00(0.684, 0.316)650 Example 2461-3853-3541:12.194.4049.51(0.684, 0.316)1050

[0612]

[0613] [Comparative example compound]

[0614]

[0615] The organic light-emitting device of Experimental Example 3 is an organic light-emitting device including an electron-blocking layer or an exciton-blocking layer, and by including the same, the organic light-emitting device including the heterocyclic compound represented by Chemical Formula 1 of the present invention, or the heterocyclic compounds represented by Chemical Formulas 1 and 3, can effectively form electrons inside the light-emitting layer, and thus it can be seen that an organic light-emitting device having improved light-emitting efficiency and lifespan characteristics can be obtained. On the other hand, when the comparative example compound is included, it can be seen that it is difficult to form electrons inside the light-emitting layer, and thus it has a high driving voltage, low light-emitting efficiency, and low lifespan characteristics.

[0616]

[0617] [Explanation of symbols]

[0618] 100: Substrate

[0619] 200: Bipolar

[0620] 300: Organic layer

[0621] 301: Hole injection layer

[0622] 302: Hole transport layer

[0623] 303: Emissive layer

[0624] 304: Hole blocking layer

[0625] 305: Electron transport layer

[0626] 306: Electron injection layer

[0627] 400: Cathode

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, The above X1 and X2 are the same or different from each other, and are each independently O; or S, wherein R1 to R9 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; And -NR101R102, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, The above a, e and g are the same as or different from each other, and are each independently an integer from 0 to 4, and when a is 2 or more, R1 is the same as or different from each other, when e is 2 or more, R7 is the same as or different from each other, and when g is 2 or more, R9 is the same as or different from each other, The above b and c are equal to or different from each other, and are each independently an integer from 0 to 5, and when the above b is 2 or more, R4 are equal to or different from each other, and when the above c is 2 or more, R5 are equal to or different from each other, The above d and f are the same as or different from each other, and are each independently an integer from 0 to 3. When the above d is 2 or more, R6 is the same as or different from each other, and when the above f is 2 or more, R8 is the same as or different from each other.

2. In paragraph 1, The heterocyclic compound represented by the above chemical formula 1 is a heterocyclic compound represented by the following chemical formula 1-1 or 1-2: [Chemical Formula 1-1] [Chemical Formula 1-2] In the above chemical formulas 1-1 and 1-2, The above h is an integer from 0 to 2, and when the above h is 2 or greater, R6 are the same or different from each other, The above i is an integer from 0 to 3, and when the above i is 2 or greater, R7 are equal to or different from each other, The above X1, X2, R1 to R9 and a to g are the same as defined in the above chemical formula 1.

3. In paragraph 1, A heterocyclic compound wherein R1 to R9 are the same or different and each independently represent hydrogen or deuterium.

4. In paragraph 1, The heterocyclic compound represented by the above chemical formula 1 is a heterocyclic compound that does not contain deuterium as a substituent or has a deuterium content of 1% to 100% with respect to the total number of hydrogen atoms and deuterium atoms.

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

6. First electrode; A second electrode provided opposite to the first electrode; and An organic light-emitting device comprising 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 a heterocyclic compound according to any one of claims 1 to 5.

7. In paragraph 6, The above organic layer includes a light-emitting layer, An organic light-emitting device, wherein the light-emitting layer comprises a heterocyclic compound according to any one of claims 1 to 5.

8. In paragraph 6, An organic light-emitting device, wherein the organic layer further comprises a heterocyclic compound represented by the following chemical formula 3: [Chemical Formula 3] In the above chemical formula 3, The above R21, R23 and R25 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; And -NR201R202, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R201, R202 and R203 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, The above j is an integer from 0 to 4, and when the above j is 2 or more, R21 are equal to or different from each other, The above k is an integer from 0 to 3, and when the above k is 2 or more, R25 are equal to or different from each other, The above R22 and R24 are different from each other and are represented by the following chemical formula 4 or chemical formula 5, [Chemical Formula 4] [Chemical Formula 5] In the above chemical formulas 4 and 5, The above L1 to L4 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, The above l is an integer from 0 to 5, and when the above l is 2 or more, L1 is equal to or different from each other, The above m is an integer from 0 to 5, and when the above m is 2 or greater, L2 are equal to or different from each other, The above n is an integer from 0 to 5, and when the above n is 2 or greater, L3 are equal to or different from each other, The above o is an integer from 0 to 5, and when the above o is 2 or more, L4 are equal to or different from each other, The above Ar1 to Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

9. In paragraph 8, The heterocyclic compound represented by the above chemical formula 3 is an organic light-emitting device represented by the following chemical formula 3-1 or 3-2: [Chemical Formula 3-1] [Chemical Formula 3-2] In the above chemical formulas 3-1 and 3-2, The above R21, R23, R25, j and k are the same as the definitions in the above chemical formula 3, The above L1 to L3, Ar1, Ar2 and l to n are the same as the definitions in the above chemical formula 4, The above L4, Ar3 and o are the same as defined in the above chemical formula 5.

10. In paragraph 8, The above organic layer includes a light-emitting layer, An organic light-emitting device, wherein the light-emitting layer comprises a heterocyclic compound according to any one of claims 1 to 5 and a heterocyclic compound represented by the chemical formula 3.

11. In paragraph 8, The heterocyclic compound represented by the above chemical formula 3 is an organic light-emitting device represented by any one of the following compounds: .

12. In paragraph 8, An organic light-emitting device in which the heterocyclic compound represented by the above chemical formula 3 does not contain deuterium as a substituent or has a deuterium content of 1% to 100% with respect to the total number of hydrogen atoms and deuterium atoms.

13. In paragraph 6, An organic light-emitting device, wherein the organic light-emitting device further comprises 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.

14. A composition for an organic layer comprising a heterocyclic compound according to any one of claims 1 to 5 and a heterocyclic compound represented by the following chemical formula 3: [Chemical Formula 3] In the above chemical formula 3, The above R21, R23 and R25 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; And -NR201R202, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R201, R202 and R203 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, The above j is an integer from 0 to 4, and when the above j is 2 or more, R21 are equal to or different from each other, The above k is an integer from 0 to 3, and when the above k is 2 or more, R25 are equal to or different from each other, The above R22 and R24 are different from each other and are represented by the following chemical formula 4 or chemical formula 5, [Chemical Formula 4] [Chemical Formula 5] In the above chemical formulas 4 and 5, The above L1 to L4 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, The above l is an integer from 0 to 5, and when the above l is 2 or more, L1 is equal to or different from each other, The above m is an integer from 0 to 5, and when the above m is 2 or greater, L2 are equal to or different from each other, The above n is an integer from 0 to 5, and when the above n is 2 or greater, L3 are equal to or different from each other, The above o is an integer from 0 to 5, and when the above o is 2 or more, L4 are equal to or different from each other, The above Ar1 to Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

15. In paragraph 14, A composition for an organic layer, wherein the weight ratio of the heterocyclic compound represented by the above chemical formula 1 to the heterocyclic compound represented by the above chemical formula 3 is 1:9 to 9:1.

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