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

Abstract

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

Description

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

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

[0002] This application claims the benefit of Korean Patent Application No. 10-2023-0087779, filed with the Korean Intellectual Property Office on July 6, 2023, the entire contents of which are incorporated herein by reference.

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

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

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

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

[0007] <Prior Art Literature>

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

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

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

[0011] [Chemical Formula 1]

[0012]

[0013] In the above chemical formula 1,

[0014] L and L1 to L3 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0015] l, l1 and l2 are each integers from 1 to 3, and if each is 2 or greater, the substituents in the parentheses are the same or different,

[0016] Ar1 and Ar2 are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0017] R is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0018] r is an integer from 1 to 4, and when r is 2 or greater, L3 and R are each equal or different,

[0019] H1 is hydrogen; or deuterium, and if r is 2 or less, H1 is the same or different,

[0020] Y is O; S; C(R10)(R11) or N(R12),

[0021] R1 to R12 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0022] At least one of R1 to R9 is deuterium,

[0023] q is 1 or 2, and if q is 2, R5 is equal or different.

[0024] In another embodiment of the present specification, an organic light-emitting device is provided, comprising: a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers includes at least one type of the heterocyclic compound.

[0025] In another embodiment of the present specification, a composition for forming an organic layer of an organic light-emitting device comprising the heterocyclic compound is provided.

[0026] The heterocyclic compound described herein, when used in an organic light-emitting device, can lower the operating voltage of the device, improve the luminous efficiency, and enhance the lifespan characteristics of the device. Specifically, the heterocyclic compound of the present invention includes a structure in which a carbazole condensed derivative substituent and a triazine group are bonded by a linker including a substituted phenylene group, as shown in Chemical Formula 1, wherein the carbazole condensed derivative substituent includes at least one deuterium, thereby including the substituent at the ortho position. The linker appropriately separates the HOMO electron cloud distributed in the condensed carbazole and the LUMO electron cloud distributed in the triazine derivative, thereby forming a more stable exciton than a compound without a substituent. In addition, one or more substituted deuterium atoms are heavier than light hydrogen and have lower molecular vibrational energy, so that they can exhibit a lifespan-enhancing effect when applied to a device.

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

[0028] <Explanation of symbols>

[0029] 100: Substrate

[0030] 200: Bipolar

[0031] 300: Organic layer

[0032] 301: Hole injection layer

[0033] 302: Hole transport layer

[0034] 303: Emissive layer

[0035] 304: Hole blocking layer

[0036] 305: Electron transport layer

[0037] 306: Electron injection layer

[0038] 400: Cathode

[0039] In the above, the terphenyl group can be selected from the following structures.

[0040]

[0041] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0042] When the above fluorenyl group is substituted, the structures below can be formed, but are not limited thereto.

[0043]

[0044] In the present specification, a heteroaryl group includes S, O, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic ring means a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms.Specific examples of the above heteroaryl group include a pyridine group, a pyrrole group, a pyrimidine group, a pyridazine group, a furan group, a thiophene group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, a triazole group, a furazan group, an oxadiazole group, a thiadiazole group, a dithiazole group, a tetrazolyl group, a pyran group, a thiopyran group, a diazine group, an oxazine group, a thiazine group, a dioxin group, a triazine group, a tetrazine group, a quinoline group, an isoquinoline group, a quinazoline group, an isoquinazoline group, a quinozoline group, a naphthyridine group, an acridine group, a phenanthridine group, an imidazopyridine group, a diazanaphthalene group, a triazaindene group, an indole group, an indolizine group, a benzothiazole group, Benzoxazole group, benzimidazole group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazole group, benzocarbazole group, dibenzocarbazole group, phenazine group, dibenzosilole group, spirobi(dibenzosilole), dihydrophenazine group, phenoxazine group, phenanthridine group, thienyl group, indolo[2,3-a]carbazole group, indolo[2,3-b]carbazole group, indoline group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridine group, phenanthrazine group, phenothiathiazine group, phthalazine group, phenanthroline group, naphthobenzofuran group, naphthobenzothiophene group, benzo[c][1,2,5]thiadiazole group, Examples thereof include, but are not limited to, 2,3-dihydrobenzo[b]thiophene group, 2,3-dihydrobenzofuran group, 5,10-dihydrodibenzo[b,e][1,4]azacillin group, pyrazolo[1,5-c]quinazoline group, pyrido[1,2-b]indazole group, pyrido[1,2-a]imidazo[1,2-e]indolin group, and 5,11-dihydroindeno[1,2-b]carbazole group.

[0045] In the present specification, the benzocarbazole group may have any of the following structures.

[0046]

[0047] In the present specification, the dibenzocarbazole group may have any of the following structures.

[0048]

[0049] In the present specification, when the substituent is a carbazole group, a benzocarbazole group, or a dibenzocarbazole group, it means that it is bonded to the nitrogen or carbon of the carbazole group, the benzocarbazole group, or the dibenzocarbazole group.

[0050] In the present specification, when a carbazole group, a benzocarbazole group, or a dibenzocarbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole group, the benzocarbazole group, or the dibenzocarbazole group.

[0051] In the present specification, the naphthobenzofuran group may have any of the following structures.

[0052]

[0053] In the present specification, the naphthobenzothiophene group may have any of the following structures.

[0054]

[0055] In the present specification, a silyl group is a substituent that contains Si and is directly connected to the Si atom as a radical, and is represented by -Si(R107)(R108)(R109), and R107 to R109 are the same as or different from each other, and may each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. Specific examples of the silyl group include, but are not limited to, the following structures.

[0056] (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group)

[0057] In the present specification, a phosphine oxide group is represented by -P(=O)(R110)(R111), and R110 and R111 are the same as or different from each other, and can each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. Specifically, it can be substituted with an alkyl group or an aryl group, and the above-described examples can be applied to the alkyl group and the aryl group. For example, the phosphine oxide group includes, but is not limited to, a dimethylphosphine oxide group, a diphenylphosphine oxide group, and dinaphthylphosphine oxide.

[0058] In the present specification, an amine group is represented by -N(R112)(R113), and R112 and R113 are the same as or different from each other, and can each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. The amine group can be selected from the group consisting of -NH2; a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; a dialkylamine group; a diarylamine group; a diheteroarylamine group; an alkylarylamine group; an alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the above amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group.

[0059] In this specification, the description of the aryl group described above may be applied, except that the arylene group is divalent.

[0060] In this specification, the description of the heteroaryl group described above may be applied, except that the heteroarylene group is divalent.

[0061] One embodiment of the present specification provides a heterocyclic compound of the above chemical formula 1.

[0062] In one embodiment of the present specification, L and L1 to L3 of the chemical formula 1 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0063] In one embodiment of the present specification, L may be a direct bond; or a substituted or unsubstituted C6 to C60 arylene group.

[0064] In one embodiment of the present specification, L may be a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

[0065] In one embodiment of the present specification, L may be a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0066] In one embodiment of the present specification, L may be a direct bond; or a substituted or unsubstituted phenylene group.

[0067] In one embodiment of the present specification, L may be a direct bond; or an arylene group having C6 to C40 substituted or unsubstituted with deuterium.

[0068] In one embodiment of the present specification, L may be a direct bond; or a C6 to C20 arylene group substituted or unsubstituted with deuterium.

[0069] In one embodiment of the present specification, L may be a direct bond; or a phenylene group substituted or unsubstituted with deuterium.

[0070] In one embodiment of the present specification, l is the number of repetitions of L and is an integer from 1 to 3, and when l is 2 or more, 2 or more Ls are the same or different.

[0071] For example, if l is 2, it can be represented as -L-L'-, where L' is identical to the definition of L.

[0072] In one embodiment of the present specification, L1 and L2 may each independently be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0073] In one embodiment of the present specification, L1 and L2 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.

[0074] In one embodiment of the present specification, L1 and L2 may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted divalent dibenzofuran group; or a substituted or unsubstituted divalent dibenzothiophene group.

[0075] In one embodiment of the present specification, L1 and L2 may each independently be a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0076] In one embodiment of the present specification, L1 and L2 may each independently be a direct bond; or a substituted or unsubstituted phenylene group.

[0077] In one embodiment of the present specification, L1 and L2 may each independently be a direct bond; a C6 to C20 arylene group; or a C2 to C20 heteroarylene group.

[0078] In one embodiment of the present specification, L1 and L2 may each independently be a direct bond; or a C6 to C20 arylene group.

[0079] In one embodiment of the present specification, l1 is the number of repetitions of L1 and is an integer from 1 to 3, and when l1 is 2 or more, 2 or more L1 are the same or different.

[0080] For example, if l1 is 2, it can be represented as -L1-L1'-, and L1' is identical to the definition of L1.

[0081] In one embodiment of the present specification, l2 is the repetition number of L2 and is an integer from 1 to 3, and when l2 is 2 or more, 2 or more L2 are the same or different.

[0082] For example, if l2 is 2, it can be represented as -L2-L2'-, where L2' is identical to the definition of L2.

[0083] In one embodiment of the present specification, L3 may be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0084] In one embodiment of the present specification, L3 may be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0085] In one embodiment of the present specification, L3 may be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted divalent dibenzofuran group; or a substituted or unsubstituted divalent dibenzothiophene group.

[0086] In one embodiment of the present specification, L3 may be a direct bond; a C6 to C20 arylene group substituted or unsubstituted with deuterium; or a C2 to C20 heteroarylene group substituted or unsubstituted with deuterium.

[0087] In one embodiment of the present specification, Ar1 and Ar2 of the chemical formula 1 are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0088] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0089] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0090] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0091] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group.

[0092] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a C6 to C20 aryl group substituted or unsubstituted with an alkyl group; or a C2 to C20 heteroaryl group substituted or unsubstituted with an aryl group.

[0093] In one embodiment of the present specification, Ar1 and Ar2 may each independently be a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a dimethylfluorenyl group; a triphenylene group; a dibenzofuran group substituted or unsubstituted with a phenyl group; a dibenzothiophene group substituted or unsubstituted with a phenyl group; or a carbazole group substituted or unsubstituted with a phenyl group.

[0094] In one embodiment of the present specification, Ar1 may be a phenyl group; a biphenyl group; a naphthyl group; or a carbazole group substituted or unsubstituted with a phenyl group.

[0095] In one embodiment of the present specification, Ar1 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted carbazole group.

[0096] In one embodiment of the present specification, Ar2 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 dimethylfluorenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group.

[0097] In one embodiment of the present specification, Ar2 may be a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a dimethylfluorenyl group; a triphenylene group; a dibenzofuran group substituted or unsubstituted with a phenyl group; a dibenzothiophene group substituted or unsubstituted with a phenyl group; or a carbazole group substituted or unsubstituted with a phenyl group.

[0098] In one embodiment of the present specification, R in the chemical formula 1 is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0099] In one embodiment of the present specification, R may be a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0100] In one embodiment of the present specification, R may be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0101] In one embodiment of the present specification, R may be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0102] In one embodiment of the present specification, R 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 triphenylene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group.

[0103] In one embodiment of the present specification, R may be a C6 to C20 aryl group unsubstituted or substituted with one or more substituents selected from deuterium, an alkyl group, and a heteroaryl group; or a C2 to C20 heteroaryl group unsubstituted or substituted with one or more substituents selected from deuterium and an aryl group.

[0104] In one embodiment of the present specification, R may be a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a fluorenyl group substituted or unsubstituted with one or more substituents selected from deuterium and an alkyl group; a triphenylene group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with one or more substituents selected from deuterium and an aryl group; a dibenzothiophene group substituted or unsubstituted with one or more substituents selected from deuterium and an aryl group; or a carbazole group substituted or unsubstituted with one or more substituents selected from deuterium and an aryl group.

[0105] In one embodiment of the present specification, r is the number of -L3-R substituted on the benzene ring and is an integer from 1 to 4, and when r is 2 or more, 2 or more L3 and R are each the same or different.

[0106] For example, when r is 2, the benzene ring is substituted with two substituents denoted as -L3-R and -L3'-R', where L3' is the same as defined for L3, and R' is the same as defined for R.

[0107] In one embodiment of the present specification, r may be 1.

[0108] In one embodiment of the present specification, H1 in the chemical formula 1 is hydrogen; or deuterium.

[0109] In one embodiment of the present specification, 4-r is the number of -H1 substituted on the benzene ring, and when r is 2 or less, 2 or more H1 are the same or different.

[0110] In one embodiment of the present specification, the sum of the number of substituents -L3-R and the number of substituents -H1 is 4.

[0111] In one embodiment of the present specification, Y in the chemical formula 1 is O; S; C(R10)(R11) or N(R12), and R10 to R12 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0112] In one embodiment of the present specification, Y may be O.

[0113] In one embodiment of the present specification, Y may be S.

[0114] In one embodiment of the present specification, Y is C(R10)(R11), and R10 and R11 can each independently be a substituted or unsubstituted C1 to C10 alkyl group.

[0115] In one embodiment of the present specification, Y is C(R10)(R11), and R10 and R11 can each independently be a substituted or unsubstituted methyl group.

[0116] In one embodiment of the present specification, Y is N(R12), and R12 may be a substituted or unsubstituted C6 to C20 aryl group.

[0117] In one embodiment of the present specification, Y is N(R12), and R12 may be a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group.

[0118] In one embodiment of the present specification, Y is N(R12), and R12 may be a C6 to C20 aryl group substituted or unsubstituted with deuterium.

[0119] In one embodiment of the present specification, Y is N(R12), and R12 may be a phenyl group substituted or unsubstituted with deuterium; or a biphenyl group substituted or unsubstituted with deuterium.

[0120] In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-3.

[0121] [Chemical Formula 1-1]

[0122]

[0123] [Chemical Formula 1-2]

[0124]

[0125] [Chemical Formula 1-3]

[0126]

[0127] In the above chemical formulas 1-1 to 1-3,

[0128] The definition of each substituent is the same as that in the chemical formula 1 above.

[0129] In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following chemical formulas 1-4 to 1-9.

[0130] [Chemical Formula 1-4]

[0131]

[0132] [Chemical Formula 1-5]

[0133]

[0134] [Chemical Formula 1-6]

[0135]

[0136] [Chemical Formula 1-7]

[0137]

[0138] [Chemical Formula 1-8]

[0139]

[0140] [Chemical Formula 1-9]

[0141]

[0142] In the above chemical formulas 1-4 to 1-9,

[0143] The definition of each substituent is the same as that in the chemical formula 1 above.

[0144] In one embodiment of the present specification, R1 to R9 of the chemical formula 1 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and at least one of R1 to R9 is deuterium.

[0145] In one embodiment of the present specification, R1 to R9 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and at least one of R1 to R9 is deuterium.

[0146] In one embodiment of the present specification, R1 to R9 may each independently be hydrogen; deuterium; 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, and at least one of R1 to R9 is deuterium.

[0147] In one embodiment of the present specification, R1 to R9 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group, and at least one of R1 to R9 is deuterium.

[0148] In one embodiment of the present specification, R1 to R9 may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group, and at least one of R1 to R9 is deuterium.

[0149] In one embodiment of the present specification, R1 to R9 may each independently be hydrogen; deuterium; or a substituted or unsubstituted phenyl group, and at least one of R1 to R9 is deuterium.

[0150] In one embodiment of the present specification, R1 to R9 may each independently be hydrogen; deuterium; or a C6 to C20 aryl group substituted or unsubstituted with deuterium, and at least one of R1 to R9 is deuterium.

[0151] In one embodiment of the present specification, R1 to R9 may each independently be hydrogen; deuterium; or a phenyl group substituted or unsubstituted with deuterium, and at least one of R1 to R9 is deuterium.

[0152] In one embodiment of the present specification, R1 to R9 may each independently be hydrogen or deuterium, and at least one of R1 to R9 is deuterium.

[0153] In one embodiment of the present specification, q is the number of substituents R5 and is 1 or 2, and when q is 2, two R5 are the same or different.

[0154] For example, when q is 2, the benzene ring having an additional condensed ring in carbazole is substituted with substituents R5 and R5', and the definition of R5' is the same as the definition of R5.

[0155] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be greater than 0% and less than or equal to 100%.

[0156] The deuterium substitution rate of a heterocyclic compound according to one embodiment of the present specification means the deuterium substitution rate with respect to the total number of hydrogens and deuteriums contained in the compound.

[0157] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 10% to 100%.

[0158] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 30% to 100%.

[0159] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 50% to 100%.

[0160] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 70% to 100%.

[0161] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be greater than 0% and less than 100%.

[0162] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 10% to 99%.

[0163] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 30% to 90%.

[0164] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 50% to 90%.

[0165] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 70% to 90%.

[0166] In one embodiment of the present specification, the deuterium content of the heterocyclic compound of the chemical formula 1 satisfies the above range, and the photochemical characteristics of the compound not containing deuterium and the compound containing deuterium are almost similar, but when deposited in a thin film, the material containing deuterium tends to be packed with a narrower intermolecular distance.

[0167] Accordingly, by fabricating an EOD (Electron Only Device) and a HOD (Hole Only Device) and checking the current density according to the voltage, it can be confirmed that the heterocyclic compound of chemical formula 1 of the present invention exhibits much more balanced charge transport characteristics than a compound that does not contain deuterium of the same structure.

[0168] Additionally, when looking at the surface of the thin film with an atomic force microscope (AFM), it can be confirmed that the thin film made of a compound containing deuterium is deposited with a more uniform surface without any aggregated areas.

[0169] Additionally, since the single bond dissociation energy of carbon and deuterium is higher than the single bond dissociation energy of carbon and hydrogen, the heterocyclic compound of chemical formula 1 of the present invention has the effect of increasing the stability of the entire molecule, thereby improving the device lifespan.

[0170] In one embodiment of the present specification, the chemical formula 1 is represented by [structure A]-[structure B]-[structure C], and the structure A may be represented by the following chemical formula A, the structure B may be represented by the following chemical formula B, and the structure C may be represented by the following chemical formula C.

[0171] [Chemical Formula A]

[0172]

[0173] [Chemical Formula B]

[0174]

[0175] [Chemical Formula C]

[0176]

[0177] In the above chemical formulas A to C,

[0178] The definition of each substituent is the same as that in the above chemical formula 1,

[0179] Chemical formula A is of chemical formula B is combined with,

[0180] Chemical formula B is of chemical formula C is combined with

[0181] In one embodiment of the present specification, the deuterium substitution rate of the structure A may be from 0% to 100%.

[0182] The deuterium substitution rate of the above structure A refers to the deuterium substitution rate with respect to the total number of hydrogens and deuteriums included in the above chemical formula A.

[0183] In one embodiment of the present specification, the deuterium substitution rate of the structure A may be 0%. That is, the structure A may not contain deuterium.

[0184] In one embodiment of the present specification, the deuterium substitution rate of the structure B may be 0% to 100%.

[0185] The deuterium substitution rate of the above structure B means the deuterium substitution rate with respect to the total number of hydrogens and deuteriums included in the above chemical formula B.

[0186] In one embodiment of the present specification, the deuterium substitution rate of the structure B may be 0%, or may be greater than 0% and less than or equal to 100%. That is, the structure B may not contain deuterium, or may contain at least one deuterium.

[0187] In one embodiment of the present specification, the deuterium substitution rate of the structure C is greater than 0% and less than or equal to 100%.

[0188] The deuterium substitution rate of the above structure C means the deuterium substitution rate with respect to the total number of hydrogens and deuteriums included in the above chemical formula C.

[0189] In one embodiment of the present specification, the deuterium substitution rate of the structure C may be 10% to 100%.

[0190] In one embodiment of the present specification, the deuterium substitution rate of the structure C may be 30% to 100%.

[0191] In one embodiment of the present specification, the deuterium substitution rate of the structure C may be 50% to 100%.

[0192] In one embodiment of the present specification, the deuterium substitution rate of the structure C may be 70% to 100%.

[0193] In one embodiment of the present specification, the deuterium substitution rate of the structure C may be 80% to 100%.

[0194] In one embodiment of the present specification, the deuterium substitution rate of the structure A is 0%, the deuterium substitution rate of the structure B is 0% to 100%, and the deuterium substitution rate of the structure C may be greater than 0% and less than or equal to 100%.

[0195] In one embodiment of the present specification, the deuterium substitution rate of the structure A may be 0%, the deuterium substitution rate of the structure B may be 0% to 100%, and the deuterium substitution rate of the structure C may be 50% to 100%.

[0196] In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following compounds.

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225] In the above compound structure, the deuterium position indicates an arbitrary position, and the substitution position is not specified as long as it satisfies the deuterium substitution rate in the structure in which deuterium is substituted.

[0226] In addition, by introducing various substituents into the structure of the above chemical formula 1, compounds having the unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, a material satisfying the conditions required for each organic layer can be synthesized.

[0227] 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.

[0228] In another embodiment of the present specification, an organic light-emitting device is provided, comprising: a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one layer of the organic layer comprises at least one heterocyclic compound of the chemical formula 1.

[0229] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include one or more types of the heterocyclic compound.

[0230] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include one type of the heterocyclic compound.

[0231] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, and the host may include one or more of the heterocyclic compounds.

[0232] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, and the host may include one type of the heterocyclic compound.

[0233] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, the host includes a green host, and the green host may include one or more of the heterocyclic compounds.

[0234] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, the host includes a red host, and the red host may include one or more of the heterocyclic compounds.

[0235] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, the host includes a blue host, and the blue host may include one or more of the heterocyclic compounds.

[0236] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include the heterocyclic compound as an N-type host.

[0237] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may further include a compound of the following chemical formula 2 or 3 in addition to the heterocyclic compound.

[0238] [Chemical Formula 2]

[0239]

[0240] [Chemical Formula 3]

[0241]

[0242] In the above chemical formulas 2 and 3,

[0243] L21 to L23 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0244] m, n and s are each an integer from 1 to 3, and when each is 2 or greater, the substituents in the parentheses are the same or different,

[0245] Ar21 to Ar24 are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0246] R21 to R24 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0247] o and p are each an integer from 1 to 7, t is an integer from 1 to 6, u is an integer from 1 to 4, and when o, p, t, and u are each 2 or more, the substituents in the parentheses are the same or different.

[0248] In one embodiment of the present specification, L21 and L22 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.

[0249] In one embodiment of the present specification, L21 and L22 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 containing O.

[0250] In one embodiment of the present specification, L21 and L22 may each independently be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted divalent dibenzofuran group.

[0251] In one embodiment of the present specification, L21 and L22 may each independently be a direct bond; a C6 to C30 arylene group substituted or unsubstituted with deuterium; or a C2 to C30 heteroarylene group substituted or unsubstituted with deuterium.

[0252] In one embodiment of the present specification, L21 and L22 may each independently be a direct bond; or a substituted or unsubstituted C6 to C30 arylene group.

[0253] In one embodiment of the present specification, L21 and L22 may each independently be a direct bond; or a substituted or unsubstituted phenylene group.

[0254] In one embodiment of the present specification, L21 and L22 may each independently be a direct bond; or a C6 to C30 arylene group substituted or unsubstituted with deuterium.

[0255] In one embodiment of the present specification, Ar21 and Ar22 may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0256] In one embodiment of the present specification, Ar21 and Ar22 may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group containing O or S.

[0257] In one embodiment of the present specification, Ar21 and Ar22 may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0258] In one embodiment of the present specification, Ar21 and Ar22 may each independently be a C6 to C30 aryl group substituted or unsubstituted with deuterium; or a C2 to C30 heteroaryl group substituted or unsubstituted with deuterium and containing O or S.

[0259] In one embodiment of the present specification, Ar21 and Ar22 may each independently be a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a triphenylene group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; or a dibenzothiophene group substituted or unsubstituted with deuterium.

[0260] In one embodiment of the present specification, R21 and R22 may each independently be hydrogen; deuterium; 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.

[0261] In one embodiment of the present specification, R21 and R22 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0262] In one embodiment of the present specification, R21 and R22 may each independently be hydrogen or deuterium.

[0263] In one embodiment of the present specification, Ar23 and Ar24 may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0264] In one embodiment of the present specification, Ar23 and Ar24 may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group containing O.

[0265] In one embodiment of the present specification, Ar23 and Ar24 may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenylene group; or a substituted or unsubstituted dibenzofuran group.

[0266] In one embodiment of the present specification, Ar23 and Ar24 may each independently be a C6 to C30 aryl group substituted or unsubstituted with deuterium; or a C2 to C30 heteroaryl group substituted or unsubstituted with deuterium and containing O.

[0267] In one embodiment of the present specification, Ar23 and Ar24 may each independently be a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a triphenylene group substituted or unsubstituted with deuterium; or a dibenzofuran group substituted or unsubstituted with deuterium.

[0268] In one embodiment of the present specification, R23 and R24 may each independently be hydrogen; deuterium; 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.

[0269] In one embodiment of the present specification, R23 and R24 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0270] In one embodiment of the present specification, R23 and R24 may each independently be hydrogen or deuterium.

[0271] In one embodiment of the present specification, the light-emitting layer may further include a compound of the chemical formula 2 or 3 as a P-type host in addition to the heterocyclic compound.

[0272] In one embodiment of the present specification, the chemical formula 2 may be represented by any one of the following compounds.

[0273]

[0274]

[0275]

[0276]

[0277] In one embodiment of the present specification, the chemical formula 3 may be represented by any one of the following compounds.

[0278]

[0279]

[0280]

[0281]

[0282] The organic layer of the organic light-emitting device of the present invention may be formed as a single-layer structure, but may also be formed as a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0283] In one embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

[0284] In another embodiment of the present specification, the first electrode may be a cathode and the second electrode may be an anode.

[0285] An organic light-emitting device according to one embodiment of the present specification can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the heterocyclic compound of the above-described chemical formula 1.

[0286] The heterocyclic compound of the above chemical formula 1 can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0287] In one embodiment of the present specification, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound of the chemical formula 1 may be used as a material of the blue organic light-emitting device. For example, the heterocyclic compound of the chemical formula 1 may be included in a light-emitting layer of the blue organic light-emitting device.

[0288] In another embodiment of the present specification, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound of the chemical formula 1 may be used as a material of the green organic light-emitting device. For example, the heterocyclic compound of the chemical formula 1 may be included in a light-emitting layer of the green organic light-emitting device.

[0289] In another embodiment of the present specification, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound of the chemical formula 1 may be used as a material of the red organic light-emitting device. For example, the heterocyclic compound of the chemical formula 1 may be included in a light-emitting layer of the red organic light-emitting device.

[0290] The organic light-emitting device of the present invention may further include one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0291] The stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present disclosure is exemplified in Figures 1 to 3. However, the scope of the present application is not intended to be limited by these drawings, and the structure of an organic light-emitting device known in the art may also be applied to the present application.

[0292] 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.

[0293] 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), an electron blocking layer (303), a light-emitting 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.

[0294] The organic layer containing the heterocyclic compound of the above chemical formula 1 may additionally contain other substances as needed.

[0295] In an organic light-emitting device according to one embodiment of the present specification, materials other than the heterocyclic compound of the above chemical formula 1 are exemplified below, but these are only for exemplification and are not intended to limit the scope of the present application, and may be replaced with materials known in the art.

[0296] 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.

[0297] 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.

[0298] As the hole injection material, a known hole injection material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a starburst amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), a soluble conductive polymer such as polyaniline / dodecylbenzenesulfonic acid, or Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrenesulfonate) can be used.

[0299] Pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used as hole transport materials, and low molecular weight or high molecular weight materials can also be used.

[0300] As the electron transport material, metal complexes of oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinoline and derivatives thereof, etc. can be used, and not only low molecular weight substances but also high molecular weight substances can be used.

[0301] For example, LiF is a representative material used in the art, but the present application is not limited thereto.

[0302] Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. At this time, two or more light-emitting materials may be deposited and used as individual sources, or may be premixed and deposited and used as a single source. In addition, a fluorescent material may be used as the light-emitting material, but it may also be used as a phosphorescent material. A material that emits light by combining holes and electrons injected from the anode and cathode, respectively, may be used as the light-emitting material, but materials in which both the host material and the dopant material participate in light emission may also be used.

[0303] When using a mixture of hosts for light-emitting materials, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, two or more types of materials, either N-type host materials or P-type host materials, may be selected and used as the host materials for the light-emitting layer.

[0304] An organic light-emitting device according to one embodiment of the present specification may be a front-emitting, back-emitting, or double-sided emitting device depending on the material used.

[0305] The heterocyclic compound according to one embodiment of the present specification can function in organic electronic devices, including organic solar cells, organic photoconductors, organic transistors, etc., by a similar principle to that applied to organic light-emitting devices.

[0306] 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.

[0307] In one embodiment of the present specification, a composition for forming an organic layer including the heterocyclic compound is provided.

[0308] In one embodiment of the present specification, the composition for forming the organic layer may further include a compound of the chemical formula 2 or 3.

[0309] In one embodiment of the present specification, the composition for forming the organic layer may include the heterocyclic compound and the compound of the chemical formula 2 or 3 in a weight ratio of 1:10 to 10:1.

[0310] In one embodiment of the present specification, the composition for forming the organic layer may include the heterocyclic compound and the compound of the chemical formula 2 or 3 in a weight ratio of 1:5 to 5:1.

[0311] In one embodiment of the present specification, a method for manufacturing an organic light-emitting device is provided, comprising: preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer, wherein the forming of the organic layer comprises forming one or more organic layers using an organic layer forming composition including the heterocyclic compound.

[0312] In one embodiment of the present specification, a method for manufacturing an organic light-emitting device is provided, comprising: a step of preparing a substrate; a step of forming a first electrode on the substrate; a step of forming one or more organic layers on the first electrode; and a step of forming a second electrode on the organic layer, wherein the step of forming the organic layer includes a step of forming one or more organic layers using an organic layer forming composition comprising the heterocyclic compound and the compound of Chemical Formula 2 or 3.

[0313] In one embodiment of the present specification, a method for manufacturing an organic light-emitting device is provided, wherein the step of forming the organic layer comprises pre-mixing a heterocyclic compound represented by the chemical formula 1 and a compound of the chemical formula 2 or 3 and forming the organic layer using a thermal vacuum deposition method.

[0314] The above pre-mixing means that the heterocyclic compound represented by the above chemical formula 1 and the compound of the above chemical formula 2 or 3 are mixed in one container before being deposited on the organic layer.

[0315] The premixed material may be referred to as a composition for forming an organic layer according to one embodiment of the present specification.

[0316] Hereinafter, the present specification will be described in more detail through examples, but these are only intended to illustrate the present application and are not intended to limit the scope of the present application.

[0317] <Manufacturing Example 1> Preparation of compound 9C

[0318]

[0319] Compound 9C-1 (12H-benzo[4,5]thieno[2,3-a]carbazole) (20 g, 73.16 mmol) was dissolved in 200 mL of D6-Benzene, and then Triflic acid (45 mL, 512.16 mmol) was slowly added. The reaction temperature was raised to 60°C, and the mixture was stirred for 1 hour. Then, a solution of Na2CO3 (15 g, 146.32 mmol) dissolved in 150 mL of D2O was added to neutralize the mixture. Excessive ethyl acetate (EA) was added to perform extraction, and the organic layer was dried over anhydrous MgSO4 and filtered with silica gel. The filtrate was used to remove the solvent using a rotary evaporator to obtain 19 g of compound 9C as a brown solid in a 92% yield (100% D substitution rate).

[0320] The target compound was synthesized by the same method as in the above manufacturing example 1, except that intermediate 1 of Table 1 was used instead of compound 9C-1.

[0321] [Table 1]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329] <Manufacturing Example 2> Preparation of compound 9

[0330]

[0331] 1) Preparation of compound P-3

[0332] Compound P-4 (2-bromo-4-chloro-1-fluorobenzene) (20 g, 95.49 mmol), compound 9C (27 g, 95.49 mmol), and Cs2CO3 (62 g, 190.98 mmol) were dissolved in 300 mL of dimethyl acetamide (DMA), and stirred at a reaction temperature of 150°C for 8 hours. After the reaction was completed, the solution was cooled to room temperature, and an excess of H2O was added to precipitate a solid. The precipitated solid was filtered, washed with H2O and methanol (MeOH), and dried. The dried solid was dissolved in an excess of methylene chloride (MC), and then filtered through silica gel. The filtrate was purified by removing the solvent using a rotary evaporator, and recrystallized with EA to obtain 39 g of compound P-3 as a pale brown solid in an 87% yield.

[0333] 2) Preparation of compound P-2

[0334] Compound P-3 (39 g, 82.48 mmol), Phenylboronic acid (A) (10 g, 82.48 mmol), Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium(0)) (4.7 g, 4.15 mmol), and K2CO3 (17 g, 123.72 mmol) were dissolved in 500 mL of 1,4-dioxane / 100 mL of H2O, and stirred at a reaction temperature of 100°C for 4 hours. After the reaction was completed, the solution was cooled to room temperature and the solvent was removed using a rotary evaporator. The concentrated solution was dissolved in an excess of MC, extracted with H2O, and the organic layer was dried over anhydrous MgSO4 and filtered through silica gel. The filtrate was purified by removing the solvent using a rotary evaporator and recrystallized with EA to obtain 31 g of compound P-2 as a pale yellow solid in a yield of 79%.

[0335] 3) Preparation of compound P-1

[0336] Compound P-2 (31 g, 55.26 mmol), B2Pin2 (28 g, 110.52 mmol), Pd2(dba)3 (tris(dibenzylideneacetone)dipalladium(0)) (5.1 g, 5.53 mmol), XPhos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) (6.3 g, 11.06 mmol), KOAc (potassium acetate) (11 g, 110.52 mmol) were dissolved in 500 mL of 1,4-dioxane and stirred at a reaction temperature of 100°C for 14 hours. After completion of the reaction, the solution was cooled to room temperature and the inorganic salt was removed by filtration. The filtrate was concentrated using a rotary evaporator, dissolved in an excess of MC, and filtered through silica gel. The solvent was removed from the residue using a rotary evaporator and recrystallized with MeOH to obtain 27 g of compound P-1 as a yellow solid in 87% yield.

[0337] 4) Preparation of compound 9

[0338] Compound P-1 (10 g, 17.81 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine(B)(6.4 g, 17.81 mmol), Pd(PPh3)4(tetrakis(triphenylphosphine)palladium(0)) (1.1 g, 0.89 mmol), and K2CO3 (5 g, 35.62 mmol) were dissolved in 1,4-dioxane 120 mL / H2O 30 mL, and stirred at a reaction temperature of 100°C for 4 hours. After the reaction was completed, the solution was cooled to room temperature and the solvent was removed using a rotary evaporator. The concentrated solution was dissolved in an excess of MC, extracted with H2O, and the organic layer was dried over anhydrous MgSO4 and filtered through silica gel. The solvent was removed from the filtrate using a rotary evaporator, and chlorobenzene (CB) / hexane (Hex) was recrystallized to obtain 9.2 g of compound 9 as a pale ivory solid in a yield of 67%.

[0339] The final compound of Table 3 was synthesized in the same manner as in Manufacturing Example 2, except that Intermediate 2 of Table 2 was used instead of Compound P-4, Intermediate 3 of Table 2 was used instead of Compound 9C, Intermediate 4 of Table 2 was used instead of Compound (A), and Intermediate 5 of Table 2 was used instead of Compound (B).

[0340] [Table 2]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347] [Table 3]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357] <Manufacturing Example 3> Preparation of compound 381C

[0358]

[0359] 1) Preparation of compound S-3

[0360] Compound S-4 (2-bromo-4-chloro-1-fluorobenzene) (20 g, 95.49 mmol), 12H-benzo[4,5]thieno[2,3-a]carbazole(C) (25 g, 95.49 mmol), and Cs2CO3 (62 g, 190.98 mmol) were dissolved in 300 mL of DMA and stirred at a reaction temperature of 160°C for 15 hours. After the reaction was completed, the solution was cooled to room temperature and an excess of H2O was added to precipitate a solid. The precipitated solid was filtered, washed with H2O and MeOH, and dried. The dried solid was dissolved in an excess of MC and filtered through silica gel. The filtrate was purified by removing the solvent using a rotary evaporator and recrystallized with acetone to obtain 33 g of compound S-3 as a pale yellow solid in a yield of 78%.

[0361] 2) Preparation of compound S-2

[0362] Compound S-3 (33 g, 71.31 mmol), Phenylboronic acid (D) (8.7 g, 71.31 mmol), Pd(PPh3)4 (4.1 g, 3.55 mmol), and K2CO3 (19 g, 142.62 mmol) were dissolved in 500 mL of 1,4-dioxane / 100 mL of H2O, and stirred at a reaction temperature of 100°C for 6 hours. After completion of the reaction, the solution was cooled to room temperature and the solvent was removed using a rotary evaporator. The concentrated solution was dissolved in an excess of MC, extracted with H2O, and the organic layer was dried over anhydrous MgSO4 and filtered through silica gel. The filtrate was purified by removing the solvent using a rotary evaporator and recrystallized with EA to obtain 26 g of compound S-2 as an ivory solid in a yield of 81%.

[0363] 3) Preparation of compound 381C

[0364] Compound S-2 (26 g, 56.52 mmol) was dissolved in 130 mL of D6-benzene, and then triflic acid (35 mL, 395.64 mmol) was slowly added. The reaction temperature was raised to 60°C and stirred for 1 hour. After the reaction was completed, the temperature of the reaction solution was lowered to 0°C and 30 mL of D2O in which triethylamine (TEA) (31 mL, 226.08 mmol) was dissolved was added to neutralize. The organic layer was separated, dried over MgSO4, and filtered with silica gel. The filtrate was used to remove the solvent using a rotary evaporator, and acetone was recrystallized to obtain 23 g of compound 381C as an ivory solid in 85% yield (83% D substitution rate).

[0365] The target compound was synthesized by the same method as in Manufacturing Example 3 except that intermediate 6 of Table 4 was used instead of compound S-4, intermediate 7 of Table 4 was used instead of compound (C), and intermediate 8 of Table 4 was used instead of compound (D).

[0366] [Table 4]

[0367]

[0368]

[0369] <Manufacturing Example 4> Preparation of compound 381

[0370]

[0371] 1) Preparation of compound S-1

[0372] Compound 381C (23 g, 48.12 mmol), B2Pin2(bis(pinacolato)diboron) (25 g, 96.24 mmol), Pd2(dba)3 (4.4 g, 4.82 mmol), XPhos (4.6 g, 9.62 mmol), KOAc 9.5 g, 96.24 mmol) were dissolved in 400 mL of 1,4-dioxane and stirred at a reaction temperature of 100°C for 15 hours. After completion of the reaction, the solution was cooled to room temperature and the inorganic salts were removed by filtration. The filtrate was concentrated using a rotary evaporator, dissolved in an excess of MC, and filtered through silica gel. The filtrate was subjected to removal of the solvent using a rotary evaporator and recrystallized with MeOH to obtain 22 g of compound S-1 as a yellow solid in a yield of 81%.

[0373] 2) Preparation of compound 381

[0374] Compound S-1 (10 g, 17.57 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine(E)(6 g, 17.57 mmol), Pd(PPh3)4(1 g, 0.88 mmol), and K2CO3(4.8 g, 35.14 mmol) were dissolved in 120 mL of 1,4-dioxane / 30 mL of H2O, and stirred at a reaction temperature of 100°C for 5 hours. After the reaction was completed, the solution was cooled to room temperature and the solvent was removed using a rotary evaporator. The concentrated solution was dissolved in an excess of MC, extracted with H2O, and the organic layer was dried over anhydrous MgSO4 and filtered through silica gel. The filtrate was purified by removing the solvent using a rotary evaporator and recrystallized with CB / Acetone to obtain 8 g of compound 381 as a white solid in a yield of 62%.

[0375] The final compound was synthesized using the same method as in Manufacturing Example 4 above, except that Intermediate 9 in Table 5 below was used instead of Compound 381C, and Intermediate 10 in Table 5 below was used instead of Compound (E).

[0376] [Table 5]

[0377]

[0378]

[0379] <Manufacturing Example 5> Preparation of Compound 2-2

[0380]

[0381] 1) Preparation of compound M-1

[0382] Compound M-2 (9H,9'H-3,3'-bicarbazole) (20 g, 60.16 mmol), Bromobenzene(H) (9.4 g, 60.16 mmol), Pd2(dba)3 (5.5 g, 6.02 mmol), XPhos (5.7 g, 12.03 mmol), and K2CO3 (12.5 g, 90.24 mmol) were dissolved in 300 mL of 1,4-dioxane and stirred at a reaction temperature of 110°C for 6 hours. After the reaction was completed, the solution was cooled to room temperature and the solvent was removed using a rotary evaporator. The concentrated solution was dissolved in an excess of MC, extracted with H2O, and the organic layer was dried over anhydrous MgSO4 and filtered through silica gel. The filtrate was purified by removing the solvent using a rotary evaporator and recrystallized with EA to obtain 20 g of compound M-1 as a white solid in a yield of 81%.

[0383] 2) Preparation of compound 2-2

[0384] Compound M-1 (20 g, 49.02 mmol), 4-bromo-1,1'-biphenyl(I)(12 g, 49.02 mmol), Pd2(dba)3(4.5 g, 4.9 mmol), P(tBu)3(tri-tert-butylphosphine) (1.9 g, 9.81 mmol), NaOtBu(sodium tert-butoxide) (9.5 g, 98.04 mmol) were dissolved in 300 mL of toluene and stirred at a reaction temperature of 110°C for 15 hours. After completion of the reaction, the solution was cooled to room temperature and the solvent was removed using a rotary evaporator. The concentrated solution was dissolved in an excess of MC, extracted with H2O, and the organic layer was dried over anhydrous MgSO4 and filtered through silica gel. The solvent was removed from the residue using a rotary evaporator and recrystallized from CB to obtain 217 g of compound 2 as a white solid in 63% yield.

[0385] The final compound was synthesized using the same method as in Manufacturing Example 5 above, except that Intermediate 11 of Table 6 below was used instead of Compound M-2, Intermediate 12 of Table 6 below was used instead of Compound (H), and Intermediate 13 was used instead of Compound (I).

[0386] [Table 6]

[0387]

[0388]

[0389] <Manufacturing Example 6> Preparation of compound 2-42

[0390]

[0391] Compound 2-2 (9-([1,1'-biphenyl]-4-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole) (20 g, 35.66 mmol) was dissolved in 200 mL of D6-Benzene, and then Triflic acid (23 mL, 249.69 mmol) was slowly added. The reaction temperature was raised to 60°C, and the mixture was stirred for 1 hour. Then, a solution of TEA (20 mL, 142.64 mmol) dissolved in 20 mL of D2O was added to neutralize the mixture. Excess EA was added to perform extraction, and the organic layer was dried over anhydrous MgSO4 and filtered through silica gel. The solvent was removed from the filtrate using a rotary evaporator to obtain 19.8 g of compound 2-42 as a brown solid in a 94% yield (100% D substitution rate).

[0392] The final compound was synthesized by the same method as in the above manufacturing example 6, except that intermediate 14 of the following table 7 was used instead of compound 2-2.

[0393] [Table 7]

[0394]

[0395]

[0396] The compound synthesized in the above manufacturing example is 1 It was confirmed through H-NMR and FD-mass spectrometry. Tables 8 and 9 are 1 These are the measured values ​​of H NMR (CDCl3, 300 MHz), and Tables 10 and 11 are the measured values ​​of FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0397] NO 1H NMR(CDCl3, 300MHz)97.21-7.23 (m, 4H), 7.31-7.39 (m, 3H), 7.41-7.45 (m, 3H), 7.57 (d, 1H), 7.69 (d, 1H), 7.82 (d, 1H), 7.98 (d, 1H), 8.01 (d, 1H), 8.08 (s, 1H), 8.36 (dd, 2H), 8.39-8.41 (m, 2H)127.19-7.20 (d, 4H), 7.41 (td, 1H), 7.49-7.51 (m, 6H), 7.61 (dd, 1H), 7.73 (t, 1H), 7.94 (s, 1H), 8.01 (d, 1H), 8.08 (s, 1H), 8.11 (dd, 2H), 8.38-8.40 (m, 4H)137.26-7.28 (m, 4H), 7.31 (d, 1H), 7.39 (td, 1H), 7.41-7.43 (m, 3H), 7.49-7.51 (m, 6H), 7.98 (d, 1H), 8.01 (dd, 2H), 8.08 (s, 1H), 8.11 (dd, 1H), 8.36-8.38 (m, 4H)177.20-7.22 (d, 4H), 7.30-7.35 (m, 3H), 7.40-7.43 (m, 3H), 7.50-7.51 (m, 2H), 7.52-7.53 (m, 2H), 7.98 (dd, 1H), 8.01 (s, 1H), 8.10 (d, 1H), 8.25 (d, 1H), 8.36 (dd, 1H), 8.98 (d, 1H)287.19-7.21 (d, 4H), 7.32-7.39 (m, 4H), 7.41-7.44 (m, 3H), 7.52 (dd, 2H), 7.70 (d, 1H), 7.80 (d, 1H), 7.89-7.90 (m, 2H), 8.18 (s, 1H), 8.26 (dd, 2H), 8.35-8.37 (m, 2H)291.69 (s, 6H), 7.19-7.20 (m, 4H), 7.28 (d, 1H), 7.38 (dd, 2H), 7.41-7.43 (m, 5H), 7.47 (d, 1H), 7.65 (d, 1H), 7.78 (dd, 1H), 7.90 (d, 1H), 8.01 (d, 1H), 8.08 (s, 1H), 8.11 (d, 1H), 8.36 (dd, 2H)327.20-7.22 (d, 4H), 7.29-7.30 (m, 3H), 7.47 (d, 1H), 7.50-7.52 (m, 2H), 7.66 (d, 1H), 7.77 (s, 1H), 7.80 (d, 1H), 7.89-7.90 (m, 2H), 8.18 (s, 1H), 8.26 (dd, 2H), 8.35-8.37 (m, 2H), 8.41 (d, 1H), 8.44 (d, 1H)387.16-7.17 (m, 3H), 7.35 (t, 1H), 7.46 (d, 1H), 7.50-7.52 (m, 6H), 7.50 (dd, 1H), 7.66 (d, 1H), 7.80 (t, 1H), 7.91 (d, 1H), 7.92 (d, 1H), 8.08-8.11 (m, 3H), 8.15 (s, 1H), 8.26 (dd, 2H), 8.35-8.37 (m, 4H), 8.55 (d, 1H)417.19-7.21 (d, 4H), 7.41 (t, 1H), 7.41-7.44 (m, 4H), 7.49 (s, 1H), 7.52 (dd, 2H), 8.01 (s, 1H), 8.08-8.10 (m, 2H), 8.35-8.37 (m, 4H)467.19-7.22 (d, 4H), 7.25 (dd, 2H), 7.47 (t, 1H), 7.50-7.52 (m, 4H), 7.55-7.58 (m, 2H), 7.62 (d, 1H), 7.78-7.80 (m, 2H), 7.89-7.90 (m, 2H), 8.11 (s, 1H), 8.16 (dd, 1H), 8.35-8.37 (m, 2H), 8.41-8.42 (m, 2H)477.35-7.36 (m, 2H), 7.45-7.47 (m, 4H), 7.50-7.52 (m, 2H), 7.55-7.58 (m, 2H), 7.61 (dd, 1H), 7.75-7.76 (m, 3H), 7.80-7.82 (m, 2H), 7.94 (s, 1H), 8.10 (s, 1H), 8.14 (dd, 1H), 8.35-8.36 (m, 2H), 8.40-8.42 (m, 2H)597.41-7.43 (m, 4H), 7.49-7.50 (m, 5H), 7.60 (dd, 2H), 7.65 (s, 1H), 7.79 (dd, 2H), 7.96 (dd, 2H), 8.01 (s, 1H), 8.09 (d, 1H), 8.11 (d, 1H), 8.37-8.38 (m, 4H), 8.42 (dd, 2H)631.69 (s, 6H), 7.19-7.20 (m, 4H), 7.28 (d, 1H), 7.33-7.35 (m, 3H), 7.41 (t, 1H), 7.84 (s, 1H), 8.10 (d, 1H), 8.14 (dd, 1H), 8.19-8.22 (m, 3H), 8.35-8.36 (m, 2H), 8.40-8.42 (m, 2H)801.69 (s, 6H), 7.19-7.20 (m, 4H), 7.32-7.33 (m, 3H), 7.41 (td, 1H), 7.49-7.51 (m, 4H), 7.60 (dd, 2H), 7.96 (dd, 2H), 7.99 (dd, 2H), 8.01 (d, 1H), 8.08 (s, 1H), 8.11 (d, 1H), 8.36-8.37 (m, 4H)977.40-7.41 (m, 3H), 7.59-7.61 (m, 4H), 7.79 (dd, 2H), 8.02 (d, 1H), 8.10 (d, 1H), 8.18 (dd, 2H), 8.33 (dd, 2H), 8.39 (dd, 2H), 8.40 (s, 1H), 8.49 (dd, 2H), 9.00 (s, 2H)1067.20-7.22 (m, 4H), 7.25-7.26 (m, 3H), 7.40-7.43 (m, 4H), 7.48-7.49 (m, 2H), 7.55 (d, 1H), 7.58 (dd, 2H), 7.61 (dd, 1H), 7.75-7.76 (m, 2H), 7.84 (s, 1H), 8.12 (s, 1H), 8.16 (dd, 1H), 8.37-8.38 (m, 2H), 8.41-8.42 (m, 2H)1117.16-7.19 (m, 4H), 7.19-7.22 (m, 4H), 7.29-7.31 (m, 4H), 7.46 (d, 1H), 7.55 (d, 1H), 7.60 (dd, 2H), 7.68 (dd, 1H), 7.75-7.76 (m, 2H), 7.94 (dd, 2H), 8.10 (d, 1H), 8.19 (d, 1H), 8.40 (s, 1H), 8.55 (d, 1H)1137.49-7.50 (m, 3H), 7.54-7.56 (m, 4H), 7.68 (td, 1H), 7.93 (d, 1H), 7.95 (dd, 2H), 8.01 (d, 1H), 8.03 (d, 1H), 8.10 (d, 1H), 8.22 (dd, 2H), 8.35-8.36 (m, 4H), 8.40 (dd, 1H)1351.70 (s, 6H), 7.19-7.21 (m, 4H), 7.26-7.28 (m, 4H), 7.30 (dd, 2H), 7.34-7.35 (m, 3H), 7.43 (t, 1H), 7.46-7.48 (m, 2H), 7.55 (dd, 2H), 7.77 (s, 1H), 7.89 (s, 1H), 8.10 (s, 1H), 8.35-8.36 (m, 2H)1367.40-7.42 (m, 3H), 7.50 (d, 1H), 7.52-7.55 (m, 4H), 7.60 (dd, 2H), 7.70 (d, 1H), 7.74 (d, 1H), 7.79 (dd, 2H), 7.94 (s, 1H), 8.03 (d, 1H), 8.10 (d, 1H), 8.22 (dd, 1H), 8.30 (m, 2H), 8.35 (m, 2H), 8.40 (s, 1H), 8.55 (d, 1H)1387.35-7.38 (m, 4H), 7.41-7.46 (m, 4H), 7.55 (s, 1H), 7.60 (dd, 2H), 7.68-7.70 (m, 5H), 7.75-7.76 (m, 3H), 7.80 (d, 1H), 7.94 (dd, 2H), 8.03 (d, 1H), 8.10 (d, 1H), 8.16 (d, 1H), 8.36 (dd, 2H), 8.40 (s, 1H), 8.55 (dd, 2H)1541.70 (s, 6H), 7.19-7.21 (m, 4H), 7.26-7.28 (m, 3H), 7.30 (d, 1H), 7.34-7.35 (m, 2H), 7.43 (t, 1H), 7.46-7.48 (m, 2H), 7.55 (dd, 2H), 7.70 (d, 1H), 8.10 (s, 1H), 8.14 (dd, 1H), 8.35-8.36 (m, 2H), 8.40-8.42 (m, 2H)1667.25-7.29 (m, 3H), 7.32 (d, 1H), 7.34-7.35 (m, 2H), 7.41 (t, 1H), 7.47-7.48 (m, 2H), 7.57 (dd, 2H), 7.81 (d, 1H), 8.10 (s, 1H), 8.14 (dd, 1H), 8.35-8.36 (m, 2H), 8.40-8.42 (m, 2H)1787.25 (dd, 4H), 7.41-4.42 (m, 4H), 7.49 (td, 1H), 7.49-7.50 (m, 6H), 7.60 (dd, 2H), 7.75 (dd, 2H), 7.80 (s, 1H), 7.90 (d, 1H), 7.96 (dd, 2H), 8.10 (d, 1H), 8.35-8.36 (m, 4H)1797.16 (t, 1H), 7.35 (t, 1H), 7.40 (dd, 2H), 7.49-7.51 (m, 4H), 7.53 (dd, 1H), 7.55-7.58 (m, 4H), 7.93-7.94 (m, 2H), 8.06 (d, 1H), 8.09 (dd, 1H), 8.11 (d, 1H), 8.29 (d, 1H), 8.36-8.37 (m, 4H), 8.40 (s, 1H), 8.55 (d, 1H)1807.20-7.23 (m, 4H), 7.25-7.27 (m, 3H), 7.30 (d, 1H), 7.34 (d, 1H), 7.37-7.39 (m, 3H), 7.47 (dd, 2H), 7.65-7.68 (m, 2H), 8.10 (s, 1H), 8.18 (dd, 1H), 8.35-8.36 (m, 2H), 8.40-8.42 (m, 2H)1867.16 (t, 1H), 7.35 (dd, 1H), 7.41-7.43 (m, 4H), 7.48-7.50 (m, 6H), 7.75 (dd, 2H), 7.77 (d, 1H), 7.87 (d, 1H), 7.89 (s, 1H), 7.99 (d, 1H), 8.06 (dd, 2H), 8.34 (s, 1H), 8.36-8.37 (m, 4H), 8.55 (dd, 1H)1967.30-7.32 (m, 4H), 7.34-7.35 (m, 5H), 7.39-7.41 (m, 4H), 7.48 (dd, 2H), 7.57 (dd, 1H), 7.60-7.62 (m, 2H), 7.81 (d, 1H), 8.07 (s, 1H), 8.11 (dd, 1H),8.29 (d, 1H), 8.35-8.36 (m, 2H), 8.40-8.42 (m, 2H), 8.55 (s, 1H)1977.19-7.20 (m, 4H), 7.35 (t, 1H), 7.52-7.54 (m, 4H), 7.90 (d, 1H), 8.03 (dd, 2H), 8.10 (dd, 2H), 8.25 (d, 1H), 8.30 (dd, 2H), 8.40 (d, 1H), 8.43 (d, 1H), 8.97 (dd, 2H)2077.39-7.40 (m, 4H), 7.42-7.45 (m, 5H), 7.62 (dd, 2H), 7.73-7.74 (m, 4H), 7.94 (s, 1H), 7.81 (d, 1H), 8.11 (dd, 1H), 8.29 (d, 1H), 8.35-8.36 (m, 2H), 8.39 (s, 1H), 8.40-8.42 (m, 2H), 8.55 (s, 1H)2147.19-7.20 (m, 4H), 7.38 (t, 1H), 7.42-7.44 (,m, 3H), 7.51-7.53 (m, 3H), 7.92 (d, 1H), 8.10 (d, 1H), 8.39 (s, 1H), 8.40-8.41 (m, 4H)2261.68 (s, 6H), 7.35-7.37 (m, 4H), 7.40-7.43 (m, 3H), 7.52 (d, 1H), 7.68 (d, 1H), 7.74 (dd, 2H), 7.81 (d, 1H), 7.85-7.88 (m, 2H), 7.97 (d, 1H), 8.11 (s, 1H), 8.29 (d, 1H), 8.35-8.36 (m, 2H), 8.40 (d, 1H)2477.41-7.42 (m, 4H), 7.50-7.52 (m, 6H), 7.61 (dd, 2H), 7.63 (d, 1H), 7.72 (dd, 2H), 7.91 (s, 1H), 8.02 (d, 1H), 8.10 (d, 1H), 8.40 (s, 1H), 8.42-8.43 (m, 4H)2517.15-7.17 (m, 4H), 7.20-7.23 (m, 3H), 7.35 (dd, 2H), 7.39-7.41 (m, 5H), 7.46 (d, 1H), 7.50-7.52 (m, 2H), 7.65 (d, 1H), 7.79 (dd, 2H), 8.02 (d, 1H), 8.10 (d, 1H), 8.19 (d, 1H), 8.33 (dd, 1H), 8.40 (s, 1H), 8.55 (d, 1H)2537.17-7.19 (m, 4H), 7.22 (td, 1H), 7.35-7.41 (m, 5H), 7.47 (dd, 2H), 7.50 (dd, 2H), 7.65-7.67 (m, 3H), 8.01 (s, 1H), 8.34 (dd, 2H), 8.40 (dd, 2H)2587.20-7.23 (m, 4H), 7.21-7.23 (m, 3H), 7.39-7.41 (m, 3H), 7.46 (d, 1H), 7.50-7.52 (m, 2H), 7.65 (d, 1H), 8.20 (d, 1H), 8.36 (dd, 2H), 8.39 (s, 1H), 8.40 (dd, 2H)2787.16-7.19 (m, 4H), 7.22-7.25 (m, 4H), 7.35 (dd, 2H), 7.46 (d, 1H), 7.50-7.52 (m, 5H), 7.65 (d, 1H), 7.79 (dd, 2H), 8.02 (dd, 2H), 8.10 (s, 1H), 8.31-8.33 (m, 5H), 8.40 (s, 1H), 8.55 (d, 1H)2981.68 (s, 6H), 1.72 (s, 6H), 7.34-7.37 (m, 6H), 7.40-7.42 (m, 3H), 7.52 (d, 1H), 7.68 (d, 1H), 7.74 (dd, 2H), 7.81 (d, 1H), 7.85-7.88 (m, 2H), 7.97 (d, 1H), 8.03 (s, 1H), 8.12 (d, 1H), 8.20 (d, 1H), 8.29 (d, 1H), 8.35-8.36 (m, 2H), 8.40 (dd, 2H), 8.51 (s, 1H)3177.36-7.39 (m, 4H), 7.40-7.45 (m, 4H), 7.47 (dd, 2H), 7.49-7.52 (m, 4H), 7.66 (dd, 2H), 7.69 (d, 1H), 7.79 (dd, 2H), 8.02 (dd, 2H), 8.33 (d, 1H), 8.55 (d, 1H), 9.27 (s, 1H), 9.60 (d, 1H)3357.30-7.33 (m, 4H), 7.41-7.42 (m, 2H), 7.47 (dd, 2H), 7.49-7.52 (m, 3H), 7.66 (dd, 2H), 7.69 (d, 1H), 7.79 (dd, 2H), 7.85 (dd, 1H), 7.94 (s, 1H), 8.02 (dd, 2H), 8.13 (d, 1H), 8.33 (d, 1H)3527.29-7.31 (m, 4H), 7.35-7.39 (m, 3H), 7.45-7.47 (m, 4H), 7.55 (d, 1H), 7.66 (dd, 2H), 7.69 (d, 1H), 7.79 (dd, 2H), 7.85 (dd, 1H), 7.95 (s, 1H), 8.13 (d, 1H), 8.33 (dd, 2H), 8.38 (d, 1H)3761.69 (s, 6H), 7.26-7.28 (m, 2H), 7.36-7.39 (m, 3H), 7.45-7.49 (m, 4H), 7.55-7.57 (m, 3H), 7.75 (dd, 2H), 7.77 (dd, 2H), 7.80 (d, 1H), 7.85 (dd, 1H), 7.92 (d, 1H), 8.01 (d, 1H), 8.04 (s, 3H), 8.22 (d, 1H), 8.36 (dd, 2H)3967.27-7.29 (m, 2H), 7.35-7.39 (m, 3H), 7.58 (dd, 1H), 7.70-7.72 (m, 4H), 8.22 (d, 2H), 8.36 (dd, 2H)4187.29 (d, 1H), 7.51-7.52 (m, 2H), 7.75 (dd, 2H), 7.91-7.92 (m, 4H), 8.23 (d, 1H), 8.37 (dd, 2H)4267.29 (d, 1H), 7.51-7.52 (m, 3H), 7.75 (dd, 1H), 7.91-7.92 (m, 4H), 8.23 (d, 1H), 8.37 (dd, 2H)4407.30 (dd, 1H), 7.70-7.75 (m, 4H), 7.88 (dd, 1H), 8.01 (s, 1H), 7.90-7.92 (m, 3H), 8.23 (d, 1H), 8.37 (dd, 2H)4487.21-7.22 (t, 1H), 7.29-7.30 (m, 3H), 7.55-7.57 (m, 4H), 7.75 (dd, 2H), 7.77 (dd, 2H), 7.80-7.82 (m, 3H), 7.92 (d, 1H), 8.01-8.04 (m, 3H), 8.22 (d, 1H), 8.36 (dd, 2H), 8.55 (dd, 1H)4567.28 (d, 1H), 7.36-7.37 (m, 3H), 7.70-7.75 (m, 4H), 7.88-7.90 (m, 3H), 8.23 (d, 1H), 8.37 (dd, 2H)4617.21-7.22 (dd, 1H), 7.30-7.32 (m, 3H), 7.44 (dd, 1H), 7.55-7.57 (m, 4H), 7.75 (dd, 2H), 7.77 (dd, 2H), 7.80-7.82 (m, 3H), 8.01-8.04 (m, 3H), 8.36 (dd, 2H), 8.55 (dd, 1H)4797.21-7.22 (dd, 1H), 7.29-7.31 (m, 2H), 7.55-7.57 (m, 4H), 7.75 (dd, 2H), 7.77 (dd, 2H), 7.80-7.82 (m, 3H), 8.01-8.04 (m, 3H), 8.21 (dd, 1H), 8.36 (dd, 2H), 8.55 (dd, 1H)4887.30-7.31 (m, 2H), 7.55 (dd, 1H), 7.69-7.70 (m,3H), 7.75 (dd, 2H), 7.77 (dd, 2H), 7.82 (s, 1H), 8.01-8.04 (m, 3H), 8.21 (dd, 1H), 8.36 (dd, 2H), 8.55 (dd, 1H)4957.28-7.31 (m, 4H), 7.50 (s, 1H), 7.60-7.62 (m,2H), 7.71 (dd, 1H), 8.01-8.04 (m, 3H),8.10-8.11 (m, 4H), 8.21 (dd, 1H), 8.36 (dd, 2H), 8.41 (s, 1H), 8.55 (dd, 1H)4977.28 (dd, 1H), 7.36-7.37 (m, 4H), 7.70-7.75 (m, 4H), 7.88-7.90 (m, 3H), 8.11-8.12 (m, 3H), 8.23 (d, 1H), 8.37 (dd, 2H)5207.36-7.37 (m, 3H), 7.40-7.45 (m, 3H), 7.47 (dd, 2H), 7.49-7.52 (m, 4H), 7.66 (dd, 2H), 7.69 (d, 1H), 7.79 (dd, 2H), 8.02 (dd, 2H), 8.33 (d, 1H), 8.55 (d, 1H),5427.22-7.24 (m, 4H), 7.32 (t, 1H), 7.40-7.44 (m, 3H), 7.50-7.52 (m, 4H), 7.70-7.75 (m, 2H), 7.75 (dd, 2H), 7.80-7.82 (m, 3H), 7.90 (s, 1H), 8.01-8.04 (m, 3H), 8.36 (dd, 2H), 8.55 (dd, 1H)5607.23-7.26 (m, 3H), 7.40 (m, 2H), 7.42-7.45 (m, 5H), 7.55 (dd, 1H), 7.60-7.62 (m, 4H), 7.79 (d, 1H), 8.02 (dd, 1H), 8.34-8.35 (m, 4H).

[0398] NO 1 H NMR(CDCl3, 300MHz)2-27.20-7.24 (m, 4H), 7.30-7.33 (m, 5H), 7.41-7.42 (m, 3H), 7.75 (dd, 2H), 7.89 (s, 2H), 7.94-7.96 (m, 4H), 8.00-8.03 (m, 2H), 8.11 (d, 2H), 8.19 (d, 1H), 8.30 (d, 1H), 8.55 (dd, 2H)2-47.21-7.23 (m, 3H), 7.30-7.33 (m, 6H), 7.38 (s, 1H), 7.41-7.43 (m, 4H), 7.75 (dd, 2H), 7.87-7.90 (m, 4H), 7.94-7.96 (m, 4H), 8.00-8.03 (m, 2H), 8.11 (d, 2H), 8.19 (d, 1H), 8.30 (d, 1H), 8.55 (dd, 2H)2-157.19-7.21 (m, 5H), 7.25-7.27 (m, 3H), 7.30-7.33 (m, 6H), 7.38 (s, 1H), 7.41-7.43 (m, 4H), 7.75 (dd, 2H), 7.87-7.90 (m, 4H), 7.94-7.96 (m, 4H), 8.00-8.03 (m, 2H), 8.11 (d, 2H), 8.19 (d, 1H), 8.30 (d, 1H), 8.55 (dd, 2H)2-317.19-7.21 (m, 3H), 7.23-7.25 (m, 3H), 7.30-7.32 (m, 6H), 7.41-7.43 (m, 4H), 7.75 (dd, 2H), 7.87-7.90 (m, 4H), 7.94-7.96 (m, 4H), 8.00-8.03 (m, 2H), 8.11 (d, 2H), 8.19 (d, 1H), 8.25 (s, 1H), 8.30 (d, 1H), 8.55 (dd, 2H)2-51중수소 함량 100%로 1<h2 style=";text-align:left;direction:ltr">H NMR peak 없음2-557.49 (s, 1H), 8.52 (s, 1H),2-687.52 (s, 1H), 7.66 (m, 2H)2-867.16 (t, 2H), 7.23-7.26 (m, 3H), 7.35-7.37 (m, 4H), 7.40-7.41 (m, 5H), 7.49 (dd, 2H), 7.65 (dd, 2H), 7.75 (d, 2H), 7.91-7.95 (m, 4H), 7.99 (dd, 2H), 8.56 (dd, 2H)2-1077.19 (t, 2H), 7.20-7.21 (m, 4H), 7.23-7.26 (m, 3H), 7.35-7.37 (m, 4H), 7.40-7.41 (m, 5H), 7.49 (dd, 2H), 7.65 (dd, 2H), 7.75 (d, 2H), 7.91-7.95 (m, 4H), 7.99 (dd, 2H), 8.56 (dd, 2H)2-1177.16 (t, 2H), 7.23-7.26 (m, 3H), 7.35-7.37 (m, 4H), 7.40-7.41 (m, 5H), 7.49 (dd, 2H), 7.65 (dd, 2H), 7.75 (d, 2H), 7.81 (s, 1H), 7.91-7.95 (m, 3H), 7.99 (dd, 2H), 8.56 (dd, 2H)2-123중수소 함량 100%로<h2 style=";text-align:left;direction:ltr"> 1 <h2 style=";text-align:left;direction:ltr"> H NMR peak 없음2-1337.21-7.23 (m, 3H), 7.38 (s, 1H), 7.55 (m, 2H)2-1357.50 (s, 1H)2-1447.16 (s, 1H), 7.29 (m, 2H)2-1517.55 (s, 1H)2-1557.26 (s, 1H), 7.52 (m, 2H)<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0399] <h2 style=";text-align:left;direction:ltr"> 화합물FD-MS화합물FD-MS1m / z=667.87(C)<h2 style=";text-align:left;direction:ltr"> 45 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 19 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 10 <h2 style=";text-align:left;direction:ltr"> N4S)281m / z=676.89(C<h2 style=";text-align:left;direction:ltr"> 48 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 24 <h2 style=";text-align:left;direction:ltr"> D<h2 style=";text-align:left;direction:ltr"> 10 <h2 style=";text-align:left;direction:ltr"> N4)2m / z=666.87(C<h2 style=";text-align:left;direction:ltr"> 45 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 18 <h2 style=";text-align:left;direction:ltr"> D10 N4S)282m / z=676.89(C 48 H 24 D 10 N4)3m / z=668.87(C 45 H 20 D 10 N4S)283m / z=676.89(C 48 H 24 D 10 N4)4m / z=666.87(C 45 H 18 D 10 N4S)284m / z=676.89(C 48 H 24 D 10 H4)5m / z=666.87(C 45 H 18 D 10 N4S)285m / z=676.89(C 48 H 24 D 10 N4)6m / z=667.87(C 45 H 19 D 10 N4S)286m / z=676.89(C 48 H 24 D 10 N4)7m / z=742.97(C 51 H 22 D 10 N4S)287m / z=752.99(C 54 H 28 D 10 N4)8m / z=818.05(C 57 H 25 D 10 N4S)288m / z=752.99(C 54 H 28 D 10 H4)9m / z=756.95(C 51 H 20 D 10 N4SO)289m / z=766.97(C 54 H 26 D 10 H4O)10m / z=820.06(C 57 H 27 D 10 N4S)290m / z=752.99(C 54 H 28 D10 N4)11m / z=758.97(C 51 H 24 D 10 N5S)291m / z=855.08(C 60 H 30 D 10 N6)12m / z=743.97(C 51 H 23 D 10 N4S)292m / z=752.99(C 54 H 28 D 10 N4)13m / z=833.05(C 57 H 24 D 10 N4SO)293m / z=766.97(C 54 H 26 D 10 N4O)14m / z=742.97(C 51 H 22 D 10 N4S)294m / z=752.99(C 54 H 28 D 10 N4)15m / z=820.06(C 57 H 27 D 10 N4S)295m / z=752.99(C 54 H 28 D 10 N4)16m / z=775.01(C 51 H 22 D 10 N4S2)296m / z=843.07(C 60 H 30 D 10 N4O)17m / z=716.93(C 49 H 20 D 10 N4S)297m / z=726.95(C 52 H 26 D 10 N4)18m / z=850.11(C 57 H 25 D 10 N4S2)298m / z=869.15(C 63 H 36 D 10 N4)19m / z=718.93(C 49 H22 D 10 N4S)299m / z=726.95(C 52 H 26 D 10 N4)20m / z=743.97(C 51 H 23 D 10 N4S)300m / z=752.99(C 54 H 28 D 10 N4)21m / z=650.81(C 45 H 18 D 10 N4O)301m / z=666.87(C 45 H 18 D 10 N4S)22m / z=650.81(C 45 H 18 D 10 N4O)302m / z=666.87(C 45 H 18 D 10 N4S)23m / z=651.81(C 45 H 19 D 10 N4O)303m / z=666.87(C 45 H 18 D 10 N4S)24m / z=652.81(C 45 H 20 D 10 N4O)304m / z=666.87(C 45 H 18 D 10 N4S)25m / z=651.81(C 45 H 19 D 10 N4O)305m / z=666.87(C 45 H 18 D 10 N4S)26m / z=650.81(C 45 H 18 D 10 N4O)306m / z=666.87(C 45 H 18 D 10 N4S)27m / z=727.91(C 51 H 23 D 10 N4O)307m / z=742.97(C51 H 22 D 10 N4S)28m / z=726.91(C 51 H 22 D 10 N4O)308m / z=742.97(C 51 H 22 D 10 N4S)29m / z=767.97(C 54 H 27 D 10 N4O)309m / z=756.95(C 51 H 20 D 10 N4OS)30m / z=726.91(C 51 H 22 D 10 N4O)310m / z=742.97(C 51 H 22 D 10 N4S)31m / z=740.90(C 51 H 22 D 10 N5O)311m / z=845.06(C 57 H 24 D 10 N6S)32m / z=726.91(C 51 H 22 D 10 N4O)312m / z=742.97(C 51 H 22 D 10 N4S)33m / z=741.89(C 51 H 21 D 10 N4O2)313m / z=756.95(C 51 H 20 D 10 N4OS)34m / z=729.91(C 51 H 25 D 10 N4O)314m / z=742.97(C 51 H 22 D 10 N4S)35m / z=805.00(C 57 H 28 D 10 N4O)315m / z=742.97(C 51 H 22 D 10N4S)36m / z=834.05(C 57 H 25 D 10 N4OS)316m / z=783.03(C 54 H 26 D 10 N4S)37m / z=700.87(C 49 H 20 D 10 N4O)317m / z=817.05(C 51 H 20 D 10 N4OS)38m / z=818.00(C 57 H 27 D 10 N5O)318m / z=849.11(C 57 H 24 D 10 N4S2)39m / z=700.87(C 49 H 20 D 10 N4O)319m / z=716.93(C 49 H 20 D 10 N4S)40m / z=728.91(C 51 H 24 D 10 N4O)320m / z=742.97(C 57 H 24 D 10 N4S)41m / z=731.95(C 51 H 19 D 15 N5)321m / z=650.81(C 45 H 18 D 10 N4O)42m / z=734.95(C 51 H 22 D 15 N5)322m / z=650.81(C 45 H 18 D 10 N4O)43m / z=732.95(C 51 H 20 D 15 N5)323m / z=650.81(C 45 H 18 D 10 N4O)44m / z=731.95(C 51 H 19 D15 N5)324m / z=650.81(C 45 H 18 D 10 N4O)45m / z=734.95(C 51 H 22 D 15 N5)325m / z=650.81(C 45 H 18 D 10 N4O)46m / z=732.95(C 51 H 20 D 15 N5)326m / z=650.81(C 45 H 18 D 10 N4O)47m / z=810.05(C 57 H 25 D 15 N5)327m / z=726.91(C 51 H 22 D 10 N4O)48m / z=808.05(C 57 H 23 D 15 N5)328m / z=726.91(C 51 H 22 D 10 N4O)49m / z=821.03(C 57 H 20 D 15 N5O)329m / z=740.89(C 51 H 20 D 10 N4O2)50m / z=808.05(C 57 H 23 D 15 N5)330m / z=726.91(C 51 H 22 D 10 N4O)51m / z=820.05(C 57 H 21 D 15 N6)331m / z=739.90(C 51 H 21 D 10 N5O)52m / z=812.05(C 57 H 27 D 15 N5)332m / z=726.91(C 51 H 22D 10 N4O)53m / z=901.13(C 63 H 28 D 15 N5O)333m / z=740.89(C 51 H 20 D 10 N4O2)54m / z=808.05(C 57 H 23 D 15 N5)334m / z=726.91(C 51 H 22 D 10 N4O)55m / z=885.15(C 63 H 28 D 15 N5)335m / z=726.91(C 51 H 22 D 10 N4O)56m / z=900.13(C 63 H 27 D 15 N5O)336m / z=803.00(C 57 H 26 D 10 N4O)57m / z=782.01(C 55 H 21 D 15 N5)337m / z=800.99(C 57 H 24 D 10 N4O)58m / z=917.19(C 63 H 28 D 15 N5S)338m / z=833.05(C 57 H 24 D 10 N4OS)59m / z=810.05(C 57 H 25 D 15 N5)339m / z=700.87(C 49 H 20 D 10 N4O)60m / z=812.05(C 57 H 27 D 15 N5)340m / z=740.89(C 51 H 20 D 10 N4O2)61m / z=676.89(C 48 H24 D 10 N4)341m / z=730.95(C 51 H 18 D 15 N5)62m / z=676.89(C 48 H 24 D 10 N4)342m / z=730.95(C 51 H 18 D 15 N5)63m / z=677.89(C 48 H 25 D 10 N4)343m / z=730.95(C 51 H 18 D 15 N5)64m / z=677.89(C 48 H 25 D 10 N4)344m / z=730.95(C 51 H 18 D 15 N5)65m / z=678.89(C 48 H 26 D 10 N4)345m / z=730.95(C 51 H 18 D 15 N5)66m / z=676.89(C 48 H 24 D 10 N4)346m / z=730.95(C 51 H 18 D 15 N5)67m / z=755.99(C 54 H 31 D 10 N4)347m / z=807.05(C 57 H 22 D 15 N5)68m / z=752.99(C 54 H 28 D 10 N4)348m / z=881.13(C 63 H 24 D 15 N5)69m / z=843.07(C 60 H 30 D 10 N4O)349m / z=897.13(C 63 H24 D 15 N5O)70m / z=753.99(C 54 H 29 D 10 N4)350m / z=807.05(C 57 H 22 D 15 N5)71m / z=767.99(C 54 H 29 D 10 N5)351m / z=820.05(C 57 H 21 D 15 N6)72m / z=754.99(C 54 H 30 D 10 N4)352m / z=807.05(C 57 H 22 D 15 N5)73m / z=766.97(C 54 H 26 D 10 N4O)353m / z=837.09(C 57 H 20 D 15 N5S)74m / z=752.99(C 54 H 28 D 10 N4)354m / z=807.05(C 57 H 22 D 15 N5)75m / z=830.09(C 60 H 33 D 10 N4)355m / z=807.05(C 57 H 22 D 15 N5)76m / z=843.07(C 60 H 30 D 10 N4O)356m / z=897.13(C 63 H 24 D 15 N5O)77m / z=728.95(C 52 H 28 D 10 N4)357m / z=781.01(C 55 H 20 D 15 N5)78m / z=843.07(C 60 H30 D 10 N4O)358m / z=913.19(C 63 H 24 D 15 N5S)79m / z=726.95(C 52 H 26 D 10 N4)359m / z=807.05(C 57 H 22 D 15 N5)80m / z=753.99(C 54 H 29 D 10 N4)360m / z=807.05(C 57 H 22 D 15 N5)81m / z=666.87(C 45 H 18 D 10 N4S)361m / z=676.89(C 48 H 24 D 10 N4)82m / z=666.87(C 45 H 18 D 10 N4S)362m / z=676.89(C 48 H 24 D 10 N4)83m / z=668.87(C 45 H 20 D 10 N4S)363m / z=676.89(C 48 H 24 D 10 N4)84m / z=667.87(C 45 H 19 D 10 N4S)364m / z=676.89(C 48 H 24 D 10 N4)85m / z=666.87(C 45 H 18 D 10 N4S)365m / z=675.89(C 48 H 25 D9N4)86m / z=667.87(C 45 H 19 D 10 N4S)366m / z=676.89(C 48 H 24D 10 N4)87m / z=742.97(C 51 H 22 D 10 N4S)367m / z=752.99(C 54 H 28 D 10 N4)88m / z=742.97(C 51 H 22 D 10 N4S)368m / z=752.99(C 54 H 28 D 10 N4)89m / z=759.95(C 51 H 23 D 10 N4SO)369m / z=766.97(C 54 H 26 D 10 N4O)90m / z=743.97(C 51 H 23 D 10 N4S)370m / z=750.99(C 54 H 30 D8N4)91m / z=756.97(C 51 H 22 D 10 N5S)371m / z=853.08(C 60 H 32 D8N6)92m / z=742.97(C 51 H 22 D 10 N4S)372m / z=749.99(C 54 H 31 D7N4)93m / z=756.95(C 51 H 20 D 10 N4SO)373m / z=766.97(C 54 H 26 D 10 N4O)94m / z=744.97(C 51 H 24 D 10 N4S)374m / z=752.99(C 54 H 28 D 10 N4)95m / z=819.06(C 57 H 26 D 10N4S)375m / z=749.99(C 54 H 31 D7N4)96m / z=776.01(C 51 H 23 D 10 N4S2)376m / z=829.09(C 60 H 32 D 10 N4)97m / z=766.99(C 53 H 22 D 10 N4S)377m / z=826.07(C 60 H 31 D9N4)98m / z=833.05(C 57 H 24 D 10 N4SO)378m / z=829.09(C 60 H 32 D 10 N4)99m / z=743.97(C 51 H 23 D 10 N4S)379m / z=726.95(C 52 H 26 D 10 N4)100m / z=742.97(C 51 H 22 D 10 N4S)380m / z=752.99(C 54 H 28 D 10 N4)101m / z=650.81(C 45 H 18 D 10 N4O)381m / z=682.93(C 48 H 18 D 16 N4)102m / z=651.81(C 45 H 18 D 10 N4O)382m / z=680.91(C 48 H 20 D 14 N4)103m / z=650.81(C 45 H 18 D 10 N4O)383m / z=680.92(C 48 H 18 D 15N4)104m / z=652.81(C 45 H 20 D 10 N4O)384m / z=683.93(C 48 H 17 D 17 N4)105m / z=653.81(C 45 H 21 D 10 N4O)385m / z=680.92(C 48 H 18 D 15 N4)106m / z=650.81(C 45 H 18 D 10 N4O)386m / z=680.92(C 48 H 18 D 15 N4)107m / z=726.91(C 51 H 22 D 10 N4O)387m / z=680.91(C 48 H 20 D 14 N4)108m / z=727.91(C 51 H 23 D 10 N4O)388m / z=762.04(C 54 H 19 D 19 N4)109m / z=743.89(C 51 H 23 D 10 N4O2)389m / z=760.03(C 54 H 21 D 17 N4)110m / z=803.00(C 57 H 26 D 10 N4O)390m / z=762.04(C 54 H 19 D 19 N4)111m / z=816.00(C 57 H 25 D 10 N5O)391m / z=733.97(C 51 H 15 D 18 N5)112m / z=726.91(C 51 H 22 D10 N4O)392m / z=735.98(C 51 H 13 D 20 N5)113m / z=757.95(C 51 H 21 D 10 N4OS)393m / z=735.98(C 51 H 13 D 20 N5)114m / z=728.91(C 51 H 24 D 10 N4O)394m / z=733.97(C 51 H 15 D 18 N5)115m / z=805.00(C 57 H 28 D 10 N4O)395m / z=736.99(C 51 H 12 D 21 N5)116m / z=833.05(C 57 H 24 D 10 N4OS)396m / z=817.11(C 57 H 12 D 25 N5)117m / z=700.87(C 49 H 20 D 10 N4O)397m / z=812.08(C 57 H 17 D 20 N5)118m / z=819.99(C 57 H 27 D 10 N4O2)398m / z=817.11(C 57 H 12 D 25 N5)119m / z=701.87(C 49 H 21 D 10 N4O)399m / z=816.10(C 57 H 13 D 24 N5)120m / z=726.91(C 51 H 22 D 10 N4O)400m / z=822.04(C 57 H19 D 16 N5)121m / z=731.95(C 51 H 19 D 15 N5)401m / z=672.90(C 45 H 12 D 16 N4S)122m / z=732.95(C 51 H 20 D 15 N5)402m / z=671.90(C 45 H 13 D 15 N4S)123m / z=733.95(C 51 H 21 D 15 N5)403m / z=671.90(C 45 H 13 D 15 N4S)124m / z=731.95(C 51 H 19 D 15 N5)404m / z=673.90(C 45 H 11 D 17 N4S)125m / z=732.95(C 51 H 20 D 15 N5)405m / z=674.92(C 45 H 10 D 18 N4S)126m / z=733.95(C 51 H 21 D 15 N5)406m / z=753.03(C 51 H 12 D 20 N4S)127m / z=807.05(C 57 H 22 D 15 N5)407m / z=673.90(C 45 H 11 D 17 N4S)128m / z=808.05(C 57 H 23 D 15 N5)408m / z=671.90(C 45 H 13 D 15 N4S)129m / z=821.03(C57 H 20 D 15 N5O)409m / z=671.90(C 45 H 13 D 15 N4S)130m / z=808.05(C 57 H 23 D 15 N5)410m / z=673.90(C 45 H 11 D 17 N4S)131m / z=823.05(C 57 H 24 D 15 N6)411m / z=842.10(C 57 H 15 D 19 N4OS)132m / z=807.05(C 57 H 22 D 15 N5)412m / z=655.84(C 45 H 13 D 15 N4O)133m / z=823.03(C 57 H 22 D 15 N5O)413m / z=655.84(C 45 H 13 D 15 N4O)134m / z=808.05(C 57 H 23 D 15 N5)414m / z=657.85(C 45 H 11 D 17 N4O)135m / z=850.11(C 60 H 29 D 15 N4)415m / z=657.85(C 45 H 11 D 17 N4O)136m / z=842.09(C 57 H 25 D 15 N5OS)416m / z=736.97(C 51 H 12 D 20 N4O)137m / z=781.01(C 55 H 20 D 15N5)417m / z=734.96(C 51 H 14 D 18 N4O)138m / z=898.13(C 63 H 25 D 15 N5O)418m / z=747.95(C 51 H 13 D 18 N5O)139m / z=808.05(C 57 H 23 D 15 N5)419m / z=655.84(C 45 H 13 D 15 N4O)140m / z=810.05(C 57 H 25 D 15 N5)420m / z=828.05(C 57 H 13 D 21 N4O2)141m / z=676.89(C 48 H 24 D 10 N4)421m / z=682.93(C 48 H 18 D 16 N4)142m / z=676.89(C 48 H 24 D 10 N4)422m / z=681.92(C 48 H 19 D 15 N4)143m / z=678.89(C 48 H 26 D 10 N4)423m / z=681.92(C 48 H 19 D 15 N4)144m / z=677.89(C 48 H 25 D 10 N4)424m / z=683.93(C 48 H 17 D 17 N4)145m / z=676.89(C 48 H 24 D 10 N4)425m / z=684.93(C 48 H 16 D18 N4)146m / z=676.89(C 48 H 24 D 10 N4)426m / z=762.04(C 54 H 19 D 19 N4)147m / z=754.99(C 54 H 30 D 10 N4)427m / z=760.03(C 54 H 21 D 17 N4)148m / z=753.99(C 54 H 29 D 10 N4)428m / z=775.02(C 54 H 18 D 18 N4O)149m / z=844.07(C 60 H 31 D 10 N4O)429m / z=758.02(C 54 H 23 D 15 N4)150m / z=752.99(C 54 H 28 D 10 N4)430m / z=764.04(C 54 H 17 D 21 N4)151m / z=766.99(C 54 H 28 D 10 N5)431m / z=826.09(C 57 H 14 D 21 N5O)152m / z=755.99(C 54 H 31 D 10 N4)432m / z=735.98(C 51 H 13 D 20 N5)153m / z=829.09(C 60 H 32 D 10 N4)433m / z=736.99(C 51 H 12 D 21 N5)154m / z=752.99(C 54 H 28D 10 N4)434m / z=735.98(C 51 H 13 D 20 N5)155m / z=753.99(C 54 H 29 D 10 N4)435m / z=734.98(C 51 H 14 D 19 N5)156m / z=766.97(C 54 H 26 D 10 N4O)436m / z=816.10(C 57 H 13 D 24 N5)157m / z=728.95(C 52 H 28 D 10 N4)437m / z=817.11(C 57 H 12 D 25 N5)158m / z=846.07(C 60 H 33 D 10 N4O)438m / z=823.07(C 57 H 18 D 18 N6)159m / z=726.95(C 52 H 26 D 10 N4)439m / z=810.07(C 57 H 19 D 18 N5)160m / z=753.99(C 54 H 29 D 10 N4)440m / z=827.07(C 57 H 14 D 21 N5O)161m / z=666.87(C 45 H 18 D 10 N4S)441m / z=742.97(C 51 H 22 D 10 N4S)162m / z=667.87(C 45 H 19 D 10 N4S)442m / z=742.97(C 51 H22 D 10 N4S)163m / z=666.87(C 45 H 18 D 10 N4S)443m / z=832.06(C 57 H 25 D 10 N4S)164m / z=666.87(C 45 H 18 D 10 N4S)444m / z=741.96(C 51 H 23 D9N4S)165m / z=668.87(C 45 H 20 D 10 N4S)445m / z=742.97(C 51 H 22 D 10 N4S)166m / z=666.87(C 45 H 18 D 10 N4S)446m / z=756.97(C 51 H 22 D 10 N5S)167m / z=742.97(C 51 H 22 D 10 N4S)447m / z=726.91(C 51 H 22 D 10 N4O)168m / z=742.97(C 51 H 22 D 10 N4S)448m / z=648.81(C 45 H 20 D8N4O)169m / z=759.95(C 51 H 23 D 10 N4OS)449m / z=726.91(C 51 H 22 D 10 N4O)170m / z=742.97(C 51 H 22 D 10 N4S)450m / z=803.00(C 57 H 26 D 10 N4O)171m / z=756.97(C 51 H22 D 10 N5S)451m / z=739.88(C 51 H 21 D9N4O2)172m / z=742.97(C 51 H 22 D 10 N4S)452m / z=726.91(C 51 H 22 D 10 N4O)173m / z=756.95(C 51 H 20 D 10 N4OS)453m / z=816.99(C 57 H 24 D 10 N4O2)174m / z=742.97(C 51 H 22 D 10 N4S)454m / z=650.81(C 45 H 18 D 10 N4O)175m / z=822.06(C 57 H 29 D 10 N4S)455m / z=832.04(C 57 H 25 D9N4O2)176m / z=832.06(C 57 H 25 D 10 N5S)456m / z=742.97(C 51 H 22 D 10 N4S)177m / z=717.93(C 49 H 21 D 10 N4S)457m / z=832.06(C 57 H 25 D 10 N5S)178m / z=821.06(C 57 H 28 D 10 N4S)458m / z=756.97(C 51 H 20 D 10 N4OS)179m / z=832.06(C 57 H 25 D 10 N5S)459m / z=755.97(C 51 H21 D9N4OS)180m / z=742.97(C 51 H 22 D 10 N4S)460m / z=819.06(C 57 H 26 D 10 N4S)181m / z=650.81(C 45 H 18 D 10 N4O)461m / z=802.02(C 57 H 27 D 10 N5)182m / z=650.81(C 45 H 18 D 10 N4O)462m / z=804.03(C 57 H 25 D 12 N5)183m / z=650.81(C 45 H 18 D 10 N4O)463m / z=819.04(C 57 H 22 D 14 N6)184m / z=650.81(C 45 H 18 D 10 N4O)464m / z=802.02(C 57 H 27 D 10 N5)185m / z=650.81(C 45 H 18 D 10 N4O)465m / z=821.03(C 57 H 20 D 15 N5O)186m / z=650.81(C 45 H 18 D 10 N4O)466m / z=896.13(C 63 H 25 D 14 N5O)187m / z=726.91(C 51 H 22 D 10 N4O)467m / z=806.04(C 57 H 23 D 14 N5)188m / z=726.91(C 51H 22 D 10 N4O)468m / z=730.95(C 51 H 18 D 15 N5)189m / z=740.89(C 51 H 20 D 10 N4O2)469m / z=728.94(C 51 H 20 D 13 N5)190m / z=726.91(C 51 H 22 D 10 N4O)470m / z=881.14(C 63 H 28 D 13 N5)191m / z=739.90(C 51 H 21 D 10 N5O)471m / z=802.02(C 57 H 27 D 10 N5)192m / z=726.91(C 51 H 22 D 10 N4O)472m / z=806.04(C 57 H 23 D 14 N5)193m / z=740.89(C 51 H 20 D 10 N4O2)473m / z=817.03(C 57 H 24 D 12 N6)194m / z=726.91(C 51 H 22 D 10 N4O)474m / z=728.94(C 51 H 20 D 13 N5)195m / z=726.91(C 51 H 22 D 10 N4O)475m / z=821.03(C 57 H 20 D 15 N5O)196m / z=816.00(C 57 H 25 D 10N5O)476m / z=826.06(C 57 H 15 D 20 N5O)197m / z=750.93(C 53 H 22 D 10 N4)477m / z=891.20(C 63 H 18 D 23 N5)198m / z=816.99(C 57 H 24 D 10 N4O2)478m / z=735.98(C 51 H 13 D 20 N5)199m / z=700.87(C 49 H 20 D 10 N4O)479m / z=916.21(C 63 H 21 D 18 N5S)200m / z=726.91(C 51 H 22 D 10 N4O)480m / z=901.15(C 63 H 20 D 19 N5O)201m / z=730.95(C 51 H 18 D 15 N5)481m / z=744.98(C 51 H 20 D 12 N4S)202m / z=730.95(C 51 H 18 D 15 N5)482m / z=748.00(C 51 H 17 D 15 N4S)203m / z=730.95(C 51 H 18 D 15 N5)483m / z=759.99(C 51 H 17 D 14 N5S)204m / z=730.95(C 51 H 18 D 15 N5)484m / z=743.97(C 51 H 21 D11 N4S)205m / z=730.95(C 51 H 18 D 15 N5)485m / z=761.98(C 51 H 15 D 15 N4OS)206m / z=730.95(C 51 H 18 D 15 N5)486m / z=751.01(C 51 H 14 D 18 N4S)207m / z=807.05(C 57 H 22 D 15 N5)487m / z=731.94(C 51 H 17 D 15 N4O)208m / z=807.05(C 57 H 22 D 15 N5)488m / z=726.91(C 51 H 22 D 10 N4O)209m / z=897.13(C 63 H 24 D 15 N5O)489m / z=761.98(C 51 H 15 D 15 N4OS)210m / z=807.05(C 57 H 22 D 15 N5)490m / z=807.03(C 57 H 22 D 14 N4O)211m / z=820.05(C 57 H 21 D 15 N6)491m / z=735.96(C 51 H 13 D 19 N4O)212m / z=807.05(C 57 H 22 D 15 N5)492m / z=746.92(C 51 H 14 D 16 N4O2)213m / z=821.03(C 57 H20 D 15 N5O)493m / z=842.10(C 57 H 15 D 19 N4OS)214m / z=807.05(C 57 H 22 D 15 N5)494m / z=809.04(C 57 H 20 D 16 N4O)215m / z=807.05(C 57 H 22 D 15 N5)495m / z=735.96(C 51 H 13 D 19 N4O)216m / z=897.13(C 63 H 24 D 15 N5O)496m / z=840.09(C 57 H 17 D 17 N4OS)217m / z=857.11(C 61 H 24 D 15 N5)497m / z=751.01(C 51 H 14 D 18 N4S)218m / z=883.15(C 63 H 26 D 15 N5)498m / z=762.99(C 51 H 14 D 16 N4OS)219m / z=807.05(C 57 H 22 D 15 N5)499m / z=821.07(C 57 H 20 D 14 N4S)220m / z=807.05(C 57 H 22 D 15 N5)500m / z=916.19(C 63 H 21 D 17 N4OS)221m / z=676.89(C 48 H 24 D 10 N4)501m / z=832.04(C57 H 25 D9N4S)222m / z=676.89(C 48 H 24 D 10 N4)502m / z=818.06(C 57 H 27 D9N4S)223m / z=676.89(C 48 H 24 D 10 N4)503m / z=742.97(C 51 H 22 D 10 N4S)224m / z=676.89(C 48 H 24 D 10 N4)504m / z=832.06(C 57 H 25 D 10 N5S)225m / z=676.89(C 48 H 24 D 10 N4)505m / z=664.86(C 45 H 20 D8N4S)226m / z=676.89(C 48 H 24 D 10 N4)506m / z=742.97(C 51 H 22 D 10 N4S)227m / z=752.99(C 54 H 28 D 10 N4)507m / z=740.89(C 51 H 20 D 10 N4O2)228m / z=752.99(C 54 H 28 D 10 N4)508m / z=803.00(C 57 H 26 D 10 N4O)229m / z=783.03(C 54 H 26 D 10 N4S)509m / z=650.81(C 45 H 18 D 10 N4O)230m / z=752.99(C 54 H 28D 10 N4)510m / z=724.89(C 51 H 24 D8N4O)231m / z=765.99(C 54 H 27 D 10 N5)511m / z=893.08(C 63 H 28 D 10 N4O2)232m / z=752.99(C 54 H 28 D 10 N4)512m / z=725.90(C 51 H 23 D9N4O)233m / z=766.97(C 54 H 26 D 10 N4O)513m / z=725.90(C 51 H 23 D9N4O)234m / z=752.99(C 54 H 28 D 10 N4)514m / z=803.00(C 57 H 26 D 10 N4O)235m / z=752.99(C 54 H 28 D 10 N4)515m / z=877.09(C 63 H 28 D 10 N4O)236m / z=842.08(C 60 H 31 D 10 N5)516m / z=816.04(C 57 H 25 D9N4S)237m / z=777.01(C 56 H 26 D 10 N4)517m / z=849.11(C 57 H 24 D 10 N4S2)238m / z=843.07(C 60 H 30 D 10 N4O)518m / z=742.97(C 51 H 22 D 10 N4S)239m / z=726.95(C52 H 26 D 10 N4)519m / z=819.09(C 57 H 26 D 10 N4S)240m / z=752.99(C 54 H 28 D 10 N4)520m / z=742.97(C 51 H 22 D 10 N4S)241m / z=666.87(C 45 H 18 D 10 N4S)521m / z=831.30(C 57 H 25 D9N4OS)242m / z=666.87(C 45 H 18 D 10 N4S)522m / z=819.09(C 57 H 26 D 10 N4S)243m / z=666.87(C 45 H 18 D 10 N4S)523m / z=742.97(C 51 H 22 D 10 N4S)244m / z=666.87(C 45 H 18 D 10 N4S)524m / z=832.06(C 57 H 25 D 10 N5S)245m / z=666.87(C 45 H 18 D 10 N4S)525m / z=664.86(C 45 H 20 D8N4S)246m / z=666.87(C 45 H 18 D 10 N4S)526m / z=742.97(C 51 H 22 D 10 N4S)247m / z=742.97(C 51 H 22 D 10 N4S)527m / z=740.30(C51 H 20 D 10 N4S2)248m / z=742.97(C 51 H 22 D 10 N4S)528m / z=802.35(C 57 H 26 D 10 N4O)249m / z=756.95(C 51 H 20 D 10 N4OS)529m / z=650.29(C 45 H 18 D 10 N4O)250m / z=742.97(C 51 H 22 D 10 N4S)530m / z=724.89(C 51 H 24 D8N4O)251m / z=845.06(C 57 H 24 D 10 N6S)531m / z=892.36(C 63 H 28 D 10 N4O2)252m / z=742.97(C 51 H 22 D 10 N4S)532m / z=725.90(C 51 H 23 D9N4O)253m / z=756.95(C 51 H 20 D 10 N4OS)533m / z=725.90(C 51 H 23 D9N4O)254m / z=742.97(C 51 H 22 D 10 N4S)534m / z=802.35(C 57 H 26 D 10 N4O)255m / z=742.97(C 51 H 22 D 10 N4S)535m / z=877.09(C 63 H 28 D 10 N4O)256m / z=783.03(C 54 H26 D 10 N4S)536m / z=816.04(C 57 H 25 D9N4S)257m / z=716.93(C 49 H 20 D 10 N4S)537m / z=849.11(C 57 H 24 D 10 N4S2)258m / z=755.97(C 51 H 25 D 10 N5S)538m / z=742.97(C 51 H 22 D 10 N4S)259m / z=716.93(C 49 H 20 D 10 N4S)539m / z=819.09(C 57 H 26 D 10 N4S)260m / z=742.97(C 51 H 22 D 10 N4S)540m / z=742.97(C 51 H 22 D 10 N4S)261m / z=730.95(C 51 H 18 D 15 N5)541m / z=742.97(C 51 H 22 D 10 N4S)262m / z=730.95(C 51 H 18 D 15 N5)542m / z=819.09(C 57 H 26 D 10 N4S)263m / z=730.95(C 51 H 18 D 15 N5)543m / z=746.99(C 51 H 18 D 14 N4S)264m / z=730.95(C 51 H 18 D 15 N5)544m / z=743.97(C 51H 21 D 11 N4S)265m / z=730.95(C 51 H 18 D 15 N5)545m / z=739.95(C 51 H 25 D7N4S)266m / z=730.95(C 51 H 18 D 15 N5)546m / z=728.92(C 51 H 20 D 12 N4O)267m / z=807.05(C 57 H 22 D 15 N5)547m / z=805.02(C 57 H 24 D 12 N4O)268m / z=807.05(C 57 H 22 D 15 N5)548m / z=804.02(C 57 H 25 D 11 N4O)269m / z=897.13(C 63 H 24 D 15 N5O)549m / z=725.30(C 51 H 23 D9N4O)270m / z=807.05(C 57 H 22 D 15 N5)550m / z=805.02(C 57 H 24 D 12 N4O)271m / z=820.05(C 57 H 21 D 15 N6)551m / z=920.43(C 66 H 32 D 12 N4O)272m / z=807.05(C 57 H 22 D 15 N5)552m / z=830.42(C 60 H 30 D 12 N4)273m / z=821.03(C 57 H 20D 15 N5O)553m / z=753.99(C 54 H 27 D 11 N4)274m / z=807.05(C 57 H 22 D 15 N5)554m / z=830.42(C 60 H 30 D 12 N4)275m / z=807.05(C 57 H 22 D 15 N5)555m / z=754.38(C 54 H 26 D 12 N4)276m / z=897.13(C 63 H 24 D 15 N5O)556m / z=880.42(C 63 H 28 D 13 N5)277m / z=831.07(C 59 H 22 D 15 N5)557m / z=909.37(C 63 H 27 D 12 N5S)278m / z=913.19(C 63 H 24 D 15 N5OS)558m / z=880.42(C 63 H 28 D 13 N5)279m / z=807.05(C 57 H 22 D 15 N5)559m / z=806.40(C 57 H 22 D 15 N5)280m / z=807.05(C 57 H 22 D 15 N5)560m / z=807.41(C 57 H 22 D 16 N5 )

[0400] 화합물FD-MS화합물FD-MS2-1m / z=484.60(C 36 H 24N2)2-81m / z=484.60(C 36 H 24 N2)2-2m / z=560.70(C 42 H 28 N2)2-82m / z=560.70(C 42 H 28 N2)2-3m / z=560.70(C 42 H 28 N2)2-83m / z=560.70(C 42 H 28 N2)2-4m / z=636.80(C 48 H 32 N2)2-84m / z=560.70(C 42 H 28 N2)2-5m / z=636.80(C 48 H 32 N2)2-85m / z=560.70(C 42 H 28 N2)2-6m / z=636.80(C 48 H 32 N2)2-86m / z=560.70(C 42 H 28 N2)2-7m / z=634.78(C 48 H 30 N2)2-87m / z=636.80(C 48 H 32 N2)2-8m / z=636.80(C 48 H 32 N2)2-88m / z=636.80(C 48 H 32 N2)2-9m / z=575.68(C 42 H 26 N2)2-89m / z=636.80(C 48 H 32 N2)2-10m / z=650.78(C 48 H 30 N2O)2-90m / z=636.80(C 48 H 32 N2)2-11m / z=636.80(C 48 H 32 N2)2-91m / z=560.70(C 42 H 28 N2)2-12m / z=636.80(C 48 H32 N2)2-92m / z=636.80(C 48 H 32 N2)2-13m / z=712.90(C 54 H 36 N2)2-93m / z=636.80(C 48 H 32 N2)2-14m / z=650.78(C 48 H 30 N2O)2-94m / z=636.80(C 48 H 32 N2)2-15m / z=712.90(C 54 H 36 N2)2-95m / z=636.80(C 48 H 32 N2)2-16m / z=712.90(C 54 H 36 N2)2-96m / z=636.80(C 48 H 32 N2)2-17m / z=636.80(C 48 H 32 N2)2-97m / z=558.68(C 42 H 26 N2)2-18m / z=650.78(C 48 H 30 N2O)2-98m / z=712.90(C 54 H 36 N2)2-19m / z=712.90(C 54 H 36 N2)2-99m / z=498.58(C 36 H 22 N2O)2-20m / z=710.88(C 54 H 34 N2)2-100m / z=712.90(C 54 H 36 N2)2-21m / z=636.80(C 48 H 32 N2)2-101m / z=484.60(C 36 H 24 N2)2-22m / z=636.80(C 48 H 32 N2)2-102m / z=560.70(C 42 H 28N2)2-23m / z=636.80(C 48 H 32 N2)2-103m / z=498.58(C 36 H 22 N2O)2-24m / z=590.74(C 42 H 26 N2S)2-104m / z=560.70(C 42 H 28 N2)2-25m / z=788.99(C 60 H 40 N2)2-105m / z=558.68(C 42 H 26 N2)2-26m / z=712.90(C 54 H 36 N2)2-106m / z=560.70(C 42 H 28 N2)2-27m / z=788.99(C 60 H 40 N2)2-107m / z=636.80(C 48 H 32 N2)2-28m / z=712.90(C 54 H 36 N2)2-108m / z=712.90(C 54 H 36 N2)2-29m / z=788.99(C 60 H 40 N2)2-109m / z=636.80(C 48 H 32 N2)2-30m / z=712.90(C 54 H 36 N2)2-110m / z=636.80(C 48 H 32 N2)2-31m / z=726.88(C 54 H 34 N2O)2-111m / z=560.70(C 42 H 28 N2)2-32m / z=560.70(C 42 H 28 N2)2-112m / z=636.80(C 48 H 32 N2)2-33m / z=636.80(C 48 H 32 N2)2-113m / z=636.80(C48 H 32 N2)2-34m / z=636.80(C 48 H 32 N2)2-114m / z=560.70(C 42 H 28 N2)2-35m / z=712.90(C 54 H 36 N2)2-115m / z=574.68(C 42 H 26 N2O)2-36m / z=636.80(C 48 H 32 N2)2-116m / z=484.60(C 36 H 24 N2)2-37m / z=712.90(C 54 H 36 N2)2-117m / z=560.70(C 42 H 28 N2)2-38m / z=712.90(C 54 H 36 N2)2-118m / z=560.70(C 42 H 28 N2)2-39m / z=574.68(C 42 H 26 N2O)2-119m / z=560.70(C 42 H 28 N2)2-40m / z=788.99(C 60 H 40 N2)2-120m / z=636.80(C 48 H 32 N2)2-41m / z=508.75(C 36 D 24 N2)2-121m / z=508.75(C 36 D 24 N2)2-42m / z=587.86(C 42 HD 27 N2)2-122m / z=588.87(C 42 D 28 N2)2-43m / z=588.75(C 42 D 28 N2)2-123m / z=588.87(C 42 D 28 N2)2-44m / z=666.98(C 48 H2D30 N2)2-124m / z=586.86(C 42 H2D 26 N2)2-45m / z=668.98(C 48 D 32 N2)2-125m / z=588.87(C 42 D 28 N2)2-46m / z=665.98(C 48 H3D 29 N2)2-126m / z=588.87(C 42 D 28 N2)2-47m / z=662.98(C 48 H2D 28 N2)2-127m / z=588.87(C 42 D 28 N2)2-48m / z=668.98(C 48 D 32 N2)2-128m / z=666.98(C 48 H2D 30 N2)2-49m / z=600.84(C 42 D 26 N2O)2-129m / z=665.98(C 48 H3D 29 N2)2-50m / z=678.98(C 48 H2D 28 N2)2-130m / z=668.98(C 48 D 32 N2)2-51m / z=668.98(C 48 D 32 N2)2-131m / z=588.87(C 42 D 28 N2)2-52m / z=667.98(C 48 HD 31 N2)2-132m / z=664.98(C 48 H4D 28 N2)2-53m / z=748.12(C 54 HD 35 N2)2-133m / z=663.96(C 48 H5D 27 N2)2-54m / z=680.96(C 48 D 30 N2O)2-134m / z=668.98(C 48 D32 N2)2-55m / z=747.10(C 54 H2D 34 N2)2-135m / z=667.98(C 48 HD 31 N2)2-56m / z=739.05(C 54 H 10 D 26 N2)2-136m / z=585.87(C 42 H3D 25 N2)2-57m / z=668.98(C 48 D 32 N2)2-137m / z=582.83(C 42 H2D 24 N2)2-58m / z=677.98(C 48 H3D 27 N2O)2-138m / z=749.12(C 54 D 36 N2)2-59m / z=746.10(C 54 H3D 33 N2)2-139m / z=518.71(C 36 H2D 20 N2O)2-60m / z=744.08(C 54 HD 33 N2)2-140m / z=748.12(C 54 HD 35 N2)2-61m / z=668.98(C 48 D 32 N2)2-141m / z=508.75(C 36 D 24 N2)2-62m / z=666.98(C 48 H2D 30 N2)2-142m / z=588.87(C 42 D 28 N2)2-63m / z=667.98(C 48 HD 31 N2)2-143m / z=520.72(C 36 D 22 N2O)2-64m / z=614.89(C 42 H2D 24 N2S)2-144m / z=583.84(C 42 H5D 23 N2)2-65m / z=826.22(C60 H3D 37 N2)2-145m / z=583.84(C 42 HD 25 N2)2-66m / z=747.10(C 54 H2D 34 N2)2-146m / z=588.87(C 42 D 28 N2)2-67m / z=829.24(C 60 D 40 N2)2-147m / z=668.98(C 48 D 32 N2)2-68m / z=746.10(C 54 H3D 33 N2)2-148m / z=746.12(C 54 H3D 33 N2)2-69m / z=829.24(C 60 D 40 N2)2-149m / z=665.97(C 48 H3D 29 N2)2-70m / z=747.10(C 54 H2D 34 N2)2-150m / z=668.98(C 48 D 32 N2)2-71m / z=759.09(C 54 H2D 32 N2)2-151m / z=587.87(C 42 HD 27 N2)2-72m / z=588.75(C 42 D 28 N2)2-152m / z=668.98(C 48 D 32 N2)2-73m / z=668.98(C 48 D 32 N2)2-153m / z=666.98(C 48 H2D 30 N2)2-74m / z=668.98(C 48 D 32 N2)2-154m / z=588.87(C 42 D 28 N2)2-75m / z=749.12(C 54 D 36 N2)2-155m / z=596.82(C42 H4D 22 N2O)2-76m / z=666.98(C 48 H2D 30 N2)2-156m / z=508.75(C 36 D 24 N2)2-77m / z=824.21(C 60 H5D 35 N2)2-157m / z=588.87(C 42 D 28 N2)2-78m / z=829.24(C 60 D 40 N2)2-158m / z=586.86(C 42 H2D 26 N2)2-79m / z=598.83(C 42 H2D 24 N2)2-159m / z=588.87(C 42 D 28 N2)2-80m / z=862.22(C 60 H3D 37 N2)2-160m / z=668.99(C 48 D 32 N2)

[0401] <Experimental Example 1>1) Fabrication of organic light-emitting devices

[0402] A glass substrate coated with a 1,500 Å thick ITO film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes in a UV cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), where it was plasma-treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.

[0403] A common layer, a hole injection layer 2-TNATA (4,4',4''-Tris[2-naphthyl (phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), were formed on the ITO transparent electrode (anode).

[0404] On top of that, a light-emitting layer was thermally vacuum-deposited as follows. The light-emitting layer used a heterocyclic compound of Chemical Formula 1 or a comparative example compound described in Table 12 below as a host, and Ir(ppy)3(tris(2-phenylpyridine)iridium) as a green phosphorescent dopant. The host was doped with 7% Ir(ppy)3 and deposited to a thickness of 360Å. Then, BCP was deposited to a thickness of 60Å as a hole-blocking layer, and Alq3 was deposited to a thickness of 200Å as an electron-transporting layer thereon. Finally, lithium fluoride (LiF) was deposited to a thickness of 10Å on the electron-transporting layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1200Å on the electron injection layer to form a cathode, thereby manufacturing an organic electroluminescent device.

[0405] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -8 ~10 -6 It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0406] Compounds Ref. 1 to Ref. 12 used as the above comparative examples are as follows.

[0407]

[0408] 2) Driving voltage and luminous efficiency of organic field effect devices

[0409] The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured using M7000 from Max Science, and the standard luminance was determined to be 6,000 cd / m using the life measurement equipment (M6000) manufactured by Max Science based on the measurement results. 2 At that time, T90 was measured.

[0410] 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 were as shown in Table 12 below.

[0411] Compound Driving voltage (V) Luminous efficacy (cd / A) Color coordinate Lifespan (T90) Comparative example 1 Ref. 16.49 20.5 Green 10 Comparative example 2 Ref. 26.60 19.7 Green 25 Comparative example 3 Ref. 36.50 20.5 Green 30 Comparative example 4 Ref. 46.68 20.6 Green 25 Comparative example 5 Ref. 56.74 18.8 Green 19 Comparative example 6 Ref. 66.66 20.5 Green 25 Comparative example 7 Ref. 76.70 19.5 Green 20 Comparative example 8 Ref. 86.01 24.1 Green 25 Comparative example 9 Ref. 96.11 20.3 Green 23 Comparative example 10Ref.105.8819.1Green19Comparative Example 11Ref.115.9821.3Green34Comparative Example 12Ref.126.4016.5Green16Example 194.2041.5Green150Example 2124.1245.2Green162Example 3134.9540.0Green80Example 4174.0844.6Green160Example 5284.1543.5Green159Example 6294.0045.1Green165Example 7324.0544.8Green170Example 8384.9839.2Green75Example Example 9415.1133.9Green58Example 10465.2834.0Green69Example 11475.0531.1Green50Example 12595.6733.2Green66Example 13634.2242.5Green154Example 14804.1143.5Green158Example 15974.0944.7Green172Example 161064.0546.6Green156Example 171114.0243.2Green164Example 181134.9435.8Green101Example 191355.5330.9Green40 Example 201365.4934.1Green52Example 211385.7730.0Green49Example 221545.7034.5Green51Example 231664.0545.3Green156Example 241784.0846.6Green169Example 251795.5030.7Green43Example 261804.0145.1Green170Example 271964.1944.2Green163Example 281974.0246.8Green150Example 292075.6127.9Green59Example 302145.7033.6Green42Example 312264.1645.3Green149Example 322474.0543.8Green165Example 332514.1045.1Green176Example 342534.4940.6Green82Example 352785.7131.9Green76Example 362984.2942.2Green156Example 373174.0442.1Green165Example 383354.0043.0Green170Example 393525.5734.5Green50Example 403764.2641.5Green149Example 413964.1544.1Green158Example 424185.6131.5Gr een45 Example 434264.0943.0Green159 Example 444404.6140.1Green65 Example 454484.5542.9Green166 Example 464565.5033.2Green52 Example 474614.1643.1Green152 Example 484794.4838.5Green76 Example 494884.1243.5Green156 Example 504955.7033.1Green55 Example 514975.5930.0Green60 Example 525204.6639.5Green50 Example 535424.7045.2Green145 Example 545605.6631.8Green48.

[0412] Through the results in Table 12 above, it can be seen that the driving voltage, luminous efficiency, and lifespan of the organic light-emitting device manufactured using the heterocyclic compound of the present invention as a light-emitting layer material are all superior to those of the comparative example.

[0413] In particular, the compound used in Comparative Example 1 is a compound that does not contain a triazine group and does not contain deuterium in the carbazole condensation derivative substituent, and thus has a high driving voltage, low luminous efficiency, and significantly short lifespan. On the other hand, the compounds of the present invention contain a triazine group that can accept electrons to form excitons, and thus can form stable excitons with an appropriate balance of holes and electrons. Therefore, when a device is manufactured using the compound of the present invention, it exhibits high luminous efficiency and lifespan.

[0414] In addition, the compounds used in Comparative Examples 2 to 5 are compounds whose structures contain a triazine group and do not contain deuterium in the carbazole condensation derivative substituent, and thus, it can be confirmed that their performance is inferior to that of the examples. This is because, in the case of compounds substituted with deuterium, which is heavier than light hydrogen, the molecular vibration energy decreases, weakening the intermolecular interaction, thereby forming a durable element, thereby obtaining high life results.

[0415] Compounds of Comparative Examples 6 and 7 are compounds containing a carbazole group, not a carbazole condensation derivative. The carbazole condensation derivative of the present invention exhibits faster hole mobility than the carbazole group due to its strong hole mobility. Therefore, it exhibits excellent driving characteristics and forms a balanced mobility with the triazine group, which has fast electron mobility, resulting in excellent efficiency and lifespan.

[0416] Compound 8 of Comparative Example is a compound in which deuterium is incorporated into a triazine group rather than a carbazole condensation derivative substituent. When deuterium is substituted into a triazine group, the structural stability is superior to that of carbazole, and the stable basis energy and vibrational energy effects due to deuterium substitution are not as great as when deuterium is substituted into carbazole.

[0417] Compounds of Comparative Examples 9 and 10 are compounds in which the linker of the triazine group and the carbazole condensation derivative substituent is an unsubstituted phenylene group. In the case of the compound of the present invention having a substituted phenylene linker, separation of HOMO and LUMO occurs, thereby forming a stable HOMO energy value compared to a compound having an unsubstituted phenylene group as a linker. This allows the formation of a stable exciton, thereby exhibiting excellent efficiency and lifetime when applied to devices.

[0418] The compound of Comparative Example 11 is a compound whose linker is dibenzofuran, and the compound of Comparative Example 12 is a compound without a linker. It can be seen that the driving voltage, luminous efficiency, and lifespan of Comparative Examples 11 and 12, which use compounds that do not satisfy the linker conditions of the present invention, are worse than those of the examples using the heterocyclic compound of the present invention.

[0419] Experimental Example 2

[0420] 1) Fabrication of organic light-emitting devices

[0421] A glass substrate coated with a 1,500 Å thick ITO film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes in a UV cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), where it was plasma-treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.

[0422] A common layer, a hole injection layer 2-TNATA (4,4',4''-Tris[2-naphthyl (phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), were formed on the ITO transparent electrode (anode).

[0423] On top of that, a light-emitting layer was thermally vacuum-deposited as follows. The light-emitting layer was pre-mixed with one heterocyclic compound of the chemical formula 1 and one compound of the chemical formula 2 or 3, as shown in Table 13 below, as a host, and then deposited at 360Å in one hole, and the green phosphorescent dopant was doped with Ir(ppy)3 at 7% of the thickness of the light-emitting layer deposition and deposited. After that, 60Å of BCP was deposited as a hole-blocking layer, and 200Å of Alq3 was deposited as an electron-transporting layer thereon. Finally, lithium fluoride (LiF) was deposited on the electron-transporting layer to a thickness of 10Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200Å to form a cathode, thereby manufacturing an organic electroluminescent device.

[0424] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -8 ~10 -6 It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0425] 2) Driving voltage and luminous efficiency of organic field effect devices

[0426] The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured using M7000 from Max Science, and the standard luminance was determined to be 6,000 cd / m using the life measurement equipment (M6000) manufactured by Max Science based on the measurement results. 2 At that time, T90 was measured.

[0427] 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 as shown in Table 13 below.

[0428] [Table 13]

[0429]

[0430] Comparing the results in Tables 12 and 13 above, it can be confirmed that when the heterocyclic compound of Chemical Formula 1 of the present invention and the compound of Chemical Formula 2 or 3 are used together as a light-emitting layer material, the performance of the organic light-emitting device is improved, and in particular, remarkable effects are shown in terms of luminous efficiency and lifespan. Specifically, it can be seen that the luminous efficiency is increased by about 1.5 times, and the lifespan is extended by about 2 times.

Claims

1. A heterocyclic compound of the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, L and L1 to L3 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, l, l1 and l2 are each integers from 1 to 3, and if each is 2 or greater, the substituents in the parentheses are the same or different, Ar1 and Ar2 are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, R is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, r is an integer from 1 to 4, and when r is 2 or greater, L3 and R are each equal or different, H1 is hydrogen; or deuterium, and if r is 2 or less, H1 is the same or different, Y is O; S; C(R10)(R11) or N(R12), R1 to R12 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, At least one of R1 to R9 is deuterium, q is 1 or 2, and if q is 2, R5 is equal or different.

2. In claim 1, the chemical formula 1 is a heterocyclic compound represented by any one of the following chemical formulas 1-1 to 1-3: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] In the above chemical formulas 1-1 to 1-3, The definition of each substituent is the same as that in the chemical formula 1 above.

3. A heterocyclic compound according to claim 1, wherein R is a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

4. In claim 1, the chemical formula 1 is represented by [Structure A]-[Structure B]-[Structure C], the structure A is represented by the following chemical formula A, the structure B is represented by the following chemical formula B, the structure C is represented by the following chemical formula C, the deuterium substitution rate of the structure A is 0%, the deuterium substitution rate of the structure B is 0% to 100%, and the deuterium substitution rate of the structure C is more than 0% and 100% or less, a heterocyclic compound: [Chemical Formula A] [Chemical Formula B] [Chemical Formula C] In the above chemical formulas A to C, The definition of each substituent is the same as that in the above chemical formula 1, Chemical formula A is of chemical formula B is combined with, Chemical formula B is of chemical formula C is combined with 5. A heterocyclic compound according to claim 1, wherein the deuterium substitution rate of the chemical formula 1 is 10% to 99%.

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

7. An organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, An organic light-emitting device, wherein at least one of the organic layers comprises at least one heterocyclic compound according to any one of claims 1 to 6.

8. An organic light-emitting device according to claim 7, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes at least one type of the heterocyclic compound.

9. An organic light-emitting device according to claim 8, wherein the light-emitting layer comprises a host, and the host comprises at least one heterocyclic compound.

10. In claim 8, the organic light-emitting device further comprises a compound of the following chemical formula 2 or 3: [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, L21 to L23 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, m, n and s are each an integer from 1 to 3, and when each is 2 or greater, the substituents in the parentheses are the same or different, Ar21 to Ar24 are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, R21 to R24 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, o and p are each an integer from 1 to 7, t is an integer from 1 to 6, u is an integer from 1 to 4, and when o, p, t, and u are each 2 or more, the substituents in the parentheses are the same or different.

11. In claim 10, the organic light-emitting device wherein the chemical formula 2 is represented by any one of the following compounds:

12. In claim 10, the organic light-emitting device wherein the chemical formula 3 is represented by any one of the following compounds:

13. A composition for forming an organic layer of an organic light-emitting device comprising the heterocyclic compound of claim 1.

14. A composition for forming an organic layer of an organic light-emitting device, comprising a compound of the following chemical formula 2 or 3, in claim 13: [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, L21 to L23 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, m, n and s are each an integer from 1 to 3, and when each is 2 or greater, the substituents in the parentheses are the same or different, Ar21 to Ar24 are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, R21 to R24 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, o and p are each an integer from 1 to 7, t is an integer from 1 to 6, u is an integer from 1 to 4, and when o, p, t, and u are each 2 or more, the substituents in the parentheses are the same or different.

15. A composition for forming an organic layer of an organic light-emitting device, comprising the heterocyclic compound and the compound of the chemical formula 2 or 3 in a weight ratio of 1:10 to 10:1 in claim 14.

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