KR102580638B1 - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

This specification relates to a heterocyclic compound represented by Formula 1 and an organic light-emitting device containing the same.

Description

Heterocyclic compound and organic light-emitting device containing the same {HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

This specification relates to heterocyclic compounds and organic light-emitting devices containing the same.

Electroluminescent devices are a type of self-luminous display devices and have the advantages of a wide viewing angle, excellent contrast, and fast response speed.

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 with this structure, electrons and holes injected from two electrodes combine in the organic thin film to form a pair and then disappear, emitting light. The organic thin film may be composed of a single layer or multiple layers, depending on need.

The material of the organic thin film may have a light-emitting function as needed. For example, as an organic thin film material, a compound that can independently form a light-emitting layer may be used, or a compound that can act as a host or dopant of a host-dopant-based light-emitting layer may be used. In addition, as a material for the organic thin film, compounds that can perform roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.

In order to improve the performance, lifespan, or efficiency of organic light-emitting devices, the development of organic thin film materials is continuously required.

US Patent No. 4,356,429

The present application seeks to provide a novel heterocyclic compound and an organic light-emitting device containing the same.

An exemplary embodiment of the present application provides a heterocyclic compound represented by the following formula (1).

[Formula 1]

In Formula 1,

A is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle,

X ₁ and X ₂ are the same as or different from each other and are each independently directly bonded; O; or S,

Ra is hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar ₁ is a substituted or unsubstituted alkyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group; A substituted or unsubstituted monocyclic or polycyclic heteroaryl group; P(=O)R _x R _y ; SiR _x R _y R _z ; Or a substituted or unsubstituted amine group,

R ₁ , R ₂ , R _x , R _y and R _z are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring, n is an integer of 1 to 3, and n When m is 2 or more, R ₂ is the same as or different from each other, m is an integer from 1 to 4, and when m is 2 or more, R ₁ is the same as or different from each other,

When Ar ₁ is a substituted or unsubstituted N-containing tricyclic heteroaryl group, A is a substituted or unsubstituted polycyclic aromatic hydrocarbon ring.

Additionally, according to an exemplary embodiment of the present application, a first electrode; a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a heterocyclic compound represented by Formula 1. provides.

The compounds described in this specification can be used as organic layer materials for organic light-emitting devices. The above compounds can serve as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials in organic light-emitting devices. In particular, the above compound can be used as a light-emitting layer material of an organic light-emitting device. For example, the compound may be used alone as a light-emitting material or as a host material for a light-emitting layer.

In particular, Formula 1 has a stable core structure by combining a substituent with hole characteristics at the phenyl position of the carbazole group. By introducing substituents with various electronic properties into this core part, appropriate energy levels and thermal stability are provided to the device. Using these compounds, organic light-emitting devices with improved lifespan, operational stability, and efficiency can be manufactured.

1 to 3 are diagrams schematically showing the stacked structure of an organic light-emitting device according to an exemplary embodiment of the present application.

The present application will be described in detail below.

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.

In this specification, the halogen may be fluorine, chlorine, bromine, or iodine.

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

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

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

In the present specification, the alkoxy group may be straight chain, branched chain, or ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It may be possible, but it is not limited to this.

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

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

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

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

When the fluorenyl group is substituted, , , , , , It may be, but is not limited to this.

In the present specification, the heteroaryl group includes S, O, Se, N, or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic refers to 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, heterocycloalkyl group, or aryl group. The carbon number of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heteroaryl group include pyridyl group, pyrrolyl group, pyrimidyl group, pyridazinyl group, furanyl group, thiophene group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, and thiazolyl group. group, isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , thiazinyl group, deoxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyryl group, naphthyridyl group, acridinyl group, phenanthridide Nyl group, imidazopyridinyl group, diazanaphthalenyl group, triazindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group , dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilol group, spirobi (dibenzosilol), dihydrophenazinyl group, Phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10, 11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiathiazinyl group, phthalazinyl group, naphthylidinyl group, phenanthrolinyl group, Benzo[c][1,2,5]thiadiazolyl group, 5,10-dihydrodibenzo[b,e][1,4]azacylinyl, pyrazolo[1,5-c]quinazolinyl group , pyrido [1,2-b] indazolyl group, pyrido [1,2-a] imidazo [1,2-e] indolinyl group, 5,11-dihydroindeno [1,2-b ] Carbazolyl group, etc. may be mentioned, but it is not limited thereto.

In the present specification, the amine group is a monoalkylamine group; monoarylamine group; Monoheteroarylamine group; -NH ₂ ; dialkylamine group; Diarylamine group; Diheteroarylamine group; Alkylarylamine group; Alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, dibiphenylamine group, anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenyl fluorescein Examples include a nylamine group, phenyltriphenylenylamine group, and biphenyltriphenylenylamine group, but are not limited to these.

In the present specification, the phosphine oxide group may be specifically substituted with an aryl group, and the examples described above may be applied to the aryl group. For example, the phosphine oxide group includes diphenylphosphine oxide group, dinaphthylphosphine oxide, etc., but is not limited thereto.

As used herein, an “adjacent” group may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in terms of structure, or another substituent substituted on the atom on which the substituent is substituted. You can. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as “adjacent” groups.

The structures exemplified by the cycloalkyl group described above can be applied to the aliphatic hydrocarbon ring that can be formed by adjacent groups, except that it is not monovalent, and the structures exemplified by the aryl group can be applied to the aromatic hydrocarbon ring, except that it is not monovalent. The structures exemplified by the heterocycloalkyl group described above can be applied, except that the aliphatic heterocycle is not monovalent, and the structures exemplified by the heteroaryl group described above can be applied, except that the aromatic heterocycle is not monovalent. may be applied.

In an exemplary embodiment of the present application, a compound represented by Formula 1 is provided.

In an exemplary embodiment of the present application, the compound represented by Formula 1 may be used as a red host material for the light-emitting layer of an organic light-emitting device.

In an exemplary embodiment of the present application, Ar ₁ is a substituted or unsubstituted alkyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group; A substituted or unsubstituted monocyclic or polycyclic heteroaryl group; P(=O)R _x R _y ; SiR _x R _y R _z ; Or, it may be a substituted or unsubstituted amine group.

In another embodiment, Ar ₁ is a substituted or unsubstituted C1 to C60 alkyl group; A substituted or unsubstituted monocyclic or polycyclic C6 to C60 aryl group; Substituted or unsubstituted monocyclic or polycyclic C2 to C60 heteroaryl group; P(=O)R _x R _y ; SiR _x R _y R _z ; Or, it may be a substituted or unsubstituted amine group.

In another embodiment, Ar ₁ is a substituted or unsubstituted C1 to C40 alkyl group; A substituted or unsubstituted monocyclic or polycyclic C6 to C40 aryl group; Substituted or unsubstituted monocyclic or polycyclic C2 to C40 heteroaryl group; P(=O)R _x R _y ; SiR _x R _y R _z ; Or, it may be a substituted or unsubstituted amine group.

In another embodiment, Ar ₁ is a monocyclic or polycyclic C6 to C40 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a C1 to C40 alkyl group and a C6 to C40 aryl group; A monocyclic or polycyclic C2 to C40 heteroaryl group substituted or unsubstituted with a C6 to C40 aryl group; P(=O)R _x R _y ; SiR _x R _y R _z ; Alternatively, it may be an amine group substituted or unsubstituted with a C6 to C40 aryl group.

In an exemplary embodiment of the present application, Formula 1 may be represented by any one of the following Formulas 2 to 4.

[Formula 2]

[Formula 3]

[Formula 4]

In Formulas _{2 to 4 , the definitions} of X ₁ ,

B is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle,

Y is O; S; CRR'; or NR",

Y ₁ to Y ₅ are CR ₄₁ ; or N,

When Y is NR", at least one of A and B is a substituted or unsubstituted polycyclic aromatic hydrocarbon ring,

R, R', R" and R ₃ are the same or different from each other, and are each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkyl Nyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phos A pin oxide group; and two or more groups selected from the group consisting of a substituted or unsubstituted amine group, or adjacent to each other, combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring, and p is 1 to 3 If it is an integer and p is 2 or more, R ₃ is the same or different,

R ₄₁ is hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, or two or more groups adjacent to each other may be combined to form a substituted or unsubstituted monocyclic aromatic hydrocarbon ring or a substituted or unsubstituted monocyclic heterocycle.

In an exemplary embodiment of the present application, A and B are the same or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring; Alternatively, it may be a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle.

In another embodiment, A and B are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aromatic hydrocarbon ring; Alternatively, it may be a substituted or unsubstituted C2 to C60 monocyclic or polycyclic aromatic heterocycle.

In another embodiment, A and B are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C40 monocyclic or polycyclic aromatic hydrocarbon ring; Alternatively, it may be a substituted or unsubstituted C2 to C40 monocyclic or polycyclic aromatic heterocycle.

In another embodiment, A and B are the same or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 monocyclic or polycyclic aromatic hydrocarbon ring.

In another embodiment, A and B may be the same or different from each other, and may each independently be a C6 to C40 monocyclic or polycyclic aromatic hydrocarbon ring.

In another exemplary embodiment, A and B are the same or different from each other, and are each independently benzene; Or it may be a naphthyl group.

In an exemplary embodiment of the present application, when Y in Formula 2 is NR", at least one of A and B may be a substituted or unsubstituted polycyclic aromatic hydrocarbon ring.

In another embodiment, when Y in Formula 2 is NR", at least one of A and B may be a substituted or unsubstituted C6 to C40 polycyclic aromatic hydrocarbon ring.

In another embodiment, when Y in Formula 2 is NR", at least one of A and B may be a C6 to C40 polycyclic aromatic hydrocarbon ring.

In another exemplary embodiment, when Y in Formula 2 is NR", at least one of A and B may be a naphthyl group.

In an exemplary embodiment of the present application, when Ar ₁ is a substituted or unsubstituted N-containing tricyclic heteroaryl group, A may be a substituted or unsubstituted polycyclic aromatic hydrocarbon ring.

In another embodiment, when Ar ₁ is a substituted or unsubstituted N-containing tricyclic heteroaryl group, A may be a polycyclic aromatic hydrocarbon ring.

In another embodiment, when Ar ₁ is a substituted or unsubstituted N-containing tricyclic heteroaryl group, A may be a naphthyl group.

In another embodiment, when Ar ₁ is a carbazole group substituted with a phenyl group, A may be a naphthyl group.

In an exemplary embodiment of the present application, R _x , R _y and R _z are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, or two or more groups adjacent to each other may be combined with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring.

In another embodiment, R _x , R _y and R _z are the same or different from each other, and are each independently hydrogen; Or it may be a phenyl group.

In an exemplary embodiment of the present application, R ₄₁ is hydrogen; Or, it is selected from the group consisting of a substituted or unsubstituted aryl group, or two or more groups adjacent to each other can be combined with each other to form a substituted or unsubstituted monocyclic aromatic hydrocarbon ring or a substituted or unsubstituted monocyclic heterocycle.

In another exemplary embodiment, R ₄₁ is hydrogen; Alternatively, it may be selected from the group consisting of a substituted or unsubstituted C6 to C40 aryl group, or two or more groups adjacent to each other may be combined with each other to form a monocyclic aromatic hydrocarbon ring or a monocyclic heterocycle.

In another exemplary embodiment, R ₄₁ is hydrogen; Or, it may be selected from the group consisting of a substituted or unsubstituted C6 to C40 aryl group, or two or more groups adjacent to each other may be bonded to each other to form a monocyclic aromatic hydrocarbon ring or a monocyclic heterocycle.

In another exemplary embodiment, R ₄₁ is hydrogen; phenyl group; Alternatively, it may be a biphenyl group, or two or more groups adjacent to each other may be combined with each other to form a benzene ring or a pyridine ring.

In an exemplary embodiment of the present application, Formula 2 may be represented by any one of the following Formulas 2-1 to 2-3.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Formulas 2-1 to 2-3, the definitions of X ₁ , X ₂ , Y, R ₁ to R ₃ , Ra, m, n and p are the same as defined in Formula 2,

R ₁₁ to R ₁₈ are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group.

In an exemplary embodiment of the present application, X ₁ and X ₂ are the same as or different from each other and are each independently directly bonded; O; Or it may be S.

In an exemplary embodiment of the present application, one of X ₁ and X ₂ may be a direct bond, and the other may be O or S.

In an exemplary embodiment of the present application, X ₁ may be a direct bond, and X ₂ may be O.

In an exemplary embodiment of the present application, X ₁ may be a direct bond, and X ₂ may be S.

In an exemplary embodiment of the present application, X ₁ may be O, and X ₂ may be a direct bond.

In an exemplary embodiment of the present application, X ₁ may be S, and X ₂ may be a direct bond.

In an exemplary embodiment of the present application, Y is O; S; CRR'; or NR".

In an exemplary embodiment of the present application, Y may be O.

In an exemplary embodiment of the present application, Y may be S.

In an exemplary embodiment of the present application, Y may be CRR'.

In an exemplary embodiment of the present application, Y may be NR".

In an exemplary embodiment of the present application, R, R', and R" are the same as or different from each other, and are each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group ; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group ; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, or two or more groups adjacent to each other may be combined with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring. You can.

In another embodiment, R, R', and R" may be the same or different from each other, and may each independently be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

In another embodiment, R, R' and R" are the same or different from each other, and are each independently hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group. It could be a sign.

In another embodiment, R, R' and R" are the same or different from each other, and are each independently hydrogen; a substituted or unsubstituted C1 to C40 alkyl group; or a substituted or unsubstituted C6 to C40 aryl group. It could be a sign.

In another embodiment, R, R', and R" may be the same or different from each other, and may each independently be hydrogen; a C1 to C40 alkyl group; or a C6 to C40 aryl group.

In another embodiment, R, R', and R" may be the same or different from each other, and may each independently be hydrogen; a methyl group; or a phenyl group.

In an exemplary embodiment of the present application, R ₁ to R ₃ are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring, and n and p are each an integer of 1 to 3. , when n is 2 or more, R ₂ is the same as or different from each other, and when p is 2 or more, R ₃ is the same or different from each other, m is an integer from 1 to 4, and when m is 2 or more, R ₁ is the same or different from each other. may be different.

In another exemplary embodiment, R ₁ to R ₃ may be hydrogen.

In an exemplary embodiment of the present application, Ra is hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group.

In another embodiment, Ra is a substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group.

In another embodiment, Ra is a substituted or unsubstituted aryl group of C6 to C60; Or it may be a substituted or unsubstituted C2 to C60 heteroaryl group.

In another embodiment, Ra is a substituted or unsubstituted aryl group of C6 to C40; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In another embodiment, Ra is a C6 to C40 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a C6 to C40 alkyl group and a C6 to C40 aryl group; Alternatively, it may be a C2 to C40 heteroaryl group substituted or unsubstituted with a C6 to C40 aryl group.

In another embodiment, Ra is a C6 to C20 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of a C6 to C20 alkyl group and a C6 to C20 aryl group; Alternatively, it may be a C2 to C20 heteroaryl group substituted or unsubstituted with a C6 to C20 aryl group.

In another exemplary embodiment, Ra is a phenyl group substituted or unsubstituted with a phenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; Biphenyl group; phenanthrenyl group; Dibenzofuran group; Dibenzothiophene group; Carbazole group substituted or unsubstituted with a phenyl group; Naphtho[2,1-b]benzofuran group; Benzo[b]naphtho[1,2-d]thiophene group; Or it may be a dimethylfluorene group.

In another exemplary embodiment, Ra is a phenyl group substituted or unsubstituted with a phenyl group; Biphenyl group; Dibenzofuran group; Dibenzothiophene group; Carbazole group substituted or unsubstituted with a phenyl group; Naphtho[2,1-b]benzofuran group; Benzo[b]naphtho[1,2-d]thiophene group; Or it may be a dimethylfluorene group.

In an exemplary embodiment of the present application, Ra of Formula 1 may be represented by any one of the following Formulas 5 to 7.

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 5 to 7,

means the connected part,

Y _a and Y _b are the same or different from each other, and are each independently O; S; CRR'; or NR",

R ₂₁ , R ₂₂ , R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted Substituted alkynyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted heterocycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; substituted or unsubstituted may be selected from the group consisting of a ringed phosphine oxide group; and a substituted or unsubstituted amine group, a1 is an integer of 0 to 3, and when a1 is 2 or more, R ₂₁ is the same or different from each other, and a2 is 0 to 3 is an integer of 4, and if a2 is 2 or more, R ₂₂ is the same or different,

Xa to Xe are CR ₃₁ ; or N,

R ₃₁ is hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; and a substituted or unsubstituted heteroaryl group, or two or more groups adjacent to each other may be combined with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring.

In an exemplary embodiment of the present application, Y _a may be O.

In an exemplary embodiment of the present application, Y _a may be S.

In an exemplary embodiment of the present application, Y _a may be CRR'.

In an exemplary embodiment of the present application, Y _a may be NR".

In an exemplary embodiment of the present application, R ₂₁ and R ₂₂ may be hydrogen.

In an exemplary embodiment of the present application, among Xa to Xe, Xd may be N, and the remainder may be CR ₃₁ .

In an exemplary embodiment of the present application, Xa to Xe may be CR ₃₁ .

In an exemplary embodiment of the present application, R ₃₁ is hydrogen; Alternatively, it may be a C6 to C40 aryl group, or two or more adjacent groups may be combined with each other to form a C6 to C40 aromatic hydrocarbon ring substituted or unsubstituted with a C6 to C40 aryl group.

In another exemplary embodiment, R ₃₁ is hydrogen; Alternatively, it may be a phenyl group, or two or more groups adjacent to each other may be combined with each other to form a benzene ring.

In another exemplary embodiment, R ₃₁ is hydrogen; Alternatively, it may be a phenyl group, or two or more adjacent groups may be combined with each other to form a benzene ring substituted or unsubstituted by a phenyl group.

According to an exemplary embodiment of the present application, Formula 1 may be represented by any one of the following compounds, but is not limited thereto.

Additionally, by introducing various substituents into the structure of Formula 1, a compound having the unique properties of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport 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, the conditions required for each organic material layer are met. You can synthesize the desired substance.

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

Additionally, in an exemplary embodiment of the present application, a first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a heterocyclic compound according to Formula 1 above. to provide.

Specific details about the heterocyclic compound represented by Formula 1 are the same as described above.

In an exemplary embodiment of the present application, the first electrode may be an anode, and the second electrode may be a cathode.

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

In an exemplary embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound according to Formula 1 may be used as a material for the blue organic light-emitting device. For example, the heterocyclic compound according to Formula 1 may be included in the host material of the blue light-emitting layer of the blue organic light-emitting device.

In an exemplary embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound according to Formula 1 may be used as a material for the green organic light-emitting device. For example, the heterocyclic compound according to Formula 1 may be included in the host material of the green light-emitting layer of the green organic light-emitting device.

In an exemplary embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound according to Formula 1 may be used as a material for the red organic light-emitting device. For example, the heterocyclic compound according to Formula 1 may be included in the host material of the red light-emitting layer of the red organic light-emitting device.

The organic light-emitting device of the present invention can be manufactured using conventional organic light-emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the heterocyclic compound described above.

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

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

In the organic light-emitting device of the present invention, the organic material layer may include a light-emitting layer, and the light-emitting layer may include the heterocyclic compound.

In another organic light-emitting device, the organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material may include the heterocyclic compound.

In another organic light emitting device, the light emitting layer includes a red host material, and the red host material includes the heterocyclic compound.

As another example, the organic material layer containing the heterocyclic compound includes the heterocyclic compound represented by Formula 1 as a host and can be used together with an iridium-based dopant.

In the organic light emitting device of the present invention, the organic material layer includes an electron injection layer or an electron transport layer, and the electron transport layer or electron injection layer may include the heterocyclic compound.

In another organic light emitting device, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or hole blocking layer may include the heterocyclic compound.

The organic light emitting device of the present invention includes a light emitting layer, a hole injection layer, and a hole transport layer. It may further include one or two layers selected from the group consisting of an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

1 to 3 illustrate the stacking order of electrodes and organic material layers of an organic light-emitting device according to an exemplary embodiment of the present application. However, it is not intended that the scope of the present application be limited by these drawings, and structures of organic light-emitting devices known in the art may also be applied to the present application.

According to Figure 1, an organic light emitting device is shown in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, it is not limited to this structure, and an organic light-emitting device may be implemented in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate, as shown in FIG. 2.

Figure 3 illustrates the case where the organic material layer is multi-layered. The organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited by this laminated structure, and if necessary, the remaining layers except the light-emitting layer may be omitted, and other necessary functional layers may be added.

The organic material layer containing the compound of Formula 1 may further include other materials as needed.

In the organic light emitting device according to an exemplary embodiment of the present application, materials other than the compound of Formula 1 are illustrated below, but these are for illustrative purposes only and are not intended to limit the scope of the present application, and are known in the art. It can be replaced with used materials.

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

As the cathode material, materials with a relatively low work function can be used, and metals, metal oxides, or conductive polymers can be used. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are multi-layer structure materials such as LiF/Al or LiO ₂ /Al, but they are not limited to these.

As the hole injection material, known hole injection materials may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or described in Advanced Material, 6, p.677 (1994). Starburst type amine derivatives 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), polyaniline/dodecylbenzenesulfonic acid, a soluble conductive polymer, or poly( 3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate), Polyaniline/Camphor sulfonic acid or polyaniline/ Poly(4-styrenesulfonate) (Polyaniline/Poly(4-styrene-sulfonate)) can be used.

As hole transport materials, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. may be used, and low molecular or high molecular materials may also be used.

Electron transport materials include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, and fluorenone. Derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc. may be used, and not only low molecular substances but also high molecular substances may be used.

For example, LiF is typically used as an electron injection material in the industry, but the present application is not limited thereto.

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. At this time, two or more light emitting materials can be deposited and used from individual sources, or they can be premixed and deposited from a single source. Additionally, a fluorescent material can be used as a light-emitting material, but it can also be used as a phosphorescent material. As a light-emitting material, a material that emits light by combining holes and electrons injected from an anode and a cathode, respectively, may be used, but materials that participate in light emission together with a host material and a dopant material may also be used.

When using a mixture of hosts of a light emitting material, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, any two or more types of materials, such as an n-type host material or a p-type host material, can be selected and used as the host material of the light-emitting layer.

The organic light emitting device according to an exemplary embodiment of the present application may be a front emitting type, a rear emitting type, or a double-sided emitting type depending on the material used.

The heterocyclic compound according to an exemplary embodiment of the present application may function in organic electronic devices, including organic solar cells, organic photoreceptors, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.

Below, the present specification is described in more detail through examples, but these are only for illustrating the present application and are not intended to limit the scope of the present application.

< Manufacturing example >

< Manufacturing example 1> Preparation of intermediates A to X

Synthesis of Intermediates A to V

Compound a (1eq) of Table 1 below, compound b (1eq) of Table 1 below, Pd(PPh ₃ ) ₄ (0.05eq), and K ₂ CO ₃ (3eq) were placed in a round bottom flask, and 1,4-diox was added. Add 1,4-dioxane and H ₂ O (10v/w) to dissolve and then stir at 100°C. When the reaction is complete, the temperature is cooled to room temperature and extracted using water and methylene chloride (MC). The organic layer was dried over Mg ₂ SO ₄ and concentrated, and then purified using a silica-gel column to obtain intermediate compounds A to V (yield: 58% to 78%) shown in Table 1 below.

Synthesis of intermediates W and

Compound a (1eq) of Table 1 below, compound b (1eq) of Table 1 below, Pd ₂ (dba) ₃ (0.05eq), P( t -Bu) ₃ , and NaOtBu (3eq) were placed in a round bottom flask, Add toluene (10v/w) to dissolve and then stir at 110°C. When the reaction is complete, the temperature is cooled to room temperature and extracted using water and methylene chloride (MC). The organic layer was dried over Mg ₂ SO ₄ and concentrated, and then purified using a silica-gel column to obtain intermediate compounds W and

< Manufacturing example 2> Synthesis of target compound

The intermediate (1eq) prepared in Preparation Example 1 and compound c (1eq) in Table 2 below were placed in a round bottom flask, dissolved in DMF (10v/w), then NaH was added and stirred at 70°C. When the reaction was completed, the precipitated solid was filtered and washed with H ₂ O and DMF to obtain the target compound shown in Table 2 below (yield: 72% to 88%).

The remaining compounds other than those listed in Table 2 were also prepared in the same manner as described in the above-described preparation example.

Tables 3 and 4 below show FD-MS data and 1H NMR data of the synthesized compounds, and through the following data, it can be confirmed that the target compound was synthesized.

compound FD-Mass compound FD-Mass One m/z=718.88(C ₅₀ H ₃₀ N ₄ S, 718.22) 2 m/z=768.94(C ₅₄ H ₃₂ N ₄ S, 768.23) 3 m/z=794.98(C ₅₆ H ₃₄ N ₄ S, 794.25) 4 m/z=794.98(C ₅₆ H ₃₄ N ₄ S, 794.25) 5 m/z=808.96(C ₅₆ H ₃₂ N ₄ OS, 808.23) 6 m/z=825.02(C ₅₆ H ₃₂ N ₄ S ₂ , 824.21) 7 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 8 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 9 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 10 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 11 m/z=875.08(C ₆₀ H ₃₄ N ₄ S ₂ , 874.22) 12 m/z=875.08(C ₆₀ H ₃₄ N ₄ S ₂ , 874.22) 13 m/z=875.08(C ₆₀ H ₃₄ N ₄ S ₂ , 874.22) 14 m/z=875.08(C ₆₀ H ₃₄ N ₄ S ₂ , 874.22) 15 m/z=884.07(C ₆₂ H ₃₇ N ₅ S, 883.28) 16 m/z=835.04(C ₅₉ H ₃₈ N ₄ S, 834.28) 17 m/z=718.88(C ₅₀ H ₃₀ N ₄ S, 718.22) 18 m/z=794.98(C ₅₆ H ₃₄ N ₄ S, 794.25) 19 m/z=808.96(C ₅₆ H ₃₂ N ₄ OS, 808.23) 20 m/z=825.02(C ₅₆ H ₃₂ N ₄ S ₂ , 824.21) 21 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 22 m/z=875.08(C ₆₀ H ₃₄ N ₄ S ₂ , 874.22) 23 m/z=884.07(C ₆₂ H ₃₇ N ₅ S, 883.28) 24 m/z=835.04(C ₅₉ H ₃₈ N ₄ S, 834.28) 25 m/z=702.82(C ₅₀ H ₃₀ N ₄ O, 702.24) 26 m/z=752.88(C ₅₄ H ₃₂ N ₄ O, 752.26) 27 m/z=778.92(C ₅₆ H ₃₄ N ₄ O, 778.27) 28 m/z=778.92(C ₅₆ H ₃₄ N ₄ O, 778.27) 29 m/z=792.90(C ₅₆ H ₃₂ N ₄ O ₂ , 792.25) 30 m/z=808.96(C ₅₆ H ₃₂ N ₄ OS, 808.23) 31 m/z=842.96(C ₆₀ H ₃₄ N ₄ O ₂ , 842.27) 32 m/z=842.96(C ₆₀ H ₃₄ N ₄ O ₂ , 842.27) 33 m/z=842.96(C ₆₀ H ₃₄ N ₄ O ₂ , 842.27) 34 m/z=842.96(C ₆₀ H ₃₄ N ₄ O ₂ , 842.27) 35 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 36 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 37 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 38 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 39 m/z=868.01(C ₆₂ H ₃₇ N ₅ O, 867.30) 40 m/z=818.98(C ₅₉ H ₃₈ N ₄ O, 818.30) 41 m/z=718.88 (C ₅₀ H ₃₀ NS, 718.22) 42 m/z=768.94(C ₅₄ H ₃₂ N ₄ S, 768.23) 43 m/z=794.98(C ₅₆ H ₃₄ N ₄ S, 794.25) 44 m/z=794.98(C ₅₆ H ₃₄ N ₄ S, 794.25) 45 m/z=808.96(C ₅₆ H ₃₂ N ₄ OS, 808.23) 46 m/z=825.02(C ₅₆ H ₃₂ N ₄ S ₂ , 824.21) 47 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 48 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 49 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 50 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 51 m/z=875.08(C ₆₀ H ₃₄ N ₄ S ₂ , 874.22) 52 m/z=875.08(C ₆₀ H ₃₄ N ₄ S ₂ , 874.22) 53 m/z=875.08(C ₆₀ H ₃₄ N ₄ S ₂ , 874.22) 54 m/z=875.08(C ₆₀ H ₃₄ N ₄ S ₂ , 874.22) 55 m/z=884.07(C ₆₂ H ₃₇ N ₅ S, 883.28) 56 m/z=835.04(C ₅₉ H ₃₈ N ₄ S, 834.28) 57 m/z=718.88(C ₅₀ H ₃₀ N ₄ S, 718.22) 58 m/z=794.98(C ₅₆ H ₃₄ N ₄ S, 794.25) 59 m/z=808.96(C ₅₆ H ₃₂ N ₄ OS, 808.23) 60 m/z=825.02(C ₅₆ H ₃₂ N ₄ S ₂ , 824.21) 61 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 62 m/z=875.08(C ₆₀ H ₃₄ N ₄ S ₂ , 874.22) 63 m/z=884.07(C ₆₂ H ₃₇ N ₅ S, 883.28) 64 m/z=835.04(C ₅₉ H ₃₈ N ₄ S, 834.28) 65 m/z=702.82(C ₅₀ H ₃₀ N ₄ O, 702.24) 66 m/z=752.88(C ₅₄ H ₃₂ N ₄ O, 725.26) 67 m/z=778.92(C ₅₆ H ₃₄ N ₄ O, 778.27) 68 m/z=778.92(C ₅₆ H ₃₄ N ₄ O, 778.27) 69 m/z=792.90(C ₅₆ H ₃₂ N ₄ O ₂ , 792.25) 70 m/z=808.96(C ₅₆ H ₃₂ N ₄ OS, 808.23) 71 m/z=842.96(C ₆₀ H ₃₄ N ₄ O ₂ , 842.27) 72 m/z=842.96(C ₆₀ H ₃₄ N ₄ O ₂ , 842.27) 73 m/z=842.96(C ₆₀ H ₃₄ N ₄ O ₂ , 842.27) 74 m/z=842.96(C ₆₀ H ₃₄ N ₄ O ₂ , 842.27) 75 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 76 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 77 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 78 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 79 m/z=868.01(C ₆₂ H ₃₇ N ₅ O, 867.30) 80 m/z=818.98(C ₅₉ H ₃₈ N ₄ O, 818.30) 81 m/z=768.94(C ₅₄ H ₃₂ N ₄ S, 768.23) 82 m/z=819.00(C ₅₈ H ₃₄ N ₄ S, 818.25) 83 m/z=845.04(C ₆₀ H ₃₆ N ₄ S, 844.27) 84 m/z=845.04(C ₆₀ H ₃₆ N ₄ S, 844.27) 85 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 86 m/z=875.08(C ₆₀ H ₃₄ N ₄ S ₂ , 874.22) 87 m/z=909.08(C ₆₄ H ₃₆ N ₄ OS, 908.26) 88 m/z=909.08(C ₆₄ H ₃₆ N ₄ OS, 908.26) 89 m/z=909.08(C ₆₄ H ₃₆ N ₄ OS, 908.26) 90 m/z=909.08(C ₆₄ H ₃₆ N ₄ OS, 908.26) 91 m/z=925.14(C ₆₄ H ₃₆ N ₄ S ₂ , 924.24) 92 m/z=925.14(C ₆₄ H ₃₆ N ₄ S ₂ , 924.24) 93 m/z=925.14(C ₆₄ H ₃₆ N ₄ S ₂ , 924.24) 94 m/z=925.14(C ₆₄ H ₃₆ N ₄ S ₂ , 924.24) 95 m/z=934.13(C ₆₆ H ₃₉ N ₅ S, 933.29) 96 m/z=885.10(C ₆₃ H ₄₀ N ₄ S, 884.30) 97 m/z=768.94(C ₅₄ H ₃₂ N ₄ S, 768.23) 98 m/z=845.04(C ₆₀ H ₃₆ N ₄ S, 844.27) 99 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 100 m/z=875.08(C ₆₀ H ₃₄ N ₄ S ₂ , 874.22) 101 m/z=909.08(C ₆₄ H ₃₆ N ₄ OS, 908.26) 102 m/z=925.14(C ₆₄ H ₃₆ N ₄ S ₂ , 924.24) 103 m/z=934.13(C ₆₆ H ₃₉ N ₅ S, 933.29) 104 m/z=885.10(C ₆₃ H ₄₀ N ₄ S, 884.30) 105 m/z=752.88(C ₅₄ H ₃₂ N ₄ O, 752.26) 106 m/z=802.94(C ₅₈ H ₃₄ N ₄ O, 802.27) 107 m/z=828.98(C ₆₀ H ₃₆ N ₄ O, 828.29) 108 m/z=828.98(C ₆₀ H ₃₆ N ₄ O, 828.29) 109 m/z=842.96(C ₆₀ H ₃₄ N ₄ O, 842.27) 110 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 111 m/z=893.02(C ₆₄ H ₃₆ N ₄ O ₂ , 892.28) 112 m/z=893.02(C ₆₄ H ₃₆ N ₄ O ₂ , 892.28) 113 m/z=893.02(C ₆₄ H ₃₆ N ₄ O ₂ , 892.28) 114 m/z=893.02(C ₆₄ H ₃₆ N ₄ O ₂ , 892.28) 115 m/z=909.08(C ₆₄ H ₃₆ N ₄ OS, 908.26) 116 m/z=909.08(C ₆₄ H ₃₆ N ₄ OS, 908.26) 117 m/z=909.08(C ₆₄ H ₃₆ N ₄ OS, 908.26) 118 m/z=909.08(C ₆₄ H ₃₆ N ₄ OS, 908.26) 119 m/z=918.07(C ₆₆ H ₃₉ N ₅ O, 917.32) 120 m/z=869.04(C ₆₃ H ₄₀ N ₄ O, 868.32) 121 m/z=659.82(C ₄₄ H ₂₅ N ₃ S ₂ , 659.15) 122 m/z=709.88(C ₄₈ H ₂₇ N ₃ S ₂ , 709.16) 123 m/z=735.92(C ₅₀ H ₂₉ N ₃ S ₂ , 735.18) 124 m/z=735.92(C ₅₀ H ₂₉ N ₃ S ₂ , 735.18) 125 m/z=749.91(C ₅₀ H ₂₇ N ₃ OS ₂ , 749.16) 126 m/z=765.97(C ₅₀ H ₂₇ N ₃ S ₃ , 765.14) 127 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 128 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 129 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 130 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 131 m/z=816.03(C ₅₄ H ₂₉ N ₃ S ₃ , 815.15) 132 m/z=816.03(C ₅₄ H ₂₉ N ₃ S ₃ , 815.15) 133 m/z=816.03(C ₅₄ H ₂₉ N ₃ S ₃ , 815.15) 134 m/z=816.03(C ₅₄ H ₂₉ N ₃ S ₃ , 815.15) 135 m/z=825.02(C ₅₆ H ₃₂ N ₄ S ₂ , 824.21) 136 m/z=775.99(C ₅₃ H ₃₃ N ₃ S ₂ , 775.21) 137 m/z=659.82(C ₄₄ H ₂₅ N ₃ S ₂ , 659.15) 138 m/z=735.92(C ₅₀ H ₂₉ N ₃ S ₂ , 735.18) 139 m/z=749.91(C ₅₀ H ₂₇ N ₃ OS ₂ , 749.16) 140 m/z=765.97(C ₅₀ H ₂₇ N ₃ S ₃ , 765.14) 141 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 142 m/z=816.03(C ₅₄ H ₂₉ N ₃ S ₃ , 815.15) 143 m/z=825.02(C ₅₆ H ₃₂ N ₄ S ₂ , 824.21) 144 m/z=775.99(C ₅₃ H ₃₃ N ₃ S ₂ , 775.21) 145 m/z=643.76(C ₄₄ H ₂₅ N ₃ OS, 643.17) 146 m/z=693.82(C ₄₈ H ₂₇ N ₃ OS, 693.19) 147 m/z=719.86(C ₅₀ H ₂₉ N ₃ OS, 719.20) 148 m/z=719.86(C ₅₀ H ₂₉ N ₃ OS, 719.20) 149 m/z=733.85(C ₅₀ H ₂₇ N ₃ O ₂ S, 733.18) 150 m/z=749.91(C ₅₀ H ₂₇ N ₃ OS ₂ , 749.16) 151 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 152 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 153 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 154 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 155 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 156 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 157 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 158 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 159 m/z=808.96(C ₅₆ H ₃₂ N ₄ OS, 808.23) 160 m/z=759.93(C ₅₃ H ₃₃ N ₃ OS, 759.23) 161 m/z=659.82(C ₄₄ H ₂₅ N ₃ S ₂ , 659.15) 162 m/z=709.88(C ₄₈ H ₂₇ N ₃ S ₂ , 709.16) 163 m/z=735.92(C ₅₀ H ₂₉ N ₃ S ₂ , 735.18) 164 m/z=735.92(C ₅₀ H ₂₉ N ₃ S ₂ , 735.18) 165 m/z=749.91(C ₅₀ H ₂₇ N ₃ OS ₂ , 749.16) 166 m/z=765.97(C ₅₀ H ₂₇ N ₃ S ₃ , 765.14) 167 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 168 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 169 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 170 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 171 m/z=816.03(C ₅₄ H ₂₉ N ₃ S ₃ , 815.15) 172 m/z=816.03(C ₅₄ H ₂₉ N ₃ S ₃ , 815.15) 173 m/z=816.03(C ₅₄ H ₂₉ N ₃ S ₃ , 815.15) 174 m/z=816.03(C ₅₄ H ₂₉ N ₃ S ₃ , 815.15) 175 m/z=825.02(C ₅₆ H ₃₂ N ₄ S ₂ , 824.21) 176 m/z=775.99(C ₅₃ H ₃₃ N ₃ S ₂ , 775.21) 177 m/z=659.82(C ₄₄ H ₂₅ N ₃ S ₂ , 659.15) 178 m/z=735.92(C ₅₀ H ₂₉ N ₃ S ₂ , 735.18) 179 m/z=749.91(C ₅₀ H ₂₇ N ₃ OS ₂ , 749.16) 180 m/z=765.97(C ₅₀ H ₂₇ N ₃ S ₃ , 765.14) 181 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 182 m/z=816.03(C ₅₄ H ₂₉ N ₃ S ₃ , 815.15) 183 m/z=825.02(C ₅₆ H ₃₂ N ₄ S ₂ , 824.21) 184 m/z=775.99(C ₅₃ H ₃₃ N ₃ S ₂ , 775.21) 185 m/z=643.76(C ₄₄ H ₂₅ N ₃ OS, 643.17) 186 m/z=693.82(C ₄₈ H ₂₇ N ₃ OS, 693.19) 187 m/z=719.86(C ₅₀ H ₂₉ N ₃ OS, 719.20) 188 m/z=719.86(C ₅₀ H ₂₉ N ₃ OS, 719.20) 189 m/z=733.85(C ₅₀ H ₂₇ N ₃ O ₂ S, 733.18) 190 m/z=749.91(C ₅₀ H ₂₇ N ₃ OS ₂ , 749.16) 191 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 192 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 193 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 194 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 195 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 196 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 197 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 198 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 199 m/z=808.96(C ₅₆ H ₃₂ N ₄ OS, 808.23) 200 m/z=759.93(C ₅₃ H ₃₃ N ₃ OS, 759.23) 201 m/z=709.88(C ₄₈ H ₂₇ N ₃ S ₂ , 709.16) 202 m/z=759.94(C ₅₂ H ₂₉ N ₃ S ₂ , 759.18) 203 m/z=785.98(C ₅₄ H ₃₁ N ₃ S ₂ , 785.20) 204 m/z=785.98(C ₅₄ H ₃₁ N ₃ S ₂ , 785.20) 205 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 206 m/z=816.03(C ₅₄ H ₂₉ N ₃ S ₃ , 815.15) 207 m/z=850.03(C ₅₈ H ₃₁ N ₃ OS ₂ , 849.19) 208 m/z=850.03(C ₅₈ H ₃₁ N ₃ OS ₂ , 849.19) 209 m/z=850.03(C ₅₈ H ₃₁ N ₃ OS ₂ , 849.19) 210 m/z=850.03(C ₅₈ H ₃₁ N ₃ OS ₂ , 849.19) 211 m/z=866.09(C ₅₈ H ₃₁ N ₃ S ₃ , 865.17) 212 m/z=866.09(C ₅₈ H ₃₁ N ₃ S ₃ , 865.17) 213 m/z=866.09(C ₅₈ H ₃₁ N ₃ S ₃ , 865.17) 214 m/z=866.09(C ₅₈ H ₃₁ N ₃ S ₃ , 865.17) 215 m/z=875.08(C ₆₀ H ₃₄ N ₄ S ₂ , 874.22) 216 m/z=826.05(C ₅₇ H ₃₅ N ₃ S ₂ , 825.23) 217 m/z=709.88(C ₄₈ H ₂₇ N ₃ S ₂ , 709.16) 218 m/z=785.98(C ₅₄ H ₃₁ N ₃ S ₂ , 785.20) 219 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 220 m/z=816.03(C ₅₄ H ₂₉ N ₃ S ₃ , 815.15) 221 m/z=850.03(C ₅₈ H ₃₁ N ₃ OS ₂ , 849.19) 222 m/z=866.09(C ₅₈ H ₃₁ N ₃ S ₃ , 865.17) 223 m/z=875.08(C ₆₀ H ₃₄ N ₄ S ₂ , 874.22) 224 m/z=826.05(C ₅₇ H ₃₅ N ₃ S ₂ , 825.23) 225 m/z=693.82(C ₄₈ H ₂₇ N ₃ OS, 693.19) 226 m/z=743.88(C ₅₂ H ₂₉ N ₃ OS, 743.20) 227 m/z=769.92(C ₅₄ H ₃₁ N ₃ OS, 769.22) 228 m/z=769.92(C ₅₄ H ₃₁ N ₃ OS, 769.22) 229 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 230 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 231 m/z=833.96(C ₅₈ H ₃₁ N ₃ O ₂ S, 833.21) 232 m/z=833.96(C ₅₈ H ₃₁ N ₃ O ₂ S, 833.21) 233 m/z=833.96(C ₅₈ H ₃₁ N ₃ O ₂ S, 833.21) 234 m/z=833.96(C ₅₈ H ₃₁ N ₃ O ₂ S, 833.21) 235 m/z=850.03(C ₅₈ H ₃₁ N ₃ OS ₂ , 849.19) 236 m/z=850.03(C ₅₈ H ₃₁ N ₃ OS ₂ , 849.19) 237 m/z=850.03(C ₅₈ H ₃₁ N ₃ OS ₂ , 849.19) 238 m/z=850.03(C ₅₈ H ₃₁ N ₃ OS ₂ , 849.19) 239 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 240 m/z=809.99(C ₅₇ H ₃₅ N ₃ OS, 809.25) 241 m/z=643.76(C ₄₄ H ₂₅ N ₃ OS, 643.17) 242 m/z=693.82(C ₄₈ H ₂₇ N ₃ OS, 693.19) 243 m/z=719.86(C ₅₀ H ₂₉ N ₃ OS, 719.20) 244 m/z=719.86(C ₅₀ H ₂₉ N ₃ OS, 719.20) 245 m/z=733.85(C ₅₀ H ₂₇ N ₃ O ₂ S, 733.18) 246 m/z=749.91(C ₅₀ H ₂₇ N ₃ OS ₂ , 749.16) 247 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 248 m/z=783.90(C ₅₄ H ₂₉ N ₃ OS ₂ , 783.20) 249 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 250 m/z=783.90(C ₅₄ H ₂₉ N ₃ OS ₂ , 783.20) 251 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 252 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 253 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 254 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 255 m/z=808.96(C ₅₆ H ₃₂ N ₄ OS, 808.23) 256 m/z=759.93(C ₅₃ H ₃₃ N ₃ OS, 759.23) 257 m/z=643.76(C ₄₄ H ₂₅ N ₃ OS, 643.17) 258 m/z=719.86(C ₅₀ H ₂₉ N ₃ OS, 719.20) 259 m/z=733.85(C ₅₀ H ₂₇ N ₃ O ₂ S, 733.18) 260 m/z=749.91(C ₅₀ H ₂₇ N ₃ OS ₂ , 749.16) 261 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 262 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 263 m/z=808.96(C ₅₆ H ₃₂ N ₄ OS, 808.23) 264 m/z=759.93(C ₅₃ H ₃₃ N ₃ OS, 759.23) 265 m/z=627.70(C ₄₄ H ₂₅ N ₃ O ₂ , 627.19) 266 m/z=677.76(C ₄₈ H ₂₇ N ₃ O ₂ , 677.21) 267 m/z=703.80(C ₅₀ H ₂₉ N ₃ O ₂ , 703.23) 268 m/z=703.80(C ₅₀ H ₂₉ N ₃ O ₂ , 703.23) 269 m/z=717.78(C ₅₀ H ₂₇ N ₃ O ₃ , 717.21) 270 m/z=733.85(C ₅₀ H ₂₇ N ₃ O ₂ S, 733.18) 271 m/z=767.84(C ₅₄ H ₂₉ N ₃ O ₃ , 767.22) 272 m/z=767.84(C ₅₄ H ₂₉ N ₃ O ₃ , 767.22) 273 m/z=767.84(C ₅₄ H ₂₉ N ₃ O ₃ , 767.22) 274 m/z=767.84(C ₅₄ H ₂₉ N ₃ O ₃ , 767.22) 275 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 276 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 277 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 278 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 279 m/z=792.90(C ₅₆ H ₃₂ N ₄ O ₂ , 792.25) 280 m/z=743.87(C ₅₃ H ₃₃ N ₃ O ₂ , 743.26) 281 m/z=643.76(C ₄₄ H ₂₅ N ₃ OS, 643.17) 282 m/z=693.82(C ₄₈ H ₂₇ N ₃ OS, 693.19) 283 m/z=719.86(C ₅₀ H ₂₉ N ₃ OS, 719.20) 284 m/z=719.86(C ₅₀ H ₂₉ N ₃ OS, 719.20) 285 m/z=733.85(C ₅₀ H ₂₇ N ₃ O ₂ S, 733.18) 286 m/z=749.91(C ₅₀ H ₂₇ N ₃ OS ₂ , 749.16) 287 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 288 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 289 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 290 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 291 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 292 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 293 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 294 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 295 m/z=808.96(C ₅₆ H ₃₂ N ₄ OS, 808.23) 296 m/z=759.93(C ₅₃ H ₃₃ N ₃ OS, 759.23) 297 m/z=643.76(C ₄₄ H ₂₅ N ₃ OS, 643.17) 298 m/z=719.86(C ₅₀ H ₂₉ N ₃ OS, 719.20) 299 m/z=733.85(C ₅₀ H ₂₇ N ₃ O ₂ S, 733.18) 300 m/z=749.91(C ₅₀ H ₂₇ N ₃ OS ₂ , 749.16) 301 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 302 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 303 m/z=808.96(C ₅₆ H ₃₂ N ₄ OS, 808.23) 304 m/z=759.93(C ₅₃ H ₃₃ N ₃ OS, 759.23) 305 m/z=627.70(C ₄₄ H ₂₅ N ₃ O ₂ , 627.19) 306 m/z=677.76(C ₄₈ H ₂₇ N ₃ O ₂ , 677.21) 307 m/z=703.80(C ₅₀ H ₂₉ N ₃ O ₂ , 703.23) 308 m/z=703.80(C ₅₀ H ₂₉ N ₃ O ₂ , 703.23) 309 m/z=717.78(C ₅₀ H ₂₇ N ₃ O ₃ , 717.21) 310 m/z=733.85(C ₅₀ H ₂₇ N ₃ O ₂ S, 733.18) 311 m/z=767.84(C ₅₄ H ₂₉ N ₃ O ₃ , 767.22) 312 m/z=767.84(C ₅₄ H ₂₉ N ₃ O ₃ , 767.22) 313 m/z=767.84(C ₅₄ H ₂₉ N ₃ O ₃ , 767.22) 314 m/z=767.84(C ₅₄ H ₂₉ N ₃ O ₃ , 767.22) 315 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 316 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 317 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 318 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 319 m/z=792.90(C ₅₆ H ₃₂ N ₄ O ₂ , 792.25) 320 m/z=743.87(C ₅₃ H ₃₃ N ₃ O ₂ , 743.26) 321 m/z=693.82(C ₄₈ H ₂₇ N ₃ OS, 693.19) 322 m/z=743.88(C ₅₂ H ₂₉ N ₃ OS, 743.20) 323 m/z=769.92(C ₅₄ H ₃₁ N ₃ OS, 769.22) 324 m/z=769.92(C ₅₄ H ₃₁ N ₃ OS, 769.22) 325 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 326 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 327 m/z=833.96(C ₅₈ H ₃₁ N ₃ O ₂ S, 833.21) 328 m/z=833.96(C ₅₈ H ₃₁ N ₃ O ₂ S, 833.21) 329 m/z=833.96(C ₅₈ H ₃₁ N ₃ O ₂ S, 833.21) 330 m/z=833.96(C ₅₈ H ₃₁ N ₃ O ₂ S, 833.21) 331 m/z=850.03(C ₅₈ H ₃₁ N ₃ OS ₂ , 849.19) 332 m/z=850.03(C ₅₈ H ₃₁ N ₃ OS ₂ , 849.19) 333 m/z=850.03(C ₅₈ H ₃₁ N ₃ OS ₂ , 849.19) 334 m/z=850.03(C ₅₈ H ₃₁ N ₃ OS ₂ , 849.19) 335 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 336 m/z=809.99(C ₅₇ H ₃₅ N ₃ OS, 809.25) 337 m/z=693.82(C ₄₈ H ₂₇ N ₃ OS, 693.19) 338 m/z=769.92(C ₅₄ H ₃₁ N ₃ OS, 769.22) 339 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 340 m/z=799.97(C ₅₄ H ₂₉ N ₃ OS ₂ , 799.18) 341 m/z=833.96(C ₅₈ H ₃₁ N ₃ O ₂ S, 833.21) 342 m/z=850.03(C ₅₈ H ₃₁ N ₃ OS ₂ , 849.19) 343 m/z=859.02(C ₆₀ H ₃₄ N ₄ OS, 858.25) 344 m/z=809.99(C ₅₇ H ₃₅ N ₃ OS, 809.25) 345 m/z=677.76(C ₄₈ H ₂₇ N ₃ O ₂ , 677.21) 346 m/z=727.82(C ₅₂ H ₂₉ N ₃ O ₂ , 727.23) 347 m/z=753.86(C ₅₄ H ₃₁ N ₃ O ₂ , 753.24) 348 m/z=753.86(C ₅₄ H ₃₁ N ₃ O ₂ , 753.24) 349 m/z=767.84(C ₅₄ H ₂₉ N ₃ O ₃ , 767.22) 350 m/z=783.90(C ₅₄ H ₂₉ N ₃ O ₂ S, 783.20) 351 m/z=817.90(C ₅₈ H ₃₁ N ₃ O ₃ , 817.24) 352 m/z=817.90(C ₅₈ H ₃₁ N ₃ O ₃ , 817.24) 353 m/z=817.90(C ₅₈ H ₃₁ N ₃ O ₃ , 817.24) 354 m/z=817.90(C ₅₈ H ₃₁ N ₃ O ₃ , 817.24) 355 m/z=833.96(C ₅₈ H ₃₁ N ₃ O ₂ S, 833.21) 356 m/z=833.96(C ₅₈ H ₃₁ N ₃ O ₂ S, 833.21) 357 m/z=833.96(C ₅₈ H ₃₁ N ₃ O ₂ S, 833.21) 358 m/z=833.96(C ₅₈ H ₃₁ N ₃ O ₂ S, 833.21) 359 m/z=842.96(C ₆₀ H ₃₄ N ₄ O ₂ , 842.27) 360 m/z=793.93(C ₅₇ H ₃₅ N ₃ O ₂ , 793.27) 361 m/z=719.91(C ₅₁ H ₃₃ N ₃ S, 719.24) 362 m/z=745.94(C ₅₃ H ₃₅ N ₃ S, 745.26) 363 m/z=759.93(C ₅₃ H ₃₃ N ₃ OS, 759.23) 364 m/z=775.99(C ₅₃ H ₃₃ N ₃ S ₂ , 775.21) 365 m/z=775.99(C ₅₃ H ₃₃ N ₃ S ₂ , 775.21) 366 m/z=826.05(C ₅₇ H ₃₅ N ₃ S ₂ , 825.23) 367 m/z=809.99(C ₅₇ H ₃₅ N ₃ OS, 809.25) 368 m/z=826.05(C ₅₇ H ₃₅ N ₃ S ₂ , 825.23) 369 m/z=705.88(C ₅₀ H ₃₁ N ₃ S, 705.22) 370 m/z=679.84(C ₄₈ H ₂₉ N ₃ S, 679.21) 371 m/z=630.77(C ₄₃ H ₂₆ N ₄ S, 630.19) 372 m/z=694.81(C ₄₇ H ₂₆ N ₄ OS, 694.18) 373 m/z=812.02(C ₅₆ H ₃₃ N ₃ S ₂ , 811.21) 374 m/z=709.88(C ₄₈ H ₂₇ N ₃ S ₂ , 709.16) 375 m/z=769.92(C ₅₄ H ₃₁ N ₃ OS, 769.22) 376 m/z=842.12(C ₅₆ H ₃₅ N ₃ O ₂ Si, 841.20) 377 m/z=814.00(C ₅₄ H ₃₁ N ₅ S ₂ , 813.20) 378 m/z=814.99(C ₅₃ H ₃₀ N ₆ S ₂ , 814.20) 379 m/z=809.99(C ₅₆ H ₃₅ N ₅ S, 809.26) 380 m/z=811.02(C ₅₇ H ₃₈ N ₄ S, 810.28)

Example ^1H NMR (CDCl ₃ , 200Mz) One δ = 9.25(d, 1H), 9.16(d, 1H), 8.87(d, 1H), 8.66(d, 1H), 8.46~8.42(m, 4H), 8.36(d, 1H), 8.06~8.01( m, 2H), 7.89(d, 1H), 7.77~7.69(m, 7H), 7.59~7.56(m, 2H), 7.50~7.45(m, 8H), 7.31(t, 1H). 2 δ = 9.24(d, 1H), 9.13(d, 1H), 8.85(d, 1H), 8.64(d, 1H), 8.44~8.40(m, 4H), 8.34(d, 1H), 8.06~8.02( m, 2H), 7.88(d, 1H), 7.76~7.70(m, 9H), 7.60~7.56(m, 2H), 7.51~7.46(m, 8H), 7.31(t, 1H). 3 δ = 9.25(d, 1H), 9.14(d, 1H), 8.87(d, 1H), 8.65(d, 1H), 8.45~8.40(m, 4H), 8.35(d, 1H), 8.07~8.02( m, 2H), 7.89(d, 1H), 7.78~7.72(m, 9H), 7.61~7.56(m, 4H), 7.52~7.46(m, 8H), 7.32(t, 1H). 4 δ = 9.26(d, 1H), 9.16(d, 1H), 8.89(d, 1H), 8.67(d, 1H), 8.47~8.40(m, 4H), 8.37(d, 1H), 8.07~8.03( m, 2H), 7.90(d, 1H), 7.79~7.72(m, 9H), 7.62~7.56(m, 4H), 7.53~7.46(m, 8H), 7.33(t, 1H). 5 δ = 9.33(d, 1H), 9.21(d, 1H), 8.91(d, 1H), 8.76(d, 1H), 8.56~8.51(m, 4H), 8.43(d, 1H), 8.10~8.05( m, 2H), 7.95(d, 1H), 7.85~7.79(m, 7H), 7.76~7.65(m, 4H), 7.59~7.50(m, 8H), 7.41(t, 1H). 6 δ = 9.30(d, 1H), 9.19(d, 1H), 8.90(d, 1H), 8.71(d, 1H), 8.51~8.49(m, 4H), 8.39(d, 1H), 8.07~8.04( m, 2H), 7.92(d, 1H), 7.85~7.79(m, 7H), 7.71~7.65(m, 4H), 7.55~7.50(m, 8H), 7.37(t, 1H). 8 δ = 9.29(d, 1H), 9.18(d, 1H), 8.89(d, 1H), 8.72(d, 1H), 8.52~8.48(m, 4H), 8.42(d, 1H), 8.21(s, 1H), 8.06~8.03(m, 2H), 7.93(d, 1H), 7.85~7.79(m, 8H), 7.72~7.67(m, 4H), 7.57~7.52(m, 8H), 7.33(t, 1H). 12 δ = 9.31(d, 1H), 9.20(d, 1H), 8.91(d, 1H), 8.73(d, 1H), 8.51~8.49(m, 4H), 8.30(d, 1H), 8.10(s, 1H), 8.05~8.01(m, 2H), 7.92(d, 1H), 7.85~7.79(m, 8H), 7.71~7.65(m, 4H), 7.57~7.51(m, 8H), 7.34(t, 1H). 15 δ = 9.21(d, 1H), 9.11(d, 1H), 8.82(d, 1H), 8.69(d, 1H), 8.59(d, 1H), 8.51~8.45(m, 4H), 8.30(d, 1H), 8.20(d, 1H), 8.11(s, 1H), 8.05~8.01(m, 2H), 7.92(d, 1H), 7.85~7.79(m, 8H), 7.71~7.65(m, 4H) , 7.57~7.51(m, 9H), 7.34(t, 1H). 16 δ = 9.11(d, 1H), 9.09(d, 1H), 8.81(d, 1H), 8.75(d, 1H), 8.61(d, 1H), 8.48~8.41(m, 3H), 8.20(d, 1H), 8.19(d, 1H), 8.05(s, 1H), 8.01~7.95(m, 2H), 7.88(d, 1H), 7.84~7.76(m, 6H), 7.70~7.63(m, 4H) , 7.54~7.49(m, 9H), 7.29(t, 1H), 1.69(s, 6H). 19 δ = 9.29(d, 1H), 9.19(d, 1H), 8.90(d, 1H), 8.69(d, 1H), 8.51~8.49(m, 4H), 8.35(d, 1H), 8.07~8.04( m, 2H), 7.88(d, 1H), 7.85~7.74(m, 7H), 7.71~7.68(m, 4H), 7.51~7.47(m, 8H), 7.31(t, 1H). 20 δ = 9.22(d, 1H), 9.18(d, 1H), 8.93(d, 1H), 8.71(d, 1H), 8.55~8.49(m, 4H), 8.37(d, 1H), 8.10~8.04( m, 2H), 7.89(d, 1H), 7.86(s, 1H), 7.83~7.74(m, 7H), 7.70~7.68(m, 4H), 7.57~7.47(m, 8H), 7.21(t, 1H). 29 δ = 9.31(d, 1H), 9.21(d, 1H), 8.91(d, 1H), 8.69(d, 1H), 8.51~8.47(m, 4H), 8.31(d, 1H), 8.09~8.05( m, 2H), 7.91(d, 1H), 7.84(s, 1H), 7.81~7.74(m, 7H), 7.69~7.64(m, 4H), 7.61~7.45(m, 8H), 7.19(t, 1H). 30 δ = 9.29(d, 1H), 9.19(d, 1H), 8.91(d, 1H), 8.71(d, 1H), 8.51~8.49(m, 4H), 8.35(d, 1H), 8.07~8.04( m, 2H), 7.88(d, 1H), 7.85(s, 1H), 7.81~7.78(m, 6H), 7.71~7.65(m, 4H), 7.51~7.47(m, 8H), 7.32(t, 1H). 41 δ = 9.11(d, 1H), 9.05(d, 1H), 8.77(d, 1H), 8.61(s, 1H), 8.45~8.39(m, 4H), 8.31(d, 1H), 8.01~7.99( m, 2H), 7.85(d, 1H), 7.71~7.69(m, 7H), 7.55~7.53(m, 2H), 7.49~7.45(m, 8H), 7.31(t, 1H). 42 δ = 9.18(d, 1H), 9.07(d, 1H), 8.78(d, 1H), 8.61(s, 1H), 8.48~18.40(m, 4H), 8.32(d, 1H), 8.02(s, 1H), 7.99~7.91(m, 2H), 7.80(d, 1H), 7.71~7.68(m, 6H), 7.55~7.52(m, 2H), 7.45~7.37(m, 8H), 7.31(t, 1H). 43 δ = 9.21(d, 1H), 9.11(d, 1H), 8.78(d, 1H), 8.61(s, 1H), 8.48~8.40(m, 4H), 8.32(d, 1H), 8.00~7.92( m, 3H), 7.81(d, 1H), 7.72~7.68(m, 6H), 7.56~7.52(m, 3H), 7.45~7.39(m, 8H), 7.35(t, 1H). 44 δ = 9.25(d, 1H), 9.17(d, 1H), 8.78(d, 1H), 8.61(s, 1H), 8.41~8.39(m, 4H), 8.32(d, 1H), 8.12(s, 1H), 1H 8.00~7.92(m, 2H), 7.81(d, 1H), 7.72~7.68(m, 5H), 7.56~7.52(m, 3H), 7.45~7.39(m, 8H), 7.36(t) , 1H). 45 δ = 9.39(d, 1H), 9.25(d, 1H), 8.99(d, 1H), 8.88(d, 1H), 8.71~8.61(m, 4H), 8.51(d, 1H), 8.26~8.14( m, 2H), 7.96(d, 1H), 7.84~7.79(m, 7H), 7.77~7.65(m, 4H), 7.59~7.50(m, 8H), 7.41(t, 1H). 46 δ = 9.38(d, 1H), 9.27(d, 1H), 9.01(d, 1H), 8.79(d, 1H), 8.66~8.56(m, 4H), 8.49(d, 1H), 8.20~8.09( m, 2H), 7.94(d, 1H), 7.85~7.80(m, 7H), 7.66~7.61(m, 4H), 7.49~7.41(m, 8H), 7.38(t, 1H). 48 δ = 9.29(d, 1H), 9.19(d, 1H), 8.91(d, 1H), 8.72(d, 1H), 8.52~8.48(m, 4H), 8.42(d, 1H), 8.11(s, 1H), 8.06~8.03(m, 2H), 7.89(d, 1H), 7.81~7.77(m, 8H), 7.69~7.64(m, 4H), 7.57~7.52(m, 8H), 7.32(t, 1H). 52 δ = 9.31(d, 1H), 9.20(d, 1H), 8.91(d, 1H), 8.73(d, 1H), 8.51~8.49(m, 4H), 8.30(d, 1H), 8.10(s, 1H), 8.05~8.01(m, 2H), 7.92(d, 1H), 7.85~7.79(m, 8H), 7.71~7.65(m, 4H), 7.57~7.51(m, 8H), 7.34(t, 1H). 55 δ = 9.22(d, 1H), 9.11(d, 1H), 8.91(d, 1H), 8.69(d, 1H), 8.59(d, 1H), 8.51~8.45(m, 4H), 8.30(d, 1H), 8.21(d, 1H), 8.12(s, 1H), 8.05~8.01(m, 2H), 7.92(d, 1H), 7.85~7.79(m, 8H), 7.71~7.65(m, 4H) , 7.57~7.51(m, 9H), 7.34(t, 1H). 56 δ = 9.13(d, 1H), 9.09(d, 1H), 8.86(d, 1H), 8.75(d, 1H), 8.61(d, 1H), 8.54~8.41(m, 3H), 8.20(d, 1H), 8.19(d, 1H), 8.05(s, 1H), 8.01~7.95(m, 2H), 7.88(d, 1H), 7.84~7.76(m, 6H), 7.70~7.63(m, 4H) , 7.54~7.49(m, 9H), 7.29(t, 1H), 1.69(s, 6H). 59 δ = 9.28(d, 1H), 9.19(d, 1H), 8.94(d, 1H), 8.69(d, 1H), 8.51~8.49(m, 4H), 8.35(d, 1H), 8.07~8.04( m, 2H), 7.88(d, 1H), 7.81~7.74(m, 7H), 7.69~7.61(m, 4H), 7.51~7.47(m, 8H), 7.21(t, 1H). 60 δ = 9.23(d, 1H), 9.18(d, 1H), 8.93(d, 1H), 8.81(d, 1H), 8.55~8.49(m, 4H), 8.39(d, 1H), 8.10~8.04( m, 2H), 7.89(d, 1H), 7.86(s, 1H), 7.83~7.74(m, 7H), 7.69~7.65(m, 4H), 7.57~7.47(m, 8H), 7.21(t, 1H). 69 δ = 9.29(d, 1H), 9.22(d, 1H), 8.91(d, 1H), 8.69(d, 1H), 8.51~8.47(m, 4H), 8.31(d, 1H), 8.12~8.05( m, 2H), 7.91(d, 1H), 7.84(s, 1H), 7.81~7.74(m, 7H), 7.69~7.64(m, 4H), 7.61~7.45(m, 8H), 7.19(t, 1H). 70 δ = 9.27(d, 1H), 9.19(d, 1H), 8.93(d, 1H), 8.71(d, 1H), 8.61~8.49(m, 4H), 8.35(d, 1H), 8.07~8.04( m, 2H), 7.89(d, 1H), 7.85(s, 1H), 7.80~7.76(m, 6H), 7.71~7.65(m, 4H), 7.52~7.45(m, 8H), 7.30(t, 1H). 81 δ = 9.28(d, 1H), 9.12(d, 1H), 9.01(d, 1H), 8.67(s, 1H), 8.46~8.42(m, 4H), 8.36~8.25(m, 3H), 8.12( d, 1H), 7.99~7.77(m, 7H), 7.69(d, 1H), 7.59~7.53(m, 3H), 7.50~7.45(m, 8H), 7.31(t, 1H). 83 δ = 9.23(d, 1H), 9.15(d, 1H), 8.96(d, 1H), 8.86(s, 1H), 8.68~8.42(m, 4H), 8.36~8.25(m, 3H), 8.06( d, 1H), 7.85~7.73(m, 7H), 7.65(d, 1H), 7.59~7.55(m, 4H), 7.50~7.145(m, 8H), 7.31(t, 1H), 6.99(t, 1H). 84 δ = 9.25(d, 1H), 9.16(d, 1H), 8.87(d, 1H), 8.66(s, 1H), 8.55~8.42(m, 4H), 8.32~8.25(m, 3H), 8.03( d, 1H), 7.89~7.74(m, 7H), 7.68(d, 1H), 7.61(s,1H), 7.59~7.56(m, 4H), 7.50~7.45(m, 8H), 7.31(t, 1H). 85 δ = 9.24(d, 1H), 9.15(d, 1H), 9.05(d, 1H), 8.71(d, 1H), 8.64~8.55(m, 4H), 8.19(d, 1H), 8.07~8.04( m, 2H), 7.88(d, 1H), 7.85(s, 1H), 7.81~7.78(m, 6H), 7.71~7.65(m, 6H), 7.51~7.47(m, 8H), 7.32(t, 1H). 86 δ = 9.19(d, 1H), 9.08(d, 1H), 8.90(d, 1H), 8.69(d, 1H), 8.51~8.49(m, 4H), 8.35(d, 1H), 8.17~8.09( m, 2H), 7.88(d, 1H), 7.85~7.74(m, 7H), 7.71~7.68(m, 4H), 7.51~7.47(m, 8H), 7.31(t, 1H). 88 δ = 9.29(d, 1H), 9.18(d, 1H), 9.01(d, 1H), 8.79(d, 1H), 8.67(d, 1H), 8.21(s, 1H), 8.06~8.03(m, 2H), 7.93(d, 1H), 7.85~7.79(m, 8H), 7.72~7.67(m, 8H), 7.57~7.52(m, 10H), 7.33(t, 1H). 92 δ = 9.27(d, 1H), 9.18(d, 1H), 8.84(d, 1H), 8.73(d, 1H), 8.49~8.41(m, 4H), 8.29(d, 1H), 8.11(s, 1H), 8.04~7.99(m, 2H), 7.91(d, 1H), 7.84~7.78(m, 8H), 7.70~7.65(m, 6H), 7.55~7.50(m, 8H), 7.33(t, 1H). 95 δ = 9.22(d, 1H), 9.17(s, 1H), 8.91(d, 1H), 8.79(d, 1H), 8.63(d, 1H), 8.54~8.45(m, 4H), 8.38~8.21( m, 4H), 8.12(s, 1H), 7.99~7.95(m, 4H), 7.92(d, 1H), 7.85~7.79(m, 8H), 7.69~7.65(m, 4H), 7.59~7.53( m, 8H), 7.20(t, 1H). 96 δ = 9.09(d, 1H), 8.99(s, 1H), 8.82(d, 1H), 8.75(d, 1H), 8.50(d, 1H), 8.47~8.41(m, 3H), 8.16(d, 1H), 8.07(d, 1H), 8.01(s, 1H), 7.98~7.95(m, 4H), 7.88(d, 1H), 7.85~7.76(m, 6H), 7.69~7.63(m, 4H) , 7.53~7.49(m, 9H), 7.29(t, 1H), 1.69(s, 6H). 121 δ = 9.14(d, 1H), 8.89(s, 1H), 8.76(s, 1H), 8.66(d, 1H), 8.43~8.40(m, 4H), 8.27(d, 1H), 8.09~8.01( m, 5H), 7.89(d, 1H), 7.72~7.69(m, 4H), 7.55~7.46(m, 5H), 6.91(t, 1H). 123 δ = 9.13(d, 1H), 8.90(s, 1H), 8.78(s, 1H), 8.64(d, 1H), 8.45~8.39(m, 4H), 8.22(d, 1H), 8.10~8.01( m, 5H), 7.85(d, 1H), 7.73~7.69(m, 6H), 7.57~7.46(m, 7H), 6.90(t, 1H). 124 δ = 9.12(d, 1H), 8.91(s, 1H), 8.81(s, 1H), 8.74(d, 1H), 8.54~8.41(m, 4H), 8.32(d, 1H), 8.15~8.04( m, 5H), 7.80(d, 1H), 7.75(s, 1H), 7.69~7.61(m, 6H), 7.54~7.46(m, 6H), 6.81(t, 1H). 126 δ = 9.14(d, 1H), 8.92(s, 1H), 8.85(d, 1H), 8.79(s, 1H), 8.73(d, 1H), 8.64~8.51(m, 4H), 8.21(d, 1H), 8.10~8.04(m, 6H), 7.89(d, 1H), 7.70~7.61(m, 6H), 7.55~7.46(m, 6H), 6.89(t, 1H). 128 δ = 9.26(d, 1H), 9.01(s, 1H), 8.92(d, 1H), 8.85(s, 1H), 8.79(d, 1H), 8.73(d, 1H), 8.61~8.55(m, 4H), 8.21(d, 1H), 8.10~8.04(m, 6H), 7.89(d, 1H), 7.75~7.61(m, 8H), 7.56~7.42(m, 6H), 7.01(t, 1H) . 132 δ = 9.23(d, 1H), 9.02(s, 1H), 8.91(d, 1H), 8.81(s, 1H), 8.72(d, 1H), 8.61~8.55(m, 4H), 8.21(d, 1H), 8.12~8.05(m, 8H), 7.89(d, 1H), 7.76~7.65(m, 8H), 7.56~7.39(m, 6H), 7.10(t, 1H). 161 δ = 9.21(d, 1H), 8.93(s, 1H), 8.70(d, 1H), 8.45~8.40(m, 4H), 8.31(d, 1H), 8.10~8.01(m, 5H), 7.88( d, 1H), 7.72~7.69(m, 5H), 7.50~7.46(m, 5H), 6.95(t, 1H). 163 δ = 9.13(d, 1H), 8.92(s, 1H), 8.78(s, 1H), 8.65(d, 1H), 8.45~8.39(m, 4H), 8.29(d, 1H), 8.10~8.01( m, 5H), 7.86(d, 1H), 7.73~7.69(m, 6H), 7.56~7.46(m, 7H), 6.96(t, 1H). 164 δ = 9.14(d, 1H), 8.91(s, 1H), 8.82(s, 1H), 8.74(d, 1H), 8.53~8.41(m, 4H), 8.32(d, 1H), 8.16~8.04( m, 5H), 7.80(d, 1H), 7.76(s, 1H), 7.69~7.61(m, 6H), 7.53~7.46(m, 6H), 6.81(t, 1H). 166 δ = 9.15(d, 1H), 8.92(s, 1H), 8.85(d, 1H), 8.80(s, 1H), 8.73(d, 1H), 8.64~8.51(m, 4H), 8.21(d, 1H), 8.11~8.04(m, 6H), 7.90(d, 1H), 7.70~7.61(m, 6H), 7.57~7.46(m, 6H), 6.96(t, 1H). 168 δ = 9.23(d, 1H), 9.00(s, 1H), 8.93(d, 1H), 8.85(s, 1H), 8.80(d, 1H), 8.73(d, 1H), 8.62~8.55(m, 4H), 8.21(d, 1H), 8.10~8.04(m, 6H), 7.90(d, 1H), 7.75~7.61(m, 8H), 7.56~7.42(m, 6H), 7.01(t, 1H) . 172 δ = 9.22(d, 1H), 9.03(s, 1H), 8.91(d, 1H), 8.80(s, 1H), 8.72(d, 1H), 8.60~8.55(m, 4H), 8.21(d, 1H), 8.13~8.05(m, 8H), 7.89(d, 1H), 7.76~7.65(m, 8H), 7.57~7.39(m, 6H), 7.10(t, 1H). 201 δ = 9.24(d, 1H), 9.18(d, 1H), 8.85(d, 1H), 8.61(d, 1H), 8.46~8.42(m, 4H), 8.36(d, 1H), 8.10~8.01( m, 2H), 7.89(d, 1H), 7.77~7.69(m, 4H), 7.58~7.56(m, 7H), 7.50~7.45(m, 5H), 7.31(t, 1H). 203 δ = 9.26(d, 1H), 9.13(d, 1H), 8.87(d, 1H), 8.65(d, 1H), 8.50~8.40(m, 4H), 8.35(d, 1H), 8.07~8.02( m, 2H), 7.93(d, 1H), 7.78~7.72(m, 4H), 7.61~7.56(m, 4H), 7.52~7.46(m, 5H), 7.32(t, 1H). 204 δ = 9.27(d, 1H), 9.16(d, 1H), 8.89(d, 1H), 8.67(d, 1H), 8.47~8.40(m, 4H), 8.42(d, 1H), 8.07~8.03( m, 2H), 7.90(d, 1H), 7.80~7.72(m, 4H), 7.62~7.56(m, 4H), 7.53~7.46(m, 5H), 7.23(t, 1H). 206 δ = 9.15(d, 1H), 8.92(s, 1H), 8.85(d, 1H), 8.80(s, 1H), 8.73(d, 1H), 8.64~8.51(m, 4H), 8.21(d, 1H), 8.11~8.04(m, 6H), 7.90(d, 1H), 7.70~7.61(m, 4H), 7.57~7.46(m, 6H), 6.96(t, 1H). 208 δ = 9.23(d, 1H), 9.00(s, 1H), 8.94(d, 1H), 8.85(s, 1H), 8.80(d, 1H), 8.74(d, 1H), 8.62~8.55(m, 4H), 8.24(d, 1H), 8.10~8.04(m, 6H), 7.90(d, 1H), 7.75~7.61(m, 4H), 7.56~7.42(m, 4H), 7.04(t, 1H) . 212 δ = 9.22(d, 1H), 9.04(s, 1H), 8.91(d, 1H), 8.84(s, 1H), 8.72(d, 1H), 8.64~8.55(m, 4H), 8.21(d, 1H), 8.13~8.05(m, 8H), 7.89(d, 1H), 7.76~7.65(m, 4H), 7.57~7.34(m, 4H), 7.10(t, 1H). 241 δ = 9.24(d, 1H), 8.89(s, 1H), 8.76(s, 1H), 8.66(d, 1H), 8.46~8.40(m, 4H), 8.27(d, 1H), 8.09~8.01( m, 5H), 7.89(d, 1H), 7.72~7.69(m, 4H), 7.55~7.46(m, 5H), 6.92(t, 1H). 243 δ = 9.13(d, 1H), 8.94(s, 1H), 8.78(s, 1H), 8.64(d, 1H), 8.45~8.39(m, 4H), 8.20(d, 1H), 8.10~8.01( m, 5H), 7.85(d, 1H), 7.73~7.69(m, 6H), 7.57~7.46(m, 7H), 6.90(t, 1H). 244 δ = 9.12(d, 1H), 8.91(s, 1H), 8.84(s, 1H), 8.74(d, 1H), 8.54~8.41(m, 4H), 8.32(d, 1H), 8.15~8.04( m, 5H), 7.79(d, 1H), 7.75(s, 1H), 7.69~7.61(m, 6H), 7.54~7.46(m, 6H), 6.81(t, 1H). 246 δ = 9.14(d, 1H), 8.92(s, 1H), 8.85(d, 1H), 8.79(s, 1H), 8.74(d, 1H), 8.64~8.51(m, 4H), 8.21(d, 1H), 8.10~8.04(m, 6H), 7.89(d, 1H), 7.71~7.61(m, 6H), 7.55~7.46(m, 6H), 6.89(t, 1H). 248 δ = 9.14(d, 1H), 8.92(s, 1H), 8.85(d, 1H), 8.79(s, 1H), 8.73(d, 1H), 8.64~8.51(m, 4H), 8.21(d, 1H), 8.10~8.04(m, 6H), 7.89(d, 1H), 7.70~7.61(m, 6H), 7.55~7.46(m, 6H), 6.89(t, 1H). 252 δ = 9.26(d, 1H), 9.01(s, 1H), 8.92(d, 1H), 8.85(s, 1H), 8.79(d, 1H), 8.73(d, 1H), 8.61~8.55(m, 4H), 8.21(d, 1H), 8.10~8.04(m, 6H), 7.89(d, 1H), 7.75~7.61(m, 8H), 7.56~7.42(m, 6H), 7.01(t, 1H) . 281 δ = 9.24(d, 1H), 8.89(s, 1H), 8.76(s, 1H), 8.66(d, 1H), 8.52~8.40(m, 4H), 8.27(d, 1H), 8.09~8.01( m, 5H), 7.89(d, 1H), 7.72~7.69(m, 4H), 7.55~7.46(m, 5H), 6.92(t, 1H). 283 δ = 9.21(d, 1H), 8.94(s, 1H), 8.78(s, 1H), 8.64(d, 1H), 8.45~8.39(m, 4H), 8.20(d, 1H), 8.10~8.01( m, 5H), 7.85(d, 1H), 7.73~7.69(m, 6H), 7.57~7.46(m, 7H), 6.91(t, 1H). 284 δ = 9.12(d, 1H), 8.94(s, 1H), 8.84(s, 1H), 8.74(d, 1H), 8.54~8.41(m, 4H), 8.32(d, 1H), 8.15~8.04( m, 5H), 7.79(d, 1H), 7.75(s, 1H), 7.69~7.61(m, 6H), 7.54~7.46(m, 6H), 6.89(t, 1H). 286 δ = 9.14(d, 1H), 8.92(s, 1H), 8.82(d, 1H), 8.79(s, 1H), 8.74(d, 1H), 8.64~8.51(m, 4H), 8.33(d, 1H), 8.10~8.04(m, 6H), 7.89(d, 1H), 7.71~7.61(m, 6H), 7.55~7.46(m, 6H), 7.00(t, 1H). 288 δ = 9.14(d, 1H), 8.92(s, 1H), 8.85(d, 1H), 8.76(s, 1H), 8.73(d, 1H), 8.64~8.51(m, 4H), 8.21(d, 1H), 8.18~8.04(m, 6H), 7.89(d, 1H), 7.70~7.61(m, 6H), 7.59~7.46(m, 6H), 6.99(t, 1H). 292 δ = 9.26(d, 1H), 9.01(s, 1H), 8.92(d, 1H), 8.85(s, 1H), 8.78(d, 1H), 8.73(d, 1H), 8.61~8.55(m, 4H), 8.21(d, 1H), 8.10~8.04(m, 6H), 7.75(d, 1H), 7.70~7.61(m, 8H), 7.56~7.42(m, 6H), 7.01(t, 1H) . 321 δ = 9.12(d, 1H), 8.99(d, 1H), 8.72(d, 1H), 8.53(d, 1H), 8.43~8.40(m, 4H), 8.32(d, 1H), 8.07~8.01( m, 3H), 7.81(d, 1H), 7.76~7.65(m, 4H), 7.55~7.52(m, 4H), 7.49~7.45(m, 5H), 7.00(t, 1H). 323 δ = 9.15(d, 1H), 9.03(d, 1H), 8.87(d, 1H), 8.66(d, 1H), 8.53~8.45(m, 4H), 8.35(d, 1H), 8.05~8.02( m, 3H), 7.91(d, 1H), 7.78~7.72(m, 6H), 7.60~7.56(m, 6H), 7.50~7.46(m, 5H), 7.06(t, 1H). 324 δ = 9.20(d, 1H), 9.10(d, 1H), 8.89(d, 1H), 8.67(d, 1H), 8.47~8.40(m, 4H), 8.42(d, 1H), 8.07~8.03( m, 3H), 7.90(d, 1H), 7.80~7.72(m, 6H), 7.65(s, 1H), 7.62~7.56(m, 4H), 7.52~7.46(m, 5H), 6.99(t, 1H). 326 δ = 9.22(d, 1H), 8.95(d, 1H), 8.82(s, 1H), 8.73(d, 1H), 8.67~8.59(m, 4H), 8.31(d, 1H), 8.13~8.04( m, 6H), 7.92(d, 1H), 7.71~7.61(m, 6H), 7.55~7.46(m, 6H), 6.99(t, 1H). 328 δ = 9.23(d, 1H), 9.01(s, 1H), 8.94(d, 1H), 8.85(s, 1H), 8.80(d, 1H), 8.75(d, 1H), 8.65~8.55(m, 4H), 8.25(d, 1H), 8.10~8.04(m, 6H), 7.90(d, 1H), 7.76~7.61(m, 6H), 7.56~7.40(m, 4H), 7.05(t, 1H) . 332 δ = 9.22(d, 1H), 8.99(d, 1H), 8.85(s, 1H), 8.72(d, 1H), 8.65~8.55(m, 4H), 8.25(d, 1H), 8.15~8.05( m, 8H), 7.89(d, 1H), 7.75~7.65(m, 6H), 7.57~7.34(m, 4H), 7.09(t, 1H). 361 δ = 8.99(d, 1H), 8.85(d, 1H), 8.74(d, 1H), 8.57~8.45(m, 3H), 8.22(d, 1H), 8.15(d, 1H), 8.07(s, 1H), 8.02~7.97(m, 2H), 7.88(d, 1H), 7.82~7.76(m, 4H), 7.70~7.63(m, 4H), 7.49~7.44(m, 6H), 7.02(t, 1H), 1.69(s, 6H). 362 δ = 9.02(d, 1H), 8.81(d, 1H), 8.72(d, 1H), 8.62~8.49(m, 3H), 8.20(d, 1H), 8.16(d, 1H), 8.11(s, 1H), 8.05~7.97(m, 2H), 7.91(d, 1H), 7.86~7.76(m, 6H), 7.72~7.65(m, 4H), 7.51~7.42(m, 6H), 7.03(t, 1H), 1.69(s, 6H). 364 δ = 9.12(d, 1H), 8.82(d, 1H), 8.79(s, 1H), 8.65(d, 1H), 8.60~8.53(m, 4H), 8.21(d, 1H), 8.17~8.12( m, 6H), 7.98(d, 1H), 7.70~7.65(m, 6H), 7.53~7.46(m, 4H), 7.03(t, 1H), 1.69(s, 6H). 365 δ = 9.05(d, 1H), 8.92(d, 1H), 8.70(s, 1H), 8.60(d, 1H), 8.59~8.55(m, 4H), 8.31(d, 1H), 8.21~8.12( m, 5H), 8.02(d, 1H), 7.88~7.76(m, 6H), 7.55~7.49(m, 5H), 7.05(t, 1H), 1.69(s, 6H). 366 δ = 9.08(d, 1H), 8.88(d, 1H), 8.72(s, 1H), 8.65(d, 1H), 8.69~8.58(m, 4H), 8.28(d, 1H), 8.18~8.10( m, 6H), 7.95(d, 1H), 7.79~7.69(m, 6H), 7.58~7.46(m, 6H), 6.98(t, 1H), 1.69(s, 6H). 367 δ = 9.18(d, 1H), 9.04(s, 1H), 8.95(d, 1H), 8.81(s, 1H), 8.71(d, 1H), 8.62(d, 1H), 8.59~8.51(m, 4H), 8.24(d, 1H), 8.11~8.05(m, 6H), 7.81(d, 1H), 7.75~7.68(m, 6H), 7.60~7.54(m, 4H), 7.04(t, 1H) , 1.69(s, 6H). 368 δ = 9.12(d, 1H), 9.01(s, 1H), 8.91(d, 1H), 8.72(s, 1H), 8.64(d, 1H), 8.60~8.55(m, 4H), 8.25(d, 1H), 8.12~8.09(m, 5H), 7.91(d, 1H), 7.78~7.65(m, 6H), 7.60~7.53(m, 6H), 7.01(t, 1H), 1.69(s, 6H) .

< Experiment example 1>- Fabrication of organic light emitting devices

1) Fabrication of organic light emitting device (red host)

A glass substrate coated with a thin film of ITO with a thickness of 1,500 Å was washed with distilled water ultrasonic waves. After washing with distilled water, it was ultrasonic washed with solvents such as acetone, methanol, and isopropyl alcohol, dried, and treated with UV for 5 minutes using UV light in a UV cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), then 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.

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

A light emitting layer was thermally vacuum deposited thereon as follows. The light-emitting layer was deposited at 500 Å by using a compound listed in Table 5 below as a red host and (piq)2(Ir)(acac) as a red phosphorescent dopant, doping 3% of (piq)2(Ir)(acac) into the host. Afterwards, 60Å of BCP was deposited as a hole blocking layer, and 200Å of Alq3 was deposited on top of it as an electron transport layer. Afterwards, 60Å of BCP was deposited as a hole blocking layer, and 200Å of Alq3 was deposited on top of it as an electron transport layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200Å on the electron injection layer to form the cathode, thereby forming an organic An electroluminescent device was manufactured.

Meanwhile, all organic compounds required for OLED device production were purified by vacuum sublimation under 10-6 to 10-8 torr for each material and used for OLED production.

2) Organic electric field Driving voltage and luminous efficiency of light emitting elements

The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured using the M7000 from McScience, and the standard luminance was measured to be 6,000 using the lifespan measurement equipment (M6000) manufactured by McScience based on the measurement results. When cd/m ² , T90 was measured. The characteristics of the organic electroluminescent device of the present invention are shown in Table 5 below.

compound Driving voltage (V) Efficiency (cd/A) Color coordinates (x, y) Lifespan (T ₉₀ ) Comparison example 1 One 5.52 12.9 0.687, 0.313 39 Comparison example 2 2 5.62 12.1 0.688, 0.312 40 Comparison example 3 3 5.42 13.8 0.689, 0.310 58 Comparison example 4 4 5.22 14.0 0.691, 0.309 63 Comparison example 5 5 5.82 14.5 0.674, 0.325 61 Comparison example 6 6 5.68 14.2 0.672, 0.327 38 Comparison example 7 7 5.24 13.9 0.684, 0.316 49 Comparison example 8 8 5.13 14.1 0.691, 0.309 53 Comparison example 9 9 5.10 15.8 0.691, 0.309 54 Comparison example 10 10 4.96 16.6 0.689, 0.310 25 Comparison example 11 11 5.96 11.5 0.689, 0.310 23 Comparison Example 12 12 5.22 16.2 0.689, 0.310 28 Example 1 Compound 1 4.29 24.2 0.676, 0.324 138 Example 2 compound 2 4.20 22.0 0.678, 0.322 109 Example 3 Compound 3 4.28 25.7 0.679, 0.321 161 Example 4 Compound 4 4.25 25.2 0.682, 0.317 159 Example 5 Compound 5 4.32 19.2 0.685, 0.314 124 Example 6 Compound 6 4.08 28.6 0.678, 0.321 187 Example 7 Compound 8 4.19 24.0 0.687, 0.313 130 Example 8 Compound 12 4.12 24.2 0.688, 0.312 120 Example 9 Compound 15 4.48 18.4 0.689, 0.310 109 Example 10 Compound 16 4.39 18.7 0.691, 0.309 98 Example 11 Compound 19 4.37 19.2 0.674, 0.325 103 Example 12 Compound 20 4.55 17.2 0.678, 0.321 100 Example 13 Compound 29 4.59 17.1 0.685, 0.314 97 Example 14 Compound 30 4.57 18.0 0.684, 0.316 99 Example 15 Compound 41 4.25 25.2 0.680, 0.319 131 Example 16 Compound 42 4.23 22.6 0.684, 0.315 106 Example 17 Compound 43 4.22 25.5 0.683, 0.317 158 Example 18 Compound 44 4.21 24.9 0.682, 0.317 153 Example 19 Compound 45 4.35 19.8 0.682, 0.317 120 Example 20 Compound 46 4.10 28.0 0.680, 0.319 177 Example 21 Compound 48 4.20 24.6 0.682, 0.318 133 Example 22 Compound 52 4.15 24.5 0.681, 0.319 122 Example 23 Compound 55 4.42 17.9 0.680, 0.319 119 Example 24 Compound 56 4.33 17.2 0.681, 0.319 101 Example 25 Compound 59 4.35 18.2 0.687, 0.313 93 Example 26 Compound 60 4.50 17.5 0.688, 0.312 103 Example 27 Compound 69 4.51 17.0 0.689, 0.310 99 Example 28 Compound 70 4.52 18.9 0.691, 0.309 94 Example 29 Compound 81 4.30 24.2 0.674, 0.325 140 Example 30 Compound 83 4.28 21.6 0.672, 0.327 117 Example 31 Compound 84 4.27 24.5 0.676, 0.324 169 Example 32 Compound 85 4.26 23.9 0.678, 0.322 164 Example 33 Compound 86 4.40 18.8 0.679, 0.321 131 Example 34 Compound 88 4.15 27.0 0.682, 0.317 175 Example 35 Compound 92 4.25 23.6 0.685, 0.314 144 Example 36 Compound 95 4.20 23.5 0.678, 0.321 133 Example 37 Compound 96 4.42 16.9 0.681, 0.319 120 Example 38 Compound 121 4.23 20.2 0.678, 0.321 108 Example 39 Compound 123 4.21 22.0 0.685, 0.314 99 Example 40 Compound 124 4.25 23.7 0.684, 0.316 96 3Example 41 Compound 126 4.32 21.2 0.680, 0.319 120 Example 42 Compound 128 4.30 19.2 0.684, 0.315 98 Example 43 Compound 132 4.28 18.6 0.683, 0.317 100 Example 44 Compound 161 4.28 20.2 0.682, 0.317 108 Example 45 Compound 163 4.25 20.0 0.682, 0.317 102 Example 46 Compound 164 4.27 21.2 0.680, 0.319 99 Example 47 Compound 166 4.42 20.2 0.682, 0.318 125 Example 48 Compound 168 4.30 18.2 0.681, 0.319 99 Example 49 Compound 172 4.28 19.6 0.680, 0.319 97 Example 50 compound 201 4.33 18.2 0.687, 0.313 98 Example 51 Compound 203 4.29 19.0 0.688, 0.312 101 Example 52 Compound 204 4.25 20.3 0.689, 0.310 92 Example 53 Compound 206 4.31 19.8 0.691, 0.309 112 Example 54 Compound 208 4.35 18.9 0.674, 0.325 92 Example 55 Compound 212 4.38 20.6 0.672, 0.327 88 Example 56 Compound 241 4.38 22.9 0.676, 0.324 90 Example 57 Compound 243 4.39 21.9 0.678, 0.322 103 Example 58 Compound 244 4.30 21.7 0.679, 0.321 80 Example 59 Compound 246 4.29 19.9 0.682, 0.317 89 Example 60 Compound 248 4.49 21.9 0.685, 0.314 121 Example 61 Compound 252 4.32 19.7 0.678, 0.321 98 Example 62 Compound 281 4.32 19.0 0.681, 0.319 111 Example 63 Compound 283 4.29 17.8 0.678, 0.321 119 Example 64 Compound 286 4.52 19.9 0.685, 0.314 110 Example 65 Compound 288 4.51 17.9 0.684, 0.316 137 Example 66 Compound 292 4.37 19.9 0.680, 0.319 129 Example 67 Compound 321 4.51 22.9 0.684, 0.315 121 Example 68 Compound 323 4.39 22.0 0.683, 0.317 108 Example 69 Compound 324 4.64 18.8 0.682, 0.317 120 Example 70 Compound 326 4.38 23.9 0.682, 0.317 94 Example 71 Compound 328 4.37 22.6 0.680, 0.319 98 Example 72 Compound 332 4.34 22.7 0.682, 0.318 96 Example 73 Compound 361 4.32 21.9 0.681, 0.319 99 Example 74 Compound 362 4.33 22.5 0.680, 0.319 101 Example 75 Compound 364 4.49 18.6 0.681, 0.319 121 Example 76 Compound 365 4.58 20.2 0.687, 0.313 98 Example 77 Compound 366 4.44 21.9 0.688, 0.312 100 Example 78 Compound 367 4.47 20.8 0.689, 0.310 97 Example 79 Compound 368 4.69 19.9 0.691, 0.309 96 Example 80 Compound 369 4.58 21.3 0.674, 0.325 92 Example 81 Compound 370 4.21 18.8 0.672, 0.327 101 Example 82 Compound 371 4.39 22.9 0.676, 0.324 80 Example 83 Compound 372 4.39 22.7 0.678, 0.322 101 Example 84 Compound 373 4.28 19.9 0.679, 0.321 88 Example 85 Compound 374 4.37 20.9 0.682, 0.317 89 Example 86 Compound 375 4.48 19.8 0.685, 0.314 84 Example 87 Compound 376 4.59 18.9 0.678, 0.321 96 Example 88 Compound 377 4.57 20.4 0.681, 0.319 99 Example 89 Compound 378 4.51 20.9 0.678, 0.321 97 Example 90 Compound 379 4.27 17.9 0.685, 0.314 88 Example 91 Compound 380 4.31 19.8 0.684, 0.316 89

As can be seen from the results in Table 5, the organic light-emitting device using the heterocyclic compound of the present invention as the light-emitting layer host of the red organic light-emitting device had a lower driving voltage and significantly improved luminous efficiency and lifespan compared to Comparative Examples 1 to 12. I was able to confirm.

Looking at the results in Table 5 above, it is possible to meet the conditions required by the light emitting layer by creating a compound with the same appropriate band gap by introducing various substituents into the core portion of the compound. This improves electron transfer ability, resulting in excellent driving and efficiency effects, while also improving thermal stability and lifespan characteristics.

In addition, when Ar1 of Formula 1 was replaced with a carbazole core substituted with one more ring rather than a simple carbazole core, it was found that the drive, efficiency, and lifespan were improved compared to the other cases (Comparative Examples 3 and 4). , of Formula 1 In the case of a structure directly linked to the N of carbazole without a linker, it was confirmed that the operation, efficiency, and lifespan were improved compared to the case without a linker (Comparative Example 11).

100: substrate
200: anode
300: Organic layer
301: hole injection layer
302: hole transport layer
303: light emitting layer
304: hole blocking layer
305: electron transport layer
306: electron injection layer
400: cathode

Claims (14)

Heterocyclic compounds represented by any one of the following formulas 1, 2-1 to 2-3, 3 and 4:
[Formula 1]

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 3]

[Formula 4]

In Formulas 1, 2-1 to 2-3, 3 and 4,
A is a substituted or unsubstituted C6 to C40 monocyclic or polycyclic aromatic hydrocarbon ring,
X ₁ and X ₂ are the same as or different from each other and are each independently directly bonded; O; or S,
Ra is a substituted or unsubstituted C6 to C40 aryl group; Or a substituted or unsubstituted C2 to C40 heteroaryl group,
Ar ₁ is a substituted or unsubstituted amine group,
R ₁ to R ₃ and R ₁₁ to R ₁₈ are the same as or different from each other, and are each independently hydrogen; or deuterium,
_{R _ _ _} or different, m is an integer from 1 to 4, and when m is 2 or more, R ₁ is the same as or different from each other, p is an integer from 1 to 3, and when p is 2 or more, R ₃ is the same as or different from each other,
Y is O; S; CRR'; or NR",
Y ₁ to Y ₅ are CR41; or N,
At least one of Y ₁ to Y ₅ is N,
R, R' and R" are the same or different from each other and are each independently a substituted or unsubstituted C1 to C40 alkyl group; or a C6 to C10 aryl group,
R41 is hydrogen; Substituted or unsubstituted aryl group of C6 to C40; Or a substituted or unsubstituted C2 to C40 heteroaryl group;
The following compounds are excluded.
delete delete The method according to claim 1, wherein Ra of Formula 1 is a heterocyclic compound represented by any one of the following Formulas 5 to 7:
[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 5 to 7,
means the connected part,
Y _a and Y _b are the same or different from each other, and are each independently O; S; CRR'; or NR",
R ₂₁ , R ₂₂ , R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; substituted or unsubstituted C1 to C40 alkyl group; substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted heteroaryl group of C2 to C40, a1 is an integer of 0 to 3, and when a1 is 2 or more, R ₂₁ are the same or different from each other, a2 is an integer of 0 to 4, and a2 is 2 In case of more than R ₂₂ are the same or different,
Xa to Xe are CR ₃₁ ; or N,
R ₃₁ is hydrogen; Substituted or unsubstituted C1 to C40 alkyl group; Substituted or unsubstituted C6 to C40 aryl group; and a substituted or unsubstituted C2 to C40 heteroaryl group, or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring. The method according to claim 1, wherein R ₁ and R ₂ are hydrogen. The method of claim 4, wherein R ₃₁ is hydrogen; or a C6 to C40 aryl group, or a heterocyclic compound in which two or more groups adjacent to each other are combined to form a C6 to C40 aromatic hydrocarbon ring substituted or unsubstituted with a C6 to C40 aryl group. The heterocyclic compound according to claim 1, wherein any one of Formulas 1, 2-1 to 2-3, 3, and 4 is represented by any one of the following compounds:

first electrode; a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the heterocyclic compound according to any one of claims 1 and 4 to 7. An organic light-emitting device. The organic light-emitting device of claim 8, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound. The organic light-emitting device of claim 8, wherein the organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes the heterocyclic compound. The organic light-emitting device of claim 10, wherein the light-emitting layer includes a red host material, and the red host material includes the heterocyclic compound. The organic light-emitting device of claim 8, wherein the organic layer includes an electron injection layer or an electron transport layer, and the electron transport layer or electron injection layer includes the heterocyclic compound. The organic light-emitting device of claim 8, wherein the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the heterocyclic compound. The method according to claim 8, wherein the organic light emitting device comprises a light emitting layer, a hole injection layer, and a hole transport layer. An organic light-emitting device further comprising one or two layers selected from the group consisting of an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

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