KR20190097577A - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a heterocyclic compound represented by chemical formula 1 and an organic light emitting device comprising the same. A compound described in the present specification can be used as a material of an organic material layer of the organic light emitting device. The present invention can manufacture the organic light emitting device with improved lifespan, driving stability, and efficiency by using the compound.

Description

Heterocyclic compound and organic light-emitting device including the same TECHNICAL FIELD

The present specification relates to a heterocyclic compound and an organic light emitting device including the same.

The electroluminescent device is a kind of self-luminous display device, and has an advantage of having a wide viewing angle, excellent contrast, and fast response speed.

The organic light emitting element has a structure in which an organic thin film is arranged between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from two electrodes are combined in the organic thin film to form a pair, then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers as necessary.

The material of the organic thin film may have a light emitting function as needed. For example, as the organic thin film material, a compound which may itself constitute a light emitting layer may be used, or a compound that may serve as a host or a dopant of a host-dopant-based light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing a role of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, or the like may be used.

In order to improve the performance, lifespan, or efficiency of an organic light emitting element, development of the material of an organic thin film is continuously required.

U.S. Patent 4,356,429

The present application is to provide a novel heterocyclic compound and an organic light emitting device comprising the same.

An exemplary embodiment of the present application provides a heterocyclic compound represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1,

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

X ₁ and X ₂ are the same as or different from each other, and each independently a direct bond; 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; Substituted or unsubstituted monocyclic or polycyclic aryl group; Substituted or unsubstituted monocyclic or polycyclic heteroaryl group; P (= 0) 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 as or different from each other, and 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; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And substituted or unsubstituted amine groups, or two or more groups adjacent to each other combine 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, n When 2 or more, R ₂ is the same as or different from each other, m is an integer of 1 to 4, when m is 2 or more, R ₁ is the same 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.

In addition, according to an exemplary embodiment of the present application, the first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a heterocyclic compound represented by Chemical Formula 1. To provide.

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

In particular, the general formula (1) is bonded to the phenyl position of the carbazole group, a substituent having a hall characteristic is bonded to have a stable core structure. The introduction of substituents with various electronic properties into this core portion imparts appropriate energy levels and thermal stability to the device. Using these compounds, an organic light emitting device having improved lifetime, driving stability, and efficiency can be manufactured.

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

Hereinafter, the present application will be described in detail.

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

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

In the present specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. Carbon number of the alkyl group may be 1 to 60, specifically 1 to 40, 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, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 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 and the like, but is not limited thereto.

In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. Carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20. Specific examples thereof 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, and 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 and the like, but are not limited thereto.

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

In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. 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 and the like It may be, but is not limited thereto.

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 other substituents. Here, polycyclic means a group in which a cycloalkyl group is directly connected or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may be another type of ring group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, or the like. Carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, 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 and the like, but is not limited thereto.

In the present specification, the heterocycloalkyl group includes O, S, 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 other substituents. Here, polycyclic means a group in which a heterocycloalkyl group is directly connected or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may be another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, or the like. Carbon number of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, 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, the polycyclic means a group in which an aryl group is directly connected or condensed with another ring group. Here, the other ring group may be an aryl group, but may be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, or the like. The aryl group includes a spiro group. Carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. 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, phenenyl group, pyre Neyl group, tetrasenyl group, pentaxenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof Etc., but is not limited thereto.

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

,

,

,

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

,

,

,

Etc., but is not limited thereto.

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 means a group in which a heteroaryl group is directly connected or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, or the like. Carbon number of the heteroaryl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 25. Specific examples of the heteroaryl group include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophene, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl and thiazolyl Group, isothiazolyl group, triazolyl group, furazanyl group, oxdiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , Thiazinyl group, dioxyyl group, triazinyl group, tetragenyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyl group, naphthyridyl group, acridinyl group, phenanthrididi Nyl group, imidazopyridinyl group, diazanaphthalenyl group, triaza indene group, indolyl group, indolinyl 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-dihydro Acridinyl group, phenanthrazinyl group, phenothiathiazinyl group, phthalazinyl group, naphthyridinyl group, phenanthrolinyl group, benzo [c] [1,2,5] thiadiazolyl group, 5,10-di Hydrodibenzo [b, e] [1,4] azasilinyl, 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, and the like, but are not limited thereto.

In the present specification, the amine group is a monoalkylamine group; Monoarylamine group; Monoheteroarylamine group; -NH ₂ ; Dialkylamine groups; Diarylamine group; Diheteroarylamine group; Alkylarylamine group; Alkyl heteroaryl amine group; And it may be selected from the group consisting of arylheteroarylamine group, carbon number 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, biphenylfluore And a phenylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but are not limited thereto.

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

As used herein, the term "adjacent" means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted. Can be. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as “adjacent” groups.

The structures exemplified by the cycloalkyl group described above may be applied except that the aliphatic hydrocarbon ring which adjacent groups may form is not the monovalent group, and the structures exemplified by the aryl group except that the aromatic hydrocarbon ring is not monovalent The structures exemplified above can be applied except that the aliphatic heterocycle is not monovalent, and the structure exemplified above is the heteroaryl group except that the aromatic heterocycle is not monovalent. Can be applied.

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

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

In one embodiment of the present application, Ar ₁ is a substituted or unsubstituted alkyl group; Substituted or unsubstituted monocyclic or polycyclic aryl group; Substituted or unsubstituted monocyclic or polycyclic heteroaryl group; P (= 0) R _x R _y ; SiR _x R _y R _z ; Or a substituted or unsubstituted amine group.

In another exemplary embodiment, Ar ₁ is a substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted monocyclic or polycyclic C6 to C60 aryl group; Substituted or unsubstituted monocyclic or polycyclic C2 to C60 heteroaryl group; P (= 0) R _x R _y ; SiR _x R _y R _z ; Or a substituted or unsubstituted amine group.

In another exemplary embodiment, Ar ₁ is a substituted or unsubstituted C1 to C40 alkyl group; Substituted or unsubstituted monocyclic or polycyclic C6 to C40 aryl group; Substituted or unsubstituted monocyclic or polycyclic C2 to C40 heteroaryl group; P (= 0) R _x R _y ; SiR _x R _y R _z ; Or a substituted or unsubstituted amine group.

In another exemplary 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 C1 to C40 alkyl groups and C6 to C40 aryl groups; Monocyclic or polycyclic C2 to C40 heteroaryl group unsubstituted or substituted with C6 to C40 aryl group; P (= 0) R _x R _y ; SiR _x R _y R _z ; Or an amine group unsubstituted or substituted with an aryl group of C6 to C40.

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

[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4, X ₁ , X ₂ , R ₁ , R ₂ , Ra, m, n, R _x , R _y , R _z , and A are the same as defined in Formula 1,

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

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 as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alky A substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted force Two or more groups selected from the group consisting of a pin oxide group and 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 Is an integer and p is 2 or more, then R ₃ is the same or different from each other

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 combine with each other to form a substituted or unsubstituted monocyclic aromatic hydrocarbon ring or a substituted or unsubstituted monocyclic hetero ring.

In one embodiment of the present application, A and B are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic or polycyclic aromatic hetero ring.

In another exemplary embodiment, A and B are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aromatic hydrocarbon ring; Or a substituted or unsubstituted C2 to C60 monocyclic or polycyclic aromatic hetero ring.

In another exemplary embodiment, A and B are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C40 monocyclic or polycyclic aromatic hydrocarbon ring; Or a substituted or unsubstituted C2 to C40 monocyclic or polycyclic aromatic hetero ring.

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

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

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

In one embodiment of the present application, when the Y in the general formula (2) is NR ", at least one of A and B may be a substituted or unsubstituted 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 substituted or unsubstituted 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 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 exemplary embodiment, when Ar ₁ is a substituted or unsubstituted N-containing tricyclic heteroaryl group, A may be a polycyclic aromatic hydrocarbon ring.

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

In another exemplary 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, the R _x , R _y And R _z are the same as or different from each other, and 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; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And substituted or unsubstituted amine groups, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring.

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

In one embodiment of the present application, R ₄₁ is hydrogen; Or two or more groups selected from the group consisting of substituted or unsubstituted aryl groups, or adjacent to each other, may combine with each other to form a substituted or unsubstituted monocyclic aromatic hydrocarbon ring or a substituted or unsubstituted monocyclic hetero ring.

In yet one embodiment, R ₄₁ is hydrogen; Or 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 hetero ring.

In yet one embodiment, R ₄₁ is hydrogen; Or a C6 to C40 aryl group unsubstituted or substituted with a 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 hetero ring.

In yet one embodiment, R ₄₁ is hydrogen; Phenyl group; Or a biphenyl group, or two or more groups adjacent to each other may be bonded to each other to form a benzene ring or a pyridine ring.

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

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Chemical 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 Chemical Formula 2,

R ₁₁ to R ₁₈ are the same as or different from each other, and 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; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And it may be selected from the group consisting of a substituted or unsubstituted amine group.

In one embodiment of the present application, X ₁ and X ₂ are the same as or different from each other, and each independently a direct bond; O; Or S.

In one embodiment of the present application, one of the X _One And X ₂ It is a direct bond, the other may be O or S.

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

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

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

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

In one embodiment of the present application, Y is O; S; CRR '; Or NR ".

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

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

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

In one embodiment of the present application, Y may be NR ″.

In one embodiment of the present application, R, R 'and R "are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group A substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; a 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 combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring. Can be.

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

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

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

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

In another exemplary embodiment, R, R ', and R "are the same as or different from each other, and each independently hydrogen, a methyl group, or a phenyl group.

In one embodiment of the present application, the R _{One To} R _{3 They} are the same as or different from each other, and 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; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And at least two groups selected from the group consisting of substituted or unsubstituted amine groups, or adjacent to each other, combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring, n and p each represent 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 as or different from each other, m is an integer of 1 to 4, and when m is 2 or more, R ₁ is the same as or different from each other; Can be different.

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

In one embodiment of the present application, Ra is hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

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

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

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

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

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

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

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

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

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 5 to 7,

은 연결되는 부위를 의미하며,

Means the connecting portion,

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

R ₂₁ , R ₂₂ , R, R 'and R "are the same as or different from each other, and 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 It may be selected from the group consisting of a ring phosphine oxide group and a substituted or unsubstituted amine group, a1 is an integer of 0 to 3, when a1 is 2 or more, R ₂₁ is the same as or different from each other, a2 is 0 to An integer of 4 and when a2 is 2 or more, R ₂₂ is the same as or different from each other,

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 combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring.

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

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

In one embodiment of the present application, Y _a may be CRR ′.

In one embodiment of the present application, Y _a may be NR ″.

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

In one embodiment of the present application, Xd of Xa to Xe may be N, and the rest may be CR ₃₁ .

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

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

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

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

In addition, by introducing various substituents into the structure of the formula (1) it is possible to synthesize a compound having the intrinsic properties of the introduced substituents. For example, by introducing a substituent mainly used in the hole injection layer material, the hole transporting material, the light emitting layer material, the electron transporting material and the charge generating layer material used in the manufacture of the organic light emitting device to meet the requirements required for each organic material layer The substance to make can be synthesize | combined.

In addition, by introducing a variety of substituents in the structure of the formula (1) it is possible to finely control the energy bandgap, on the other hand to improve the characteristics at the interface between the organic material and to vary the use of the material.

In addition, in an exemplary embodiment of the present application, the first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a heterocyclic compound according to Chemical Formula 1. to provide.

Details of the heterocyclic compound represented by Formula 1 are the same as described above.

In one 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 Chemical Formula 1 may be used as a material of 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 Chemical Formula 1 may be used as a material of 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 Chemical Formula 1 may be used as a material of 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 may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic material layers are formed using the heterocyclic compound described above.

The heterocyclic compound may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer 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 and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto 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 may include a light emitting layer, the light emitting layer may include a host material, and the host material may include the heterocyclic compound.

In another organic light emitting device, the light emitting layer comprises a red host material, the red host material comprises the heterocyclic compound provides an organic light emitting device.

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

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

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

The organic light emitting device of the present invention is a light emitting layer, a hole injection layer, a hole transport layer. It may further include one or two or more 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 a lamination order of an electrode and an organic material layer of an organic light emitting diode according to an exemplary embodiment of the present application. However, these drawings are not intended to limit the scope of the present application, the structure of the organic light emitting device known in the art can be applied to the present application.

Referring to FIG. 1, an organic light emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is illustrated. However, the present invention is not limited thereto, and as illustrated in FIG. 2, an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.

3 illustrates a case where the organic material layer is a multilayer. The organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited by such a laminated structure, and other layers except for the light emitting layer may be omitted, and other functional layers may be added as needed.

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

In the organic light emitting device according to the exemplary embodiment of the present application, materials other than the compound of Chemical Formula 1 are exemplified 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. Material may be replaced.

As the anode material, materials having a relatively large work function may be used, and a transparent conductive oxide, a metal, or a conductive polymer may be used. Specific examples of the positive electrode 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), indium zinc oxide (IZO); A combination of a metal and an 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, and the like, but are not limited thereto.

As the cathode material, materials having a relatively low work function may be used, and a metal, a metal oxide, or a conductive polymer may be used. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

As the hole injection material, a well-known hole injection material 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 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, or poly (line) 3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) (Poly (3,4-ethylenedioxythiophene) / Poly (4-styrenesulfonate)), polyaniline / Camphor sulfonic acid or polyaniline / Poly (4-styrenesulfonate) (Polyaniline / Poly (4-styrene-sulfonate)) etc. can be used.

As the hole transporting material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like may be used, and low molecular or polymer materials may be used.

Examples of the electron transporting material include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthhraquinomethane and derivatives thereof, and fluorenone Derivatives, diphenyl dicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like can be used, as well as high molecular weight materials as well as high molecular materials.

As the electron injection material, for example, LiF is representatively used in the art, but the present application is not limited thereto.

As the light emitting material, a red, green or blue light emitting material may be used, and if necessary, two or more light emitting materials may be mixed. In this case, two or more light emitting materials may be deposited and used as separate sources, or premixed and deposited as one source. In addition, although a fluorescent material can be used as a light emitting material, it can also be used as a phosphorescent material. As the light emitting material, a material which combines holes and electrons injected from the anode and the cathode, respectively, to emit light may be used, but materials in which both the host material and the dopant material are involved in light emission may be used.

In the case of mixing and using a host of luminescent materials, the host of the same series may be mixed and used, or the host of another series may be mixed and used. For example, any two or more kinds of n-type host materials or p-type host materials may be selected and used as the host material of the light emitting layer.

The organic light emitting device according to the exemplary embodiment of the present application may be a top emission type, a bottom emission type, or a double-sided emission type according to a material used.

The heterocyclic compound according to the exemplary embodiment of the present application may act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like.

Hereinafter, the present specification will be described in more detail with reference to Examples, but these are merely to illustrate the present application and are not intended to limit the scope of the present application.

< Production Example >

< Production Example  1> Preparation of Intermediates A to X

Synthesis of Intermediates A to V

To compound a (1eq) of Table 1, compound b (1eq) of Table 1, Pd (PPh ₃ ) ₄ (0.05eq), K ₂ CO ₃ (3eq) in a round bottom flask, 1,4-diox It is dissolved in putin (1,4-dioxane), H ₂ O (10v / w) and stirred at 100 ℃. When the reaction is completed, 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 , concentrated, and purified by silica-gel column to obtain intermediate compounds A to V (yield: 58% to 78%) of Table 1 below.

Synthesis of Intermediates W and X

To compound a (1eq) of Table 1, compound b (1eq) of Table 1, Pd ₂ (dba) ₃ (0.05eq), P ( t -Bu) ₃ , NaOtBu (3eq) in a round bottom flask, Toluene (10v / w) was added to dissolve and stirred at 110 ° C. When the reaction is completed, 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 , concentrated, and purified by silica-gel column to obtain intermediate compounds W and X (yield: 66% to 73%) of Table 1 below.

< Production Example  2> Synthesis of Target Compound

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

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

Table 3 and Table 4 are FD-MS data and 1H NMR data of the synthesized compound, and the following data can confirm that the desired 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 ¹ H NMR (CDCl ₃ , 200 Mz) 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 to 8.51 (m, 4H), 8.43 (d, 1H), 8.10 to 8.05 ( m, 2H), 7.95 (d, 1H), 7.85-7.79 (m, 7H), 7.76-7.75 (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), 7.71-7.75 (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), 7.71-7.75 (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), 7.71-7.75 (m, 4H) , 7.57 to 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), 7.84-7.72 (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), 7.69-7.74 (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), 7.71-7.75 (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), 8.00-7.72 ( 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), 7.77-7.75 (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), 7.71-7.75 (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 to 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), 7.84-7.72 (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), 7.69-7.75 (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), 7.69-7.74 (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), 7.80-7.72 (m, 6H), 7.71-7.75 (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), 7.71-7.75 (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), 7.72-7.57 (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), 7.70-7.75 (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, 1 H). 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), 7.85-7.72 (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), 7.76-7.75 (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), 7.76-7.75 (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 to 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), 7.76-7.75 (m, 4H), 7.57-7.74 (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 to 8.04 (m, 6H), 7.75 (d, 1H), 7.70 to 7.61 (m, 8H), 7.56 to 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), 7.76-7.75 (m, 4H), 7.55-7.75 (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 to 8.59 (m, 4H), 8.31 (d, 1H), 8.13 to 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 to 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 to 8.55 (m, 4H), 8.25 (d, 1H), 8.15 to 8.05 ( m, 8H), 7.89 (d, 1H), 7.75-7.75 (m, 6H), 7.57-7.74 (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), 7.82-7.72 (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), 7.86-7.72 (m, 6H), 7.72-7.75 (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), 7.70-7.75 (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 to 8.58 (m, 4H), 8.28 (d, 1H), 8.18 to 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 to 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, 6 H). 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) .

< Experimental Example  1>-Fabrication of organic light emitting device

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

A glass substrate coated with a thin film of ITO to a thickness of 1,500 kPa was washed by distilled water ultrasonically. After washing the distilled water, ultrasonic washing with a solvent such as acetone, methanol, isopropyl alcohol and the like was dried and then UVO treated for 5 minutes using UV in a UV cleaner. Subsequently, the substrate was transferred to a plasma cleaner (PT), and then plasma-treated to remove ITO work function and residual film in a vacuum state, and then transferred to an organic deposition thermal deposition apparatus.

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

The light emitting layer was thermally vacuum deposited on it as follows. The light emitting layer was deposited at 500 Å with 3% doping of (piq) 2 (Ir) (acac) on the host using (piq) 2 (Ir) (acac) as a red phosphorescent dopant as a compound shown in Table 5 below as a red host. Thereafter, 60 B of BCP was deposited as the hole blocking layer, and 200 Å of Alq3 was deposited thereon as the electron transport layer. Thereafter, 60 B of BCP was deposited as the hole blocking layer, and 200 Å of Alq3 was deposited thereon as the electron transport layer. Finally, lithium fluoride (LiF) is deposited on the electron transport layer to form a electron injecting layer by depositing 10 Å thick. Then, an aluminum (Al) cathode is deposited to a thickness of 1,200 위에 on the electron injecting layer to form a cathode. An electroluminescent device was manufactured.

On the other hand, all the organic compounds required for OLED device fabrication was used for OLED fabrication by vacuum sublimation purification under 10-6 ~ 10-8torr for each material.

2) organic Electric field  Driving voltage and luminous efficiency of light emitting device

The electroluminescent (EL) characteristics of the organic electroluminescent device manufactured as described above were measured by Maxiers M7000, and the reference luminance was 6,000 through the life equipment measuring equipment (M6000) manufactured by McScience Inc. with the measurement results. T90 was measured at cd / m ² . The characteristics of the organic EL device of the present invention are shown in Table 5 below.

compound Drive voltage (V) Efficiency (cd / A) Color coordinates  (x, y) Life (T ₉₀ ) Comparative Example 1 One 5.52 12.9 0.687, 0.313 39 Comparative Example 2 2 5.62 12.1 0.688, 0.312 40 Comparative Example 3 3 5.42 13.8 0.689, 0.310 58 Comparative Example 4 4 5.22 14.0 0.691, 0.309 63 Comparative Example 5 5 5.82 14.5 0.674, 0.325 61 Comparative Example 6 6 5.68 14.2 0.672, 0.327 38 Comparative Example 7 7 5.24 13.9 0.684, 0.316 49 Comparative Example 8 8 5.13 14.1 0.691, 0.309 53 Comparative Example 9 9 5.10 15.8 0.691, 0.309 54 Comparative Example 10 10 4.96 16.6 0.689, 0.310 25 Comparative Example 11 11 5.96 11.5 0.689, 0.310 23 Comparative 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 3 Example 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 of Table 5, the organic light emitting device using the heterocyclic compound of the present invention as a light emitting layer host of the red organic light emitting device has a lower driving voltage and significantly improved luminous efficiency and lifetime compared to Comparative Examples 1 to 12. I could confirm it.

Looking at the results of Table 5, by introducing a variety of substituents in the core portion of the compound to make a compound having the same band gap can meet the conditions required in the light emitting layer. This improves electron transfer capability, resulting in superior driving and efficiency, while also improving thermal stability and lifetime characteristics.

링커 없이 카바졸의 N에 직접 연결된 구조의 경우, 그렇지 않은 경우(비교예 11)에 비하여 구동 및 효율, 수명이 향상되었음을 확인할 수 있었다.In addition, when Ar1 of Formula 1 is replaced by a carbazole core in which one more ring is substituted than the simple carbazole core, it can be seen that driving, efficiency, and lifespan are improved as compared with the case where it is not (Comparative Example 3, Comparative Example 4). Of Formula 1

In the case of a structure directly connected to N of carbazole without a linker, it was confirmed that the driving, efficiency, and lifespan were improved as compared with the case where it was not (Comparative Example 11).

100: substrate
200: anode
300: organic material 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 the formula (1):
[Formula 1]

In Chemical Formula 1,
A is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic or polycyclic aromatic hetero ring,
X ₁ and X ₂ are the same as or different from each other, and each independently a direct bond; 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; Substituted or unsubstituted monocyclic or polycyclic aryl group; Substituted or unsubstituted monocyclic or polycyclic heteroaryl group; P (= 0) 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 as or different from each other, and 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; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And substituted or unsubstituted amine groups, or two or more groups adjacent to each other combine 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, n When 2 or more, R ₂ is the same as or different from each other, m is an integer of 1 to 4, when m is 2 or more, R ₁ is the same 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. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any one of Formulas 2 to 4 below:
[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4, X ₁ , X ₂ , R ₁ , R ₂ , Ra, m, n, R _x , R _y , R _z , and A are the same as defined in Formula 1,
B is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic or polycyclic aromatic hetero ring,
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 as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alky A substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted force Two or more groups selected from the group consisting of a pin oxide group and 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 Is an integer and p is 2 or more, then R ₃ is the same or different from each other
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 combine with each other to form a substituted or unsubstituted monocyclic aromatic hydrocarbon ring or a substituted or unsubstituted monocyclic hetero ring. The heterocyclic compound according to claim 2, wherein Formula 2 is represented by any one of Formulas 2-1 to 2-3:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Chemical 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 Chemical Formula 2,
R ₁₁ to R ₁₈ are the same as or different from each other, and 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; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; Substituted or unsubstituted phosphine oxide group; And it may be selected from the group consisting of a substituted or unsubstituted amine group. The heterocyclic compound according to claim 1, wherein Ra of Formula 1 is represented by any one of the following Formulas 5 to 7:
[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 5 to 7,

Means the connecting portion,
Y _a and Y _b are the same as or different from each other, and each independently O; S; CRR '; Or NR ",
R ₂₁ , R ₂₂ , R, R 'and R "are the same as or different from each other, and 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 A phosphine oxide group and a substituted or unsubstituted amine group, a1 is an integer of 0 to 3, when a1 is 2 or more, R ₂₁ is the same as or different from each other, and a2 is 0 to 4 An integer, and when a2 is 2 or more, R ₂₂ is the same as or different from each other,
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 combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or hetero ring. The heterocyclic compound of 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 two or more adjacent groups are bonded to each other to form a C6 to C40 aromatic hydrocarbon ring unsubstituted or substituted with a C6 to C40 aryl group. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

A first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a heterocyclic compound according to any one of claims 1 to 7. Phosphorescent organic light-emitting device. The organic light emitting device of claim 8, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises 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 comprises a host material, and the host material includes the heterocyclic compound. The organic light emitting diode of claim 10, wherein the light emitting layer comprises a red host material, and the red host material includes the heterocyclic compound. The organic light emitting diode of claim 8, wherein the organic material layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the 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 of claim 8, wherein the organic light emitting device is a light emitting layer, a hole injection layer, a hole transport layer. The organic light emitting device further comprises one or two or more 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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