KR20190033911A - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a heterocyclic compound represented by chemical formula 1 and an organic light-emitting device comprising the same. According to the present invention, the heterocyclic compound represented by the chemical formula 1 may be used in an organic material layer of an organic light-emitting device, thereby lowering the driving voltage of the device and improving the light efficiency of the device. Furthermore, due to thermal stability of the compound, lifetime characteristics of the device may be improved.

Description

TECHNICAL FIELD [0001] The present invention relates to a heterocyclic compound and an organic light emitting device including the heterocyclic compound. [0002]

TECHNICAL FIELD The present invention relates to heterocyclic compounds and organic light emitting devices comprising the same.

An electroluminescent device is one type of self-luminous display device, and has advantages of wide viewing angle, excellent contrast, and high response speed.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes couple to each other in the organic thin film and form a pair, which then extinguishes and emits light. The organic thin film may be composed of a single layer or a multilayer, if 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 capable of forming a light emitting layer by itself may be used, or a compound capable of serving as a host or a dopant of a host-dopant light emitting layer may be used. In addition, as the material of the organic thin film, a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, etc. may be used.

In order to improve the performance, life or efficiency of an organic light emitting device, development of materials for organic thin films is continuously required.

U.S. Patent No. 4,356,429

The present invention provides a heterocyclic compound and an organic light emitting device including the heterocyclic compound.

In one embodiment of the present application, there is provided a heterocyclic compound represented by the following general formula (1).

[Chemical Formula 1]

In Formula 1,

X is O or S,

L ₁ and L ₂ are substituted or unsubstituted arylene groups; Or a substituted or unsubstituted heteroarylene group,

Z ₂ is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -SiRR'R "; or -P (= O) RR '

X ₁ to X ₃ are the same or different from each other and each independently represent N; CR ₃ ; Or P,

R ₁ and R ₂ are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or P (= O) RR '

R ₃ is hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or P (= O) RR '

R _a and R _b are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group; A 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; -SiRR'R "; -P (= O) RR ', and an amine group substituted or unsubstituted with a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group 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,

R, R 'and R "are the same or different from each other and each independently represents hydrogen, deuterium, -CN, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, An unsubstituted heteroaryl group,

m is an integer of 0 to 4,

p and n are integers of 0 to 3,

q is an integer of 0 to 3,

s is an integer of 1 to 4,

When q is an integer of 0 and Z ₂ is hydrogen, n is an integer of 2 or 3, and R _b is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring.

In addition, in one embodiment of the present application, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a heterocyclic compound represented by Formula 1, Lt; / RTI >

The compound described in this specification can be used as an organic layer material of an organic light emitting device. The compound can act as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, and the like in an organic light emitting device. In particular, the heterocyclic compound represented by Formula 1 may be used as an electron transporting layer material, a hole blocking layer material, or a charge generating layer material of an organic light emitting device. In addition, when the compound represented by Chemical Formula 1 is used in an organic material layer, the driving voltage of the device can be lowered, the light efficiency can be improved, and the lifetime characteristics of the device can be improved by the thermal stability of the compound.

The compound of Formula 1 is a bipolar type compound having both P-type and N-type substituents in its core structure. When the compound is used as an organic material layer of an organic light emitting device, it can prevent hole leakage and effectively excite the exciton You can hold it. Further, the hole characteristics are strengthened in the specific device structure, and the electron mobility changes relatively slowly, so that the electron and the hole are balanced in the light emitting layer, and the recombination region of the exciton is appropriately formed to increase the efficiency and lifetime.

FIGS. 1 to 4 schematically show a laminated structure of an organic light emitting diode according to one embodiment of the present application.

The present application will be described in detail below.

The term " substituted " means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as 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 chain or a branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, more specifically 1 to 20. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, Ethyl, propyl, isopropyl, n-butyl, isobutyl, isobutyl, isobutyl, An n-pentyl group, a tert-butyl group, a tert-butyl group, a 3-methylbutyl group, a 3-methylbutyl group, a 2-ethylbutyl group, a heptyl group, 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 chain or a branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20. Specific examples include a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-yl group, But are not limited to, - (naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like.

In the present specification, the alkynyl group includes a straight chain or a branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The 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. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In the present specification, the cycloalkyl group includes monocyclic or polycyclic rings having 3 to 60 carbon atoms, and may be further substituted by other substituents. Herein, the term "polycyclic" means a group in which a cycloalkyl group is directly connected to another ring group or condensed therewith. Here, the other ring group may be a cycloalkyl group, but may be another ring group such as a heterocycloalkyl group, an aryl group, a heteroaryl group and the like. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, more particularly 5 to 20. Specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, , 3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but are not limited thereto.

In the present specification, the heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic ring means a group in which the heterocycloalkyl group is directly connected to another ring group or condensed. Here, the other ring group may be a heterocycloalkyl group, but may be another ring group such as a cycloalkyl group, an aryl group, a heteroaryl group and the like. The number of carbon atoms 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 monocyclic or polycyclic rings having 6 to 60 carbon atoms, and may be further substituted by other substituents. Herein, a polycyclic ring means a group in which an aryl group is directly connected to another ring group or condensed with another ring group. Here, the other ring group may be an aryl group, but may be another kind of ring group such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group and the like. The aryl group includes a spiro group. The 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 a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthryl group, a klychenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, An acenaphthyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, a condensed ring group thereof, a thiophenecarbonyl group, , But are not limited thereto.

In this specification, the silyl group is a substituent including Si and a direct connection as the Si atom radical, R is represented by -SiR _{104 105} R _106, R ₁₀₄ to R ₁₀₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; An aryl group; And a heterocyclic group. Specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group and a phenylsilyl group. 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,

,

,

,

,

,

And the like, but the present invention is not limited thereto.

In the present specification, the heteroaryl group includes S, O, Se, N or Si as a hetero atom and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be further substituted by other substituents. Herein, the polycyclic ring means a group in which the heteroaryl group is directly connected to another ring group or condensed therewith. Here, the other ring group may be a heteroaryl group, but may be another ring group such as a cycloalkyl group, a heterocycloalkyl group, an aryl group and the like. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more specifically 3 to 25 carbon atoms. Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, A thiazolyl group, a thiazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a paranyl group, a thiopyranyl group, a diazinyl group, , A thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, a quinolizolyl group, a naphthyridyl group, An imidazopyridinyl group, a diazanaphthalenyl group, a triazinediyl group, an indolyl group, an indolizinyl group, a benzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiophenyl group, a benzothiophenyl group , A dibenzothiophene group, a dibenzofuran group, a carbazolyl group, a benzocarbazolyl group, (Dibenzosilyl), dihydrophenazinyl, phenoxazinyl, phenanthridyl, imidazopyridinyl, thienyl, indolo [3,3-d] pyrimidinyl, 2,3-a] carbazolyl group, indolo [2,3-b] carbazolyl group, indolinyl group, 10,11-dihydrodibenzo [b, f] azepine group, 9,10-dihydro A phenanthrolinyl group, a phenanthrazinyl group, a phenothiatriazinyl group, a phthalazinyl group, a naphthyridinyl group, a phenanthrolinyl group, a benzo [c] [1,2,5] thiadiazolyl group, 1,5-c] quinazolinyl group, pyrido [l, 2-b] indazolyl group, pyrido [l, 2- a] imidazo [1,2-e] indolinyl group, and 5,11-dihydroindeno [1,2-b] carbazolyl group.

In the present specification, the amine group is a monoalkylamine group; Monoarylamine groups; A monoheteroarylamine group; -NH ₂ ; A dialkylamine group; A diarylamine group; A diheteroarylamine group; Alkylarylamine groups; Alkylheteroarylamine groups; And an arylheteroarylamine group. The number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a diphenylamine group, an anthracenylamine group, A phenylphenylamine group, a diphenylamine group, a methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, Naphthylamine amine group, phenylnaphthylamine amine group, phenylnaphthylamine amine group, biphenyltriphenylenylamine group, and the like.

In the present specification, an arylene group means a group having two bonding positions in an aryl group, that is, a divalent group. The description of the aryl group described above can be applied except that each of these is 2 groups. Further, the heteroarylene group means that the heteroaryl group has two bonding positions, i.e., divalent. The description of the above-mentioned heteroaryl groups can be applied, except that they are each 2 groups.

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.

As used herein, the term " adjacent " means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . 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 to each other.

In the present specification, the term " substituted " means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, When two or more substituents are substituted, two or more substituents may be the same as or different from each other.

As used herein, the term " substituted or unsubstituted " means straight or branched chain alkyl of C1 to C60; C2 to C60 straight or branched chain alkenyl; Straight or branched chain alkynyl of C2 to C60; C3 to C60 monocyclic or polycyclic cycloalkyl; A C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; Wherein R is selected from the group consisting of C1 to C20 alkylamines, C6 to C60 mono- or polycyclic arylamines, and C2 to C60 mono- or polycyclic heteroarylamines. Is substituted or unsubstituted with at least one substituent, or at least two substituents selected from the substituents exemplified above are substituted or unsubstituted with a substituted substituent.

In one embodiment of the present application, the compound represented by Formula 1 is provided.

In one embodiment of the present application, X in formula (1) may be O or S.

In one embodiment of the present application, X in formula (1) may be O.

In one embodiment of the present application, X in Formula 1 may be S.

In one embodiment of the present application, X ₁ to X ₃ in Formula 1 are the same or different and each independently represent N; CR ₃ ; Or P.

In another embodiment, X ₁ to X ₃ in Formula 1 are the same or different and each independently represent N; Or CR < ₃ >.

In one embodiment of the present application, X ₁ to X ₃ in Formula 1 may be N.

In one embodiment of the present application, one of X ₁ to X ₃ in Formula 1 may be N and the remainder may be CR ₃ .

In one embodiment of the present application, two of X ₁ to X ₃ in Formula 1 may be N and the remainder may be CR ₃ .

In one embodiment of the present application, X ₁ to X ₃ in Formula 1 may be CR ₃ .

In one embodiment of the present application, R < ₃ > is hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or P (= O) RR '.

In another embodiment R ₃ is selected from the group consisting of hydrogen; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; Or P (= O) RR '.

In another embodiment R ₃ is selected from the group consisting of hydrogen; A C6 to C60 aryl group; A C2 to C60 heteroaryl group; Or P (= O) RR '.

In another embodiment R ₃ is selected from the group consisting of hydrogen; Or P (= O) RR '.

In one embodiment of the present application, R _a and R _b in Formula 1 are the same or different from each other and each independently represent hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group; A 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; -SiRR'R "; -P (= O) RR ', and an amine group substituted or unsubstituted with a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group 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.

In another embodiment, R _a and R _b in Formula 1 are the same or different from each other and independently selected from the group consisting of hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heteroaryl group, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

In another embodiment, R _a and R _b in Formula 1 are the same or different from each other and independently selected from the group consisting of hydrogen; A substituted or unsubstituted C6 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

In another embodiment, R _a and R _b in Formula 1 are the same or different from each other and independently selected from the group consisting of hydrogen; A C6 to C40 aryl group; And C2 to C60 heteroaryl groups, or two or more groups adjacent to each other may be bonded to each other to form a C3 to C60 aromatic hydrocarbon ring.

In another exemplary embodiment, R _a in the formula (I) may be hydrogen.

In one embodiment of the present application, R ₁ and R ₂ in Formula 1 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or P (= O) RR '.

In another embodiment, R ₁ and R ₂ in Formula 1 are the same or different and each independently hydrogen; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; Or P (= O) RR '.

In another embodiment, R ₁ and R ₂ in Formula 1 are the same or different and each independently hydrogen; A substituted or unsubstituted C6 to C40 aryl group; A substituted or unsubstituted C2 to C40 heteroaryl group; Or P (= O) RR '.

In another embodiment, R ₁ and R ₂ in Formula 1 are the same or different and each independently hydrogen; A C6 to C40 aryl group substituted or unsubstituted with at least one substituent selected from the group consisting of C1 to C40 alkyl groups and C2 to C40 heteroaryl groups; C2 to C40 N-containing heteroaryl groups; Or P (= O) RR '.

In another embodiment, R ₁ and R ₂ in Formula 1 are the same or different and each independently hydrogen; A phenyl group substituted or unsubstituted with a carbazole group, a dibenzofurane group or a dibenzothiophene group; Biphenyl group; A fluorene group substituted or unsubstituted with a methyl group; Carbazole group; -P (= O) RR 'or a pyridine group.

In one embodiment of the present application, L ₁ and L ₂ in Formula 1 are substituted or unsubstituted arylene groups; Or a substituted or unsubstituted heteroarylene group.

In another embodiment, L ₁ and L ₂ in Formula 1 are substituted or unsubstituted C6 to C60 arylene groups; Or a substituted or unsubstituted C2 to C60 heteroarylene group.

In another embodiment, L ₁ and L ₂ in Formula 1 are substituted or unsubstituted C6 to C40 arylene groups; Or a substituted or unsubstituted C2 to C40 heteroarylene group.

In another embodiment, L ₁ and L ₂ in Formula 1 are C 6 to C 40 arylene groups; Or a C2 to C40 heteroarylene group.

In another embodiment, L < ₁ > and L < ₂ > in the above formula (1) are C6 to C30 arylene groups; Or a C2 to C30 heteroarylene group.

In another embodiment, L ₁ and L ₂ in Formula 1 are a phenylene group; Biphenylene group; A naphthalene group; Phenanthrene; Triphenylenylene group; A divalent dibenzofurane group; A divalent phenanthroline group or a divalent dibenzothiophene group.

In one embodiment of the present application, L ₁ in Formula 1 may be a substituted or unsubstituted arylene group.

In another embodiment, L ₁ in Formula ₁ may be a substituted or unsubstituted C6 to C60 arylene group.

In another embodiment, L ₁ in Formula ₁ may be a substituted or unsubstituted C6 to C40 arylene group.

In another embodiment, L < ₁ > in Formula 1 may be an C6 to C40 arylene group.

In another embodiment, L &_lt; ₁ > in Formula ₁ is a phenylene group; Or a biphenylene group.

In one embodiment of the present application, L < ₂ > in Formula 1 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In another embodiment, L ₂ in Formula 1 is a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group.

In another embodiment, L ₂ in Formula 1 is a substituted or unsubstituted C6 to C40 arylene group; Or a substituted or unsubstituted C2 to C40 heteroarylene group.

In another embodiment, L < ₂ > in the above formula (1) is C6 to C40 arylene group; Or a C2 to C40 heteroarylene group.

In another embodiment, L < ₂ > in formula (1) is a phenylene group; Naphthylene group; Phenanthrene; Triphenylenylene group; A divalent dibenzofurane group; Or a divalent dibenzothiophene group.

In one embodiment of the present application, Z ₂ in Formula 1 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -SiRR'R "; or -P (= O) RR '.

In another embodiment, Z ₂ in Formula 1 is hydrogen; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

In another embodiment, Z ₂ in Formula 1 is hydrogen; A substituted or unsubstituted C6 to C40 aryl group; Or a substituted or unsubstituted C2 to C40 heteroaryl group.

In another embodiment, Z ₂ in Formula 1 is hydrogen; A C6 to C40 aryl group; Or a C2 to C40 heteroaryl group.

In another embodiment, Z ₂ in Formula 1 is hydrogen; A phenyl group; Naphthyl group; Phenanthrene; A dibenzofurane group; Or a dibenzothiophene group.

In one embodiment of the present application, p in Formula 1 may be zero.

In one embodiment of the present application, p in formula (1) may be 1.

In one embodiment of the present application, q in formula (1) may be zero.

In one embodiment of the present application, q in formula (1) may be one.

In one embodiment of the present application, q in Formula 1 may be 2.

In one embodiment of the present application, s in formula (1) may be 1.

In one embodiment of the present application, s in Formula 1 may be 2.

In one embodiment of the present application, s in Formula 1 may be 3.

In one embodiment of the present application, s in Formula 1 may be 4.

In one embodiment of the present application, when q in Formula 1 is an integer of 0 and Z ₂ is hydrogen, n is an integer of 2 or 3, and R _b is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, 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.

In another embodiment, when q is an integer of 0 and Z < ₂ > is hydrogen, n is an integer of 2, and two adjacent R _b may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring .

In another embodiment, when q is an integer of 0 and Z < ₂ > is hydrogen, n is an integer of 2, and two adjacent R < _{b &} gt _{; s} may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring .

In another embodiment, when q is an integer of 0 and Z < ₂ > is hydrogen, n is an integer of 2, and the two adjacent R _b are bonded to each other to form a substituted or unsubstituted C3 to C60 aromatic hydrocarbon A ring can be formed.

In another embodiment, when q is an integer of 0 and Z < ₂ > is hydrogen, n is an integer of 2, and two adjacent R _b are bonded to each other to form a substituted or unsubstituted C3 to C30 aromatic hydrocarbon A ring can be formed.

In another embodiment, when q is an integer of 0 and Z < ₂ > is hydrogen, n is an integer of 2, and two adjacent R _b may combine with each other to form a C3 to C30 aromatic hydrocarbon ring have.

In another embodiment, when q is an integer of 0 and Z ₂ is hydrogen, n is an integer of 2, and two adjacent R _b may bond to each other to form a benzene ring.

A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkyl group, An unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

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

In another embodiment, R, R 'and R " are the same or different and each independently hydrogen, a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 hetero Lt; / RTI >

In another embodiment, R, R 'and R " are the same or different and are each independently a substituted or unsubstituted C6 to C60 aryl group.

In another embodiment, R, R 'and R " are the same or different and are each independently a C6 to C60 aryl group.

In another embodiment, R, R 'and R " are the same or different and are each independently a C6 to C40 aryl group.

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

The compound of Formula 1 is a bipolar type compound having both a P-type and an N-type substituent in the core structure. When the organic compound layer is used as an organic material layer of an organic light emitting device in the future, it can prevent hole leakage and effectively excite the exciton have. In addition, the hole characteristics are strengthened in the specific device structure, and the electron mobility changes relatively slowly, so that the electron and the hole are balanced in the light emitting layer, and the recombination region of the exciton is appropriately formed to increase the efficiency and lifetime.

In the case of a single substitution by a substituent having a small molecular weight, the molecular weight is small, and when it is used as an organic material layer of the organic light emitting device, its thermal stability is lowered structurally. When it is 2-substituted as shown in Formula 1, thermal stability is superior to single substitution.

In one embodiment of the present application, the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 2 to 5:

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,

X ₁ to X ₃ , R ₁ , R ₂ , L ₁ , L ₂ , Z ₂ and p are the same as defined in the above formula (1)

q and s are each an integer of 1 to 3;

In one embodiment of the present application, the heterocyclic compound represented by Formula 1 is represented by any one of Formulas 6 to 11 below.

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

In the general formulas (6) to (11)

X ₁ to X ₃ , R ₁ , R ₂ , L ₁ and p are the same as defined in the above formula (1).

In one embodiment of the present application, the present invention provides a heterocyclic compound wherein the above-mentioned formula (1) is represented by any one of the following compounds.

A compound according to one embodiment of the present application may be prepared according to the following general formula (1).

(Formula 1)

또는

이다.In the general formula (1), Rm or Rn represents a group represented by the general formula

or

to be.

Also, by introducing various substituents to the structures of the above formulas (1) to (11), it is possible to synthesize a compound having the intrinsic property of the substituent introduced. For example, by introducing a substituent mainly used for a hole injecting layer material, a hole transporting material, a light emitting layer material, an electron transporting layer material, and a charge generating layer material used in manufacturing an organic light emitting device into the core structure, Can be synthesized.

Further, by introducing various substituents into the structures of Formulas 1 to 11, it is possible to finely control the energy band gap, and the properties at the interface between the organic materials can be improved and the use of the materials can be diversified .

On the other hand, the compound has a high glass transition temperature (Tg) and is excellent in thermal stability. This increase in thermal stability is an important factor in providing drive stability to the device.

In addition, in one embodiment of the present application, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the heterocyclic compound.

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

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

In one embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound of Formula 1 may be used as a material of the blue organic light emitting device.

In one embodiment of the present application, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound of Formula 1 may be used as the material of the green organic light emitting device.

In one embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound of Formula 1 may be used as the material of the red organic light emitting device.

The details of the heterocyclic compound represented by the formula (1) are the same as described above.

The organic light emitting device of the present invention can be manufactured by a conventional method and materials for manufacturing an organic light emitting device, except that the above-described heterocyclic compound is used to form one or more organic compound layers.

The heterocyclic compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, 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 injecting layer, a hole transporting layer, a hole blocking layer, a light emitting layer, an electron transporting layer, and an electron injecting layer 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 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 a heterocyclic compound represented by the general formula (1).

In another organic light emitting device, the organic material layer includes a light emitting layer, the light emitting layer includes a host material, and the host material may include a heterocyclic compound represented by the above formula (1) as a heterocyclic compound.

As another example, the organic compound layer containing the heterocyclic compound may include a heterocyclic compound represented by the general formula (1) as a host, and may be used together with a phosphorescent dopant.

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

As the phosphorescent dopant material, those known in the art can be used.

For example, phosphorescent dopant materials represented by LL'MX, LL'L "M, LMXX ', L2MX and L3M can be used, but the scope of the present invention is not limited by these examples.

Here, L, L ', L ", X and X' are two different left ligands and M is a metal forming an octahedral complex.

M may be iridium, platinum, osmium, and the like.

L is an anionic bidentate ligand coordinated to M by sp2 carbon and a hetero atom as the iridium dopant, and X can function to trap electrons or holes. Non-limiting examples of L include 2- (1-naphthyl) benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole) -Benzoquinoline), (thiophene-pyrimidine), phenylpyridine, benzothiophene-pyrazine, 3-methoxy-2-phenylpyridine, thiophenepyridine and tolylpyridine. Non-limiting examples of X include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.

More specific examples are shown below, but are not limited to these examples.

In one embodiment of the present application, Ir (ppy) ₃ may be used as the green phosphorescent dopant as the iridium dopant.

In one embodiment of the present application, the content of the dopant may have an amount of 1% to 15%, preferably 3% to 10%, more preferably 5% to 10%, based on the entire luminescent layer.

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 injection layer or the electron transport layer may include the heterocyclic compound.

In another organic light emitting device, the organic 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.

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

The organic light emitting device of the present invention includes a light emitting layer, a hole injecting layer, and a hole transporting layer. An electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

FIGS. 1 to 3 illustrate the stacking process of the electrode and the organic layer of the organic light emitting diode according to one embodiment of the present application. However, it is not intended that the scope of the present application be limited by these drawings, and the structure of the organic light emitting device known in the art can be applied to the present application.

1, an organic light emitting device in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is shown. However, the present invention is not limited to such a structure, and 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 as shown in FIG.

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

The organic light emitting device according to one embodiment of the present application includes a first electrode, a second electrode, and two or more stacks provided between the first electrode and the second electrode, And a charge generation layer between the two or more stacks, wherein the charge generation layer comprises a heterocyclic compound represented by the above formula (1).

According to an embodiment of the present invention, there is provided an organic light emitting diode comprising a first electrode, a first stack provided on the first electrode and including a first light emitting layer, a charge generation layer provided on the first stack, A second stack provided on the charge generation layer and including a second light emitting layer, and a second electrode provided on the second stack. At this time, the charge generation layer may include a heterocyclic compound represented by the general formula (1). The first and second stacks may further include at least one of the hole injection layer, the hole transport layer, the hole blocking layer, the electron transport layer, and the electron injection layer described above independently.

The charge generation layer may be an N-type charge generation layer, and the charge generation layer may further include a dopant known in the art in addition to the heterocyclic compound represented by Formula (1).

An organic light emitting device having a two-stack tandem structure as an organic light emitting device according to one embodiment of the present application is schematically shown in Fig.

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

In the organic light emitting device according to one embodiment of the present application, materials other than the compound of Formula 1 are exemplified below, but these are for illustrative purposes only and are not intended to limit the scope of the present application. ≪ / RTI >

As the cathode material, materials having a relatively large work function can be used, and a transparent conductive oxide, a metal, or a conductive polymer can be used. Specific examples of the cathode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

As the cathode material, materials having relatively low work functions can be used, and metals, metal oxides, conductive polymers, and the like can 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; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

As the hole injecting material, a known hole injecting material may be used. For example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a compound described in Advanced Material, 6, p. 677 (1994) Star burst type amine derivatives such as tris (4-carbamoyl-9-phenyl) amine (TCTA), 4,4 ', 4 "-tri [phenyl (m- tolyl) amino] triphenylamine MTDAPA), polyaniline / dodecylbenzenesulfonic acid (poly (vinylidene fluoride)) or poly (vinylidene fluoride), which is a soluble conductive polymer, such as 1,3,5-tris [4- (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate), polyaniline / camphor sulfonic acid or polyaniline / Poly (4-styrene-sulfonate) and the like can be used.

As the hole transporting material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, or the like may be used, and a low molecular weight or a high molecular weight material 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, tetracyanoanthraquinodimethane and derivatives thereof, Derivatives thereof, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like may be used as well as low molecular weight materials and high molecular weight materials.

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

As the light emitting material, red, green or blue light emitting materials may be used, and if necessary, two or more light emitting materials may be mixed and used. At this time, two or more luminescent materials may be used as a separate source of vapor deposition, or may be premixed and deposited as a single source. Further, a fluorescent material may be used as a light emitting material, but it may be used as a phosphorescent material. As the light emitting material, a material which emits light by coupling holes and electrons respectively injected from the anode and the cathode may be used. However, materials in which both the host material and the dopant material participate in light emission may also be used.

When a host of a light emitting material is mixed and used, a host of the same series may be used in combination, or a host of another series may be mixed and used. For example, two or more kinds of materials of an n-type host material or a p-type host material may be selected and used as a host material of the light emitting layer.

The organic light emitting device according to one embodiment of the present application may be a top emission type, a back emission type, or a both-sided emission type, depending on the material used.

The heterocyclic compound according to one 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 invention will be described in more detail by way of examples, but these are for the purpose of illustrating the present application and are not intended to limit the scope of the present application.

< Manufacturing example >

< Manufacturing example  1> Preparation of compound 1

1) Preparation of Compound 1-1

(1H-indol-2-yl) boronic acid (100 g, 0.621 mol), 2-bromo-5-chloroaniline (PPh ₃ ) ₄ (35.8 g, 0.031 mol) and NaHCO ₃ (156.5 g, 1.863 mol) were dissolved in toluene (Toluene), EtOH and H ₂ O mol) and stirred at 100 ° C for 3 hours. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain Compound 1-1 (110 g, 74%) in liquid form.

2) Preparation of Compound 1-2

Compound 1-1 (110 g, 0.428 mol) and triethyl amine (89 mL, 0.642 mol) are dissolved in 1200 mL of MC. Benzoyl chloride (90.24 g, 0.642 mol) is dissolved in 300 mL of MC and then slowly added dropwise to the mixture at 0 ° C. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator to obtain a liquid type compound 1-2 (129 g, 83%).

3) Preparation of compound 1-3

Compound 1-2 (129 g, 0.355 mol) is dissolved in 1500 mL of Nitrobenzene, and POCl ₃ (50 mL, 0.533 mol) is slowly added dropwise. And reacted at 140 캜 for 15 hours. After completion of reaction, add NaHCO ₃ dissolved in distilled water to the reaction solution slowly and stir. The resulting solids are filtered and collected. The collected solid was recrystallized from MC and MeOH to obtain solid compound 1-3 (65 g, 53%).

4) Preparation of compounds 1-4

Compound (1-3) (10 g, 0.029 mol), bis (pinacolato) diboron (8.8 g, mol) and Pd (dba) 2 (1.7 g, 0.0029 mol) were dissolved in 200 mL of 1,4-dioxane and reacted at 90 ° C for 5 hours. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain Compound 1-4 (11.4 g, 90%).

5) Preparation of Compound 1

Compound 1-4 (11.4 g, 0.026 mol), 2-bromo-4,6-diphenyl-1,3,5-triazine (PPh ₃ ) ₄ (1.4 g, 0.0012 mol) and K ₂ CO ₃ (9.2 g, 0.072 mol) were dissolved in toluene, EtOH and H ₂ O, mol) and stirred at 100 ° C for 5 hours. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain Compound 1 (9.4 g, 72%).

Except that 2-bromo-4,6-diphenyl-1,3,5-triazine was used in place of 2-bromo-4,6-diphenyl- A was used in place of the compound of Preparation Example 1, to thereby synthesize a Waste compound.

2-bromo-6-chloroaniline was used in place of 2-bromo-5-chloroaniline in Production Example 1 and 2-bromo-6- Except that the intermediate B shown in the following Table 2 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine. 1, the target compound was synthesized.

2-bromo-4-chloroaniline was used in place of 2-bromo-5-chloroaniline in Production Example 1, 2-bromo-4- Except that the intermediate C in Table 3 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine. 1, the target compound was synthesized.

2-bromo-3-chloroaniline was used in place of 2-bromo-5-chloroaniline in Production Example 1, 2-bromo-3- Except that Intermediate D in Table 4 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine. 1, the target compound was synthesized.

In Production Example 1, 1-naphthoyl chloride was used instead of benzoyl chloride, and 2-bromo-4,6-diphenyl-1,3,5-triazine (2- bromo-4,6-diphenyl-1,3,5-triazine) was used instead of Intermediate E in Table 5, the target compound was synthesized.

In the same manner as in Preparation Example 1 except that 1-naphthoyl chloride was used instead of benzoyl chloride and 2-bromo-5-chloroaniline was used instead of 2-bromo-5-chloroaniline, Bromo-4,6-diphenyl-1, 2-bromo-6-chloroaniline was used instead of 2- , 3,5-triazine) instead of Intermediate F shown in Table 6, the target compound was synthesized.

In the same manner as in Preparation Example 1 except that 1-naphthoyl chloride was used instead of benzoyl chloride and 2-bromo-5-chloroaniline was used instead of 2-bromo-5-chloroaniline, Bromo-4-chloroaniline was used instead of 2-bromo-4,6-diphenyl-1,3- , 3,5-triazine) instead of Intermediate G in Table 7, the target compound was synthesized.

In the same manner as in Preparation Example 1 except that 1-naphthoyl chloride was used instead of benzoyl chloride and 2-bromo-5-chloroaniline was used instead of 2-bromo-5-chloroaniline, Bromo-4,6-diphenyl-1 (2-bromo-3-chloroaniline) , 3,5-triazine) was used instead of Intermediate H in Table 8, the target compound was synthesized.

In the same manner as in Preparation Example 1 except that 1-naphthoyl chloride was used instead of benzoyl chloride and 2-bromo-5-chloroaniline was used instead of 2-bromo-5-chloroaniline, Bromo-4,6-diphenyl-1 (2-bromo-3-chloroaniline) , 3,5-triazine) was used instead of Intermediate H in Table 8, the target compound was synthesized.

Except that 9-chlorophenanthrene was used instead of benzoyl chloride in Preparation Example 1 and 2-bromo-5-chloroaniline was used instead of 2-bromo-5-chloroaniline. Bromo-4,6-diphenyl-1, 2-bromo-6-chloroaniline was used instead of 2-bromo- 3,5-triazine) was used instead of Intermediate J in Table 10, the target compound was synthesized.

2-bromo-6-chloroaniline was used in place of 2-bromo-5-chloroaniline in Preparation Example 1, benzoyl chloride was used instead of 2-bromo-5-chloroaniline, (naphthalen-1-yl) benzoyl chloride instead of 4- (naphthalen-1-yl) benzoyl chloride, and 2-bromo-4,6-diphenyl-1,3,5-tri The target compound was synthesized in the same manner as in Preparation Example 1, except that Intermediate K of Table 11 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine.

Bromo-5-chloroaniline instead of 9-chlorophenanthrene in the same manner as in Preparation Example 1, except that 2-bromo-5-chloroaniline was used instead of 2-bromo- Bromo-4,6-diphenyl-1, 2-bromo-4-chloroaniline was obtained by using 2-bromo- 3,5-triazine) was used instead of Intermediate L in Table 12, the target compound was synthesized.

Bromo-5-chloroaniline was used instead of 9-chlorophenanthrene in place of benzoyl chloride in Preparation Example 1, and 2-bromo-5-chloroaniline was used instead of 2-bromo- Bromo-4,6-diphenyl-1, 3-chloroaniline was prepared using 2-bromo-3-chloroaniline, 3,5-triazine) was replaced by Intermediate M shown in Table 13, the target compound was synthesized.

In Production Example 1, 2-chlorotriphenylene was used instead of benzoyl chloride, and 2-bromo-4,6-diphenyl-1,3,5-triazine (2- bromo-4,6-diphenyl-1,3,5-triazine) was used instead of the intermediate N in Table 14, the target compound was synthesized.

In the same manner as in Preparation Example 1 except that 1,1'-biphenyl-4-carbonyl chloride was used instead of benzoyl chloride, and 2-bromo-4 , Except that the intermediate O in Table 15 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine. The target compound was synthesized.

Except that 2-chlorotriphenylene was used instead of benzoyl chloride in Production Example 1 and 2-bromo-5-chloroaniline was used instead of 2-bromo-5-chloroaniline. Bromo-4-chloroaniline was used instead of 2-bromo-4,6-diphenyl-1,3- , 3,5-triazine) was used instead of the intermediate P in Table 16, the target compound was synthesized.

4-naphthalene-1-yl) benzoyl chloride was used instead of benzoyl chloride in Preparation Example 1, and 2-bromo-4,6-di Except that Intermediate Q in Table 17 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine in the same manner as in Preparation Example 1 And the desired compound was synthesized.

(Naphthalene-9-yl) benzoyl chloride was used instead of benzoyl chloride in Preparation Example 1, and 2-bromo-4,6-di Except that Intermediate R in Table 18 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine in the same manner as in Preparation Example 1 And the desired compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Preparation Example 1, 2 Except that the intermediate S of the following Table 19 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine Was prepared in the same manner as in Preparation Example 1 to synthesize the desired compound.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1 and 2 Bromo-6-chloroaniline was used in place of 2-bromo-5-chloroaniline and 2-bromo-6-chloroaniline was used instead of 2- Except that Intermediate T in the following Table 20 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine in the same manner as in Preparation Example 1 And the desired compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1 and 2 Bromo-4-chloroaniline was used instead of 2-bromo-5-chloroaniline and 2-bromo-4-chloroaniline was used instead of 2- Except that the intermediate U of the following Table 21 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine in the same manner as in Preparation Example 1 And the desired compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1 and 2 Bromo-4-chloroaniline instead of 2-bromo-5-chloroaniline and replacing benzoyl chloride with 9-chloro- 2-bromo-4,6-diphenyl-1,3,5-triazine) was obtained by using 9-chlorophenanthrene, The target compound was synthesized in the same manner as in Preparation Example 1, except that Intermediate V in Table 22 was used instead.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1 and 2 Bromo-4-chloroaniline instead of 2-bromo-5-chloroaniline and replacing benzoyl chloride with 1,1-benzoyl chloride '- biphenyl-3-carbonyl chloride, and 2-bromo-4,6-diphenyl-1,3,5-triazine ( 2-bromo-4,6-diphenyl-1,3,5-triazine) was used instead of Intermediate W in Table 23, the target compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1 and 2 Bromo-3-chloroaniline was used in place of 2-bromo-5-chloroaniline and 2-bromo-3-chloroaniline was used instead of 2- Except that Intermediate X of the following Table 24 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine in the same manner as in Preparation Example 1 And the desired compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1 and 2 Bromo-3-chloroaniline was used in place of benzoyl chloride instead of 2-bromo-5-chloroaniline and 4- ( 4-naphthalen-1-yl) benzoyl chloride was used instead of 2-bromo-4,6-diphenyl- 4,6-diphenyl-1,3,5-triazine) was used instead of Intermediate Y in the following Table 25, the target compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1, 1-naphthoyl chloride was used in place of benzoyl chloride and 2-bromo-4,6- diphenyl-1,3,5-triazine) was used instead of the intermediate Z in Table 26, the target compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1, Bromo-5-chloroaniline instead of 2-bromo-5-chloroaniline by using 1-naphthoyl chloride instead of benzoyl chloride and using 2-bromo- Bromo-4,6-diphenyl-1,3,5-triazine using 2-bromo-4-chloroaniline as a starting material. ) Was replaced by Intermediate A-1 in the following Table 27, the target compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1, Bromo-5-chloroaniline instead of 2-bromo-5-chloroaniline by using 1-naphthoyl chloride instead of benzoyl chloride and using 2-bromo- Bromo-4,6-diphenyl-1,3,5-triazine (2-bromo-3-chloroaniline) ) Was replaced by Intermediate B-1 of the following Table 28, the target compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1, 9-chlorophenanthrene was used instead of benzoyl chloride and 2-bromo-4,6-diphenyl -1,3,5-triazine) was replaced by Intermediate C-1 of the following Table 29, the target compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1, Bromo-4-chloroaniline (2-bromo-5-chloroaniline) instead of 9-chlorophenanthrene instead of benzoyl chloride and 2-bromo- 2-bromo-4,6-diphenyl-1,3,5-triazine) was obtained by using 2- bromo-4- The target compound was synthesized by the same method as Preparation Example 1, except that Intermediate D-1 in Table 30 was used instead of Intermediate D-1.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1, Bromo-5-chloroaniline instead of 2-bromo-5-chloroaniline using 9-chlorophenanthrene instead of benzoyl chloride and 2-bromo- 2-bromo-4,6-diphenyl-1,3,5-triazine) was obtained by using 2- bromo-3- The target compound was synthesized in the same manner as in Preparation Example 1, except that Intermediate E-1 in Table 31 was used instead of Intermediate E-1.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1, 2-chlorotriphenylene was used in place of benzoyl chloride, and 2-bromo-4,6- diphenyl-1,3,5-triazine) was used instead of Intermediate F-1 in the following Table 32, the target compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1, Bromo-5-chloroaniline instead of 2-bromo-5-chloroaniline by using 2-chlorotriphenylene instead of benzoyl chloride and 2-bromo- Bromo-4,6-diphenyl-1,3,5-triazine using 2-bromo-4-chloroaniline as a starting material. ) Was replaced by Intermediate G-1 in the following Table 33, the target compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1, Bromo-5-chloroaniline instead of 2-bromo-5-chloroaniline by using 2-chlorotriphenylene instead of benzoyl chloride and 2-bromo- Bromo-4,6-diphenyl-1,3,5-triazine (2-bromo-3-chloroaniline) ) Was replaced by Intermediate H-1 in the following Table 34, the target compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 1, 4-naphthalene-1-yl) benzoyl chloride was used instead of 4- (naphthalen-1-yl) benzoyl chloride in place of benzoyl chloride, Was prepared in the same manner as in Preparation Example 1, except that Intermediate I-1 of the following Table 35 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine, Were synthesized.

< Manufacturing example  2> Preparation of compound 574

1) Preparation of compound 574-1

(1H-indol-2-yl) boronic acid (100 g, 0.621 mol), 2-bromo-5-chloroaniline (PPh ₃ ) ₄ (35.8 g, 0.031 mol) and NaHCO ₃ (156.5 g, 1.863 mol) were dissolved in toluene (Toluene), EtOH and H ₂ O mol) and stirred at 100 ° C for 3 hours. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain a liquid form compound 574-1 (110 g, 74%).

2) Preparation of compound 574-2

The compound 574-1 (110 g, 0.428 mol) and phenylboronic acid (89 mL, 0.574 mol) were dissolved in 200 mL of THF and 1000 mL of H ₂ O, Pd (PPh ₃ ) ₄ (24.7 g, 0.021 mol) and K ₂ CO ₃ (170 g, 1.284 mol) were added thereto, followed by stirring at 66 ° C for 3 hours. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain a liquid form compound 574-2 (112 g, 87%).

3) Preparation of compound 574-3

Compound 574-2 (112 g, 0.372 mol) and triethyl amine (78 mL, 0.558 mol) are dissolved in 1200 mL of MC. 4-Chlorobenzoyl chloride (78.12 g, 0.446 mol) is dissolved in 300 mL of MC, and then slowly added dropwise to the mixture at 0 ° C. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain a liquid form compound 574-3 (130 g, 79%).

4) Preparation of compound 574-4

Compound 574-3 (130 g, 0.295 mol) is dissolved in 1500 mL of Nitrobenzene, and POCl ₃ (50 mL, 0.443 mol) is slowly added dropwise. And reacted at 140 캜 for 15 hours. After completion of reaction, add NaHCO ₃ dissolved in distilled water to the reaction solution slowly and stir. The resulting solids are filtered and collected. The collected solid was recrystallized from MC and MeOH to obtain 574-4 (68 g, 53%) of solid form.

5) Preparation of compound 574-5

(8.8 g, 0.035 mol), KOAc (6.7 g, 0.069 mol), Sphos (1.8 g, 0.0046 mol), compound 574-4 (10 g, 0.023 mol), bis (pinacolato) diboron bis , Pd (dba) ₂ (1.3 g, 0.0023 mol) are dissolved in 200 mL of 1,4-dioxane, and reacted at 90 ° C. for 5 hours. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain a compound 574-5 (10.6 g, 90%).

6) Preparation of compound 574

Compound 574-5 (10.6 g, 0.021 mol), 2-bromo-4,6-diphenyl-1,3,5-triazine ) (7.5 g, 0.024 mol) was dissolved in 20 mL of 20 mL of toluene, EtOH, H ₂ O, and then Pd (PPh ₃ ) ₄ (1.2 g, 0.0010 mol) and K ₂ CO ₃ (8.1 g, 0.063 mol), and the mixture is stirred at 100 ° C. for 5 hours. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying over anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain Compound 574 (9.7 g, 75%).

In the same manner as in Preparation Example 2, except that the intermediate J-1 of the following Table 36 was used instead of phenylboronic acid, and 2-bromo- 4,6-diphenyl-1,3,5-triazine) was used instead of Intermediate K-1 in the following Table 36, the target compound was synthesized.

2-bromo-6-chloroaniline was used in place of 2-bromo-5-chloroaniline in Production Example 2, and phenylboronic acid ( Intermediate L-1 of the following Table 37 was used instead of 2-bromo-4,6-diphenyl-1,3-phenylboronic acid , 5-triazine) was replaced by Intermediate M-1 of the following Table 37, the target compound was synthesized.

2-bromo-6-chloroaniline was used in place of 2-bromo-5-chloroaniline in Production Example 2, and phenylboronic acid ( Except that Intermediate M-1 of Table 38 was used instead of 2-bromo-4,6-diphenyl-1,3-phenylboronic acid , 5-triazine) was replaced by Intermediate O-1 in the following Table 38, the target compound was synthesized.

Bromo-4-chloroaniline was used in place of 2-bromo-5-chloroaniline in Preparation Example 2, phenylboronic acid (2-bromo- Except that Intermediate P-1 in Table 39 was used instead of 2-bromo-4,6-diphenyl-1,3 , 5-triazine) was replaced by Intermediate Q-1 of the following Table 39, the target compound was synthesized.

Bromo-4-chloroaniline was used in place of 2-bromo-5-chloroaniline in Preparation Example 2, phenylboronic acid (2-bromo- Phenylboronic acid was used instead of the intermediate R-1 in Table 40, and 2-bromo-4,6-diphenyl-1,3 , 5-triazine) was replaced by Intermediate S-1 of the following Table 40, the target compound was synthesized.

2-bromo-3-chloroaniline was used in place of 2-bromo-5-chloroaniline in Production Example 2, and phenylboronic acid ( Phenylboronic acid was used instead of Intermediate T-1 in Table 41, and 2-bromo-4,6-diphenyl-1,3 , 5-triazine) was replaced by Intermediate U-1 of the following Table 41, the target compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Preparation Example 2, phenyl The procedure of Intermediate V-1 of Table 42 below was repeated using 2-bromo-4,6-diphenyl-1,3,5-triazine instead of Phenylboronic acid, 1,3,5-triazine) was replaced by Intermediate W-1 of the following Table 42, the target compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Preparation Example 2, phenyl The procedure of Intermediate X-1 of Table 43 below was used in the place of Phenylboronic acid, and 2-bromo-4,6-diphenyl- 1,3,5-triazine) was replaced by Intermediate Y-1 in Table 43, the target compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Preparation Example 2, and 2 Bromo-5-chloroaniline was used instead of 2-bromo-5-chloroaniline and the intermediate Z-1 of the following Table 44 was used instead of 2-bromo-5- (2-bromo-4,6-diphenyl-1,3,5-triazine) was used instead of Intermediate A-2 in Table 44, the target compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Preparation Example 2, and 2 Bromo-3-chloroaniline instead of 2-bromo-5-chloroaniline was used instead of 2-bromo-3-chloroaniline, 45 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine in place of 2-bromo-4,6-diphenyl- The target compound was synthesized in the same manner as in Preparation Example 2, except that Intermediate C-2 in the following Table 45 was used.

2-bromo-4-chloroaniline was used in place of 2-bromo-5-chloroaniline in Production Example 2, 4-chlorobenzoyl chloride Except that 3-Chlorobenzoyl chloride was used in place of 4-Chlorobenzoyl chloride and Intermediate D-2 of the following Table 46 was used instead of Phenylboronic acid. 2-Bromo- Except that Intermediate F-2 of the following Table 46 was used instead of 6-diphenyl-1,3,5-triazine (2-bromo-4,6-diphenyl- 2, the target compound was synthesized.

2-bromo-3-chloroaniline was used in place of 2-bromo-5-chloroaniline in Production Example 2, 4-chlorobenzoyl chloride Except that 3-Chlorobenzoyl chloride was used in place of 4-Chlorobenzoyl chloride and Intermediate F-2 of the following Table 47 was used instead of Phenylboronic acid, and 2-bromo-4, Except that Intermediate G-2 of the following Table 47 was used instead of 6-diphenyl-1,3,5-triazine (2-bromo-4,6-diphenyl- 2, the target compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Production Example 2 and 4 3-Chlorobenzoyl chloride was used in place of 4-Chlorobenzoyl chloride and Intermediate H-2 of the following Table 48 was used in place of Phenylboronic acid, and 2- Except that Intermediate I-2 of the following Table 48 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine The target compound was synthesized in the same manner as in Preparation Example 2,

Benzofuran-2-ylboronic acid was used in place of (1H-indol-2-yl) boronic acid in Preparation Example 2, and 2 2-bromo-4-chloroaniline was used in place of 2-bromo-5-chloroaniline, and 4-chlorobenzoyl chloride , 3-Chlorobenzoyl chloride was used instead of phenylboronic acid and Intermediate J-2 of the following Table 49 was used in place of phenylboronic acid, and 2-bromo-4,6-diphenyl-1 , Except that Intermediate K-2 of the following Table 49 was used in place of 3,5-triazine (2-bromo-4,6-diphenyl-1,3,5-triazine) To obtain the target compound.

< Manufacturing example  3> Preparation of Compound 926

1) Preparation of compound 926-1

Benzo [b] thiophen-2-ylboronic acid (100 g, 0.562 mol), 2-bromonaphthalen-1-amine 125 g, 0.562 mol) was dissolved in 200 mL of toluene (toluene), EtOH and H ₂ O (200 mL), and then Pd (PPh ₃ ) ₄ (32.4 g, 0.028 mol) and NaHCO ₃ (141.6 g, ), And the mixture is stirred at 100 ° C for 3 hours. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain a liquid form of compound 926-1 (106 g, 68%).

2) Preparation of compound 926-2

Compound 926-1 (106 g, 0.385 mol) and triethylamine (64 mL, 0.462 mol) are dissolved in 1200 mL of MC. 4-Chlorobenzoyl chloride (67.38 g, 0.385 mol) is dissolved in 300 mL of MC, and then slowly added dropwise to the mixture at 0 ° C. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain a liquid form of compound 926-2 (120 g, 75%).

4) Preparation of compound 926-3

Compound 926-2 (120 g, 0.290 mol) is dissolved in 1500 mL of Nitrobenzene, and then POCl ₃ (50 mL, 0.443 mol) is slowly added dropwise. And reacted at 140 캜 for 15 hours. After completion of reaction, add NaHCO ₃ dissolved in distilled water to the reaction solution slowly and stir. The resulting solids are filtered and collected. The collected solid was recrystallized from MC and MeOH to obtain compound 926-3 (71 g, 61%) in the form of solid.

5) Preparation of compound 926-4

(8.8 g, 0.035 mol), KOAc (6.7 g, 0.069 mol), Sphos (1.8 g, 0.0046 mol), compound 926-3 (10 g, 0.025 mol), bis (pinacolato) diboron bis , Pd (dba) ₂ (1.3 g, 0.0023 mol) is dissolved in 200 mL of 1,4-dioxane and reacted at 90 ° C. for 5 hours. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. Thereafter, the organic layer was dried over anhydrous MgSO _4, and then the solvent was removed using a rotary evaporator to obtain Compound 926-4 (9.8 g, 80%).

6) Preparation of compound 926

Compound 926-4 (9.8 g, 0.020 mol), 2-bromo-4,6-diphenyl-1,3,5-triazine ) (7.5 g, 0.024 mol) for _{Toluene, EtOH, H 2 O 100} mL: 20 mL: was dissolved in 20 mL Pd (PPh3) 4 ( 1.2 g, 0.0010 mol) and _{K 2 CO 3 (8.1 g,} 0.063 mol ) And the mixture is stirred at 100 ° C for 5 hours. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain Compound 926 (9.5 g, 80%).

Except that 2-bromo-4,6-diphenyl-1,3,5-triazine was used instead of 2-bromo-4,6-diphenyl- L-2 was used in place of L-2, the target compound was synthesized.

3-chlorobenzoyl chloride was used in place of 4-chlorobenzoyl chloride in Production Example 3, and 2-bromo-4,6-diphenyl-1,3,5- The target compound was synthesized by the same method as Preparation Example 3, except that Intermediate M-2 in the following Table 51 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine. Respectively.

Benzofuran-2-ylboronic acid was used in place of benzo [b] thiophen-2-ylboronic acid in Production Example 3, and 4- 3-chlorobenzoyl chloride was used in place of 4-chlorobenzoyl chloride, and 2-bromo- 4,6-diphenyl-1,3,5-triazine) was used instead of the intermediate N-2 shown in the following Table 52, the target compound was synthesized.

3-bromonaphthalen-2-amine was used in place of 2-bromonaphthalen-1-amine in Production Example 3, and 2-bromoaniline was used instead of 2-bromonaphthalen- Except that Intermediate O-2 of Table 53 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine The target compound was synthesized in the same manner as in Preparation Example 3,

Benzofuran-2-ylboronic acid was used in place of benzo [b] thiophen-2-ylboronic acid in Preparation Example 3, and 2- 3-bromonaphthalen-2-amine was used instead of 2-bromonaphthalen-1-amine and 2-bromo-4,6-diphenyl- Except that Intermediate P-2 in the following Table 54 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine in the same manner as in Production Example 3 To synthesize the desired compound.

1-bromonaphthalen-2-amine was used in place of 2-bromonaphthalen-1-amine in Production Example 3, and 2-bromoaniline was used instead of 2-bromonaphthalen- Except that Intermediate Q-2 in the following Table 55 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine The target compound was synthesized in the same manner as in Preparation Example 3,

In the same manner as in Production Example 3 except that 1-bromonaphthalen-2-amine was used instead of 2-bromonaphthalen-1-amine and 4-chlorobenzoyl- 3-chlorobenzoyl chloride was used instead of 4-chlorobenzoyl chloride, and 2-bromo-4, 5-triazin- 6-diphenyl-1,3,5-triazine) was replaced by Intermediate R-2 of the following Table 56, the target compound was synthesized.

Benzofuran-2-ylboronic acid was used in place of benzo [b] thiophen-2-ylboronic acid in Preparation Example 3, and 2- 1-bromonaphthalen-2-amine was used instead of 2-bromonaphthalen-1-amine, and 2-bromo-4,6-diphenyl- Except that Intermediate S-2 of the following Table 57 was used instead of 2-bromo-4,6-diphenyl-1,3,5-triazine in the same manner as in Production Example 3 To synthesize the desired compound.

The following Tables 58 and 59 are the 1 H NMR data and the FD-MS data of the synthesized compounds. From the following data, it can be confirmed that the desired compound is synthesized.

NO ^One 1 H NMR ( CDCl ₃ , 300Mz ) One (2H, m), 7.54-7.41 (12H, m), 8.12 (1H, 4 (2H, m), 7.85 (2H, d), 7.41-7.54 (11H, m), 8.02 7.25 (2H, d) 5 (2H, m), 7.85 (2H, d), 7.41-7.54 (11H, m), 8.12 9 (2H, m), 7.85 (6H, d), 7.41-7.54 (15H, m), 8.12 7.25 (6 H, d) 13 m), 7.85 (2H, d), 7.66 (1H, t), 7.41-7.54 (11H, m) 7.25 (2H, d) 24 (8H, m), 8.04 (1H, d), 7.98 (1H, s), 7.70 13H, m) 34 (1H, s), 7.45-7.83 (8H, d), 8.04 (2H, d) m), 7.45-7.52 (11H, m), 7.25 (4H, s) 44 (1H, m), 7.85 (2H, d), 7.41-7. 8 (2H, m), 8.24 7.55 (12 H, m), 7.25 (2 H, d) 57 (13H, m), 7.25 (2H, d), 7.94-8.10 (6H, m), 7.85 4H, d) 64 (2H, d), 8.44 (2H, d), 8.27-8.28 (5H, m), 8.12 (3H, d), 7.98-8.03 7.41-7.52 (8H, m), 7.25 (2H, d) 65 (2H, d), 8.55 (2H, d), 8.24-8.66 (6H, m), 8.12 7.70 (1H, s), 7.41-7.57 (10H, m) 78 (2H, d), 8.44 (2H, d), 8.24-8.28 (5H, m), 8.12 (2H, d), 7.82-7.98 7.57 (10 H, m) 84 (1H, s), 8.93 (2H, d), 8.55 (1H, d), 8.45 (1H, m), 8.21-8.28 2H, m), 7.82-7.88 (6H, m), 7.41-7.51 (8H, m), 7.25 92 (2H, d), 8.04 (1H, s), 8.42 (1H, d) (2H, d), 7.98 (1H, m), 7.82-7.90 (7H, m), 7.42-7.51 100 (2H, d), 8.21 (1H, s), 8.21 (1H, s) , 8.12 (3H, d), 7.98 ~ 8.06 (3H, m), 7.82 ~ 7.88 (5H, m), 7.38 ~ 7.61 (9H, m), 7.28 101 (1H, s), 8.12 (3H, d), 8.45 (1H, , 7.98-8.03 (2H, m), 7.77-7.88 (12H, m), 7.45-7.52 (8H, m) 102 d, 7.89 (1H, d), 7.66 (1H, d), 7.41-7.54 (11H, m) 105 d), 7.66 (1H, d), 7.32-7.54 (13H, m), 8.08 (1H, 106 (1H, d), 7.32-7.54 (11H, m), 8.08 (1H, 7.25 (6 H, t) 119 (2H, d), 7.66 (1H, d), 7.32-7.54 (11H, m), 8.01 122 (1H, d), 8.04 (1H, d), 7.85-7.90 (4H, m), 7.66 7.25 (2H, d) 124 (8H, m), 7.66 (1H, d), 7.32-7.54 (15H, m), 7.25 (1H, d), 8.01 6H, d) 135 (1H, d), 8.01 (1H, d), 8.04 (1H, d), 7.77 4H, s) 138 m), 7.32-7.66 (12H, m), 8.08-8.12 (4H, m), 7.85-7.89 ), 7.25 (2H, d) 152 (1H, d), 8.21 (1H, d), 8.04-8.10 (3H, m), 7.85-7.90 (6H, m) 7.66 (14 H, m), 7.25 (4 H, d) 159 (1H, m), 8.46 (1H, d), 8.24-8.28 (5H, m), 7.89-8.10 (6H, m), 7.32-7.66 161 (2H, d), 8.55 (1H, m), 8.42 (1H, d), 8.27-8.28 (5H, m), 8.03-8.12 7.25-7.66 (16H, m) 175 (1H, d), 8.44 (1H, s), 8.28 (4H, d), 8.12 (2H, d), 7.82-8.03 10H, m) 181 (1H, d), 8.02 (1H, d), 8.02 (1H, 7H, m), 7.66 (1H, m), 7.25-7.51 (10H, m) 192 (2H, d), 7.85-8.03 (1H, m), 7.66 (1H, d) 1H, d), 7.25-7.51 (10H, m) 195 (2H, d), 8.21 (1H, 2), 8.12 (4H, d), 8.03 (1H, d) , 7.82-7.94 (6H, m), 7.63-7.66 (2H, m), 7.29-7.51 (9H, m) 196 (1H, s), 8.12 (3H, d), 8.28 (2H, d), 8.27 , 8.03-8.06 (2H, m), 7.82-7.89 (6H, m), 7.51-7.66 (6H, m), 7.28-7.41 197 d), 8.03 (1H, d), 8.23 (1H, d), 8.12 (3H, , 7.77-7.89 (13H, m), 7.66 (1H, d), 7.45 (6H, m), 7.32-7.38 198 (2H, m), 7.79 (2H, d), 7.29-7.84 (2H, d) 7.68 (16 H, m) 202 (2H, m), 7.85-7.89 (3H, m), 7.25-7.66 (14H), 8.41-8.45 , m) 206 (2H, m), 7.79 (2H, d), 7.41 (1H, d), 8.45 7.54 (11 H, m) 210 (1H, s), 8.12 (1H, d), 7.98-8.03 (2H, m), 7.79-7.85 (6H, m) 7.41-7.54 (11 H, m), 7.25 (6 H, t) 217 (2H, m), 7.85 (4H, d), 7.41 (1H, m), 8.45 7.54 (13 H, m) 235 (1H, s), 7.85 (2H, d), 7.41-7.54 (1H, m), 8.04 13H, m) 238 (1H, m), 7.90 (1H, s), 8.21 (1H, d), 8.04 , 7.85 (6H, d), 7.41-7.54 (15H, m), 7.25 (2H, d) 248 m), 7.41-7.54 (11H, m), 7.41-7.58 (6H, m) 7.25 (2H, d) 255 (1H, d), 8.30 (2H, d), 8.27 (1H, s), 8.23 5H, m), 7.41-7.61 (12H, m), 7.25 (2H, m) 260 (1H, s), 7.98-8.12 (5H, m), 7.85 (2H, d), 8.45-8.46 (2H, m), 8.27-8.30 7.64 (1H, t), 7.41-7.55 (12H, m) 264 (1H, m), 7.85 (2H, d), 7.79 (2H, m), 8.46 2H, d), 7.64 (1H, t), 7.41-7.52 (10H, m) 272 (2H, d), 7.79 (4H, d), 7.41 (1H, d) 7.66 (12 H, m), 7.25 (2 H, d) 275 (1H, m), 8.46 (2H, m), 8.28-8.30 (4H, m), 8.23 2H, d), 7.41-7.66 (12H, m), 7.25 (2H, d) 277 (8H, m), 7.98-8.10 (4H, m), 7.85 (2H, d), 7.41-7.66 (14H, m) 283 (2H, d), 7.98-8.10 (4H, m), 7.79-7.90 (5H, m), 7.41-7.64 (13H, m), 8.45 ) 285 (2H, d), 7.98-8.10 (4H, m), 7.79-7.90 (7H, m), 7.41-7.64 (11H, m), 8.45 ) 287 (1H, m), 8.45 (2H, m), 8.23-8.30 (6H, m), 7.98-8.10 (4H, m), 7.79-7.90 ) 302 (2H, d), 7.98-8.12 (5H, m), 7.79-7.85 (6H, m), 8.42 7.50-7.61 (11H, m) 312 (2H, d), 8.44 (2H, d), 8.23-8.30 (6H, m), 8.12 (3H, d), 7.98-8.03 7.41-7.52 (8H, m) 318 (2H, d), 8.12 (2H, d), 7.98-8.02 (2H, m), 7.79-7.88 (10H, 7.66 (1H, t), 7.41-7.52 (8H, m), 7.25 (2H, d) 328 (2H, d), 8.45 (2H, d), 8.21-8.33 (2H, d) 7.52 (8 H, m), 7.25 (2 H, m) 332 (1H, m), 7.82-7.90 (1H, m), 8.12 (2H, d), 8.04 9H, m), 7.41-7.52 (10H, m) 342 (1H, s), 8.23 (1H, s), 8.12 (3H, d), 7.79-8.03 (13H, m), 7.41-7.52 (8H, m), 7.25-7.28 (4H, t) 346 (1H, d), 8.45 (1H, m), 8.21-8.30 (7H, m), 8.12 (3H, d), 7.98-8.03 2H, m), 7.82-7.88 (6H, m), 7.41-7.52 (10H, m) 348 (2H, m), 7.79 (1H, d), 8.45 (1H, 7.88 (8 H, m), 7.41-7.52 (8 H, m) 355 (1H, d), 8.21 (2H, d), 8.12 (2H, d), 8.45 , 8.04 (1H, d), 7.98 (1H, m), 7.79-7.90 (11H, m), 7.41-7.52 358 d), 8.23 (2H, d), 8.23 (1H, d), 8.45 M), 7.41-7.52 (10H, m), 8.21 (2H, d), 8.12 359 (1H, d), 8.04 (1H, d), 8.45 (1H, d) d), 7.79-7.98 (12H, m), 7.41-7.52 (8H, m), 7.25 368 (1H, d), 8.45 (1H, d), 8.23-8.30 (4H, m), 8.12 4H, d), 7.25-7.68 (15H, m) 370 (2H, m), 7.79-7.89 (5H, m), 7.66 (1H, d), 8.02 7.25-7.54 (13H, m) 372 (3H, m), 7.79 (2H, d), 7.41-7.58 (11H, m), 8.41-8.45 ), 7.25 (2H, d) 387 (1H, d), 7.41 (1H, d), 8.08 (1H, d) 7.54 (13 H, m) 394 (2H, m), 7.25-7.54 (2H, m), 8.01 (1H, d) 13H, m) 403 d, 7.79 (2H, d), 7.66 (1H, d), 7.32-7.54 (11H, m), 8.04 406 (2H, d), 8.01 (2H, d), 8.04 (1H, d), 7.79-7.90 (8H, m), 7.66 7.25 (2H, d) 415 (2H, d), 7.66 (1H, d), 7.32-7.66 (11H, m) 418 (1H, d), 7.23 (2H, d), 7.30 (1H, d) 427 (1H, s), 8.03-8.12 (4H, m), 7.89 (1H, s), 8.23 d), 7.79 (2H, d), 7.32-7.66 (12H, m) 432 (1H, s), 8.03-8.12 (4H, m), 7.79-7.85 (5H, m), 8.23 7.41-7.66 (12H, m) 447 (2H, d), 8.04-8.10 (3H, m), 7.89-7.90 (2H, m), 7.79 7.41-7.66 (12H, m) 453 (8H, m), 7.41-7.66 (12H, m), 8.04-8.10 (3H, m), 7.79-7.90 ), 7.25 (2H, d) 458 (8H, m), 8.46 (1H, d), 8.21-8.33 (2H, d), 8.04-8.10 (3H, m), 7.85-7.90 7.64-7.66 (2H, m), 7.32-7.55 (14H, m), 7.25 (2H, d) 473 (7H, m), 7.66 (1H, d), 8.04 (2H, d), 8.44 1H, d), 7.32-7.51 (8H, m) 476 (1H, s), 8.23 (1H, s), 8.12 (3H, d), 8.03 (1H, d), 7.79-7.88 m), 7.66 (1H, d), 7.32-7.51 (8H, m), 7.25 490 (2H, d), 8.04 (1H, d), 7.79-7.90 (10H, m), 7.66 1H, d), 7.32-7.51 (8H, m) 497 (2H, d), 8.04 (1H, d), 7.9-7.60 (12H, m), 7.66 1H, d), 7.32-7.51 (8H, m), 7.25 (2H, d) 505 (2H, d), 8.44 (1H, s), 8.30 (2H, d), 8.23 d), 7.32-7.52 (12H, m), 7.25 (2H, d) 509 (1H, d), 7.34 (1H, d), 8.44 (1H, s), 8.23-8.30 (7H, m) 7.52 (10 H, m), 7.25 (2 H, d) 512 (2H, d), 8.02 (1H, d), 8.23 (1H, d) , 7.79-7.89 (8H, m), 7.66 (2H, m), 7.28-7.51 (10H, m) 517 (2H, d), 8.03 (1H, d), 8.23 (1H, s), 8.23 , 7.79-7.89 (11H, m), 7.66 (1H, d), 7.25-7.51 (10H, m) 527 (2H, d), 8.04 (1H, d), 8.23 (1H, s) , 7.79-7.89 (12H, m), 7.66 (1H, d), 7.32-7.51 (8H, m), 7.25 534 (1H, d), 8.27 (1H, s), 8.27 (1H, s), 8.12 , 8.03-8.06 (2H, d), 7.79-7.88 (8H, m), 7.51-7.61 (6H, m), 7.28-7.41 536 (2H, m), 7.79 (2H, d), 7.29-7.66 (16H, m), 8.09-8.12 ) 537 (6H, m), 7.66 (2H, d), 8.03 (1H, d), 8.23 ), 7.32-7.54 (11H, m), 7.25 (2H, d) 539 (2H, m), 8.30 (4H, t), 8.27 (1H, s), 8.23 (1H, s), 8.20 (2H, d), 7.66 (1H, d), 7.66 542 (2H, d), 8.12 (1H, d), 8.45 (2H, d), 8.45 2H), 7.70 (2H, m), 7.47-7.54 (5H, m), 7.25 (4H, s), 7.14 543 d), 8.27 (1H, s), 8.12 (1H, d), 8.45 (2H, , 7.98-8.33 (2H, m), 7.70 (2H, m), 7.47-7.54 (5H, m), 7.25 547 (2H, d), 9.15 (2H, s), 8.53-8.55 (3H, m), 8.45 7.55 (4H, m), 7.64-7.70 (3H, m), 7.25 (4H, s), 7.14 551 d), 8.12 (1H, d), 8.27 (1H, s), 8.12 (3H, d) (2H, t), 7.50-7.02 (2H, m), 7.82-7.88 (4H, m) 555 (2H, d), 8.93 (2H, d), 8.45-8.55 (4H, m), 8.271H, s), 8.21 (1H, d), 9.16 ), 8.12 (3H, d), 7.98-8.03 (2H, m), 7.82-7.88 (4H, m), 7.70 (2H, t), 7.50-7.52 7.14 (2H, t) 561 (2H, d), 8.01 (1H, d), 8.02 (1H, d) , 7.66-7.70 (4H, m), 7.32-7.54 (5H, m), 7.25 (4H, s), 7.14 567 d), 8.44 (1H, s), 8.27 (1H, s), 8.12 (3H, d) , 8.03 (1H, d), 7.82-7.88 (5H, m), 7.66-7.70 (3H, m), 7.32-7.38 (2H, m), 7.25 571 (1H, s), 8.21 (1H, s), 8.31 (2H, d) (1H, d), 8.12 (3H, d), 8.03 (1H, d), 7.82-7.89 (5H, m), 7.66-7.70 (3H, m), 7.32-7.38 , 7.14 (2H, t) 574 (2H, d), 7.41 (2H, d), 8.45 (1H, m), 8.27-8.28 (5H, d) 7.52 (13 H, m) 575 (2H, m), 7.85-7.88 (4H, t), 8.12 (1H, d) 7.41-7.52 (13H, m), 7.25 (2H, d) 585 (1H, s), 7.60 (1H, t), 7.41-7.52 (1H, m), 8.45 (1H, m), 8.21-8.30 13H, m) 591 (8H, m), 7.79 (2H, d), 7.38-7.52 (12H, m), 7.28 (2H, 1H, t), 1.72 (6H, s) 594 (2H, d), 8.55 (1H, t), 8.42-8.45 (2H, m), 8.25-8.28 (3H, d), 7.98-8.12 (5H, m), 7.85-7.88 ), 7.41-7.61 (13H, m), 7.25 (2H, d) 607 (2H, d), 8.81 (2H, d), 8.45 (1H, m), 8.28 (4H, d), 8.21 m), 7.66 (1H, t), 7.41-7.52 (8H, m) 610 (1H, d), 8.12 (3H, d), 8.45 (1H, d), 7.98-8.04 (3H, m), 7.82-7.88 (6H, m), 7.41-7.52 (8H, m) 614 (1H, d), 8.18 (1H, d), 8.45 (1H, , 8.12 (2H, d), 7.82-8.04 (10H, m), 7.41-7.52 (8H, m) 618 (2H, m), 7.81-7. 89 (5H, m), 8.12 (1H, d) 7.66 (1H, d), 7.32-7.52 (11H, m) 621 (2H, m), 7.81-7.89 (5H, m), 7.66 (1H, m), 8.01 7.32-7.52 (11H, m) 627 (1H, m), 7.66 (1H, d), 7.32-7.52 (11H, m) 634 (2H, d), 8.41-8.45 (3H, m), 8.27-8.28 (5H, d), 8.20 7.41-7.58 (11 H, m) 643 (7H, m), 7.41-7.58 (11H, m), 8.08 (2H, d) 650 (2H, d), 7.88 (2H, d), 8.55 (1H, d), 8.45 (1H, m), 8.27-8.28 2H, d), 7.63-7.68 (3H, m), 7.25-7.52 (14H, m) 652 (2H, m), 7.81-7.88 (7H, m), 8.12 (1H, d) 7.66 (1H, d), 7.25-7.52 (15H, m) 657 (2H, d), 8.27-8.28 (5H, d), 8.12 (1H, d), 8.03 (1H, d), 7.85-7.88 7.52 (13H, m), 7.25 (2H, d) 667 (8H, m), 8.04 (1H, d), 7.90 (2H, d), 7.32-7.60 674 (2H, d), 8.55 (1H, m), 8.42 (1H, d), 8.25-8.28 (5H, d), 8.04-8.12 7.32-7.66 (12H, m) 684 (2H, d), 8.55 (1H, m), 8.42 (1H, d), 7.85-8.08 (12H, m), 7.32-7.61 687 (2H, d), 8.21 (1H, s), 8.12 (3H, d), 8.03 (1H, d), 7.82-7.93 d), 7.32-7.52 (12H, m), 7.25 (4H, d) 692 (2H, d), 8.01 (2H, d), 8.28 (4H, d), 8.21 m), 7.66 (1H, d), 7.32-7.51 (8H, m) 695 (2H, d), 8.81 (2H, d), 8.28 (4H, d), 8.12 (2H, d), 7.82-8.03 8H, m) 700 (2H, d), 8.02 (2H, d), 8.28 (4H, d), 8.18 m), 7.82-7.88 (7H, m), 7.66 (1H, m), 7.32-7.51 (8H, m) 708 (8H, m), 8.12 (1H, d), 8.03 (1H, d), 7.81-7.89 (4H, m), 7.32-7.66 723 d), 8.12 (1H, d), 7.98-8.03 (2H, m), 8.08 (2H, d), 8.41-8.45 (2H, m), 8.27-8.28 7.85-7.88 (5H, m), 7.66 (1H, d), 7.32-7.58 (15H, m) 729 (2H, m), 7.98-8.44 (2H, m), 7.89-7.90 (2H, d), 7.32-7.66 (13H, m) 734 (2H, m), 7.88 (2H, m), 8.28 (1H, d) 3H, d), 7.32-7.70 (16H, m) 737 (2H, d), 8.08 (2H, d), 7.88-7.94 (4H, m), 7.79 d), 7.63-7.68 (4H, m), 7.29-7.52 (14H, m) 739 (8H, m), 7.66 (2H, d), 7.25-7.52 (1H, d), 8.08 15H, m) 741 d), 8.12 (1H, d), 7.98-8.03 (2H, m), 8.08 (2H, d), 8.41-8.45 (2H, m), 8.27-8.28 7.85-7.88 (5H, m), 7.25-7.52 (16H, m) 744 (2H, m), 7.79-7.88 (1H, m), 8.23 (1H, s), 8.12 8H, m), 7.41-7.52 (13H, m), 7.25 (2H, d) 746 (2H, m), 7.85 (4H, d), 8.23 (1H, s), 8.12 d), 7.88 (2H, d), 7.41-7.52 (17H, m) 758 (1H, d), 7.90 (1H, s), 7.79 (2H, d, d), 7.41-7.52 (13H, m) 768 (2H, d), 7.79 (4H, m), 8.45 (2H, d), 7.41-7.61 (11H, m) 781 (2H, d), 7.79 (4H, m), 8.42 (2H, m), 8.23 d), 7.41-7.61 (11H, m) 789 (9H, m), 7.41-8.33 (2H, d), 8.81 (2H, d), 8.45 7.52 (8 H, m) 796 (2H, d), 8.04 (1H, d), 7.79-7.93 (2H, 13H, m), 7.41-7.52 (8H, m) 802 (2H, d), 8.81 (2H, d), 8.45 (1H, m), 8.23-8.33 (5H, m), 8.12 7.52 (8 H, m) 804 m, 7.41-7.60 (9H, m), 8.12 (2H, d), 7.79-7.98 (12H, m) 807 (2H, d), 8.45 (1H, m), 7.98-8.33 (13H, m), 7.79-7.88 (6H, 7.52 (8 H, m) 813 (2H, m), 7.79-7.89 (5H, m), 8.12 (1H, d) 7.66 (1H, d), 7.32-7.52 (11H, m) 818 (1H, d), 7.89 (2H, d), 7.89 (2H, d) 7.41-7.58 (11 H, m) 824 (2H, d), 8.27 (1H, s), 8.23 (1H, s), 8.12 , 7.94 ~ 8.03 (3H, m), 7.79 (4H, d), 7.63 ~ 7.68 (3H, m), 7.25 ~ 7.52 826 (2H, d), 8.45 (1H, m), 8.33 (2H, d), 8.27 (1H, s), 8.23 m), 7.79-7.89 (7H, m), 7.66 (1H, d), 7.25-7.52 830 (1H, d), 8.08 (2H, d), 8.27 (1H, s), 8.23 d), 7.66 (1H, d), 7.32-7.52 (13H, m) 831 (9H, m), 7.66 (1H, s), 8.23 (1H, d) d), 7.32-7.52 (13H, m), 7.25 (2H, d) 844 (2H, d), 7.79 (2H, m), 7.66 (1H, d), 7.32-7. 7.52 (13 H, m) 855 (2H, d), 8.55 (1H, m), 8.42 (1H, d), 8.28 m), 7.79 (4H, d), 7.32-7.55 (12H, m) 861 (2H, d), 8.55 (1H, m), 8.42 (1H, d), 8.21-8.28 (6H, m), 8.02-8.08 2H, d), 7.32-7.66 (13H, m) 877 (8H, m), 8.12 (3H, d), 8.03 (1H, d), 7.82-7.93 (8H, m), 7.66 1H, d), 7.32-7.51 (10H, m) 883 (2H, d), 8.01 (2H, d), 8.81 (2H, d), 8.21-8.33 1H, d), 7.32-7.51 (8H, m) 894 (2H, d), 8.23 (2H, d), 8.23 (1H, s), 8.23 , 8.03-8.12 (6H, m), 7.79-7.88 (7H, m), 7.66 (1H, d), 7.32-7.51 902 (6H, m), 7.62 (2H, d), 7.32-7.88 (2H, d), 8.27-8.33 7.51 (11 H, m) 907 (2H, d), 8.21-8.33 (6H, m), 8.02 (1H, d), 7.79-7.89 (6H, m), 7.66 (3H, m), 7.32-7.51 910 (2H, m), 7.89 (1H, d), 7.79 (1H, d), 8.45 2H, d), 7.66 (1H, d), 7.32-7.58 (11H, m) 917 (1H, s), 8.12 (3H, d), 8.45 (1H, , 7.98-8.03 (2H, m), 7.77-7.88 (21H, m), 7.45-7.52 (8H, m) 918 (2H, t), 7.29 (1H, d), 7.89 (2H, 7.51 (13 H, m) 919 (2H, d), 8.23 (1H, s), 8.06 (1H, m), 8.23 (1H, d), 7.94-7.95 7.66 (14 H, m), 1.72 (6 H, s) 920 d), 8.03 (1H, d), 8.23 (1H, s), 8.23 (1H, , 7.89-7.94 (2H, m), 7.79 (4H, d), 7.63-7.68 (4H, m), 7.25-7.52 923 (1H, s), 8.23 (1H, s), 8.12 (1H, d), 8.03 (1H, d), 7.66-7.89 (12H, m), 7.32-7.57 15H, m) 926 d, 8.06 (1H, d), 7.98 (1H, d), 8.08 (1H, d) , 7.88 (2H, d), 7.81 (1H, d), 7.67 (2H, t), 7.41-7.52 927 (2H, m), 7.81-7.79 (3H, m), 8.08 (2H, m), 8.45-8.55 m), 7.67-7.68 (4H, m), 7.60 (1H, m), 7.50-7.52 (6H, m), 7.25-7.41 928 (1H, d), 8.08 (2H, d), 8.51 (1H, t), 8.46 (1H, m), 8.24-8.28 m), 7.81-7.89 (6H, m), 7.66-7.70 (4H, m), 7.32-7.57 (10H, m) 932 d), 8.16 (1H, m), 8.41 (1H, d), 8.21 , 8.06 (1H, d), 7.98 (2H, d), 7.81-7.88 (5H, m), 7.67 936 (1H, m), 8.06 (1H, d), 7.98 (1H, s), 8.45 m), 7.88 (2H, d), 7.81 (1H, d), 7.67-7.70 (4H, m), 7.50-7.52 937 (1H, d), 7.88 (2H, d), 8.08 (2H, d) , 7.66-7.81 (9H, m), 7.45-7.52 (10H, m) 943 (2H, m), 8.28-8.30 (4H, m), 8.26 (1H, s), 8.06-8.21 (4H, m), 7.94 7.81 (1H, d), 7.66-7.67 (3H, m), 7.25-7.63 (12H, m) 945 (1H, d), 8.06 (1H, d), 7.85-7.89 (5H, m), 7.66-7.67 (3H, 7.54-7.60 (3H, m), 7.51-7.52 (8H, m), 7.32-7.41 (4H, m) 950 (1H, m), 7.88 (2H, d), 8.08 (2H, d) , 7.67-7.68 (3H, m), 7.50-7.52 (6H, m), 7.41 (2H, m) 952 (1H, s), 7.98 (1H, d), 8.04 (2H, m) (4H, m), 7.50-7.52 (4H, m), 7.32-7.48 (4H, m) 954 d), 8.16 (2H, m), 8.05 (1H, s), 7.98 (1H, d), 8.35 , 7.85 (2H, d), 7.79 (2H, d), 7.67-7.68 (2H, m), 7.50-7.52 (8H, m), 7.41 956 (2H, d), 7.88 (2H, d), 8.08 (2H, d) (2H, d), 7.85 (2H, d), 7.68 (1H, m), 7.67 (2H, d), 7.50-7.53 959 (1H, s), 8.16 (2H, m), 8.05 (1H, s), 7.79-7.98 (6H, m), 7.50-7.75 9H, m), 7.32-7.48 (5H, m) 961 (2H, d), 7.66 (1H, m), 8.06 (1H, m), 7.73-7.77 (4H, m), 7.50-7.52 (4H, m), 7.45 (5H, m) 962 (3H, m), 7.51 (2H, m), 8.08 (2H, 4H, m), 7.41 (2H, m), 7.32-7.38 (2H, m) 969 (2H, m), 7.25 (1H, s), 7.89 (1H, d), 8.08 2H, d) 971 (8H, m), 7.66-7.79 (9H, m), 7.32-7.88 (2H, d) 7.51 (7 H, m) 977 (1H, m), 8.45 (1H, m), 8.16-8.28 (6H, m), 7.98-7.99 (3H, m), 7.85 7.25 (2H, d) 978 (2H, d), 8.14 (1H, m), 8.45 (1H, m), 8.33 m), 7.85 (2H, d), 7.79 (2H, d), 7.67 980 m), 8.28 (2H, m), 8.16-8.20 (2H, d), 7.98-7.99 (4H, m), 8.41-8.45 M), 7.25 (2H, d), 7.87 (2H, d), 7.85 986 (2H, s), 7.88-7.89 (3H, m), 7.66 (1H, m) M), 7.51 (4H, m), 7.41 (2H, m), 7.32-7.38 (2H, m) 990 (2H, d), 8.54 (1H, m), 8.33 (2H, d), 8.16 (1H, m), 7.89-7. 7.67 (3H, m), 7.51-7.52 (6H, m), 7.32-7.41 (4H, m), 7.25 996 (2H, s), 8.81 (2H, d), 8.53-8.54 (3H, m), 8.16 (1H, m), 7.98-7. 7.89 (2H, d), 7.66-7.70 (5H, m), 7.32-7.38 (2H, m), 7.25 998 (2H, d), 7.81 (1H, d), 7.47-1.30 (5H, m), 7.98-8.12 7.54 (8 H, m), 7.35 (2 H, d) 999 (2H, d), 8.81 (2H, d), 8.55 (1H, m), 8.45-8.46 (1H, d), 7.64-7.66 (2H, m), 7.47-7.55 (7H, m), 7.35 1002 (1H, d), 7.47 (1H, d), 8.45 (1H, d), 8.27-8.30 (3H, m), 7.98-8.12 7.54 (9H, m), 7.35-7.41 (3H, m) 1003 d), 7.81 (1H, d), 8.55 (1H, m), 8.45 d), 7.50-7.66 (9H, m), 7.35 (2H, d), 7.28 1008 (1H, d), 8.01 (2H, d), 8.81 (2H, d), 8.44 9H, m), 7.66 (1H, d), 7.32-7.54 (7H, m) 1012 d), 7.81 (1H, d), 7.32-7.66 (15H, m), 8.01-8.10 (4H, m), 7.88-7.90 ) 1013 (8H, m), 7.81 (1H, d), 7.28-7.88 (2H, d) 7.66 (15 H, m) 1014 (1H, d), 7.47-7.54 (9H, m), 7.98-8.12 (6H, m) 7.35-7.41 (3H, d) 1016 (8H, m), 8.30 (2H, d), 8.21 (1H, d), 7.81-8.12 (14H, m), 7.47-7.54 5H, &lt; / RTI &gt; m), 7.35 (2H, d) 1018 (4H, m), 7.66 (1H, m), 7.98-8.12 (6H, m), 7.81-7.89 7.32-7.54 (10H, m) 1019 m), 7.81 (1H, d), 7.47 (1H, d), 8.41 7.66 (9 H, m), 7.35 (2 H, d) 1020 (2H, d), 7.67 (2H, d), 7.81 (2H, d) m), 7.47 ~ 7.54 (5H, m), 7.35 (2H, d) 1022 (1H, d), 7.67 (2H, d, J = 8.48 (4H, s), 8.54 (1H, m), 8.45 m), 7.47 ~ 7.54 (5H, m), 7.35 (2H, d) 1024 (2H, d), 8.21 (1H, d), 8.02-8.10 (6H, m), 7.89 (1H, d), 7.81 (1H, d), 7.32-7.66 (12H, m) 1026 m), 7.68 (1H, d), 7.32-7.54 (7H, m), 7.81 (2H, d)

compound FD-MS compound FD-MS One m / z = 542.65 (C36H22N4S = 542.16) 2 m / z = 618.75 (C42H26N4S = 618.19) 3 m / z = 694.84 (C48H30N4S = 694.22) 4 m / z = 618.75 (C42H26N4S = 618.19) 5 m / z = 694.84 (C48H30N4S = 694.22) 6 m / z = 694.84 (C48H30N4S = 694.22) 7 m / z = 770.94 (C54 H34 N4 S = 770.25) 8 m / z = 694.84 (C48H30N4S = 694.22) 9 m / z = 770.94 (C54 H34 N4 S = 770.25) 10 m / z = 618.75 (C42H26N4S = 618.19) 11 m / z = 542.65 (C36H22N4S = 542.16) 12 m / z = 694.84 (C48H30N4S = 694.22) 13 m / z = 618.75 (C42H26N4S = 618.19) 14 m / z = 694.84 (C48H30N4S = 694.22) 15 m / z = 770.94 (C54 H34 N4 S = 770.25) 16 m / z = 618.75 (C42H26N4S = 618.19) 17 m / z = 770.94 (C54 H34 N4 S = 770.25) 18 m / z = 542.65 (C36H22N4S = 542.16) 19 m / z = 618.75 (C42H26N4S = 618.19) 20 m / z = 694.84 (C48H30N4S = 694.22) 21 m / z = 618.75 (C42H26N4S = 618.19) 22 m / z = 694.84 (C48H30N4S = 694.22) 23 m / z = 770.94 (C54 H34 N4 S = 770.25) 24 m / z = 618.75 (C42H26N4S = 618.19) 25 m / z = 770.94 (C54 H34 N4 S = 770.25) 26 m / z = 542.65 (C36H22N4S = 542.16) 27 m / z = 618.75 (C42H26N4S = 618.19) 28 m / z = 694.84 (C48H30N4S = 694.22) 29 m / z = 618.75 (C42H26N4S = 618.19) 30 m / z = 694.84 (C48H30N4S = 694.22) 31 m / z = 770.94 (C54 H34 N4 S = 770.25) 32 m / z = 618.75 (C42H26N4S = 618.19) 33 m / z = 770.94 (C54 H34 N4 S = 770.25) 34 m / z = 663.76 (C45H30NOPS = 663.18) 35 m / z = 663.76 (C45H30NOPS = 663.18) 36 m / z = 592.71 (C40H24N4S = 592.17) 37 m / z = 668.81 (C46H28N4S = 668.20) 38 m / z = 668.81 (C46H28N4S = 668.20) 39 m / z = 744.90 (C52H32N4S = 744.23) 40 m / z = 668.81 (C46H28N4S = 668.20) 41 m / z = 821.00 (C 58 H 36 N 4 S = 820.27) 42 m / z = 592.71 (C40H24N4S = 592.17) 43 m / z = 668.81 (C46H28N4S = 668.20) 44 m / z = 668.81 (C46H28N4S = 668.20) 45 m / z = 744.90 (C52H32N4S = 744.23) 46 m / z = 668.81 (C46H28N4S = 668.20) 47 m / z = 821.00 (C 58 H 36 N 4 S = 820.27) 48 m / z = 592.71 (C40H24N4S = 592.17) 49 m / z = 668.81 (C46H28N4S = 668.20) 50 m / z = 668.81 (C46H28N4S = 668.20) 51 m / z = 744.90 (C52H32N4S = 744.23) 52 m / z = 821.00 (C 58 H 36 N 4 S = 820.27) 53 m / z = 668.81 (C46H28N4S = 668.20) 54 m / z = 542.65 (C36H22N4S = 542.16) 55 m / z = 618.75 (C42H26N4S = 618.19) 56 m / z = 668.81 (C46H28N4S = 668.20) 57 m / z = 744.90 (C52H32N4S = 744.23) 58 m / z = 668.81 (C46H28N4S = 668.20) 59 m / z = 668.81 (C46H28N4S = 668.20) 60 m / z = 744.90 (C52H32N4S = 744.23) 61 m / z = 744.90 (C52H32N4S = 744.23) 62 m / z = 642.77 (C44H26N4S = 642.19) 63 m / z = 718.87 (C50H30N4S = 718.22) 64 m / z = 718.87 (C50H30N4S = 718.22) 65 m / z = 718.87 (C50H30N4S = 718.22) 66 m / z = 642.77 (C44H26N4S = 642.19) 67 m / z = 794.96 (C56H34N4S = 794.25) 68 m / z = 718.87 (C50H30N4S = 718.22) 69 m / z = 794.96 (C56H34N4S = 794.25) 70 m / z = 642.77 (C44H26N4S = 642.19) 71 m / z = 718.87 (C50H30N4S = 718.22) 72 m / z = 718.87 (C50H30N4S = 718.22) 73 m / z = 794.96 (C56H34N4S = 794.25) 74 m / z = 718.87 (C50H30N4S = 718.22) 75 m / z = 642.77 (C44H26N4S = 642.19) 76 m / z = 718.87 (C50H30N4S = 718.22) 77 m / z = 794.96 (C56H34N4S = 794.25) 78 m / z = 718.87 (C50H30N4S = 718.22) 79 m / z = 718.87 (C50H30N4S = 718.22) 80 m / z = 794.96 (C56H34N4S = 794.25) 81 m / z = 794.96 (C56H34N4S = 794.25) 82 m / z = 692.83 (C 48 H 28 N 4 S = 692.20) 83 m / z = 766.91 (C54H30N4S = 766.22) 84 m / z = 768.92 (C54 H32 N4 S = 768.23) 85 m / z = 845.02 (C60H36N4S = 844.27) 86 m / z = 768.92 (C54 H32 N4 S = 768.23) 87 m / z = 692.83 (C 48 H 28 N 4 S = 692.20) 88 m / z = 768.92 (C54 H32 N4 S = 768.23) 89 m / z = 768.92 (C54 H32 N4 S = 768.23) 90 m / z = 692.83 (C 48 H 28 N 4 S = 692.20) 91 m / z = 768.92 (C54 H32 N4 S = 768.23) 92 m / z = 768.92 (C54 H32 N4 S = 768.23) 93 m / z = 768.92 (C54 H32 N4 S = 768.23) 94 m / z = 692.83 (C 48 H 28 N 4 S = 692.20) 95 m / z = 768.92 (C54 H32 N4 S = 768.23) 96 m / z = 768.92 (C54 H32 N4 S = 768.23) 97 m / z = 768.92 (C54 H32 N4 S = 768.23) 98 m / z = 768.92 (C54 H32 N4 S = 768.23) 99 m / z = 781.92 (C54 H31 N5 S = 781.23) 100 m / z = 808.99 (C 57 H 36 N 4 S = 808.27) 101 m / z = 737.84 (C51 H32 NOPS = 737.19) 102 m / z = 526.59 (C36H22N4O = 526.18) 103 m / z = 602.68 (C42H26N4O = 602.21) 104 m / z = 678.78 (C48H30N4O = 678.24) 105 m / z = 602.68 (C42H26N4O = 602.21) 106 m / z = 678.78 (C48H30N4O = 678.24) 107 m / z = 678.78 (C48H30N4O = 678.24) 108 m / z = 754.87 (C54 H34 N4 O = 754.27) 109 m / z = 678.78 (C48H30N4O = 678.24) 110 m / z = 754.87 (C54 H34 N4 O = 754.27) 111 m / z = 526.59 (C36H22N4O = 526.18) 112 m / z = 602.68 (C42H26N4O = 602.21) 113 m / z = 678.78 (C48H30N4O = 678.24) 114 m / z = 602.68 (C42H26N4O = 602.21) 115 m / z = 678.78 (C48H30N4O = 678.24) 116 m / z = 754.87 (C54 H34 N4 O = 754.27) 117 m / z = 602.68 (C42H26N4O = 602.21) 118 m / z = 754.87 (C54 H34 N4 O = 754.27) 119 m / z = 526.59 (C36H22N4O = 526.18) 120 m / z = 602.68 (C42H26N4O = 602.21) 121 m / z = 678.78 (C48H30N4O = 678.24) 122 m / z = 602.68 (C42H26N4O = 602.21) 123 m / z = 678.78 (C48H30N4O = 678.24) 124 m / z = 754.87 (C54 H34 N4 O = 754.27) 125 m / z = 602.68 (C42H26N4O = 602.21) 126 m / z = 754.87 (C54 H34 N4 O = 754.27) 127 m / z = 526.59 (C36H22N4O = 526.18) 128 m / z = 602.68 (C42H26N4O = 602.21) 129 m / z = 678.78 (C48H30N4O = 678.24) 130 m / z = 602.68 (C42H26N4O = 602.21) 131 m / z = 678.78 (C48H30N4O = 678.24) 132 m / z = 754.87 (C54 H34 N4 O = 754.27) 133 m / z = 602.68 (C42H26N4O = 602.21) 134 m / z = 754.87 (C54 H34 N4 O = 754.27) 135 m / z = 647.70 (C45 H30 NO2 P = 647.20) 136 m / z = 576.64 (C40 H24 N4 O = 576.20) 137 m / z = 652.74 (C46H28N4O = 652.23) 138 m / z = 652.74 (C46H28N4O = 652.23) 139 m / z = 728.84 (C52H32N4O = 728.26) 140 m / z = 652.74 (C46H28N4O = 652.23) 141 m / z = 804.93 (C 58 H 36 N 4 O = 804.29) 142 m / z = 576.64 (C40 H24 N4 O = 576.20) 143 m / z = 652.74 (C46H28N4O = 652.23) 144 m / z = 728.84 (C52H32N4O = 728.26) 145 m / z = 804.93 (C 58 H 36 N 4 O = 804.29) 146 m / z = 652.74 (C46H28N4O = 652.23) 147 m / z = 804.93 (C 58 H 36 N 4 O = 804.29) 148 m / z = 576.64 (C40 H24 N4 O = 576.20) 149 m / z = 652.74 (C46H28N4O = 652.23) 150 m / z = 728.84 (C52H32N4O = 728.26) 151 m / z = 652.74 (C46H28N4O = 652.23) 152 m / z = 728.84 (C52H32N4O = 728.26) 153 m / z = 804.93 (C 58 H 36 N 4 O = 804.29) 154 m / z = 652.74 (C46H28N4O = 652.23) 155 m / z = 576.64 (C40 H24 N4 O = 576.20) 156 m / z = 652.74 (C46H28N4O = 652.23) 157 m / z = 728.84 (C52H32N4O = 728.26) 158 m / z = 804.93 (C 58 H 36 N 4 O = 804.29) 159 m / z = 652.74 (C46H28N4O = 652.23) 160 m / z = 652.74 (C46H28N4O = 652.23) 161 m / z = 728.84 (C52H32N4O = 728.26) 162 m / z = 728.84 (C52H32N4O = 728.26) 163 m / z = 626.70 (C44H26N4O = 626.21) 164 m / z = 702.80 (C50H30N4O = 702.24) 165 m / z = 702.80 (C50H30N4O = 702.24) 166 m / z = 626.70 (C44H26N4O = 626.21) 167 m / z = 702.80 (C50H30N4O = 702.24) 168 m / z = 702.80 (C50H30N4O = 702.24) 169 m / z = 626.70 (C44H26N4O = 626.21) 170 m / z = 702.80 (C50H30N4O = 702.24) 171 m / z = 702.80 (C50H30N4O = 702.24) 172 m / z = 778.90 (C56H34N4O = 778.27) 173 m / z = 702.80 (C50H30N4O = 702.24) 174 m / z = 626.70 (C44H26N4O = 626.21) 175 m / z = 702.80 (C50H30N4O = 702.24) 176 m / z = 778.90 (C56H34N4O = 778.27) 177 m / z = 702.80 (C50H30N4O = 702.24) 178 m / z = 778.90 (C56H34N4O = 778.27) 179 m / z = 676.76 (C48H28N4O = 676.23) 180 m / z = 752.86 (C54 H32 N4 O = 752.26) 181 m / z = 752.86 (C54 H32 N4 O = 752.26) 182 m / z = 676.76 (C48H28N4O = 676.23) 183 m / z = 752.86 (C54 H32 N4 O = 752.26) 184 m / z = 752.86 (C54 H32 N4 O = 752.26) 185 m / z = 752.86 (C54 H32 N4 O = 752.26) 186 m / z = 676.76 (C48H28N4O = 676.23) 187 m / z = 752.86 (C54 H32 N4 O = 752.26) 188 m / z = 752.86 (C54 H32 N4 O = 752.26) 189 m / z = 752.86 (C54 H32 N4 O = 752.26) 190 m / z = 676.76 (C48H28N4O = 676.23) 191 m / z = 752.86 (C54 H32 N4 O = 752.26) 192 m / z = 752.86 (C54 H32 N4 O = 752.26) 193 m / z = 752.86 (C54 H32 N4 O = 752.26) 194 m / z = 752.86 (C54 H32 N4 O = 752.26) 195 m / z = 765.86 (C54 H31 N5 O = 765.25) 196 m / z = 792.92 (C 57 H 36 N 4 O = 792.29 197 m / z = 721.78 (C51 H32 NO2 P = 721.22) 198 m / z = 691.78 (C48H29N5O = 691.24) 199 m / z = 691.78 (C48H29N5O = 691.24) 200 m / z = 692.76 (C48H28N4O2 = 692.22) 201 m / z = 692.76 (C48H28N4O2 = 692.22) 202 m / z = 708.83 (C48H28N4OS = 708.20) 203 m / z = 708.83 (C48H28N4OS = 708.20) 204 m / z = 541.66 (C37H23N3S = 541.16) 205 m / z = 617.76 (C43H27N3S = 617.19) 206 m / z = 541.66 (C37H23N3S = 541.16) 207 m / z = 617.76 (C43H27N3S = 617.19) 208 m / z = 617.76 (C43H27N3S = 617.19) 209 m / z = 617.76 (C43H27N3S = 617.19) 210 m / z = 693.86 (C49 H31 N3 S = 693.22) 211 m / z = 693.86 (C49 H31 N3 S = 693.22) 212 m / z = 693.86 (C49 H31 N3 S = 693.22) 213 m / z = 769.95 (C 55 H 35 N 3 S = 769.26) 214 m / z = 769.95 (C 55 H 35 N 3 S = 769.26) 215 m / z = 617.76 (C43H27N3S = 617.19) 216 m / z = 693.86 (C49 H31 N3 S = 693.22) 217 m / z = 693.86 (C49 H31 N3 S = 693.22) 218 m / z = 541.66 (C37H23N3S = 541.16) 219 m / z = 617.76 (C43H27N3S = 617.19) 220 m / z = 541.66 (C37H23N3S = 541.16) 221 m / z = 617.76 (C43H27N3S = 617.19) 222 m / z = 617.76 (C43H27N3S = 617.19) 223 m / z = 617.76 (C43H27N3S = 617.19) 224 m / z = 693.86 (C49 H31 N3 S = 693.22) 225 m / z = 769.95 (C 55 H 35 N 3 S = 769.26) 226 m / z = 617.76 (C43H27N3S = 617.19) 227 m / z = 693.86 (C49 H31 N3 S = 693.22) 228 m / z = 693.86 (C49 H31 N3 S = 693.22) 229 m / z = 769.95 (C 55 H 35 N 3 S = 769.26) 230 m / z = 541.66 (C37H23N3S = 541.16) 231 m / z = 617.76 (C43H27N3S = 617.19) 232 m / z = 693.86 (C49 H31 N3 S = 693.22) 233 m / z = 541.66 (C37H23N3S = 541.16) 234 m / z = 617.76 (C43H27N3S = 617.19) 235 m / z = 617.76 (C43H27N3S = 617.19) 236 m / z = 837.06 (C59 H36 N2 S2 = 836.23) 237 m / z = 693.86 (C49 H31 N3 S = 693.22) 238 m / z = 769.95 (C 55 H 35 N 3 S = 769.26) 239 m / z = 617.76 (C43H27N3S = 617.19) 240 m / z = 693.86 (C49 H31 N3 S = 693.22) 241 m / z = 693.86 (C49 H31 N3 S = 693.22) 242 m / z = 769.95 (C 55 H 35 N 3 S = 769.26) 243 m / z = 617.76 (C43H27N3S = 617.19) 244 m / z = 617.76 (C43H27N3S = 617.19) 245 m / z = 541.66 (C37H23N3S = 541.16) 246 m / z = 617.76 (C43H27N3S = 617.19) 247 m / z = 617.76 (C43H27N3S = 617.19) 248 m / z = 617.76 (C43H27N3S = 617.19) 249 m / z = 693.86 (C49 H31 N3 S = 693.22) 250 m / z = 769.95 (C 55 H 35 N 3 S = 769.26) 251 m / z = 617.76 (C43H27N3S = 617.19) 252 m / z = 693.86 (C49 H31 N3 S = 693.22) 253 m / z = 693.86 (C49 H31 N3 S = 693.22) 254 m / z = 769.95 (C 55 H 35 N 3 S = 769.26) 255 m / z = 733.92 (C52H35N3S = 733.26) 256 m / z = 591.72 (C41 H25 N3 S = 591.18) 257 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 258 m / z = 591.72 (C41 H25 N3 S = 591.18) 259 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 260 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 261 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 262 m / z = 743.91 (C53H33N3S = 743.24) 263 m / z = 820.01 (C59 H37 N3 S = 819.27) 264 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 265 m / z = 743.91 (C53H33N3S = 743.24) 266 m / z = 743.91 (C53H33N3S = 743.24) 267 m / z = 855.03 (C 63 H 42 N 4 = 854.34) 268 m / z = 829.00 (C61 H40 N4 = 828.33) 269 m / z = 591.72 (C41 H25 N3 S = 591.18) 270 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 271 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 272 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 273 m / z = 743.91 (C53H33N3S = 743.24) 274 m / z = 820.01 (C59 H37 N3 S = 819.27) 275 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 276 m / z = 743.91 (C53H33N3S = 743.24) 277 m / z = 743.91 (C53H33N3S = 743.24) 278 m / z = 820.01 (C59 H37 N3 S = 819.27) 279 m / z = 591.72 (C41 H25 N3 S = 591.18) 280 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 281 m / z = 743.91 (C53H33N3S = 743.24) 282 m / z = 591.72 (C41 H25 N3 S = 591.18) 283 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 284 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 285 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 286 m / z = 743.91 (C53H33N3S = 743.24) 287 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 288 m / z = 743.91 (C53H33N3S = 743.24) 289 m / z = 743.91 (C53H33N3S = 743.24) 290 m / z = 591.72 (C41 H25 N3 S = 591.18) 291 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 292 m / z = 591.72 (C41 H25 N3 S = 591.18) 293 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 294 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 295 m / z = 743.91 (C53H33N3S = 743.24) 296 m / z = 820.01 (C59 H37 N3 S = 819.27) 297 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 298 m / z = 743.91 (C53H33N3S = 743.24) 299 m / z = 743.91 (C53H33N3S = 743.24) 300 m / z = 820.01 (C59 H37 N3 S = 819.27) 301 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 302 m / z = 743.91 (C53H33N3S = 743.24) 303 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 304 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 305 m / z = 641.78 (C45H27N3S = 641.19) 306 m / z = 717.88 (C51 H31 N3 S = 717.22) 307 m / z = 641.78 (C45H27N3S = 641.19) 308 m / z = 717.88 (C51 H31 N3 S = 717.22) 309 m / z = 717.88 (C51 H31 N3 S = 717.22) 310 m / z = 717.88 (C51 H31 N3 S = 717.22) 311 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 312 m / z = 717.88 (C51 H31 N3 S = 717.22) 313 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 314 m / z = 641.78 (C45H27N3S = 641.19) 315 m / z = 717.88 (C51 H31 N3 S = 717.22) 316 m / z = 641.78 (C45H27N3S = 641.19) 317 m / z = 717.88 (C51 H31 N3 S = 717.22) 318 m / z = 717.88 (C51 H31 N3 S = 717.22) 319 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 320 m / z = 717.88 (C51 H31 N3 S = 717.22) 321 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 322 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 323 m / z = 641.78 (C45H27N3S = 641.19) 324 m / z = 717.88 (C51 H31 N3 S = 717.22) 325 m / z = 641.78 (C45H27N3S = 641.19) 326 m / z = 717.88 (C51 H31 N3 S = 717.22) 327 m / z = 717.88 (C51 H31 N3 S = 717.22) 328 m / z = 717.88 (C51 H31 N3 S = 717.22) 329 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 330 m / z = 717.88 (C51 H31 N3 S = 717.22) 331 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 332 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 333 m / z = 641.78 (C45H27N3S = 641.19) 334 m / z = 717.88 (C51 H31 N3 S = 717.22) 335 m / z = 641.78 (C45H27N3S = 641.19) 336 m / z = 717.88 (C51 H31 N3 S = 717.22) 337 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 338 m / z = 717.88 (C51 H31 N3 S = 717.22) 339 m / z = 717.88 (C51 H31 N3 S = 717.22) 340 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 341 m / z = 717.88 (C51 H31 N3 S = 717.22) 342 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 343 m / z = 717.88 (C51 H31 N3 S = 717.22) 344 m / z = 691.84 (C49H29N3S = 691.21) 345 m / z = 691.84 (C49H29N3S = 691.21) 346 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 347 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 348 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 349 m / z = 691.84 (C49H29N3S = 691.21) 350 m / z = 691.84 (C49H29N3S = 691.21) 351 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 352 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 353 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 354 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 355 m / z = 691.84 (C49H29N3S = 691.21) 356 m / z = 691.84 (C49H29N3S = 691.21) 357 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 358 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 359 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 360 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 361 m / z = 691.84 (C49H29N3S = 691.21) 362 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 363 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 364 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 365 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 366 m / z = 780.93 (C 55 H 32 N 4 S = 780.23) 367 m / z = 808.00 (C 58 H 37 N 3 S = 807.27) 368 m / z = 706.85 (C49H30N4S = 706.22) 369 m / z = 706.85 (C49H30N4S = 706.22) 370 m / z = 707.84 (C49H29N3OS = 707.20) 371 m / z = 707.84 (C49H29N3OS = 707.20) 372 m / z = 723.90 (C49H29N3S2 = 723.18) 373 m / z = 723.90 (C49H29N3S2 = 723.18) 374 m / z = 525.60 (C37 H23 N3 O = 525.18) 375 m / z = 601.69 (C43H27N3O = 601.22) 376 m / z = 677.79 (C49 H31 N3 O = 677.25) 377 m / z = 525.60 (C37 H23 N3 O = 525.18) 378 m / z = 601.69 (C43H27N3O = 601.22) 379 m / z = 601.69 (C43H27N3O = 601.22) 380 m / z = 601.69 (C43H27N3O = 601.22) 381 m / z = 677.79 (C49 H31 N3 O = 677.25) 382 m / z = 677.79 (C49 H31 N3 O = 677.25) 383 m / z = 753.89 (C 55 H 35 N 3 O = 753.28) 384 m / z = 753.89 (C 55 H 35 N 3 O = 753.28) 385 m / z = 601.69 (C43H27N3O = 601.22) 386 m / z = 677.79 (C49 H31 N3 O = 677.25) 387 m / z = 677.79 (C49 H31 N3 O = 677.25) 388 m / z = 525.60 (C37 H23 N3 O = 525.18) 389 m / z = 601.69 (C43H27N3O = 601.22) 390 m / z = 525.60 (C37 H23 N3 O = 525.18) 391 m / z = 601.69 (C43H27N3O = 601.22) 392 m / z = 601.69 (C43H27N3O = 601.22) 393 m / z = 677.79 (C49 H31 N3 O = 677.25) 394 m / z = 601.69 (C43H27N3O = 601.22) 395 m / z = 677.79 (C49 H31 N3 O = 677.25) 396 m / z = 753.89 (C 55 H 35 N 3 O = 753.28) 397 m / z = 601.69 (C43H27N3O = 601.22) 398 m / z = 677.79 (C49 H31 N3 O = 677.25) 399 m / z = 677.79 (C49 H31 N3 O = 677.25) 400 m / z = 753.89 (C 55 H 35 N 3 O = 753.28) 401 m / z = 525.60 (C37 H23 N3 O = 525.18) 402 m / z = 601.69 (C43H27N3O = 601.22) 403 m / z = 525.60 (C37 H23 N3 O = 525.18) 404 m / z = 601.69 (C43H27N3O = 601.22) 405 m / z = 601.69 (C43H27N3O = 601.22) 406 m / z = 601.69 (C43H27N3O = 601.22) 407 m / z = 677.79 (C49 H31 N3 O = 677.25) 408 m / z = 753.89 (C 55 H 35 N 3 O = 753.28) 409 m / z = 601.69 (C43H27N3O = 601.22) 410 m / z = 677.79 (C49 H31 N3 O = 677.25) 411 m / z = 677.79 (C49 H31 N3 O = 677.25) 412 m / z = 753.89 (C 55 H 35 N 3 O = 753.28) 413 m / z = 525.60 (C37 H23 N3 O = 525.18) 414 m / z = 601.69 (C43H27N3O = 601.22) 415 m / z = 525.60 (C37 H23 N3 O = 525.18) 416 m / z = 601.69 (C43H27N3O = 601.22) 417 m / z = 601.69 (C43H27N3O = 601.22) 418 m / z = 601.69 (C43H27N3O = 601.22) 419 m / z = 677.79 (C49 H31 N3 O = 677.25) 420 m / z = 753.89 (C 55 H 35 N 3 O = 753.28) 421 m / z = 601.69 (C43H27N3O = 601.22) 422 m / z = 677.79 (C49 H31 N3 O = 677.25) 423 m / z = 677.79 (C49 H31 N3 O = 677.25) 424 m / z = 753.89 (C 55 H 35 N 3 O = 753.28) 425 m / z = 575.66 (C41 H25 N3 O = 575.20) 426 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 427 m / z = 575.66 (C41 H25 N3 O = 575.20) 428 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 429 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 430 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 431 m / z = 727.85 (C 53 H 33 N 3 O = 717.22) 432 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 433 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 434 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 435 m / z = 803.94 (C59 H37 N3 O = 803.29) 436 m / z = 575.66 (C41 H25 N3 O = 575.20) 437 m / z = 575.66 (C41 H25 N3 O = 641.19) 438 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 439 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 440 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 441 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 442 m / z = 803.94 (C59 H37 N3 O = 803.29) 443 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 444 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 445 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 446 m / z = 803.94 (C59 H37 N3 O = 803.29) 447 m / z = 575.66 (C41 H25 N3 O = 575.20) 448 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 449 m / z = 575.66 (C41 H25 N3 O = 575.20) 450 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 451 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 452 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 453 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 454 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 455 m / z = 803.94 (C59 H37 N3 O = 803.29) 456 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 457 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 458 m / z = 803.94 (C59 H37 N3 O = 803.29) 459 m / z = 575.66 (C41 H25 N3 O = 575.20) 460 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 461 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 462 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 463 m / z = 803.94 (C59 H37 N3 O = 803.29) 464 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 465 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 466 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 467 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 468 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 469 m / z = 651.75 (C 47 H 29 N 3 O = 793.26) 470 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 471 m / z = 625.72 (C45H27N3O = 625.22) 472 m / z = 701.81 (C51 H31 N3 O = 701.25) 473 m / z = 625.72 (C45H27N3O = 625.22) 474 m / z = 701.81 (C51 H31 N3 O = 701.25) 475 m / z = 701.81 (C51 H31 N3 O = 701.25) 476 m / z = 701.81 (C51 H31 N3 O = 701.25) 478 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 479 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 480 m / z = 625.72 (C45H27N3O = 625.22) 481 m / z = 701.81 (C51 H31 N3 O = 701.25) 482 m / z = 625.72 (C45H27N3O = 625.22) 483 m / z = 701.81 (C51 H31 N3 O = 701.25) 484 m / z = 701.81 (C51 H31 N3 O = 701.25) 485 m / z = 701.81 (C51 H31 N3 O = 701.25) 486 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 487 m / z = 701.81 (C51 H31 N3 O = 701.25) 488 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 489 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 490 m / z = 625.72 (C45H27N3O = 625.22) 491 m / z = 701.81 (C51 H31 N3 O = 701.25) 492 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 493 m / z = 625.72 (C45H27N3O = 625.22) 494 m / z = 701.81 (C51 H31 N3 O = 701.25) 495 m / z = 701.81 (C51 H31 N3 O = 701.25) 496 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 497 m / z = 701.81 (C51 H31 N3 O = 701.25) 498 m / z = 701.81 (C51 H31 N3 O = 701.25) 499 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 500 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 501 m / z = 625.72 (C45H27N3O = 625.22) 502 m / z = 701.81 (C51 H31 N3 O = 701.25) 503 m / z = 625.72 (C45H27N3O = 625.22) 504 m / z = 701.81 (C51 H31 N3 O = 701.25) 505 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 506 m / z = 701.81 (C51 H31 N3 O = 701.25) 507 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 508 m / z = 701.81 (C51 H31 N3 O = 701.25) 509 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 510 m / z = 701.81 (C51 H31 N3 O = 701.25) 511 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 512 m / z = 701.81 (C51 H31 N3 O = 701.25) 513 m / z = 675.77 (C49H29N3O = 675.23) 514 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 515 m / z = 675.77 (C49H29N3O = 675.23) 516 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 517 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 518 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 519 m / z = 675.77 (C49H29N3O = 675.23) 520 m / z = 675.77 (C49H29N3O = 675.23) 521 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 522 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 523 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 524 m / z = 675.77 (C49H29N3O = 675.23) 525 m / z = 675.77 (C49H29N3O = 675.23) 526 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 527 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 528 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 529 m / z = 675.77 (C49H29N3O = 675.23) 530 m / z = 675.77 (C49H29N3O = 675.23) 531 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 532 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 533 m / z = 764.87 (C 55 H 32 N 4 O = 764.26) 534 m / z = 791.93 (C 58 H 37 N 3 O = 791.29) 535 m / z = 690.79 (C49H30N4O = 690.24) 536 m / z = 690.79 (C49H30N4O = 690.24) 537 m / z = 691.77 (C49H29N3O2 = 691.23) 538 m / z = 691.77 (C49H29N3O2 = 691.23) 539 m / z = 707.84 (C49H29N3OS = 707.20) 540 m / z = 707.84 (C49H29N3OS = 707.20) 541 m / z = 542.65 (C36H22N4S = 542.16) 542 m / z = 618.75 (C42H26N4S = 618.19) 543 m / z = 694.84 (C48H30N4S = 694.22) 544 m / z = 542.65 (C36H22N4S = 542.16) 545 m / z = 618.75 (C42H26N4S = 618.19) 546 m / z = 592.71 (C40H24N4S = 592.17) 547 m / z = 668.81 (C46H28N4S = 668.20) 548 m / z = 592.71 (C40H24N4S = 592.17) 549 m / z = 668.81 (C46H28N4S = 668.20) 550 m / z = 642.77 (C44H26N4S = 642.19) 551 m / z = 718.87 (C50H30N4S = 718.22) 552 m / z = 642.77 (C44H26N4S = 642.19) 553 m / z = 718.87 (C50H30N4S = 718.22) 554 m / z = 692.83 (C 48 H 28 N 4 S = 692.20) 555 m / z = 768.92 (C54 H32 N4 S = 768.23) 556 m / z = 692.83 (C 48 H 28 N 4 S = 692.20) 557 m / z = 768.92 (C54 H32 N4 S = 768.23) 558 m / z = 526.59 (C36H22N4O = 526.18) 559 m / z = 602.68 (C42H26N4O = 602.21) 560 m / z = 526.59 (C36H22N4O = 526.18) 561 m / z = 602.68 (C42H26N4O = 602.21) 562 m / z = 576.64 (C40 H24 N4 O = 576.20) 563 m / z = 652.74 (C46H28N4O = 652.23) 564 m / z = 576.64 (C40 H24 N4 O = 576.20) 565 m / z = 652.74 (C46H28N4O = 652.23) 566 m / z = 626.70 (C44H26N4O = 626.21) 567 m / z = 702.80 (C50H30N4O = 702.24) 568 m / z = 626.70 (C44H26N4O = 626.21) 569 m / z = 702.80 (C50H30N4O = 702.24) 570 m / z = 676.76 (C48H28N4O = 676.23) 571 m / z = 752.86 (C54 H32 N4 O = 752.26) 572 m / z = 676.76 (C48H28N4O = 676.23) 573 m / z = 752.86 (C54 H32 N4 O = 752.26) 574 m / z = 618.75 (C42H26N4S = 618.19) 575 m / z = 694.84 (C48H30N4S = 694.22) 576 m / z = 694.84 (C48H30N4S = 694.22) 577 m / z = 770.94 (C54 H34 N4 S = 770.25) 578 m / z = 770.94 (C54 H34 N4 S = 770.25) 579 m / z = 618.75 (C42H26N4S = 618.19) 580 m / z = 618.75 (C42H26N4S = 618.19) 581 m / z = 694.84 (C48H30N4S = 694.22) 582 m / z = 618.75 (C42H26N4S = 618.19) 583 m / z = 618.75 (C42H26N4S = 618.19) 584 m / z = 694.84 (C48H30N4S = 694.22) 585 m / z = 618.75 (C42H26N4S = 618.19) 586 m / z = 618.75 (C42H26N4S = 618.19) 587 m / z = 618.75 (C42H26N4S = 618.19) 588 m / z = 770.94 (C54 H34 N4 S = 770.25) 589 m / z = 618.75 (C42H26N4S = 618.19) 590 m / z = 707.84 (C48H29N5S = 707.21) 591 m / z = 734.91 (C51H34N4S = 734.25) 592 m / z = 663.76 (C45H30NOPS = 663.18) 593 m / z = 668.81 (C46H28N4S = 668.20) 594 m / z = 744.90 (C52H32N4S = 744.23) 595 m / z = 668.81 (C46H28N4S = 668.20) 596 m / z = 744.90 (C52H32N4S = 744.23) 597 m / z = 668.81 (C46H28N4S = 668.20) 598 m / z = 668.81 (C46H28N4S = 668.20) 599 m / z = 744.90 (C52H32N4S = 744.23) 600 m / z = 668.81 (C46H28N4S = 668.20) 601 m / z = 668.81 (C46H28N4S = 668.20) 602 m / z = 744.90 (C52H32N4S = 744.23) 603 m / z = 668.81 (C46H28N4S = 668.20) 604 m / z = 718.87 (C50H30N4S = 718.22) 605 m / z = 794.96 (C56H34N4S = 794.25) 606 m / z = 718.87 (C50H30N4S = 718.22) 607 m / z = 718.87 (C50H30N4S = 718.22) 608 m / z = 794.96 (C56H34N4S = 794.25) 609 m / z = 718.87 (C50H30N4S = 718.22) 610 m / z = 768.92 (C54 H32 N4 S = 768.23) 611 m / z = 768.92 (C54 H32 N4 S = 768.23) 612 m / z = 768.92 (C54 H32 N4 S = 768.23) 613 m / z = 768.92 (C54 H32 N4 S = 768.23) 614 m / z = 768.92 (C54 H32 N4 S = 768.23) 615 m / z = 768.92 (C54 H32 N4 S = 768.23) 616 m / z = 768.92 (C54 H32 N4 S = 768.23) 617 m / z = 768.92 (C54 H32 N4 S = 768.23) 618 m / z = 708.83 (C48H28N4OS = 708.20) 619 m / z = 784.92 (C54 H32 N4 OS = 784.23) 620 m / z = 708.83 (C48H28N4OS = 708.20) 621 m / z = 708.83 (C48H28N4OS = 708.20) 622 m / z = 784.92 (C54 H32 N4 OS = 784.23) 623 m / z = 708.83 (C48H28N4OS = 708.20) 624 m / z = 708.83 (C48H28N4OS = 708.20) 625 m / z = 784.92 (C54 H32 N4 OS = 784.23) 626 m / z = 708.83 (C48H28N4OS = 708.20) 627 m / z = 708.83 (C48H28N4OS = 708.20) 628 m / z = 784.92 (C54 H32 N4 OS = 784.23) 629 m / z = 708.83 (C48H28N4OS = 708.20) 630 m / z = 784.92 (C54 H32 N4 OS = 784.23) 631 m / z = 784.92 (C54 H32 N4 OS = 784.23) 632 m / z = 784.92 (C54 H32 N4 OS = 784.23) 633 m / z = 784.92 (C54 H32 N4 OS = 784.23) 634 m / z = 724.89 (C48H28N4S2 = 724.18) 635 m / z = 800.99 (C54 H32 N4 S2 = 717.22) 636 m / z = 724.89 (C48H28N4S2 = 724.18) 637 m / z = 724.89 (C48H28N4S2 = 724.18) 638 m / z = 800.99 (C54 H32 N4 S2 = 800.21) 639 m / z = 724.89 (C48H28N4S2 = 717.22) 640 m / z = 724.89 (C48H28N4S2 = 724.18) 641 m / z = 800.99 (C51 H31 N3 S = 717.22) 642 m / z = 723.90 (C49H29N3S2 = 723.18) 643 m / z = 724.89 (C48H28N4S2 = 724.18) 644 m / z = 800.99 (C54 H32 N4 S2 = 800.21) 645 m / z = 724.89 (C48H28N4S2 = 724.18) 646 m / z = 800.99 (C54 H32 N4 S2 = 800.21) 647 m / z = 800.99 (C54 H32 N4 S2 = 800.21) 648 m / z = 800.99 (C54 H32 N4 S2 = 800.21) 649 m / z = 800.99 (C54 H32 N4 S2 = 717.22) 650 m / z = 783.94 (C54 H33 N5 S = 783.25) 651 m / z = 783.94 (C54 H33 N5 S = 783.25) 652 m / z = 784.92 (C54 H32 N4 OS = 784.23) 653 m / z = 784.92 (C54 H32 N4 OS = 784.23) 654 m / z = 800.99 (C54 H32 N4 S2 = 800.21) 655 m / z = 800.99 (C54 H32 N4 S2 = 800.21) 656 m / z = 602.68 (C42H26N4O = 602.21) 657 m / z = 678.78 (C48H30N4O = 678.24) 658 m / z = 678.78 (C48H30N4O = 678.24) 659 m / z = 754.87 (C54 H34 N4 O = 754.27) 660 m / z = 602.68 (C42H26N4O = 602.21) 661 m / z = 602.68 (C42H26N4O = 602.21) 662 m / z = 602.68 (C42H26N4O = 602.21) 663 m / z = 691.78 (C48H29N5O = 691.24) 664 m / z = 718.84 (C51 H34 N4 O = 718.27) 665 m / z = 602.68 (C42H26N4O = 602.21) 666 m / z = 678.78 (C48H30N4O = 678.24) 667 m / z = 602.68 (C42H26N4O = 602.21) 668 m / z = 678.78 (C48H30N4O = 678.24) 669 m / z = 602.68 (C42H26N4O = 602.21) 670 m / z = 602.68 (C42H26N4O = 602.21) 671 m / z = 678.78 (C48H30N4O = 678.24) 672 m / z = 602.68 (C42H26N4O = 602.21) 673 m / z = 647.70 (C45 H30 NO2 P = 647.20) 674 m / z = 652.74 (C46H28N4O = 652.23) 675 m / z = 804.93 (C 58 H 36 N 4 O = 804.29) 676 m / z = 652.74 (C46H28N4O = 652.23) 677 m / z = 652.74 (C46H28N4O = 652.23) 678 m / z = 804.93 (C 58 H 36 N 4 O = 804.29) 679 m / z = 652.74 (C46H28N4O = 641.19) 680 m / z = 652.74 (C46H28N4O = 652.23) 681 m / z = 804.93 (C 58 H 36 N 4 O = 804.29) 682 m / z = 652.74 (C46H28N4O = 652.23) 683 m / z = 652.74 (C46H28N4O = 652.23) 684 m / z = 804.93 (C 58 H 36 N 4 O = 804.29) 685 m / z = 652.74 (C46H28N4O = 652.23) 686 m / z = 702.80 (C50H30N4O = 702.24) 687 m / z = 854.99 (C62H38N4O = 854.30) 688 m / z = 702.80 (C50H30N4O = 702.24) 689 m / z = 702.80 (C50H30N4O = 702.24) 690 m / z = 854.99 (C62H38N4O = 854.30) 691 m / z = 702.80 (C50H30N4O = 702.24) 692 m / z = 702.80 (C50H30N4O = 702.24) 693 m / z = 778.90 (C56H34N4O = 778.27) 694 m / z = 702.80 (C50H30N4O = 702.24) 695 m / z = 702.80 (C50H30N4O = 702.24) 696 m / z = 778.90 (C56H34N4O = 778.27) 697 m / z = 702.80 (C50H30N4O = 702.24) 698 m / z = 752.86 (C54 H32 N4 O = 752.26) 699 m / z = 752.86 (C54 H32 N4 O = 752.26) 700 m / z = 752.86 (C54 H32 N4 O = 752.26) 701 m / z = 752.86 (C54 H32 N4 O = 752.26) 702 m / z = 752.86 (C54 H32 N4 O = 752.26) 703 m / z = 752.86 (C54 H32 N4 O = 752.26) 704 m / z = 752.86 (C54 H32 N4 O = 752.26) 705 m / z = 752.86 (C54 H32 N4 O = 752.26) 706 m / z = 692.76 (C48H28N4O2 = 692.22) 707 m / z = 768.86 (C54 H32 N4 O2 = 768.25) 708 m / z = 692.76 (C48H28N4O2 = 692.22) 709 m / z = 692.76 (C48H28N4O2 = 692.22) 710 m / z = 768.86 (C54 H32 N4 O2 = 768.25) 711 m / z = 692.76 (C48H28N4O2 = 692.22) 712 m / z = 692.76 (C48H28N4O2 = 692.22) 713 m / z = 768.86 (C54 H32 N4 O2 = 768.25) 714 m / z = 692.76 (C48H28N4O2 = 692.22) 715 m / z = 692.76 (C48H28N4O2 = 692.22) 716 m / z = 768.86 (C54 H32 N4 O2 = 768.25) 717 m / z = 692.76 (C48H28N4O2 = 692.22) 718 m / z = 768.86 (C54 H32 N4 O2 = 768.25) 719 m / z = 768.86 (C54 H32 N4 O2 = 768.25) 720 m / z = 768.86 (C54 H32 N4 O2 = 768.25) 721 m / z = 768.86 (C54 H32 N4 O2 = 768.25) 722 m / z = 708.83 (C48H28N4OS = 708.20) 723 m / z = 784.92 (C54 H32 N4 OS = 784.23) 724 m / z = 708.83 (C48H28N4OS = 708.20) 725 m / z = 708.83 (C48H28N4OS = 708.20) 726 m / z = 708.83 (C48H28N4OS = 708.20) 727 m / z = 708.83 (C48H28N4OS = 708.20) 728 m / z = 784.92 (C54 H32 N4 OS = 784.23) 729 m / z = 708.83 (C48H28N4OS = 708.20) 730 m / z = 708.83 (C48H28N4OS = 708.20) 731 m / z = 784.92 (C54 H32 N4 OS = 784.23) 732 m / z = 708.83 (C48H28N4OS = 708.20) 733 m / z = 784.92 (C54 H32 N4 OS = 784.23) 734 m / z = 784.92 (C54 H32 N4 OS = 784.23) 735 m / z = 784.92 (C54 H32 N4 OS = 784.23) 736 m / z = 784.92 (C54 H32 N4 OS = 784.23) 737 m / z = 767.87 (C54 H33 N5 O = 767.27) 738 m / z = 767.87 (C54 H33 N5 O = 767.27) 739 m / z = 768.86 (C54 H32 N4 O2 = 768.25) 740 m / z = 768.86 (C54 H32 N4 O2 = 768.25) 741 m / z = 784.92 (C54 H32 N4 OS = 784.23) 742 m / z = 784.92 (C54 H32 N4 OS = 784.23) 743 m / z = 617.76 (C43H27N3S = 617.19) 744 m / z = 693.86 (C49 H31 N3 S = 693.22) 745 m / z = 693.86 (C49 H31 N3 S = 693.22) 746 m / z = 769.95 (C 55 H 35 N 3 S = 769.26) 747 m / z = 617.76 (C43H27N3S = 617.19) 748 m / z = 693.86 (C49 H31 N3 S = 693.22) 749 m / z = 769.95 (C 55 H 35 N 3 S = 769.26) 750 m / z = 617.76 (C43H27N3S = 617.19) 751 m / z = 769.95 (C 55 H 35 N 3 S = 769.26) 752 m / z = 617.76 (C43H27N3S = 617.19) 753 m / z = 693.86 (C49 H31 N3 S = 693.22) 754 m / z = 693.86 (C49 H31 N3 S = 693.22) 755 m / z = 618.75 (C42H26N4S = 618.19) 756 m / z = 617.76 (C43H27N3S = 617.19) 757 m / z = 693.86 (C49 H31 N3 S = 693.22) 758 m / z = 617.76 (C43H27N3S = 617.19) 759 m / z = 693.86 (C49 H31 N3 S = 693.22) 760 m / z = 769.95 (C 55 H 35 N 3 S = 769.26) 761 m / z = 617.76 (C43H27N3S = 617.19) 762 m / z = 693.86 (C49 H31 N3 SS = 693.22) 763 m / z = 617.76 (C43H27N3S = 617.19) 764 m / z = 693.86 (C49 H31 N3 S = 693.22) 765 m / z = 769.95 (C 55 H 35 N 3 S = 769.26) 766 m / z = 617.76 (C43H27N3S = 617.19) 767 m / z = 617.76 (C43H27N3S = 617.19) 768 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 769 m / z = 743.91 (C53H33N3S = 743.24) 770 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 771 m / z = 743.91 (C53H33N3S = 743.24) 772 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 773 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 774 m / z = 743.91 (C53H33N3S = 743.24) 775 m / z = 743.91 (C53H33N3S = 743.24) 776 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 777 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 778 m / z = 743.24 (C53H33N3S = 743.24) 779 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 780 m / z = 743.91 (C53H33N3S = 743.24) 781 m / z = 667.21 (C 47 H 29 N 3 S = 667.21) 782 m / z = 743.91 (C53H33N3S = 743.24) 783 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 784 m / z = 743.91 (C53H33N3S = 743.24) 785 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 786 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 787 m / z = 717.88 (C51 H31 N3 S = 717.22) 788 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 789 m / z = 717.88 (C51 H31 N3 S = 717.22) 790 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 791 m / z = 717.88 (C51 H31 N3 S = 717.22) 792 m / z = 717.88 (C51 H31 N3 S = 717.22) 793 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 794 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 795 m / z = 717.88 (C51 H31 N3 S = 717.22) 796 m / z = 717.88 (C51 H31 N3 S = 717.22) 797 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 798 m / z = 717.88 (C51 H31 N3 S = 717.22) 799 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 800 m / z = 717.88 (C51 H31 N3 S = 717.22) 801 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 802 m / z = 717.88 (C51 H31 N3 S = 717.22) 803 m / z = 793.97 (C 57 H 35 N 3 S = 793.26) 804 m / z = 717.88 (C51 H31 N3 S = 717.22) 805 m / z = 717.88 (C51 H31 N3 S = 717.22) 806 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 807 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 808 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 809 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 810 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 811 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 812 m / z = 707.84 (C49H29N3OS = 707.20) 813 m / z = 707.84 (C49H29N3OS = 707.20) 814 m / z = 707.84 (C49H29N3OS = 707.20) 815 m / z = 707.84 (C49H29N3OS = 707.20) 816 m / z = 707.84 (C49H29N3OS = 707.20) 817 m / z = 723.90 (C49H29N3S2 = 723.18) 818 m / z = 723.90 (C49H29N3S2 = 723.18) 819 m / z = 723.90 (C49H29N3S2 = 723.18) 820 m / z = 723.90 (C49H29N3S2 = 723.18) 821 m / z = 723.90 (C49H29N3S2 = 723.18) 822 m / z = 706.85 (C49H30N4S = 706.22) 823 m / z = 733.92 (C52H35N3S = 733.26) 824 m / z = 782.95 (C 55 H 34 N 4 S = 782.25) 825 m / z = 782.95 (C 55 H 34 N 4 S = 782.25) 826 m / z = 783.94 (C 55 H 33 N 3 OS = 783.23) 827 m / z = 783.94 (C 55 H 33 N 3 OS = 783.23) 828 m / z = 800.00 (C 55 H 33 N 3 S 2 = 799.21) 829 m / z = 800.00 (C 55 H 33 N 3 S 2 = 799.21) 830 m / z = 601.69 (C43H27N3O = 601.22) 831 m / z = 677.79 (C49 H31 N3 O = 677.25) 832 m / z = 753.89 (C 55 H 35 N 3 O = 753.28) 833 m / z = 601.69 (C43H27N3O = 601.22) 834 m / z = 677.79 (C49 H31 N3 O = 677.25) 835 m / z = 677.79 (C49 H31 N3 O = 677.25) 836 m / z = 601.69 (C43H27N3O = 601.22) 837 m / z = 677.79 (C49 H31 N3 O = 677.25) 838 m / z = 601.69 (C43H27N3O = 601.22) 839 m / z = 677.79 (C49 H31 N3 O = 677.25) 840 m / z = 753.89 (C 55 H 35 N 3 O = 753.28) 841 m / z = 602.68 (C42H26N4O = 602.21) 842 m / z = 601.69 (C43H27N3O = 601.22) 843 m / z = 677.79 (C49 H31 N3 O = 677.25) 844 m / z = 601.69 (C43H27N3O = 601.22) 845 m / z = 677.79 (C49 H31 N3 O = 677.25) 846 m / z = 753.89 (C 55 H 35 N 3 O = 753.28) 847 m / z = 601.69 (C43H27N3O = 601.22) 848 m / z = 677.79 (C49 H31 N3 O = 677.25) 849 m / z = 601.69 (C43H27N3O = 601.22) 850 m / z = 677.79 (C49 H31 N3 O = 677.25) 851 m / z = 677.79 (C49 H31 N3 O = 677.25) 852 m / z = 753.89 (C 55 H 35 N 3 O = 753.28) 853 m / z = 601.69 (C43H27N3O = 601.22) 854 m / z = 601.69 (C43H27N3O = 601.22) 855 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 856 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 857 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 858 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 859 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 860 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 861 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 862 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 863 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 864 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 865 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 866 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 867 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 868 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 869 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 870 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 871 m / z = 727.85 (C 53 H 33 N 3 O = 727.26) 872 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 873 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 874 m / z = 701.81 (C51 H31 N3 O = 701.25) 875 m / z = 701.81 (C51 H31 N3 O = 701.25) 876 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 877 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 878 m / z = 701.81 (C51 H31 N3 O = 701.25) 879 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 880 m / z = 701.81 (C51 H31 N3 O = 701.25) 881 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 882 m / z = 701.81 (C51 H31 N3 O = 701.25) 883 m / z = 701.81 (C51 H31 N3 O = 701.25) 884 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 885 m / z = 701.81 (C51 H31 N3 O = 701.25) 886 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 887 m / z = 701.81 (C51 H31 N3 O = 701.25) 888 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 889 m / z = 701.81 (C51 H31 N3 O = 701.25) 890 m / z = 777.91 (C 57 H 35 N 3 O = 777.28) 891 m / z = 701.81 (C51 H31 N3 O = 701.25) 892 m / z = 701.81 (C51 H31 N3 O = 701.25) 893 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 894 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 895 m / z = 827.97 (C61 H37 N3 O = 827.29) 896 m / z = 827.97 (C61 H37 N3 O = 827.29) 897 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 898 m / z = 827.97 (C61 H37 N3 O = 827.29) 899 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 900 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 901 m / z = 691.77 (C49H29N3O2 = 691.23) 902 m / z = 691.77 (C49H29N3O2 = 691.23) 903 m / z = 767.87 (C 55 H 33 N 3 O 2 = 767.26) 904 m / z = 767.87 (C 55 H 33 N 3 O 2 = 767.26) 905 m / z = 691.77 (C49H29N3O2 = 691.23) 906 m / z = 767.87 (C 55 H 33 N 3 O 2 = 767.26) 907 m / z = 691.77 (C49H29N3O2 = 691.23) 908 m / z = 691.77 (C49H29N3O2 = 691.23) 909 m / z = 707.84 (C49H29N3OS = 707.20) 910 m / z = 707.84 (C49H29N3OS = 707.20) 911 m / z = 783.94 (C 55 H 33 N 3 OS = 783.23) 912 m / z = 783.94 (C 55 H 33 N 3 OS = 783.23) 913 m / z = 707.84 (C49H29N3OS = 707.20) 914 m / z = 783.94 (C 55 H 33 N 3 OS = 783.23) 915 m / z = 707.84 (C49H29N3OS = 707.20) 916 m / z = 707.84 (C49H29N3OS = 707.20) 917 m / z = 737.84 (C51 H32 NOPS = 737.19) 918 m / z = 690.79 (C49H30N4O = 690.24) 919 m / z = 717.85 (C52H35N3O = 717.28) 920 m / z = 766.88 (C 55 H 34 N 4 O = 766.27) 921 m / z = 766.88 (C 55 H 34 N 4 O = 766.27) 922 m / z = 767.87 (C 55 H 33 N 3 O 2 = 767.26) 923 m / z = 767.87 (C 55 H 33 N 3 O 2 = 767.26) 924 m / z = 783.94 (C 55 H 33 N 3 OS = 783.23) 925 m / z = 783.94 (C 55 H 33 N 3 OS = 783.23) 926 m / z = 592.71 (C40H24N4S = 592.17) 927 m / z = 757.90 (C52H31N5S = 757.23) 928 m / z = 758.89 (C52H30N4OS = 758.21) 929 m / z = 744.90 (C52H32N4S = 744.23) 930 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 931 m / z = 757.90 (C52H31N5S = 757.23) 932 m / z = 774.95 (C52H30N4S2 = 774.19) 933 m / z = 820.01 (C59 H37 N3 S = 819.27) 934 m / z = 756.91 (C53 H32 N4 S = 756.23) 935 m / z = 757.90 (C53H31N3OS = 757.22) 936 m / z = 668.81 (C46H28N4S = 668.20) 937 m / z = 637.73 (C43H28NOPS = 637.16) 938 m / z = 576.64 (C40 H24 N4 O = 576.20) 939 m / z = 741.84 (C52H31N5O = 741.25) 940 m / z = 742.82 (C52H30N4O2 = 742.24) 941 m / z = 728.84 (C52H32N4O = 728.26) 942 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 943 m / z = 741.84 (C52H31N5O = 741.25) 944 m / z = 758.89 (C52H30N4OS = 758.21) 945 m / z = 803.94 (C59 H37 N3 O = 803.29) 946 m / z = 740.85 (C 53 H 32 N 4 O = 740.26) 947 m / z = 741.83 (C 53 H 31 N 3 O 2 = 741.24) 948 m / z = 652.74 (C46H28N4O = 652.23) 949 m / z = 621.66 (C43H28NO2P = 621.19) 950 m / z = 592.71 (C40H24N4S = 592.17) 951 m / z = 757.90 (C52H31N5S = 757.23) 952 m / z = 758.89 (C52H30N4OS = 758.21) 953 m / z = 744.90 (C52H32N4S = 744.23) 954 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 955 m / z = 757.90 (C52H31N5S = 757.23) 956 m / z = 774.95 (C52H30N4S2 = 774.19) 957 m / z = 820.01 (C59 H37 N3 S = 819.27) 958 m / z = 756.91 (C53 H32 N4 S = 756.23) 959 m / z = 757.90 (C53H31N3OS = 757.22) 960 m / z = 668.81 (C46H28N4S = 668.20) 961 m / z = 637.73 (C43H28NOPS = 637.16) 962 m / z = 576.64 (C40 H24 N4 O = 576.20) 963 m / z = 741.84 (C52H31N5O = 741.25) 964 m / z = 742.82 (C52H30N4O2 = 742.24) 965 m / z = 728.84 (C52H32N4O = 728.26) 966 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 967 m / z = 741.84 (C52H31N5O = 741.25) 968 m / z = 758.89 (C52H30N4OS = 758.21) 969 m / z = 803.94 (C59 H37 N3 O = 803.29) 970 m / z = 740.85 (C 53 H 32 N 4 O = 740.26) 971 m / z = 741.83 (C 53 H 31 N 3 O 2 = 741.24) 972 m / z = 652.74 (C46H28N4O = 652.23) 973 m / z = 621.66 (C43H28NO2P = 621.19) 974 m / z = 592.71 (C40H24N4S = 592.17) 975 m / z = 757.90 (C52H31N5S = 757.23) 976 m / z = 758.89 (C52H30N4OS = 758.21) 977 m / z = 744.90 (C52H32N4S = 744.23) 978 m / z = 667.82 (C 47 H 29 N 3 S = 667.21) 979 m / z = 757.90 (C52H31N5S = 757.23) 980 m / z = 774.95 (C52H30N4S2 = 774.19) 981 m / z = 820.01 (C59 H37 N3 S = 819.27) 982 m / z = 756.91 (C53 H32 N4 S = 756.23) 983 m / z = 757.90 (C53H31N3OS = 757.22) 984 m / z = 668.81 (C46H28N4S = 668.20) 985 m / z = 637.73 (C43H28NOPS = 637.16) 986 m / z = 576.64 (C40 H24 N4 O = 576.20) 987 m / z = 741.84 (C52H31N5O = 741.25) 988 m / z = 742.82 (C52H30N4O2 = 742.24) 989 m / z = 728.84 (C52H32N4O = 728.26) 990 m / z = 651.75 (C 47 H 29 N 3 O = 651.23) 991 m / z = 741.84 (C52H31N5O = 741.25) 992 m / z = 758.89 (C52H30N4OS = 758.21) 993 m / z = 803.94 (C59 H37 N3 O = 803.29) 994 m / z = 740.85 (C 53 H 32 N 4 O = 740.26) 995 m / z = 741.83 (C 53 H 31 N 3 O 2 = 741.24) 996 m / z = 652.74 (C46H28N4O = 652.23) 997 m / z = 621.66 (C43H28NO2P = 621.19) 998 m / z = 641.78 (C45H27N3S = 641.19) 999 m / z = 691.84 (C49H29N3S = 691.21) 1000 m / z = 741.90 (C 53 H 31 N 3 S = 741.22) 1001 m / z = 791.96 (C 57 H 33 N 3 S = 791.24) 1002 m / z = 717.88 (C51 H31 N3 S = 717.22) 1003 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 1004 m / z = 717.88 (C51 H31 N3 S = 717.22) 1005 m / z = 767.94 (C 55 H 33 N 3 S = 767.24) 1006 m / z = 625.72 (C45H27N3O = 625.22) 1007 m / z = 675.77 (C49H29N3O = 675.23) 1008 m / z = 725.83 (C 53 H 31 N 3 O = 725.25) 1009 m / z = 775.89 (C 57 H 33 N 3 O = 775.26) 1010 m / z = 701.81 (C51 H31 N3 O = 701.25) 1011 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 1012 m / z = 701.81 (C51 H31 N3 O = 701.25) 1013 m / z = 751.87 (C 55 H 33 N 3 O = 751.26) 1014 m / z = 641.78 (C45H27N3S = 641.19) 1015 m / z = 691.84 (C49H29N3S = 691.21) 1016 m / z = 741.90 (C 53 H 31 N 3 S = 741.22) 1017 m / z = 791.96 (C 57 H 33 N 3 S = 791.24) 1018 m / z = 731.86 (C51 H29 N3 OS = 731.20) 1019 m / z = 747.93 (C51H29N3S2 = 747.18) 1020 m / z = 615.74 (C43H25N3S = 615.18) 1021 m / z = 615.74 (C43H25N3S = 615.18) 1022 m / z = 783.94 (C43H25N3S = 615.18) 1023 m / z = 625.72 (C45H27N3O = 625.22) 1024 m / z = 675.77 (C49H29N3O = 675.23) 1025 m / z = 725.83 (C 53 H 31 N 3 O = 725.25) 1026 m / z = 775.89 (C 57 H 33 N 3 O = 775.26) 1027 m / z = 715.79 (C51H29N3O2 = 715.23) 1028 m / z = 731.86 (C51 H29 N3 OS = 731.20) 1029 m / z = 599.68 (C43H25N3O = 599.20) 1030 m / z = 599.68 (C43H25N3O = 599.20) 1031 m / z = 599.68 (C43H25N3O = 599.20)

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

1) Fabrication of organic light emitting device

The transparent electrode ITO thin film obtained from the glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned for 5 minutes each using trichlorethylene, acetone, ethanol and distilled water sequentially, and stored in isopropanol before use.

Next, an ITO substrate was placed on a substrate folder of a vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenyl amine: 2-TNATA).

Subsequently, the chamber was evacuated until the degree of vacuum reached 10 -6 torr, and then a current was applied to the cell to evaporate 2-TNATA, thereby depositing a 600 Å thick hole injection layer on the ITO substrate.

N'-bis (? - naphthyl) -N, N'-diphenyl-4,4'-diamine (N, N'-diphenyl-4,4'-diamine: NPB) was added, and a current was applied to the cell to evaporate the hole transport layer to deposit a 300 Å thick hole transport layer.

After the hole injecting layer and the hole transporting layer were formed as described above, a blue light emitting material having the following structure was vapor-deposited as a light emitting layer thereon. Specifically, H1, a blue light emitting host material, was vacuum deposited on one cell in a vacuum vapor deposition apparatus to a thickness of 200 Å, and D1, a blue light emitting dopant material, was vacuum deposited by 5% on the host material.

Subsequently, one of the compounds shown in the following Table 60 was deposited as an electron transporting layer to a thickness of 300 ANGSTROM.

Lithium fluoride (LiF) was deposited as an electron injection layer to a thickness of 10 Å, and an Al cathode was formed to a thickness of 1,000 Å to fabricate an OLED device.

On the other hand, all organic compounds required for OLED device fabrication were vacuum sublimated and refined at 10 ^-6 to 10 ^-8 torr for each material,

Table 60 shows the results of measuring the driving voltage, the luminous efficiency, the color coordinate (CIE), and the lifetime of the blue organic light emitting device manufactured according to the present invention.

compound Driving voltage
(V) Luminous efficiency
(cd / A) CIE
(x, y) life span
(T95) Comparative Example 1 E1 5.70 6.00 (0.134, 0.102) 20 Comparative Example 2 E2 5.71 5.98 (0.134, 0.100) 22 Comparative Example 3 E3 5.70 6.03 (0.134, 0.101) 22 Comparative Example 4 E4 5.73 6.00 (0.134, 0.102) 20 Example 1 One 5.44 6.11 (0.134, 0.101) 34 Example 2 4 5.46 6.21 (0.134, 0.102) 36 Example 3 5 5.63 5.93 (0.134, 0.103) 40 Example 4 9 4.98 6.45 (0.134, 0.100) 39 Example 5 13 5.61 6.39 (0.134, 0.101) 35 Example 6 24 4.77 6.21 (0.134, 0.102) 37 Example 7 16 5.48 6.40 (0.134, 0.103) 37 Example 8 34 5.46 6.32 (0.134, 0.102) 36 Example 9 44 5.65 6.25 (0.134, 0.102) 40 Example 10 57 5.42 6.20 (0.134, 0.103) 45 Example 11 64 5.61 6.25 (0.134, 0.102) 42 Example 12 65 5.44 6.21 (0.134, 0.101) 38 Example 13 78 4.97 6.33 (0.134, 0.100) 41 Example 14 84 5.63 6.24 (0.134, 0.100) 39 Example 15 92 4.71 6.13 (0.134, 0.100) 44 Example 16 100 4.89 6.20 (0.134, 0.101) 40 Example 17 101 4.99 6.21 (0.134, 0.100) 38 Example 18 102 5.63 5.94 (0.134, 0.100) 35 Example 19 105 5.40 6.11 (0.134, 0.102) 22 Example 20 106 5.37 6.40 (0.134, 0.101) 40 Example 21 119 5.36 6.22 (0.134, 0.102) 39 Example 22 122 5.38 6.20 (0.134, 0.101) 42 Example 23 124 4.95 6.22 (0.134, 0.101) 39 Example 24 135 4.91 6.25 (0.134, 0.101) 37 Example 25 138 4.91 6.13 (0.134, 0.101) 43 Example 26 152 4.97 6.50 (0.134, 0.101) 38 Example 27 159 5.63 6.22 (0.134, 0.100) 42 Example 28 161 5.40 5.94 (0.134, 0.100) 35 Example 29 175 5.37 5.83 (0.134, 0.101) 37 Example 30 181 5.39 6.35 (0.134, 0.101) 41 Example 31 192 5.38 6.20 (0.134, 0.103) 40 Example 32 195 5.39 6.42 (0.134, 0.102) 43 Example 33 196 4.97 6.20 (0.134, 0.101) 38 Example 34 197 4.94 6.23 (0.134, 0.102) 34 Example 35 198 4.90 6.11 (0.134, 0.101) 38 Example 36 202 5.38 6.38 (0.134, 0.101) 39 Example 37 206 5.37 6.22 (0.134, 0.103) 40 Example 38 210 5.38 6.61 (0.134, 0.102) 41 Example 39 217 4.96 6.21 (0.134, 0.101) 37 Example 40 235 4.91 6.22 (0.134, 0.102) 33 Example 41 238 4.90 6.14 (0.134, 0.101) 40 Example 42 248 4.98 6.51 (0.134, 0.101) 39 Example 43 255 5.61 6.21 (0.134, 0.100) 41 Example 44 260 5.39 5.95 (0.134, 0.101) 35 Example 45 264 5.10 6.88 (0.134, 0.100) 41 Example 46 272 5.38 6.39 (0.134, 0.101) 39 Example 47 275 5.37 6.21 (0.134, 0.103) 40 Example 48 277 5.10 6.62 (0.134, 0.102) 43 Example 49 283 4.96 6.22 (0.134, 0.100) 41 Example 50 285 4.98 6.92 (0.134, 0.100) 43 Example 51 287 5.62 5.97 (0.134, 0.100) 39 Example 52 302 4.74 6.53 (0.134, 0.102) 41 Example 53 312 4.72 6.33 (0.134, 0.102) 42 Example 54 318 4.91 6.92 (0.134, 0.100) 45 Example 55 328 4.91 6.95 (0.134, 0.100) 40 Example 56 332 4.96 6.21 (0.134, 0.100) 40 Example 57 342 5.62 5.99 (0.134, 0.100) 36 Example 58 346 5.31 6.53 (0.134, 0.102) 34 Example 59 348 4.79 6.55 (0.134, 0.102) 47 Example 60 355 5.40 6.12 (0.134, 0.101) 39 Example 61 358 5.44 6.10 (0.134, 0.100) 41 Example 62 359 5.38 6.01 (0.134, 0.101) 34 Example 63 368 4.95 6.86 (0.134, 0.100) 45 Example 64 370 4.95 6.95 (0.134, 0.100) 39 Example 65 372 4.98 6.20 (0.134, 0.100) 40 Example 66 387 5.61 5.98 (0.134, 0.100) 33 Example 67 394 4.75 6.43 (0.134, 0.102) 43 Example 68 403 5.40 6.12 (0.134, 0.101) 39 Example 69 406 5.43 6.21 (0.134, 0.100) 40 Example 70 415 5.39 6.26 (0.134, 0.101) 36 Example 71 418 5.39 6.87 (0.134, 0.100) 45 Example 72 427 5.21 6.93 (0.134, 0.100) 44 Example 73 432 5.13 6.95 (0.134, 0.100) 40 Example 74 447 5.03 6.22 (0.134, 0.100) 40 Example 75 453 4.91 5.88 (0.134, 0.100) 33 Example 76 458 4.72 6.43 (0.134, 0.102) 48 Example 77 464 5.47 6.15 (0.134, 0.101) 39 Example 78 473 5.44 6.53 (0.134, 0.102) 49 Example 79 476 5.33 6.53 (0.134, 0.102) 42 Example 80 490 4.91 6.98 (0.134, 0.100) 43 Example 81 497 4.91 6.11 (0.134, 0.100) 35 Example 82 505 4.92 6.22 (0.134, 0.100) 40 Example 83 509 5.63 5.99 (0.134, 0.100) 38 Example 84 517 4.72 6.54 (0.134, 0.102) 48 Example 85 527 4.72 6.33 (0.134, 0.102) 40 Example 86 534 4.63 6.53 (0.134, 0.102) 43 Example 87 536 4.91 6.82 (0.134, 0.100) 41 Example 88 537 4.99 6.95 (0.134, 0.100) 39 Example 89 539 4.94 6.25 (0.134, 0.100) 40 Example 90 542 5.61 5.98 (0.134, 0.100) 33 Example 91 543 5.44 6.53 (0.134, 0.102) 41 Example 92 547 4.88 6.88 (0.134, 0.102) 42 Example 93 551 5.41 6.12 (0.134, 0.101) 40 Example 94 555 5.41 5.89 (0.134, 0.100) 39 Example 95 561 5.39 6.01 (0.134, 0.101) 31 Example 96 567 4.63 6.54 (0.134, 0.102) 48 Example 97 571 4.90 6.82 (0.134, 0.100) 43 Example 98 574 4.72 6.52 (0.134, 0.102) 38 Example 99 575 4.91 6.78 (0.134, 0.100) 42 Example 100 585 4.90 6.94 (0.134, 0.100) 40 Example 101 591 4.99 6.22 (0.134, 0.100) 40 Example 102 594 5.64 5.97 (0.134, 0.100) 33 Example 103 607 5.22 6.01 (0.134, 0.101) 33 Example 104 610 5.39 6.01 (0.134, 0.101) 36 Example 105 614 5.35 6.04 (0.134, 0.101) 33 Example 106 618 4.91 6.94 (0.134, 0.100) 43 Example 107 621 4.77 6.96 (0.134, 0.100) 41 Example 108 627 4.99 6.22 (0.134, 0.100) 40 Example 109 634 5.03 5.98 (0.134, 0.100) 42 Example 110 643 4.71 6.50 (0.134, 0.102) 41 Example 111 650 4.77 6.53 (0.134, 0.102) 48 Example 112 652 4.73 6.59 (0.134, 0.102) 45 Example 113 Synthesis of 657 5.42 6.12 (0.134, 0.101) 39 Example 114 667 4.72 6.53 (0.134, 0.102) 37 Example 115 674 4.91 6.78 (0.134, 0.100) 42 Example 116 684 5.45 5.89 (0.134, 0.100) 41 Example 117 687 5.36 6.03 (0.134, 0.101) 32 Example 118 692 4.96 6.83 (0.134, 0.100) 45 Example 119 695 4.94 6.93 (0.134, 0.100) 43 Example 120 700 4.94 6.95 (0.134, 0.100) 41 Example 121 708 5.34 6.13 (0.134, 0.101) 38 Example 122 723 4.86 6.77 (0.134, 0.100) 45 Example 123 729 4.95 6.73 (0.134, 0.102) 42 Example 124 734 4.91 6.55 (0.134, 0.100) 42 Example 125 737 5.31 6.29 (0.134, 0.100) 44 Example 126 739 5.26 6.10 (0.134, 0.100) 34 Example 127 741 5.34 6.25 (0.134, 0.102) 41 Example 128 744 5.31 6.57 (0.134, 0.102) 44 Example 129 746 4.72 6.53 (0.134, 0.102) 38 Example 130 758 4.79 6.54 (0.134, 0.102) 48 Example 131 768 5.41 6.13 (0.134, 0.101) 39 Example 132 781 5.13 5.89 (0.134, 0.100) 41 Example 133 789 5.31 6.03 (0.134, 0.101) 34 Example 134 796 5.19 6.88 (0.134, 0.100) 47 Example 135 802 5.26 6.71 (0.134, 0.100) 39 Example 136 804 5.21 6.66 (0.134, 0.100) 45 Example 137 807 4.94 6.83 (0.134, 0.100) 38 Example 138 813 5.34 6.53 (0.134, 0.100) 46 Example 139 818 5.33 6.04 (0.134, 0.100) 41 Example 140 824 5.11 6.88 (0.134, 0.100) 45 Example 141 826 5.11 6.88 (0.134, 0.100) 45 Example 142 [ 830 5.61 5.92 (0.134, 0.100) 33 Example 143 831 5.44 6.53 (0.134, 0.102) 40 Example 144 844 4.88 6.88 (0.134, 0.102) 42 Example 145 855 5.40 6.12 (0.134, 0.101) 41 Example 146 861 5.44 5.88 (0.134, 0.100) 39 Example 147 877 5.39 6.02 (0.134, 0.101) 31 Example 148 883 4.66 6.54 (0.134, 0.102) 48 Example 149 894 4.90 6.82 (0.134, 0.100) 40 Example 150 902 4.72 6.52 (0.134, 0.102) 38 Example 151 907 4.91 6.77 (0.134, 0.100) 42 Example 152 910 4.93 6.94 (0.134, 0.100) 40 Example 153 917 4.99 6.22 (0.134, 0.100) 40 Example 154 918 5.44 5.89 (0.134, 0.100) 41 Example 155 919 5.36 6.03 (0.134, 0.101) 38 Example 156 920 4.97 6.83 (0.134, 0.100) 45 Example 157 923 4.94 6.96 (0.134, 0.100) 44 Example 158 925 4.92 6.95 (0.134, 0.100) 39 Example 159 926 5.19 6.88 (0.134, 0.100) 47 Example 160 927 5.49 6.16 (0.134, 0.101) 39 Example 161 928 5.44 6.53 (0.134, 0.102) 48 Example 162 932 5.37 6.53 (0.134, 0.102) 42 Example 163 936 4.91 6.96 (0.134, 0.100) 44 Example 164 937 4.90 6.11 (0.134, 0.100) 35 Example 165 943 4.92 6.22 (0.134, 0.100) 42 Example 166 945 5.64 5.99 (0.134, 0.100) 38 Example 167 950 4.72 6.55 (0.134, 0.102) 48 Example 168 952 4.72 6.33 (0.134, 0.102) 41 Example 169 954 4.64 6.53 (0.134, 0.102) 43 Example 170 956 4.91 6.82 (0.134, 0.100) 43 Example 171 959 4.97 6.95 (0.134, 0.100) 39 Example 172 961 4.94 6.24 (0.134, 0.100) 40 Example 173 962 5.61 5.98 (0.134, 0.100) 34 Example 174 969 5.42 6.53 (0.134, 0.102) 41 Example 175 971 4.88 6.88 (0.134, 0.102) 45 Example 176 977 5.40 6.12 (0.134, 0.101) 40 Example 177 978 5.41 5.89 (0.134, 0.100) 39 Example 178 980 5.38 6.01 (0.134, 0.101) 31 Example 179 986 4.63 6.54 (0.134, 0.102) 46 Example 180 990 4.90 6.81 (0.134, 0.100) 43 Example 181 996 5.48 6.15 (0.134, 0.101) 40 Example 182 998 5.44 6.55 (0.134, 0.102) 49 Example 183 999 5.33 6.53 (0.134, 0.102) 41 Example 184 1002 4.90 6.98 (0.134, 0.100) 43 Example 185 1003 4.91 6.13 (0.134, 0.100) 35 Example 186 1008 4.92 6.22 (0.134, 0.100) 42 Example 187 1012 5.66 5.99 (0.134, 0.100) 38 Example 188 1013 4.72 6.54 (0.134, 0.102) 47 Example 189 1014 4.71 6.33 (0.134, 0.102) 40 Example 190 1016 4.63 6.56 (0.134, 0.102) 43 Example 191 1018 4.91 6.82 (0.134, 0.100) 40 Example 192 1019 4.98 6.95 (0.134, 0.100) 39 Example 193 1020 4.94 6.25 (0.134, 0.100) 42 Example 194 1022 5.64 5.98 (0.134, 0.100) 33 Example 195 1024 5.44 6.53 (0.134, 0.102) 40 Example 196 1026 4.87 6.88 (0.134, 0.102) 42

As can be seen from the results of Table 60, the organic light emitting device using the electron transport layer material of the blue organic light emitting device of the present invention has a driving voltage lower than that of Comparative Examples 1, 2, 3 and 4, . The reason for this result is that, when an inventive compound having an appropriate length and strength is used as an electron transporting layer, it is possible to produce an excited state compound under an electron-accepting condition, and particularly, when an excited state of a hetero- It is believed that the excited heteroskeleton site will be moved to a stable state before the excitation, and relatively stable compounds can efficiently transfer electrons because they do not undergo decomposition or destruction. These excited states when excited are aryl or acenic compounds or polyvalent heterocyclic compounds. Therefore, it is considered that the compound of the present invention improves the improved electron-transporting property or the improved stability, resulting in excellent driving, efficiency and lifetime.

< Experimental Example  2> - Fabrication of organic light emitting device

1) Fabrication of organic light emitting device

The transparent electrode ITO thin film obtained from the glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned for 5 minutes each using trichlorethylene, acetone, ethanol and distilled water sequentially, and stored in isopropanol before use.

Next, an ITO substrate was placed on a substrate folder of a vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenyl amine: 2-TNATA).

Subsequently, the chamber was evacuated until the degree of vacuum reached 10 -6 torr, and then a current was applied to the cell to evaporate 2-TNATA, thereby depositing a 600 Å thick hole injection layer on the ITO substrate.

N'-bis (? - naphthyl) -N, N'-diphenyl-4,4'-diamine (N, N'-diphenyl-4,4'-diamine: NPB) was added, and a current was applied to the cell to evaporate the hole transport layer to deposit a 300 Å thick hole transport layer.

After the hole injecting layer and the hole transporting layer were formed as described above, a blue light emitting material having the following structure was vapor-deposited as a light emitting layer thereon. Specifically, H1, a blue light emitting host material, was vacuum deposited on one cell in a vacuum vapor deposition apparatus to a thickness of 200 Å, and D1, a blue light emitting dopant material, was vacuum deposited by 5% on the host material.

Next, a compound of the following structural formula E1 was deposited as an electron transporting layer to a thickness of 300 Å.

Lithium fluoride (LiF) was deposited as an electron injection layer to a thickness of 10 Å, and an Al cathode was formed to a thickness of 1,000 Å to fabricate an OLED device.

On the other hand, all the organic compounds required for OLED device fabrication were vacuum sublimated and refined under 10-6 ~ 10-8 torr for each material, and used for OLED fabrication.

In the same manner as in Experimental Example 2, except that the electron transport layer E1 was formed to a thickness of 250 ANGSTROM in Experimental Example 2, and then the hole blocking layer was formed to a thickness of 50 ANGSTROM on the electron transport layer To prepare an organic light emitting device.

Table 61 shows the results of measuring the driving voltage, the luminous efficiency, the color coordinates (CIE), and the lifetime of the blue organic light emitting device manufactured according to the present invention.

compound Driving voltage
(V) Luminous efficiency
(cd / A) CIE
(x, y) life span
(T95) Comparative Example 5 E1 5.70 6.00 (0.134, 0.102) 20 Comparative Example 6 E2 5.71 5.98 (0.134, 0.100) 22 Comparative Example 7 E3 5.70 6.03 (0.134, 0.101) 22 Comparative Example 8 E4 5.73 6.00 (0.134, 0.102) 20 Example 197 9 5.45 6.10 (0.134, 0.101) 33 Example 198 16 5.46 6.22 (0.134, 0.102) 36 Example 199 57 5.62 5.93 (0.134, 0.103) 41 Example 200 65 4.98 6.46 (0.134, 0.100) 39 Example 201 78 5.61 6.38 (0.134, 0.101) 35 Example 202 100 4.77 6.21 (0.134, 0.102) 39 Example 203 102 5.47 6.40 (0.134, 0.103) 37 Example 204 119 5.48 6.32 (0.134, 0.102) 39 Example 205 152 5.65 6.26 (0.134, 0.102) 41 Example 206 159 5.41 6.20 (0.134, 0.103) 45 Example 207 181 5.61 6.28 (0.134, 0.102) 41 Example 208 197 5.44 6.21 (0.134, 0.101) 38 Example 209 206 4.97 6.35 (0.134, 0.100) 41 Example 210 210 5.63 6.24 (0.134, 0.100) 38 Example 211 235 4.70 6.13 (0.134, 0.100) 44 Example 212 255 4.89 6.20 (0.134, 0.101) 41 Example 213 277 4.98 6.21 (0.134, 0.100) 38 Example 214 283 5.63 5.94 (0.134, 0.100) 37 Example 215 302 5.41 6.11 (0.134, 0.102) 22 Example 216 332 5.37 6.43 (0.134, 0.101) 40 Example 217 358 5.36 6.22 (0.134, 0.102) 38 Example 218 372 5.37 6.20 (0.134, 0.101) 42 Example 219 394 4.96 6.22 (0.134, 0.101) 39 Example 220 406 4.91 6.25 (0.134, 0.101) 39 Example 221 415 4.90 6.14 (0.134, 0.101) 43 Example 222 447 4.98 6.50 (0.134, 0.101) 38 Example 223 464 5.63 6.22 (0.134, 0.100) 45 Example 224 527 5.41 5.94 (0.134, 0.100) 35 Example 225 536 5.37 5.84 (0.134, 0.101) 37 Example 226 567 5.39 6.35 (0.134, 0.101) 40 Example 227 591 5.37 6.20 (0.134, 0.103) 40 Example 228 607 5.39 6.43 (0.134, 0.102) 43 Example 229 621 4.97 6.20 (0.134, 0.101) 39 Example 230 643 4.93 6.23 (0.134, 0.102) 34 Example 231 700 4.90 6.13 (0.134, 0.101) 39 Example 232 708 5.38 6.38 (0.134, 0.101) 39 Example 233 734 5.37 6.23 (0.134, 0.103) 40 Example 234 746 5.37 6.61 (0.134, 0.101) 41 Example 235 781 4.96 6.21 (0.134, 0.101) 39 Example 236 826 4.91 6.22 (0.134, 0.102) 33 Example 237 830 4.90 6.14 (0.134, 0.101) 40 Example 238 861 4.98 6.53 (0.134, 0.101) 39 Example 239 883 5.61 6.21 (0.134, 0.100) 43 Example 240 910 5.38 5.95 (0.134, 0.101) 35 Example 241 927 5.10 6.89 (0.134, 0.100) 41 Example 242 936 5.38 6.39 (0.134, 0.101) 38 Example 243 950 5.38 6.21 (0.134, 0.103) 40 Example 244 952 5.10 6.63 (0.134, 0.102) 43 Example 245 959 4.96 6.22 (0.134, 0.100) 40 Example 246 969 4.99 6.92 (0.134, 0.100) 43 Example 247 980 5.62 5.97 (0.134, 0.100) 38 Example 248 990 4.75 6.53 (0.134, 0.102) 41 Example 249 1002 4.72 6.34 (0.134, 0.102) 42 Example 250 1008 4.91 6.92 (0.134, 0.100) 44 Example 251 1014 4.90 6.95 (0.134, 0.100) 40 Example 252 1019 5.37 6.20 (0.134, 0.103) 40 Example 253 1020 5.36 6.22 (0.134, 0.102) 38 Example 254 1026 5.37 5.84 (0.134, 0.101) 37

As can be seen from the results of Table 61, the organic light emitting device using the hole blocking layer material of the blue organic light emitting device of the present invention had lower driving voltage, luminescent efficiency and longevity than Comparative Examples 5, 6, 7 and 8 Improved. The reason for this result is that the compound of Chemical Formula 1 is a bipolar type having both p-type and n-type substituents, so that hole leakage can be prevented and the excitons can be effectively confined in the light emitting layer.

< Experimental Example  3> - Fabrication of organic light emitting device

1) Fabrication of organic light emitting device

The glass substrate coated with ITO thin film with a thickness of 1500Å was washed with distilled water ultrasonic waves. After the distilled water was washed, it was ultrasonically cleaned with a solvent such as acetone, methanol, isopropyl alcohol, dried, and UV-treated for 5 minutes using UV in a UV scrubber. Subsequently, the substrate was transferred to a plasma cleaner (PT), subjected to a plasma treatment for removing ITO work function and residual film in a vacuum state, and transferred to a thermal evaporation apparatus for organic vapor deposition.

An organic material was formed on the ITO transparent electrode (anode) in a two-stack WOLED (White Organic Light Device) structure. In the first stack, a hole transport layer was formed by thermally vacuum depositing TAPC to a thickness of 300 ANGSTROM. After forming a hole transporting layer, a light emitting layer was formed thereon by thermal vacuum deposition as follows. The light emitting layer was doped with TCp1 as a host with blue phosphorescent dopant FIrpic in an amount of 8% to deposit 300Å. The electron transport layer was formed to a thickness of 400 ANGSTROM using TmPyPB, and then doped with Cs ₂ CO ₃ to a compound shown in Table 62 below as a charge generation layer to form 100 Å.

In the second stack, first, MoO ₃ was thermally vacuum-deposited to a thickness of 50 Å to form a hole injection layer. A hole transport layer as a common layer was formed by doping TAPC with 20% MoO ₃ to form 100 Å, followed by deposition of TAPC to 300 Å. On the phosphorescent layer, dopant Ir (ppy) _3, which is a green phosphorescent dopant, And then 600 Å was formed using TmPyPB as an electron transport layer. Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer. An aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode Thereby preparing an electroluminescent device.

On the other hand, all the organic compounds required for OLED device fabrication were vacuum sublimated and refined under 10 ^-6 ~ 10 ^-8 torr for each material, and used for OLED fabrication.

compound Driving voltage
(V) Luminous efficiency
(cd / A) CIE
(x, y) life span
(T95) Comparative Example 9 E1 5.70 6.00 (0.134, 0.102) 20 Comparative Example 10 E2 5.71 5.98 (0.134, 0.100) 22 Comparative Example 11 E3 5.70 6.03 (0.134, 0.101) 22 Comparative Example 12 E4 5.73 6.00 (0.134, 0.102) 20 Example 255 1014 5.45 6.10 (0.134, 0.101) 33 Example 256 1016 5.46 6.22 (0.134, 0.102) 36 Example 257 1018 5.62 5.93 (0.134, 0.103) 41 Example 258 1019 4.98 6.46 (0.134, 0.100) 39 Example 259 1020 5.61 6.38 (0.134, 0.101) 35 Example 260 1022 4.77 6.21 (0.134, 0.102) 39 Example 261 1024 5.47 6.40 (0.134, 0.103) 37 Example 262 1026 5.48 6.32 (0.134, 0.102) 39

As can be seen from the results shown in Table 62, the organic electroluminescent device using the charge generating layer material of the two-stack white organic electroluminescent device of the present invention has a lower driving voltage than that of Comparative Examples 9, 10, 11 and 12, The efficiency was improved.

The reason for this result is that the compound of the present invention used as an N type charge generation layer composed of an inventive skeleton having appropriate length, strength and flat characteristics and a suitable hetero compound capable of binding with a metal is an alkali metal or an alkaline earth metal It is presumed that a gap state is formed in the N type charge generation layer and electrons generated from the P type charge generation layer are easily injected into the electron transport layer through the gap state fished in the N type charge generation layer . Therefore, the P-type charge generation layer can be electron-injected and electron-transferred to the N-type charge generation layer well, so that the driving voltage of the organic light emitting device is lowered and the efficiency and lifetime are improved.

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

Claims (16)

A heterocyclic compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
X is O or S,
L ₁ and L ₂ are substituted or unsubstituted arylene groups; Or a substituted or unsubstituted heteroarylene group,
Z ₂ is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -SiRR'R &quot;; or -P (= O) RR '
X ₁ to X ₃ are the same or different from each other and each independently represent N; CR ₃ ; Or P,
R ₁ and R ₂ are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or P (= O) RR '
R ₃ is hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or P (= O) RR '
R _a and R _b are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group; A 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; -SiRR'R &quot;; -P (= O) RR ', and an amine group substituted or unsubstituted with a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group 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,
R, R 'and R "are the same or different from each other and each independently represents hydrogen, deuterium, -CN, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, An unsubstituted heteroaryl group,
m is an integer of 0 to 4,
p and n are integers of 0 to 3,
q is an integer of 0 to 3,
s is an integer of 1 to 4,
When q is an integer of 0 and Z ₂ is hydrogen, n is an integer of 2 or 3, and R _b is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring. The term "substituted or unsubstituted" as used in claim 1 means a straight-chain or branched-chain alkyl of C1 to C60; C2 to C60 straight or branched chain alkenyl; Straight or branched chain alkynyl of C2 to C60; C3 to C60 monocyclic or polycyclic cycloalkyl; A C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; Wherein R is selected from the group consisting of C1 to C20 alkylamines, C6 to C60 mono- or polycyclic arylamines, and C2 to C60 mono- or polycyclic heteroarylamines. Means that at least two substituents selected from the above-exemplified substituents are substituted or unsubstituted with a substituent to which they are linked,
Wherein the definition of R, R 'and R "is the same as defined in the above formula (1). The method according to claim 1,
Wherein R & lt _{; a} & gt _; and R &lt; _b & gt _; are hydrogen. The method according to claim 1,
R ₁ and R ₂ are independently selected from the group consisting of hydrogen; A C6 to C40 aryl group substituted or unsubstituted with at least one substituent selected from the group consisting of C1 to C40 alkyl groups and C2 to C40 heteroaryl groups; P (= O) RR 'or a C2 to C40 N-containing heteroaryl group. The method according to claim 1,
Wherein L ₁ and L ₂ are C 6 to C 30 arylene groups; Or a C2 to C30 heteroarylene group,
Z &lt; ₂ &gt; is hydrogen; A C6 to C40 aryl group; Or a C2 to C40 heteroaryl group. The method according to claim 1,
Wherein the formula 1 is represented by any one of the following formulas 2 to 5:
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,
X ₁ to X ₃ , R ₁ , R ₂ , L ₁ , L ₂ , Z ₂ and p are the same as defined in the above formula (1)
q and s are each an integer of 1 to 3; The method according to claim 1,
The heterocyclic compound represented by the formula (1) is represented by any one of the following formulas (6) to (11):
[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

In the general formulas (6) to (11)
X ₁ to X ₃ , R ₁ , R ₂ , L ₁ and p are the same as defined in the above formula (1). The heterocyclic compound according to claim 1, wherein the formula 1 is represented by any one of the following compounds:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the heterocyclic compound according to any one of claims 1 to 8 Lt; / RTI &gt; The organic light emitting device according to claim 9, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound. The organic light emitting device according to claim 9, wherein the organic layer includes a light emitting layer, the light emitting layer includes a host material, and the host material includes the heterocyclic compound. The organic light emitting device according to claim 9, wherein the organic layer includes a light emitting layer, the light emitting layer includes a host material, and the host material includes the heterocyclic compound. [12] The organic light emitting device according to claim 9, wherein the organic 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. [Claim 11] The organic electroluminescent device of claim 9, wherein the organic light emitting device comprises a light emitting layer, a hole injecting layer, and a hole transporting layer. An electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. The organic electroluminescent device of claim 9, wherein the organic light emitting device comprises a first electrode, a first stack provided on the first electrode and including a first light emitting layer, a charge generating layer provided on the first stack, And a second electrode provided on the second stack, wherein the second electrode includes a second light emitting layer. 16. The organic light emitting device according to claim 15, wherein the charge generation layer comprises the heterocyclic compound.

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