CN108623545A - A kind of organic compound and its application and a kind of organic electroluminescence device - Google Patents

A kind of organic compound and its application and a kind of organic electroluminescence device Download PDF

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CN108623545A
CN108623545A CN201710168953.2A CN201710168953A CN108623545A CN 108623545 A CN108623545 A CN 108623545A CN 201710168953 A CN201710168953 A CN 201710168953A CN 108623545 A CN108623545 A CN 108623545A
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吕瑶
冯玉
贾学艺
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Green People's Science And Technology Ltd Co In Beijing
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Abstract

The present invention relates to organic electroluminescence device field, disclose a kind of organic compound and its application and a kind of organic electroluminescence device, which has a structure shown in formula (1), A and B be O, S,OrBy R1、R2、R3And R4In the group of composition any one for structure shown in formula (Y) group, by R1、R2、R3And R4In residue three and R5、R6、R7And R8In the group of composition any one for structure shown in formula (Z) group；In formula (Y), R9And R10Substituted five-membered ring is formed together, and the substituted five-membered ring so that formula (Y) is the group of structure shown in formula (Y1) or formula (Y2).Organic electroluminescence device containing aforementioned organic compound provided by the invention has that driving voltage is low, service life is long, current efficiency and the high advantage of brightness.

Description

A kind of organic compound and its application and a kind of organic electroluminescence device
Technical field
The present invention relates to organic electroluminescence device fields, and in particular, to a kind of organic compound and the organic compound Application of the object in organic electroluminescence device, and the organic electroluminescence device containing the organic compound.
Background technology
Organic electroluminescent (OLED) technology compared to traditional liquid crystal technology for, without backlight irradiation and colour filter Device, pixel itself can shine and be presented on color display panel, also, possess superelevation contrast, super wide visible angle, curved surface, thin The features such as type.
The performance of OLED is not only influenced by illuminator, in particular, forming each layer of the material of OLED all to OLED Performance there is very important influence, such as base material, hole barrier materials, electron transport material, hole mobile material With electronics or exciton-blocking material etc..Each layer of the material of the formation OLED used at present still has driving voltage height, makes With the low defect of short life, current efficiency and brightness, cause that the preferable organic electroluminescence device of performance can not be obtained.
Invention content
The purpose of the invention is to overcome driving voltage existing for the organic electroluminescence device that the prior art provides it is high, Service life is short and current efficiency and the low defect of brightness, provides and a kind of new can be used in forming organic electroluminescent The organic compound of device so that the organic electroluminescence device containing the organic compound is with driving voltage is low, uses the longevity Life length, current efficiency and the high advantage of brightness.
The present inventor has found under study for action, containing structure shown in formula (1), formula (Y) and formula (Z), and specifically, Wherein group shown in formula (Y) is by R1、R2、R3And R4Base shown in any one group and formula (Z) in the group of composition Group is by R1、R2、R3And R4In residue three and R5、R6、R7And R8When any one group in the group of composition, thus The organic compound arrived enables to organic electroluminescence device to have driving voltage when forming organic electroluminescence device It is low, service life is long, current efficiency and the high advantage of brightness.
In addition, inventor has found, the structure being connected with formula (Z) and bigeminy aniline using formula (1) can not only improve material The hole transport performance of material, and the triplet of material can be effectively improved, it is used in organic electroluminescence device In hole transmission layer, can effectively improve hole mobility, to improve the current efficiency of organic electroluminescence device, brightness, Service life reduces driving voltage.It is used in the electronic barrier layer of organic electroluminescence device, hole and electronics can be limited In luminescent layer, make its in luminescent layer in conjunction with and shine, to improve the current efficiency of organic electroluminescence device, brightness, Service life reduces driving voltage.Because it is with higher energy level, be used in the higher blue-light device of energy, can effectively by Exciton is limited in luminescent layer, and exciton is made to shine in luminescent layer, to reach improve the current efficiency of blue-light device, brightness, Service life reduces the effect of driving voltage.But this compound is not limited only to use in blue-light device, in red, green device Current efficiency, brightness, service life are improved in use, can equally reach, reduces the effect of driving voltage.
Based on this, technical scheme of the present invention is completed.
To achieve the goals above, one aspect of the present invention provides a kind of organic compound, which has shown in formula (1) Structure,
Wherein, A and B be each independently O, S,
By R1、R2、R3And R4In the group of composition any one for structure shown in formula (Y) group, by R1、R2、R3And R4In Residue three and R5、R6、R7And R8Any one in the group of composition is the group of structure shown in formula (Z), and R1、R2、R3、 R4、R5、R6、R7And R8In residue six be H；
In formula (Y), R9And R10For H；Or in formula (Y), R9And R10Substituted five-membered ring, the substitution are formed together Five-membered ring so that formula (Y) is the group of structure shown in formula (Y1) or formula (Y2), in formula (Y1), R13And R14Each independently For C1-4Alkyl or phenyl；
In formula (Z), R11And R12It is H；Or in formula (Z), R11And R12In any one be knot shown in formula (Y) The group of structure, and another is H.
On the other hand, the present invention provides organic compound the answering in organic electroluminescence device described in first aspect With.
The present invention's also has on the one hand offer to contain one or both of the organic compound described in aforementioned first aspect Above organic electroluminescence device.
Organic electroluminescence device containing aforementioned organic compound provided by the invention is with driving voltage is low, uses the longevity Life length, current efficiency and the high advantage of brightness.
Other features and advantages of the present invention will be described in detail in subsequent specific embodiment part.
Specific implementation mode
The specific implementation mode of the present invention is described in detail below.It should be understood that described herein specific Embodiment is merely to illustrate and explain the present invention, and is not intended to restrict the invention.
The endpoint of disclosed range and any value are not limited to the accurate range or value herein, these ranges or Value should be understood as comprising the value close to these ranges or value.For numberical range, between the endpoint value of each range, respectively It can be combined with each other between the endpoint value of a range and individual point value, and individually between point value and obtain one or more New numberical range, these numberical ranges should be considered as specific open herein.
“C1-4Alkyl " indicate the total number of carbon atoms be 1-4 alkyl, such as can be methyl, ethyl, n-propyl, isopropyl Base, normal-butyl, isobutyl group or tertiary butyl.
In a first aspect, the present invention provides a kind of organic compound, which has structure shown in formula (1),
Wherein, A and B be each independently O, S,
By R1、R2、R3And R4In the group of composition any one for structure shown in formula (Y) group, by R1、R2、R3And R4In Residue three and R5、R6、R7And R8Any one in the group of composition is the group of structure shown in formula (Z), and R1、R2、R3、 R4、R5、R6、R7And R8In residue six be H；
In formula (Y), R9And R10For H；Or in formula (Y), R9And R10Substituted five-membered ring, the substitution are formed together Five-membered ring so that formula (Y) is the group of structure shown in formula (Y1) or formula (Y2), in formula (Y1), R13And R14Each independently For C1-4Alkyl or phenyl；
In formula (Z), R11And R12It is H；Or in formula (Z), R11And R12In any one be knot shown in formula (Y) The group of structure, and another is H.
According to the first preferred embodiment, in organic compound provided by the invention,
A and B be each independently O, S,
By R1、R2、R3And R4In the group of composition any one for structure shown in formula (Y) group, by R1、R2、R3And R4In Residue three and R5、R6、R7And R8Any one in the group of composition is the group of structure shown in formula (Z), and R1、R2、R3、 R4、R5、R6、R7And R8In residue six be H；
In formula (Y), R9And R10For H；Or in formula (Y), R9And R10Substituted five-membered ring, the substitution are formed together Five-membered ring so that formula (Y) is the group of structure shown in formula (Y1) or formula (Y2), in formula (Y1), R13And R14Each independently For C1-4Alkyl (more preferable R13And R14It is each independently methyl or ethyl)；
In formula (Z), R11And R12It is H；Or in formula (Z), R11And R12In any one be knot shown in formula (Y3) The group of structure, and another is H,
According to second of preferred embodiment, in organic compound provided by the invention,
A and B be each independently O, S,
By R1、R2、R3And R4In the group of composition any one for structure shown in formula (Y11) or formula (Y12) group, by R1、R2、R3And R4In residue three and R5、R6、R7And R8In the group of composition any one for structure shown in formula (Z) base Group, and R1、R2、R3、R4、R5、R6、R7And R8In residue six be H；
In formula (Y11) and formula (Y12), R9And R10For H；Or
In formula (Y11) and formula (Y12), R9And R10Substituted five-membered ring is formed together, and the substituted five-membered ring makes Formula (Y11) is that the group or the substituted five-membered ring of structure shown in formula (Y111) or formula (Y112) so that formula (Y12) is formula (Y121) or the group of structure shown in formula (Y122)；
R13And R14It is each independently methyl or phenyl (more preferable R13And R14It is each independently methyl or ethyl)；
In formula (Z), R11And R12It is H；Or in formula (Z), R11And R12In any one be knot shown in formula (Y) The group (the more preferably group of structure shown in formula (Y3)) of structure, and another is H.
According to the third preferred embodiment, in organic compound provided by the invention,
A isB be O, S,
By R1、R2、R3And R4In the group of composition any one for structure shown in formula (Y11) or formula (Y12) group, by R1、R2、R3And R4In residue three and R5、R6、R7And R8In the group of composition any one for structure shown in formula (Z) base Group, and R1、R2、R3、R4、R5、R6、R7And R8In residue six be H；
In formula (Y11), R9And R10For H；Or R9And R10Substituted five-membered ring, the substituted five-membered ring are formed together So that formula (Y11) is the group of structure shown in formula (Y111) or formula (Y112),
In formula (Y12), R9And R10For H；Or R9And R10Substituted five-membered ring, the substituted five-membered ring are formed together So that formula (Y12) is the group of structure shown in formula (Y122)；
In formula (Z), R11And R12It is H；Or in formula (Z), R11And R12In any one be knot shown in formula (Y) The group (the more preferably group of structure shown in formula (Y3)) of structure, and another is H.
According to the 4th kind of preferred embodiment, organic compound provided by the invention is described in claim 6 One or more of compound.
The organic electroluminescence device that aforementioned organic compound provided by the present invention is formed is low with driving voltage, uses The high advantage of long lifespan, current efficiency and brightness.
The primary object of the present invention is the provision of a kind of can be used in organic electroluminescence device and makes it have Driving voltage is low, service life is long, and the organic compound of current efficiency and the high advantage of brightness, the present invention is to the organic of offer There is no particular limitation for the synthetic method of compound, and those skilled in the art can be according to organic compound provided by the invention Preparation method determines suitable synthetic method to structural formula in conjunction with the embodiments.For example, those skilled in the art can pass through the first step Suzuki reaction and second step aryl amination react to prepare the organic compound of the present invention.In addition, example in the preparation example of the present invention The preparation method of some organic compounds is given to property, those skilled in the art can be according to these illustrative preparation examples Preparation method obtains all organic compounds provided by the invention.
Second aspect, the present invention also provides application of the aforementioned organic compound in organic electroluminescence device.
The third aspect, the present invention provides a kind of Organic Electricities containing one or more of aforementioned organic compound Electroluminescence device.
Preferably, the organic compound is present in the hole transmission layer, luminescent layer and electricity of the organic electroluminescence device In at least one of sub- barrier layer.
Preferably, the organic electroluminescence device includes the substrate, anode, hole injection layer being cascading (HIL), hole transmission layer (HTL), optional electronic barrier layer, luminescent layer (EML), optional hole blocking layer, electron-transport Layer (ETL), electron injecting layer (EIL) and cathode.
The present invention is not particularly limited the method for preparing the organic electroluminescence device, and creativeness of the invention is main It is the inventors found that containing structure shown in formula (1), formula (Y) and formula (Z), and specifically, wherein formula (Y) institute The group shown is by R1、R2、R3And R4Group shown in any one group and formula (Z) in the group of composition is by R1、R2、 R3And R4In residue three and R5、R6、R7And R8When any one group in the group of composition, thus obtained organic compound For object when forming organic electroluminescence device, enabling to organic electroluminescence device to have, driving voltage is low, service life is long, Current efficiency and the high advantage of brightness.Therefore, what those skilled in the art may be used routine in the art prepares Organic Electricity The method of electroluminescence device come prepare the present invention organic electroluminescence device.Moreover, the embodiment of the present invention exemplary partial Ground gives the preparation method of the organic electroluminescence device of the present invention, and those skilled in the art should not be construed as to the present invention's Limitation.
It below will the present invention will be described in detail by preparation example and embodiment.In following embodiment, not special In the case of explanation, the various raw materials that use are all from commercially available.
Preparation example 1
Synthetic example 1：The synthesis of compound 1
The synthesis of intermediate 1-1：By (uncommon love (Shanghai) chemical conversion of TCI- ladders of the bromo- 4- iodine dibenzofurans of the 2- of 0.1926mol Industrial development Co., Ltd) it is dissolved in Isosorbide-5-Nitrae-dioxane solvent of 720mL, lead to stirred under nitrogen, sequentially adds 0.1926mol Dibenzofurans -4- boric acid, 0.3852mol potassium carbonate, 53mL water, 0.0019mol tetrakis triphenylphosphine palladiums, be warming up to reflux It reacts, detection raw material, which reacts, after 3h finishes, and after reaction solution decompression is spin-dried for, obtains 51.74g intermediates 1-1 by column chromatography and (receives Rate is 65 weight %).Calculated value C24H13BrO2：413.26+1.
The nuclear magnetic data of intermediate 1-1 is：1H-NMR (400MHz, CDCl3) δ=7.36~7.42 (ppm) (5H, m), 7.69~7.72 (2H, d), 7.82~7.94 (4H, m), 8.12~8.15 (2H, d).
The synthesis of compound 1：0.1024mol intermediates 1-1 is dissolved in 420mL toluene solvants, leads to stirred under nitrogen, so Sequentially add afterwards 0.1229mol bis- (4- xenyls) amine, 0.2048mol sodium tert-butoxides, 0.001mol (DBA)3Pd2、2mL (0.001) tri-tert-butylphosphine is warming up to back flow reaction, and raw material reaction is detected after 6h and is finished, reaction solution decompression is spin-dried for, column is passed through Chromatography obtains 36.8g compounds 1 (yield is 55 weight %).Calculated value C48H31NO2：653.77+1.
The nuclear magnetic data of compound 1 is：1H-NMR (400MHz, CDCl3) δ=6.72~6.75 (ppm) (4H, d), 7.35 ~7.92 (23H, m), 7.95~8.04 (4H, m).
Preparation example 2：The synthesis of compound 3
Using the method similar from preparation example 1 (be only use raw material type different) synthetic intermediate 3-1 and compound 3。
Obtain 16.5g intermediates 3-1 (63 weight % of yield).Calculated value C27H19BrO：439.34+1.
The nuclear magnetic data of intermediate 3-1 is：δ=1.72~1.75 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 7.36~7.42 (5H, m), 7.52~7.53 (2H, m), 7.69~7.72 (1H, m), 7.82~7.94 (3H, m), 8.15~ 8.18 (2H, d).
And obtain 9.6g compounds 3 (53 weight % of yield).Calculated value C51H37NO：679.85+1.
The nuclear magnetic data of compound 3 is：1H-NMR (400MHz, CDCl3) δ=1.72~1.75 (ppm) (6H, s), 6.72 ~6.75 (4H, d), 7.35~7.77 (24H, m), 7.92~8.05 (3H, m).
Preparation example 3：The synthesis of compound 46
Using the method similar from preparation example 1 (be only use raw material type different) synthetic intermediate 46-1 and compound 46。
Obtain 23.1g intermediates 46-1 (61 weight % of yield).Calculated value C27H19BrO：439.34+1.
The nuclear magnetic data of intermediate 46-1 is：δ=1.72~1.75 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 7.32~7.56 (4H, m), 7.56~7.59 (1H, d), 7.69~7.75 (3H, m), 7.79~7.82 (1H, s), 7.87~ 7.93 (3H, m), 8.12~8.15 (1H, s).
And obtain 15g compounds 46 (49 weight % of yield).Calculated value C51H37NO：679.85+1.
The nuclear magnetic data of compound 46 is：δ=1.72~1.75 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 6.72~6.75 (4H, d), 7.07~7.10 (1H, s), 7.32~7.64 (20H, m), 7.77~7.80 (1H, s), 7.87~ 7.93 (3H, m).
Preparation example 4：The synthesis of compound 53
Using the method similar from preparation example 1 (be only use raw material type different) synthetic intermediate 53-1 and compound 53。
Obtain 25.5g intermediates 53-1 (53 weight % of yield).Calculated value C27H19BrO：439.34+1.
The nuclear magnetic data of intermediate 53-1：1H-NMR (400MHz, CDCl3) δ=1.72~1.75 (ppm) (6H, s), 7.28~7.35 (3H, m), 7.56~7.59 (1H, d), 7.65~7.68 (2H, m), 7.76~7.82 (3H, m), 7.96~ 8.02 (3H, m), 8.29~8.32 (1H, s).
And obtain 16.7g compounds 53 (45 weight % of yield).Calculated value C51H37NO：679.85+1.
The nuclear magnetic data of compound 53：1H-NMR (400MHz, CDCl3) δ=1.72~1.75 (ppm) (6H, s), 6.72 ~6.84 (4H, d), 7.21~7.66 (24H, m), 7.92~7.95 (3H, m).
Preparation example 5：The synthesis of compound 67
Using the method similar from preparation example 1 (be only use raw material type different) synthetic intermediate 67-1 and compound 67。
Obtain 13.4g intermediates 67-1 (yield 57.5%).Calculated value C27H19BrO：439.34+1.
The nuclear magnetic data of intermediate 67-1：1H-NMR (400MHz, CDCl3) δ=1.72~1.75 (ppm) (6H, s), 7.42~7.48 (4H, m), 7.58~7.64 (2H, m), 7.72~7.75 (2H, m), 8.09~8.15 (3H, m).
And obtain 6.8g compounds 67 (yield 47%).Calculated value C51H37NO：679.85+1.
The nuclear magnetic data of compound 67：1H-NMR (400MHz, CDCl3) δ=1.72~1.75 (ppm) (6H, s), 6.72 ~6.75 (4H, d), 7.32~7.74 (24H, m), 7.92~7.95 (2H, m), 8.09~8.12 (1H, s).
Preparation example 6：The synthesis of compound 85
Using the method similar from preparation example 1 (be only use raw material type different) synthetic intermediate 85-1 and compound 85。
Obtain 16.8g intermediates 85-1 (42 weight % of yield).Calculated value C30H18BrNO：488.37+1.
The nuclear magnetic data of intermediate 85-1：δ=7.39~7.63 (9H, m) 1H-NMR (400MHz, CDCl3) (ppm), 7.72~7.99 (7H, m), 8.21~8.24 (1H, s), 8.58~8.61 (1H, d).
And obtain 9.6g compounds 85 (yield 53%).Calculated value C54H36N2O：728.88+1.
The nuclear magnetic data of compound 85：δ=6.42~6.45 (1H, d) 1H-NMR (400MHz, CDCl3) (ppm), 6.72 ~6.75 (4H, d), 7.32~7.86 (29H, m), 7.96~7.99 (1H, d), 8.58~8.61 (1H, d).
Preparation example 7：The synthesis of compound 90
Using the method similar from preparation example 1 (be only use raw material type different) synthetic intermediate 90-1 and compound 90。
Obtain intermediate 85-1 (62 weight % of yield).Calculated value C33H24BrN：514.45+1.
The nuclear magnetic data of intermediate 85-1：δ=1.72~1.73 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 7.25~7.33 (2H, m), 7.45~7.63 (8H, m), 7.72~7.79 (4H, m), 7.93~7.94 (2H, m), 8.18~ 8.19 (1H, d), 8.55~8.56 (1H, m).
And obtain compound 90 (yield 59%).Calculated value C57H42N2：754.96+1.
The nuclear magnetic data of compound 90：δ=1.72~1.73 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 6.58 ~6.59 (1H, m), 6.69~6.75 (5H, m), 7.25~7.63 (24H, m), 7.77~7.79 (2H, m), 7.93~7.94 (2H, m), 8.18~8.19 (1H, d), 8.55~8.56 (1H, m).
Preparation example 8：The synthesis of compound 103
Using the method similar from preparation example 1 (be only use raw material type different) synthetic intermediate 103-1 and chemical combination Object 103.
Obtain intermediate 103-1 (58 weight % of yield).Calculated value C30H18BrNO：488.37+1.
The nuclear magnetic data of intermediate 103-1：δ=7.25~7.33 (3H, m) 1H-NMR (400MHz, CDCl3) (ppm), 7.45~7.78 (10H, m), 7.87~7.95 (3H, m), 8.26~8.26 (1H, m), 8.55~8.55 (1H, m).
And obtain compound 103 (yield 53%).Calculated value C54H36N2O：728.88+1.
The nuclear magnetic data of compound 103：δ=6.33~6.33 (1H, m) 1H-NMR (400MHz, CDCl3) (ppm), 6.69 ~6.70 (4H, d), 7.25~7.75 (27H, m), 7.87~7.87 (1H, m), 7.97~7.95 (1H, m), 8.55~8.55 (1H, m).
Preparation example 9：The synthesis of compound 157
Using the method similar from preparation example 1 (be only use raw material type different) (the preparation sides synthetic intermediate 157-1 Method is with intermediate 1-1), intermediate 157-2 (preparation method is with compound 1) and compound 157 (preparation method is with compound 1).
Obtain intermediate 157-1 (64 weight % of yield).Calculated value C27H21NO：375.46+1.
The nuclear magnetic data of intermediate 157-1：δ=1.72~1.72 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 6.27~6.27 (2H, s), 6.39~6.39 (1H, d), 7.28~7.38 (4H, m), 7.55~7.56 (2H, m), 7.63~ 7.66 (2H, m), 7.77~7.77 (1H, d), 7.87~7.93 (3H, m).
And obtain intermediate 157-2 (yield 45%).Calculated value C39H29NO：527.65+1.
The nuclear magnetic data of intermediate 157-2：δ=1.72~1.72 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 4.00~4.00 (1H, s), 6.39~6.39 (1H, d), 6.69~6.69 (1H, m), 6.87~6.87 (1H, m), 7.08~ 7.16 (3H, m), 7.28~7.41 (5H, m), 7.51~7.66 (7H, m), 7.77~7.77 (1H, m), 7.87~7.93 (3H, m)。
Obtain compound 157 (yield 45%).Calculated value C64H43NO：842.03+1.
The nuclear magnetic data of compound 157：δ=1.72~1.72 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 6.39 ~6.39 (1H, d), 6.58~6.58 (1H, m), 6.69~6.69 (1H, m), 6.75~6.75 (1H, m), 6.87~6.87 (1H, m), 7.16~7.41 (16H, m), 7.55~7.62 (9H, m), 7.75~7.77 (3H, m), 7.87~7.93 (3H, m).
Preparation example 10：The synthesis of compound 158
Using the method similar from preparation example 9 (be only use raw material type different) (the preparation sides synthetic intermediate 158-1 Method is with intermediate 157-1), intermediate 158-2 (preparation method is with intermediate 157-2) and (the same chemical combination of preparation method of compound 158 Object 157).
Obtain intermediate 158-1 (62 weight % of yield).Calculated value C27H21NS：391.53.
The nuclear magnetic data of intermediate 158-1：δ=1.72~1.72 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 6.27~6.27 (2H, s), 6.94~6.94 (1H, d), 7.28~7.38 (2H, m), 7.50~7.55 (4H, m), 7.63~ 7.63 (1H, m), 7.77~7.77 (1H, d), 7.87~7.98 (3H, m), 8.45~8.45 (1H, m).
And obtain intermediate 158-2 (yield 43%).Calculated value C39H29NS：543.72.
The nuclear magnetic data of intermediate 158-2：δ=1.72~1.72 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 4.00~4.00 (1H, s), 6.69~6.69 (1H, d), 6.87~6.94 (2H, m), 7.08~7.16 (3H, m), 7.28~ 7.55 (10H, m), 7.63~7.63 (1H, m), 7.77~7.77 (1H, m), 7.87~7.98 (3H, m), 8.45~8.45 (1H, m)。
Obtain compound 158 (yield 54%).Calculated value C64H43NS：858.10.
The nuclear magnetic data of compound 158：δ=1.72~1.72 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 6.58 ~6.58 (1H, m), 6.69~6.75 (2H, m), 6.87~6.94 (2H, m), 7.16~7.63 (24H, m), 7.75~7.77 (3H, m), 7.87~7.98 (4H, m), 8.45~8.45 (1H, m).
Preparation example 11：The synthesis of compound 192
Using the method similar from preparation example 9 (be only use raw material type different) (the preparation sides synthetic intermediate 192-1 Method is with intermediate 157-1), intermediate 192-2 (preparation method is with intermediate 157-2) and (the same chemical combination of preparation method of compound 192 Object 157).
Obtain intermediate 192-1 (57.5 weight % of yield).Calculated value：C27H19BrS：455.41.
The nuclear magnetic data of intermediate 192-1：δ=1.72~1.72 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 7.56~7.63 (4H, m), 7.72~7.77 (3H, m), 7.93~8.11 (5H, m), 8.45~8.45 (1H, m).
And obtain intermediate 192-2 (yield 43%).Calculated value C39H29NS：543.72.
The nuclear magnetic data of intermediate 192-2：δ=1.72~1.72 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 4.00~4.00 (1H, s), 6.58~6.58 (1H, m), 6.69~6.75 (2H, m), 6.87~6.87 (1H, m), 7.08~ 7.16 (3H, m), 7.41~7.54 (6H, m), 7.77~7.77 (1H, d), 7.83~8.11 (5H, m), 8.45~8.45 (1H, m)。
Obtain compound 192 (yield 54%).Calculated value C64H43NS：858.10+1.
The nuclear magnetic data of compound 192：δ=1.72~1.72 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 6.58 ~6.58 (2H, m), 6.67~6.75 (3H, m), 6.87~6.87 (1H, m), 7.16~7.63 (21H, m), 7.75~7.77 (3H, m), 7.87~8.11 (6H, m), 8.45~8.45 (1H, m).
Preparation example 12：The synthesis of compound 193
Using the method similar from preparation example 9 (be only use raw material type different) (the preparation sides synthetic intermediate 193-1 Method is with intermediate 157-1), intermediate 193-2 (preparation method is with intermediate 157-2) and (the same chemical combination of preparation method of compound 193 Object 157).
Obtain intermediate 193-1 (40 weight % of yield).Calculated value C27H19BrO：439.34.
The nuclear magnetic data of intermediate 193-1：δ=1.72~1.72 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 7.32~7.38 (3H, m), 7.55~7.56 (1H, m), 7.63~7.66 (2H, m), 7.72~7.89 (7H, m).
And obtain intermediate 193-2 (yield 45%).Calculated value C39H29NO：527.65.
The nuclear magnetic data of intermediate 193-2：δ=1.72~1.72 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 4.00~4.00 (1H, s), 6.58~6.58 (1H, m), 6.69~6.75 (2H, m), 6.87~6.87 (1H, m), 7.08~ 7.16 (3H, m), 7.32~7.41 (4H, m), 7.51~7.54 (3H, m), 7.62~7.66 (3H, m), 7.77~7.89 (5H, m)。
Obtain compound 193 (yield 56%).Calculated value C64H43NO：842.03+1.
The nuclear magnetic data of compound 193：δ=1.72~1.72 (6H, s) 1H-NMR (400MHz, CDCl3) (ppm), 6.58 ~6.58 (2H, m), 6.67~6.75 (3H, m), 6.87~6.87 (1H, m), 7.08~7.38 (15H, m), 7.51~7.66 (8H, m), 7.75~7.93 (8H, m).
Preparation example 13：The synthesis of compound 201
The synthesis of intermediate 201-1：The 2- nitro dibenzothiophenes of 0.13mol is dissolved in the DMF of 150mL, is cooled to 0 DEG C, the NBS of 0.12mol is dissolved in the DMF solvent of 50mL, then NBS solution is added dropwise into substrate solution, stirring, after dripping Reaction also stops therewith.100mL water is added dropwise in reaction solution, crystallization filters, obtains intermediate 201-1 (yield 48%).
The nuclear magnetic data of intermediate 201-1：1H-NMR(400MHZ,CDCl3) δ=7.50~7.52 (ppm) (2H, t), 7.94~7.98 (1H, d), 8.41~8.46 (2H, m), 8.65~8.66 (1H, s).
The synthesis of intermediate 201-2：Intermediate 201-1, the 0.31mol iron powder of 0.062mol is added to ethyl alcohol 200mL, water 80mL in the mixed solution of concentrated hydrochloric acid 1.5mL, are warming up to reflux, react 4 hours.Reaction finishes, and acetic acid second is added Ester extracts, and organic phase makes evaporation of the solvent, column chromatography obtain intermediate 201-2 (yield 67%) by revolving.
The nuclear magnetic data of intermediate 201-2：1H-NMR(400MHZ,CDCl3) δ=6.27~6.29 (ppm) (2H, s), 6.68~6.70 (1H, s), 7.33~7.35 (1H, s), 7.50~7.52 (2H, t), 7.94~7.98 (2H, d), 8.45~ 8.46(1H,d)。
Intermediate 201-3 is synthesized using method identical with synthetic intermediate 1-1, yield 70%.
The nuclear magnetic data of intermediate 201-3：1H-NMR(400MHZ,CDCl3) δ=6.27~6.29 (ppm) (2H, s), 7.15~7.16 (1H, s), 7.25~7.28 (1H, t), 7.33~7.38 (2H, m), 7.41~7.45 (1H, m), 7.50~ 7.55 (4H, m), 7.58~7.62 (2H, t), 7.68~7.69 (1H, d), 7.75~7.77 (1H, s), 7.86~7.87 (1H, D), 7.94~7.98 (2H, d), 8.45~8.46 (1H, d), 8.55~8.56 (1H, d).
Intermediate 201-4 uses the synthesis of method identical with synthesis compound 1, yield 52%.
The nuclear magnetic data of intermediate 201-4：1H-NMR(400MHZ,CDCl3) δ=4.00~4.02 (ppm) (1H, s), 6.69~6.70 (1H, d), 6.87~6.88 (1H, t), 7.08~7.09 (2H, d), 7.15~7.16 (2H, m), 7.25~ 7.28 (1H, t), 7.33~7.38 (2H, m), 7.41~7.45 (2H, m), 7.50~7.55 (1H, m), 7.58~7.62 (2H, T), 7.68~7.69 (1H, d), 7.75~7.77 (1H, s), 7.81~7.83 (1H, d), 7.94~7.98 (2H, d), 8.45~ 8.46 (1H, d), 8.55~8.56 (1H, d).
Compound 201 is using the synthesis of method identical with synthesis compound 1, yield 45%.
The nuclear magnetic data of compound 201：1H-NMR(400MHZ,CDCl3) δ=6.58~6.59 (ppm) (1H, d), 6.69 ~6.70 (1H, d), 6.74~6.75 (1H, s), 6.87~6.88 (1H, t), 7.08~7.09 (2H, d), 7.15~7.16 (4H, m), 7.19~7.20 (2H, t), 7.25~7.28 (2H, m), 7.33~7.38 (5H, m), 7.41~7.45 (2H, m), 7.50~7.55 (8H, m), 7.58~7.62 (3H, m), 7.68~7.69 (1H, d), 7.75~7.77 (3H, m), 7.87~ 7.89 (2H, d), 7.94~7.98 (2H, t), 8.45~8.46 (1H, d), 8.55~8.56 (1H, d).
Preparation example 14：The synthesis of compound 230
The synthesis of 230-1：By the bromo- 4- dibenzothiophenes amine of the 1- of 0.05mol, 10g concentrated hydrochloric acids are added with 100mL water to burning It is put into ice salt bath in bottle, the aqueous solution that 4g sodium nitrites are prepared with 8mL water is added dropwise, after 10 DEG C of temperature of holding is hereinafter, be added dropwise 1h is reacted, reaction system is warming up to reflux, after sustained response 2h, pH value is adjusted to after alkalescent plus ethyl acetate extracts, is had Machine, which communicated revolving, makes evaporation of the solvent, column chromatography obtain intermediate 230-1 (yield 67%).
The nuclear magnetic data of intermediate 230-1：1H-NMR(400MHZ,CDCl3) δ=7.37~7.41 (ppm) (2H, t), 7.50~7.52 (2H, t), 7.94~7.98 (1H, d), 8.41~8.46 (1H, d).
Intermediate 230-2 is synthesized using method identical with synthetic intermediate 1-1, yield 65%.
The nuclear magnetic data of intermediate 230-2：1H-NMR(400MHZ,CDCl3) δ=7.25~7.28 (ppm) (1H, t), 7.33~7.38 (1H, t), 7.41~7.45 (1H, m), 7.50~7.55 (5H, m), 7.57~7.62 (2H, t), 7.75~ 7.77 (2H, m), 7.87~7.89 (2H, d), 7.94~7.98 (2H, d), 8.45~8.46 (1H, d), 8.55~8.56 (1H, d)。
Intermediate 230-3 uses method identical with synthesis compound 1 to synthesize, yield 47%.
The nuclear magnetic data of intermediate 230-3：1H-NMR(400MHZ,CDCl3) δ=4.00~4.02 (ppm) (1H, s), 6.69~6.70 (1H, d), 6.87~6.92 (2H, m), 7.08~7.09 (2H, d), 7.15~7.16 (1d, m), 7.25~ 7.28 (2H, t), 7.33~7.38 (1H, t), 7.41~7.45 (2H, m), 7.50~7.55 (7H, m), 7.57~7.62 (3H, M), 7.68~7.69 (1H, d), 7.75~7.77 (1H, m), 7.87~7.89 (1H, d), 7.94~7.98 (2H, d), 8.45~ 8.46 (1H, d), 8.55~8.56 (1H, d).
Compound 230 is used and is synthesized with 1 identical method of compound, yield 49%.
The nuclear magnetic data of compound 230：1H-NMR(400MHZ,CDCl3) δ=6.58~6.59 (ppm) (1H, d), 6.69 ~6.70 (1H, d), 6.74~6.75 (1H, s), 6.87~6.92 (2H, m), 7.08~7.09 (2H, d), 7.15~7.16 (3H, m), 7.19~7.20 (2H, t), 7.25~7.28 (2H, m), 7.33~7.38 (4H, m), 7.41~7.45 (2H, m), 7.50~7.55 (8H, m), 7.57~7.62 (4H, m), 7.68~7.69 (1H, d), 7.75~7.77 (3H, m), 7.87~ 7.89 (2H, d), 7.94~7.98 (2H, t), 8.45~8.46 (1H, d), 8.55~8.56 (1H, d).
Preparation example 15：The synthesis of compound 281
Intermediate 281-1 is synthesized using method identical with synthetic intermediate 1-1, yield 63%.
The nuclear magnetic data of intermediate 281-1：1H-NMR(400MHZ,CDCl3) δ=1.72~1.73 (ppm) (6H, s), 7.50~7.55 (3H, m), 7.61~7.66 (1H, d), 7.72~7.73 (1H, s), 7.76~7.79 (2H, s), 7.86~ 7.89 (1H, d), 7.93~7.98 (2H, m), 8.00~8.02 (2H, m), 8.45~8.46 (1H, d).
Intermediate 281-2 uses method identical with synthesis compound 1 to synthesize, yield 54%.
The nuclear magnetic data of intermediate 281-2：1H-NMR(400MHZ,CDCl3) δ=1.72~1.73 (ppm) (6H, s), 4.00~4.01 (1H, s), 6.58~6.59 (1H, d), 6.68~6.69 (2H, d), 6.74~6.75 (1H, s), 7.41~ 7.45 (1H, m), 7.50~7.55 (8H, m), 7.61~7.63 (2H, m), 7.77~7.79 (1H, s), 7.86~7.89 (1H, D), 7.93~7.98 (2H, m), 8.00~8.02 (2H, m), 8.45~8.46 (1H, d).
Compound 281 is synthesized using method identical with synthesis compound 1, yield 44%.
The nuclear magnetic data of compound 281：1H-NMR(400MHZ,CDCl3) δ=1.72~1.73 (ppm) (6H, s), 6.58 ~6.59 (2H, d), 6.68~6.68 (2H, d), 6.75~6.76 (2H, s), 7.15~7.16 (2H, t), 7.19~7.20 (2H, t), 7.25~7.28 (1H, t), 7.33~7.38 (3H, m), 7.41~7.45 (1H, m), 7.50~7.55 (9H, m), 7.62~7.63 (3H, m), 7.75~7.77 (3H, m), 7.86~7.89 (2H, d), 7.93~7.98 (2H, t), 8.00~ 8.01 (1H, d), 8.45~8.46 (1H, d).
Preparation example 16：The synthesis of compound 304
Intermediate 304-1 is synthesized using method identical with synthetic intermediate 1-1, yield 66%.
The nuclear magnetic data of intermediate 304-1：1H-NMR(400MHZ,CDCl3) δ=7.25~7.28 (ppm) (1H, t), 7.33~7.38 (3H, m), 7.41~7.45 (1H, m), 7.50~7.55 (2H, d), 7.57~7.58 (2H, t), 7.61~ 7.66 (2H, m), 7.77~7.79 (1H, d), 7.87~7.89 (1H, d), 7.93~7.95 (1H, d), 8.03~8.13 (2H, S), 8.18~8.19 (1H, d), 8.55~8.56 (1H, d).
Intermediate 304-2 uses method identical with synthesis compound 1 to synthesize, yield 51%.
The nuclear magnetic data of intermediate 304-2：1H-NMR(400MHZ,CDCl3) δ=4.00~4.01 (ppm) (1H, s), 6.68~6.68 (2H, d), 7.25~7.28 (1H, t), 7.33~7.38 (3H, m), 7.41~7.45 (2H, m), 7.50~ 7.55 (8H, m), 7.57~7.58 (3H, m), 7.61~7.66 (3H, m), 7.77~7.79 (1H, d), 7.87~7.89 (1H, D), 7.93~7.95 (1H, d), 8.18~8.19 (1H, d), 8.55~8.56 (1H, d).
Compound 304 is synthesized using method identical with synthesis compound 1, yield 46%.
The nuclear magnetic data of compound 304：1H-NMR(400MHZ,CDCl3) δ=1.72~1.73 (ppm) (6H, s), 6.58 ~6.59 (1H, d), 6.68~6.68 (2H, d), 6.75~6.76 (1H, s), 7.25~7.28 (2H, t), 7.33~7.38 (4H, m), 7.41~7.45 (2H, m), 7.50~7.55 (9H, m), 7.57~7.58 (3H, m), 7.61~7.66 (4H, m), 7.77~7.79 (1H, m), 7.87~7.89 (2H, d), 7.93~7.95 (1H, t), 8.18~8.19 (1H, d), 8.55~ 8.56(1H,d)。
Preparation example 17：The synthesis of compound 314
Intermediate 314-1 is synthesized using method identical with synthetic intermediate 1-1, yield 68%.
The nuclear magnetic data of intermediate 314-1：1H-NMR(400MHZ,CDCl3) δ=6.27~6.30 (ppm) (2H, s), 6.58~6.59 (1H, d), 7.25~7.28 (1, t), 7.33~7.38 (3, m), 7.43~7.45 (1H, m), 7.50~7.55 (2H, d), 7.56~7.58 (3H, m), 7.61~7.66 (2H, m), 7.77~7.79 (1H, d), 7.87~7.89 (1H, d), 7.93~7.95 (1H, d), 8.18~8.19 (1H, d), 8.55~8.56 (1H, d).
Intermediate 314-2 uses method identical with synthesis compound 1 to synthesize, yield 53%.
The nuclear magnetic data of intermediate 314-2：1H-NMR(400MHZ,CDCl3) δ=4.00~4.01 (ppm) (1H, s), 6.38~6.39 (1H, d), 6.68~6.68 (2H, d), 7.25~7.28 (1H, t), 7.33~7.38 (3H, m), 7.41~ 7.45 (2H, m), 7.50~7.55 (8H, m), 7.57~7.58 (3H, m), 7.61~7.66 (2H, m), 7.77~7.79 (1H, D), 7.87~7.89 (1H, d), 7.93~7.95 (1H, d), 8.18~8.19 (1H, d), 8.55~8.56 (1H, d).
Compound 314 is synthesized using method identical with synthesis compound 1, yield 47%.
The nuclear magnetic data of compound 314：1H-NMR(400MHZ,CDCl3) δ=1.72~1.73 (ppm) (6H, s), 6.38 ~6.39 (1H, d), 6.58~6.59 (1H, d), 6.68~6.68 (2H, d), 7.25~7.28 (2H, t), 7.33~7.38 (4H, m), 7.41~7.45 (2H, m), 7.50~7.55 (9H, m), 7.57~7.58 (3H, m), 7.61~7.66 (3H, m), 7.77~7.79 (1H, m), 7.87~7.89 (2H, d), 7.93~7.95 (1H, t), 8.18~8.19 (1H, d), 8.55~ 8.56(1H,d)。
Preparation example 18：The synthesis of compound 324
The synthesis of intermediate 324-1：By the bromo- 7- chlorodiphenyls of the 3- of 0.082mol and the 9- phenyl-of furans, 0.069mol 9H- carbazole -3- boric acid and 0.104mol potassium carbonate sequentially add the mixed solution of 800mL toluene, 400mL ethyl alcohol and 200mL water In, under nitrogen protection, 0.69mmol tetra- (triphenyl phosphorus palladium) is added, heating stirring is reacted 3 hours to flowing back.By reaction solution mistake Diatom soil hopper, filtrate water extraction, organic phase make evaporation of the solvent by revolving, obtain intermediate 324-1, yield 65%.
The nuclear magnetic data of intermediate 324-1：1H-NMR (400MHz, CDCl3) δ=7.13~7.15 (ppm) (1H, d), 7.28~7.30 (1H, m), 7.43~7.46 (2H, m), 7.49~7.51 (3H, m), 7.57~7.59 (2H, m), 7.62~ 7.65 (2H, m), 7.74~7.76 (1H, d), 7.77 (1H, s), 7.82~7.84 (1H, d), 7.94~7.96 (1H, d), 7.99 ~8.01 (1H, d), 8.11~8.13 (1H, d), 8.17~8.19 (1H, d).
The synthesis of compound 324：By N- (4- xenyls) -9,9- two of 0.0448mol intermediates 324-1,0.053mol Methyl-9 H-fluorene -2- amine and 0.053mol sodium tert-butoxides are dissolved in successively in 200mL toluene, and under nitrogen protection, 0.44mol is added Tri-tert-butylphosphine and 0.44mol tris(dibenzylideneacetone) dipalladiums, stirring are warming up to 90 DEG C, react about 2 hours.Gained is reacted Liquid crosses diatom soil hopper, and organic phase is made evaporation of the solvent by Rotary Evaporators, obtains compound 324, yield 70%.Calculated value C57H40N2O:LC-MS:769.94+1。
The nuclear magnetic data of compound 324：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.32~6.34 (1H, d), 6.57~6.59 (1H, d), 6.68~6.70 (2H, d), 6.75 (1H, s), 7.27~7.30 (2H, m), 7.37~ 7.39 (1H, m), 7.40~7.46 (3H, m), 7.49~7.53 (7H, m), 7.54~7.56 (3H, m), 7.57~7.59 (2H, M), 7.61~7.65 (4H, m), 7.74~7.78 (2H, m), 7.86~7.88 (1H, d), 7.94~7.96 (1H, d), 7.99~ 8.01 (1H, d), 8.11~8.13 (1H, d), 8.17~8.19 (1H, d).
Preparation example 19：The synthesis of compound 333
Intermediate 333-1 is synthesized using method identical with synthetic intermediate 324-1, yield：53%；
The nuclear magnetic data of intermediate 333-1：1H-NMR (400MHz, CDCl3) δ=7.26~7.30 (ppm) (2H, m), 7.31~7.33 (1H, m), 7.37~7.39 (1H, m), 7.44~7.46 (1H, m), 7.49~7.51 (3H, m), 7.57~ 7.59 (2H, m), 7.62~7.64 (1H, m), 7.66~7.70 (2H, m), 7.77 (1H, s), 7.88~7.90 (1H, d), 7.99 ~8.01 (1H, d), 8.11~8.13 (1H, d), 8.17~8.19 (1H, d).
Compound 333 is synthesized using method identical with synthesis compound 324, yield：63%.
The nuclear magnetic data of compound 333：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.44~6.46 (1H, d), 6.57~6.59 (1H, d), 6.68~6.70 (2H, d), 6.75 (1H, s), 7.27~7.30 (2H, m), 7.31~ 7.33 (1H, m), 7.37~7.39 (2H, m), 7.40~7.42 (1H, m), 7.44~7.46 (1H, m), 7.49~7.53 (8H, M), 7.54~7.56 (3H, m), 7.57~7.59 (2H, m), 7.61~7.65 (4H, m), 7.77 (1H, m), 7.86~7.90 (2H, m), 7.99~8.01 (1H, d), 8.11~8.13 (1H, d), 8.17~8.19 (1H, d).
Preparation example 20：The synthesis of compound 341
Intermediate 341-1 is synthesized using method identical with synthetic intermediate 324-1, yield：55%.
The nuclear magnetic data of intermediate 341-1：1H-NMR (400MHz, CDCl3) δ=7.28~7.30 (ppm) (1H, m), 7.44~7.46 (1H, m), 7.49~7.53 (5H, m), 7.57~7.59 (2H, m), 7.77 (1H, s), 7.97~8.01 (3H, M), 8.11~8.13 (1H, d), 8.17~8.19 (1H, d), 8.20 (1H, s), 8.44~8.46 (1H, d).
Compound 341 is synthesized using method identical with synthesis compound 324, yield：66%.
The nuclear magnetic data of compound 341：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.57~6.59 (1H, d), 6.68~6.70 (2H, d), 6.75 (1H, s), 7.15 (1H, s), 7.27~7.30 (2H, m), 7.37~7.39 (2H, M), 7.40~7.42 (1H, m), 7.44~7.46 (1H, m), 7.49~7.53 (9H, m), 7.54~7.56 (3H, m), 7.57~ 7.59 (2H, m), 7.61~7.64 (2H, m), 7.77 (1H, m), 7.86~7.90 (2H, m), 7.99~8.01 (1H, d), 8.11 ~8.13 (1H, d), 8.17~8.19 (1H, d), 8.44~8.46 (1H, d).
Preparation example 21：The synthesis of compound 348
Intermediate 348-1 is synthesized using method identical with synthetic intermediate 324-1, yield 50%；
The nuclear magnetic data of intermediate 348-1：1H-NMR (400MHz, CDCl3) δ=7.28~7.30 (ppm) (1H, m), 7.44~7.46 (1H, m), 7.49~7.53 (5H, m), 7.55~7.56 (1H, d), 7.57~7.59 (2H, m), 7.62~ 7.64 (1H, d), 7.73~7.75 (1H, d), 7.77 (1H, s), 7.97~8.01 (2H, m), 8.11~8.13 (1H, d), 8.17 ~8.19 (1H, d), 8.44~8.46 (1H, d).
Compound 348 is synthesized using method identical with synthesis compound 324, yield：61%.
The nuclear magnetic data of compound 348：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.57~6.59 (1H, d), 6.68~6.70 (2H, d), 6.75 (1H, s), 6.93~6.95 (1H, d), 7.27~7.30 (2H, m), 7.37~ 7.39 (1H, m), 7.40~7.42 (1H, m), 7.44~7.46 (1H, m), 7.49~7.53 (9H, m), 7.54~7.56 (4H, M), 7.57~7.59 (2H, m), 7.61~7.64 (2H, m), 7.77 (1H, m), 7.86~7.98 (1H, d), 7.99~8.01 (2H, m), 8.11~8.13 (1H, d), 8.17~8.19 (1H, d), 8.44~8.46 (1H, d).
Preparation example 22：The synthesis of compound 367
Intermediate 367-1 is synthesized using method identical with synthetic intermediate 324-1, yield：54%；
The nuclear magnetic data of intermediate 367-1：1H-NMR (400MHz, CDCl3) δ=7.28~7.30 (ppm) (1H, m), 7.44~7.46 (1H, m), 7.49~7.53 (5H, m), 7.55~7.56 (1H, d), 7.57~7.59 (2H, m), 7.62~ 7.64 (1H, d), 7.75~7.772H, m), 7.97~8.01 (2H, m), 8.11~8.13 (1H, d), 8.17~8.19 (1H, D), 8.44~8.46 (1H, d).
Compound 367 is synthesized using method identical with synthesis compound 324, yield：64%.
The nuclear magnetic data of compound 367：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.57~6.59 (1H, d), 6.68~6.70 (2H, d), 6.75 (1H, s), 6.93~6.95 (1H, d), 7.27~7.30 (2H, m), 7.37~ 7.39 (1H, m), 7.40~7.42 (1H, m), 7.44~7.46 (1H, m), 7.49~7.53 (9H, m), 7.54~7.56 (3H, M), 7.56~7.59 (3H, m), 7.61~7.64 (2H, m), 7.77 (1H, m), 7.86~7.98 (1H, d), 7.99~8.01 (2H, m), 8.11~8.13 (1H, d), 8.17~8.19 (1H, d), 8.44~8.46 (1H, d).
The present invention is also prepared for following compound, the nuclear-magnetism number of these compounds presented below using aforementioned similar method According to：
Compound 4：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.72~6.75 (4H, d), 7.28 ~7.67 (22H, m), 7.85~7.91 (3H, m)
Compound 7：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.72~6.75 (4H, d), 7.18 (1H, s), 7.29~7.32 (1H, m), 7.42~7.77 (21H, m), 7.85~7.91 (2H, m), 7.98~8.01 (1H, m), 8.45~8.48 (1H, m)
Compound 10：1H-NMR (400MHz, CDCl3) δ=6.39 (ppm) (1H, d), 6.72~6.75 (4H, d), 7.09 (1H, m), 7.25~7.28 (1H, m), 7.35~7.56 (18H, m), 7.82~7.88 (2H, m), 7.98~8.01 (1H, m), 8.21~8.24 (1H, m), 8.42~8.45 (2H, m)
Compound 11：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.42~6.45 (1H, d), 6.72 ~6.75 (4H, d), 7.09~7.12 (1H, m), 7.25~7.28 (2H, m), 7.35~7.56 (19H, m), 7.82~7.88 (4H,m)
Compound 13：1H-NMR (400MHz, CDCl3) δ=6.72~6.75 (ppm) (4H, d), 6.86~6.89 (1H, D), 7.42~7.65 (19H, m), 7.68~7.71 (1H, d), 7.82~7.88 (4H, m), 8.21~8.24 (1H, d), 8.42 ~8.45 (1H, d)
Compound 15：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.72~6.75 (4H, d), 6.86 ~6.89 (1H, d), 7.27~7.30 (2H, m), 7.42~7.65 (19H, m), 7.82~7.85 (3H, m), 8.24~8.27 (1H, d), 8.42~8.45 (1H, d)
Compound 16：1H-NMR (400MHz, CDCl3) δ=6.72~6.75 (ppm) (4H, d), 6.86~6.89 (1H, D), 7.42~7.65 (24H, m), 7.82~7.86 (2H, m), 7.96~7.99 (1H, d), 8.12~8.15 (1H, d), 8.21 ~8.24 (1H, d), 8.42~8.45 (1H, d), 8.56~8.59 (1H, d)
Compound 17：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.32~6.35 (2H, d), 6.72 ~6.75 (4H, d), 7.08~7.11 (1H, m), 7.32~7.35 (2H, m), 7.42~7.65 (18H, m), 7.75~7.78 (2H, m), 7.82~7.88 (3H, m)
Compound 19：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.42~6.45 (1H, d), 6.69 ~6.72 (4H, d), 7.28~7.63 (23H, m), 7.92~7.95 (2H, m), 8.08 (1H, s)
Compound 21：1H-NMR (400MHz, CDCl3) δ=6.72~6.75 (ppm) (4H, d), 6.86~6.89 (1H, D), 7.32~7.38 (3H, m), 7.42~7.74 (21H, m), 7.897.92 (2H, m), 8.02~8.05 (2H, m), 8.15~ 8.18 (1H, d), 8.32~8.35 (1H, d), 8.52~8.55 (1H, d)
Compound 22：1H-NMR (400MHz, CDCl3) δ=6.72~6.75 (ppm) (4H, d), 6.95~6.98 (1H, D), 7.28~7.60 (24H, m), 7.72~7.75 (1H, d), 7.78 (1H, s), 7.87~7.90 (1H, d), 7.96~7.99 (2H, m), 8.46~8.49 (1H, m), 8.56~8.59 (1H, d)
Compound 23：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.35~6.38 (1H, d), 6.72 ~6.75 (4H, d), 7.32~7.35 (1H, m), 7.42~7.66 (19H, m), 7.65~7.68 (2H, m), 7.78~7.81 (1H, m), 7.83~7.86 (2H, m), 7.96~7.99 (1H, d)
Compound 27：1H-NMR (400MHz, CDCl3) δ=6.42~6.45 (ppm) (1H, d), 6.72~6.75 (4H, D), 7.32~7.35 (1H, m), 7.42~7.66 (18H, m), 7.64~7.67 (2H, m), 7.86~7.99 (5H, m)
Compound 29：1H-NMR (400MHz, CDCl3) δ=1.72~1.73 (ppm) (6H, s), 6.69~6.70 (4H, D), 6.88~6.89 (1H, m), 7.06~7.07 (1H, m), 7.27~7.28 (1H, m), 7.38~7.55 (18H, m), 7.80 ~7.87 (3H, m), 8.05~8.11 (3H, m).
Compound 30：1H-NMR (400MHz, CDCl3) δ=6.69~6.70 (ppm) (4H, d), 6.88~6.89 (1H, M), 7.06~7.07 (1H, s), 7.29~7.31 (2H, m), 7.41~7.63 (21H, m), 7.80~7.81 (1H, d), 8.05 ~8.12 (4H, m), 8.30~8.31 (1H, m), 8.60~8.61 (1H, m).
Compound 31：1H-NMR (400MHz, CDCl3) δ=6.69~6.70 (ppm) (4H, d), 6.88~6.89 (1H, M), 7.06~7.07 (1H, s), 7.25~7.62 (23H, m), 7.79~7.80 (2H, m), 7.94~7.95 (1H, m), 8.18 ~8.20 (2H, m), 8.41~8.42 (1H, m), 8.55~8.56 (1H, m).
Compound 33：1H-NMR (400MHz, CDCl3) δ=6.39~6.40 (ppm) (1H, d), 6.69~6.70 (4H, D), 7.25~7.66 (27H, m), 7.79~7.80 (1H, m), 7.89~7.94 (2H, m), 8.55~8.56 (1H, m).
Compound 35：1H-NMR (400MHz, CDCl3) δ=1.72~1.73 (ppm) (6H, s), 6.33~6.34 (1H, M), 6.69~6.70 (4H, d), 7.28~7.55 (21H, m), 7.63~7.64 (2H, m), 7.81~7.87 (3H, m).
Compound 38：1H-NMR (400MHz, CDCl3) δ=6.69~6.70 (ppm) (4H, d), 7.02~7.03 (1H, S), 7.17~7.18 (1H, s), 7.29~7.31 (2H, m), 7.41~7.63 (23H, m), 7.98~7.99 (1H, m), 8.12 ~8.13 (1H, m), 8.30~8.31 (1H, m), 8.45~8.51 (2H, m).
Compound 42：1H-NMR (400MHz, CDCl3) δ=1.72~1.73 (ppm) (6H, s), 6.33~6.34 (1H, D), 6.69~6.70 (4H, d), 7.28~7.29 (1H, m), 7.38~7.54 (18H, m), 7.63~7.64 (2H, m), 7.77 ~7.93 (5H, m).
Compound 44：1H-NMR (400MHz, CDCl3) δ=1.72~1.73 (ppm) (6H, s), 6.39~6.40 (1H, D), 6.69~6.70 (4H, d), 7.28~7.29 (1H, m), 7.41~7.64 (21H, m), 7.75~7.76 (1H, m), 7.87 ~7.88 (1H, m), 7.95~7.96 (1H, m), 8.06~8.07 (1H, s).
Compound 48：1H-NMR (400MHz, CDCl3) δ=6.69~6.70 (ppm) (4H, d), 6.86~6.87 (1H, M), 7.25~7.54 (22H, m), 7.69~7.77 (3H, m), 7.87~7.88 (1H, m), 7.94~7.95 (1H, m), 8.05 ~8.11 (3H, m), 8.55~8.56 (1H, m).
Compound 50：1H-NMR (400MHz, CDCl3) δ=6.69~6.70 (ppm) (4H, d), 7.15~7.16 (1H, S), 7.29~7.30 (1H, m), 7.36~7.68 (25H, m), 7.98~7.99 (1H, m), 8.10~8.12 (2H, m), 8.45 ~8.47 (2H, m).
Compound 58：1H-NMR (400MHz, CDCl3) δ=6.69~6.70 (ppm) (4H, d), 6.88~6.89 (1H, M), 7.06~7.07 (1H, s), 7.25~7.58 (22H, s), 7.79~7.80 (2H, m), 7.94~7.95 (1H, m), 8.05 ~8.11 (3H, m), 8.18~8.19 (1H, m), 8.55~8.56 (1H, m).
Compound 62：1H-NMR (400MHz, CDCl3) δ=1.72~1.73 (ppm) (6H, s), 6.69~6.70 (4H, D), 6.86~6.87 (1H, m), 7.28~7.55 (20H, m), 7.63~7.64 (1H, m), 7.73~7.74 (1H, s), 7.87 ~7.88 (1H, m), 8.05~8.11 (3H, m).
Compound 69：1H-NMR (400MHz, CDCl3) δ=1.72~1.73 (ppm) (6H, s), 6.69~6.70 (4H, D), 7.28~7.66 (23H, m), 7.87~7.89 (2H, m), 8.06~8.07 (1H, s).
Compound 72：1H-NMR(400MHZ,CDCl3) δ=6.69~6.70 (ppm) (4H, d), 7.15~7.16 (1H, S), 7.36~7.38 (1H, s), 7.41~7.43 (2H, t), 7.50~7.54 (16H, m), 7.86~7.88 (1H, d), 7.98 ~8.00 (4H, m), 8.45~8.46 (2H, d),
Compound 78：1H-NMR(400MHZ,CDCl3) δ=5.93~5.95 (ppm) (2H, d), 6.69~6.70 (4H, D), 7.32~7.38 (2H, m), 7.41~7.45 (3H, m), 7.50~7.54 (14H, m), 7.56~7.58 (1H, t), 7.63 ~7.66 (2H, m), 7.69~7.69 (2H, d), 7.71~7.73 (2H, d), 7.77~7.78 (1H, s), 7.81~7.89 (3H,m),
Compound 81：1H-NMR(400MHZ,CDCl3) δ=5.93~5.95 (ppm) (1H, s), 6.69~6.70 (4H, D), 7.29~7.30 (1H, m), 7.41~7.45 (4H, m), 7.50~7.54 (17H, m), 7.56~7.58 (4H, m), 7.63 ~7.66 (2H, m), 7.69~7.73 (2H, d), 7.77~7.78 (2H, s), 7.87~7.89 (1H, d), 7.98~8.00 (1H, d), 8.12~8.18 (2H, d),
Compound 108：1H-NMR(400MHZ,CDCl3) δ=6.69~6.70 (ppm) (4H, d), 6.86~6.87 (1H, D), 7.29~7.30 (1H, t), 7.41~7.45 (3H, m), 7.50~7.54 (15H, m), 7.56~7.58 (2H, m), 7.63 ~7.66 (1H, d), 7.69~7.73 (2H, d), 7.77~7.78 (1H, s), 8.00~8.08 (3H, m), 8.12~8.18 (3H,m),
Compound 111：1H-NMR(400MHZ,CDCl3) δ=6.33~6.34 (ppm) (1H, d), 6.69~6.70 (4H, D), 7.41~7.45 (3H, m), 7.50~7.54 (14H, m), 7.63~7.66 (2H, d), 7.75~7.76 (1H, d), 7.86 ~7.87 (1H, d), 7.98~8.00 (4H, m), 8.45~8.46 (1H, d)
Compound 114：1H-NMR(400MHZ,CDCl3) δ=6.39~6.40 (ppm) (1H, d), 6.69~6.70 (4H, D), 7.41~7.45 (4H, m), 7.50~7.54 (14H, m), 7.62~7.66 (2H, d), 7.75~7.76 (1H, d), 7.86 ~7.87 (1H, d), 7.98~8.00 (3H, m), 8.45~8.46 (1H, d),
Compound 116：1H-NMR(400MHZ,CDCl3) δ=6.43~6.45 (ppm) (1H, d), 6.69~6.70 (4H, D), 7.29~7.32 (2H, m), 7.36~7.38 (1H, t), 7.41~7.45 (3H, m), 7.50~7.54 (16H, m), 7.56 ~7.58 (2H, m), 7.62~7.66 (2H, d), 7.75~7.76 (1H, s), 7.86~7.89 (1H, d), 7.98~8.00 (1H, d), 8.12~8.18 (2H, d),
Compound 127：1H-NMR(400MHZ,CDCl3) δ=6.69~6.70 (ppm) (4H, d), 6.86~6.88 (1H, D), 7.06~7.08 (1H, s), 7.25~7.28 (1H, t), 7.32~7.33 (1H, t), 7.41~7.45 (4H, m), 7.50~ 7.54 (15H, m), 7.56~7.58 (3H, m), 7.79~7.82 (3H, m), 7.94~7.96 (2H, d), 8.55~8.57 (1H, d),
Compound 134：1H-NMR(400MHZ,CDCl3) δ=1.72~1.73 (ppm) (6H, s), 6.39~6.40 (2H, D), 6.55~6.56 (1H, s), 6.69~6.70 (1H, d), 6.87~6.88 (1H, t), 7.07~7.08 (3H, m), 7.16~ 7.19 (3H, m), 7.25~7.28 (4H, m), 7.35~7.38 (6H, m), 7.41~7.42 (2H, d), 7.50~7.55 (7H, M), 7.75~7.77 (1H, d), 7.81~7.85 (3H, m), 7.87~7.89 (3H, m),
Compound 142：1H-NMR(400MHZ,CDCl3) δ=1.72~1.73 (ppm) (6H, s), 6.33~6.39 (2H, D), 6.55~6.56 (1H, s), 6.69~6.70 (1H, d), 6.87~6.88 (1H, t), 7.07~7.08 (2H, m), 7.16~ 7.19 (3H, m), 7.25~7.28 (3H, m), 7.35~7.38 (5H, m), 7.41~7.43 (2H, d), 7.50~7.55 (8H, M), 7.61~7.64 (2H, m), 7.75~7.77 (1H, d), 7.81~7.85 (2H, m), 7.87~7.89 (3H, m), 8.05~ 8.06(1H,s),
Compound 149：1H-NMR(400MHZ,CDCl3) δ=1.72~1.73 (ppm) (6H, s), 6.33~6.39 (2H, D), 6.55~6.56 (1H, s), 6.69~6.70 (1H, d), 6.87~6.88 (1H, t), 7.07~7.08 (2H, m), 7.16~ 7.19 (3H, m), 7.25~7.28 (3H, m), 7.35~7.38 (6H, m), 7.41~7.43 (2H, d), 7.50~7.55 (8H, M), 7.63~7.66 (2H, m), 7.75~7.77 (2H, d), 7.87~7.89 (3H, m), 7.93~7.95 (1H, s),
Compound 162：1H-NMR(400MHZ,CDCl3) δ=1.72~1.73 (ppm) (6H, s), 6.33~6.39 (2H, D), 6.55~6.56 (1H, s), 6.69~6.70 (1H, d), 6.87~6.88 (1H, t), 7.07~7.08 (3H, m), 7.16~ 7.19 (3H, m), 7.25~7.28 (4H, m), 7.35~7.38 (4H, m), 7.41~7.43 (2H, d), 7.50~7.55 (8H, M), 7.63~7.66 (2H, m), 7.75~7.77 (2H, d), 7.87~7.89 (3H, m), 7.93~7.95 (1H, s),
Compound 167：1H-NMR(400MHZ,CDCl3) δ=6.33~6.39 (ppm) (1H, d), 6.55~6.56 (1H, S), 6.69~6.70 (1H, d), 6.87~6.88 (1H, t), 7.07~7.08 (2H, m), 7.16~7.19 (4H, m), 7.25~ 7.28 (3H, m), 7.35~7.38 (4H, m), 7.41~7.43 (2H, d), 7.50~7.55 (11H, m), 7.56~7.58 (2H, M), 7.63~7.66 (2H, m), 7.75~7.77 (1H, d), 7.87~7.89 (2H, m), 7.96~7.98 (1H, s), 8.10~ 8.12 (2H, t), 8.45~8.49 (2H, m),
Compound 175：1H-NMR (400MHz, CDCl3) δ=6.38~6.40 (ppm) (1H, d), 6.55 (1H, s), 6.86~6.89 (2H, m), 7.05~7.09 (3H, m), 7.15~7.19 (3H, m), 7.27~7.29 (2H, m), 7.32~ 7.41 (6H, m), 7.50~7.56 (5H, m), 7.64~7.67 (2H, m), 7.75~7.80 (3H, m), 7.86~7.90 (3H, M), 7.94~7.96 (1H, m), 8.04~8.08 (2H, m), 8.10~8.12 (1H, m).
Compound 177：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.32~6.34 (1H, d), 6.38~6.40 (1H, d), 6.55 (1H, s), 6.68~6.70 (1H, d), 6.86~6.88 (1H, m), 7.07~7.09 (2H, M), 7.15~7.19 (3H, m), 7.27~7.29 (3H, m), 7.37~7.44 (5H, m), 7.50~7.57 (7H, m), 7.62~ 7.64 (3H, m), 7.74~7.78 (3H, m), 7.86~7.88 (3H, m), 7.92~7.95 (2H, m).
Compound 184：1H-NMR (400MHz, CDCl3) δ=6.38~6.40 (ppm) (1H, d), 6.54~6.56 (1H, M), 6.68~6.70 (1H, m), 6.91~6.93 (1H, m), 7.07~7.09 (3H, m), 7.15~7.19 (3H, m), 7.25~ 7.29 (3H, m), 7.32~7.38 (4H, m), 7.40~7.45 (2H, m), 7.50~7.56 (10H, m), 7.56~7.59 (3H, M), 7.74~7.79 (2H, m), 7.86~7.88 (2H, d), 7.94~7.98 (2H, m), 8.17~8.19 (1H, d), 8.44~ 8.46 (1H, d), 8.54~8.56 (1H, d).
Compound 188：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.38~6.40 (1H, m), 6.55~6.59 (2H, m), 6.68~6.70 (1H, m), 6.75~6.77 (1H, d), 7.07~7.09 (2H, m), 7.15~ 7.19 (3H, 3), 7.27~7.29 (2H, m), 7.35~7.42 (4H, m), 7.50~7.57 (9H, m), 7.61~7.64 (2H, M), 7.75~7.82 (3H, m), 7.86~7.94 (3H, m), 7.97~7.99 (1H, m), 8.44~8.46 (1H, m).
Compound 205：1H-NMR (400MHz, CDCl3) δ=6.38~6.40 (ppm) (2H, m), 6.54~6.56 (1H, M), 6.68~6.70 (1H, d), 6.86~6.88 (1H, m), 7.07~7.09 (2H, m), 7.15~7.19 (3H, m), 7.27~ 7.29 (2H, m), 7.32~7.41 (7H, m), 7.50~7.56 (6H, m), 7.64~7.67 (2H, m), 7.70~7.73 (4H, M), 7.80~7.82 (1H, m), 7.86~7.90 (3H, m).
Compound 211：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.38~6.40 (1H, m), 6.55 (1H, s), 6.68~6.70 (1H, d), 6.85~6.88 (2H, m), 7.07~7.09 (2H, m), 7.15~7.19 (3H, M), 7.27~7.29 (2H, m), 7.35~7.41 (5H, m), 7.50~7.56 (8H, m), 7.60~7.62 (1H, m), 7.74~ 7.76 (2H, m), 7.80~7.82 (1H, m), 7.86~7.90 (3H, m).
Compound 215：1H-NMR (400MHz, CDCl3) δ=6.38~6.40 (ppm) (1H, m), 6.54~6.56 (1H, D), 6.68~6.70 (1H, m), 6.86~6.88 (1H, m), 7.07~7.09 (2H, m), 7.14~7.19 (4H, m), 7.25~ 7.29 (3H, m), 7.32~7.38 (5H, m), 7.40~7.45 (2H, m), 7.50~7.59 (12H, m), 7.74~7.78 (2H, M), 7.86~7.88 (3H, m), 7.97~7.99 (1H, d), 8.44~8.46 (1H, d), 8.54~8.56 (1H, d).
Compound 222：1H-NMR (400MHz, CDCl3) δ=6.38~6.40 (ppm) (1H, m), 6.54~6.56 (1H, D), 6.68~6.70 (1H, m), 6.86~6.88 (2H, m), 7.07~7.09 (2H, m), 7.14~7.19 (3H, m), 7.25~ 7.29 (3H, m), 7.32~7.38 (4H, m), 7.40~7.45 (2H, m), 7.50~7.59 (14H, m), 7.74~7.78 (2H, M), 7.86~7.88 (4H, m), 7.93~7.95 (1H, d), 7.99~8.02 (3H, m), 8.54~8.56 (1H, m).
Compound 235：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.38~6.40 (2H, m), 6.54~6.56 (1H, m), 6.59~6.61 (1H, d), 6.86~6.88 (1H, m), 7.07~7.09 (3H, m), 7.15~ 7.19 (3H, m), 7.25~7.29 (4H, m), 7.34~7.41 (7H, m), 7.50~7.56 (8H, m), 7.62~7.64 (1H, M), 7.74~7.76 (1H, m), 7.80~7.82 (1H, m), 7.84~7.88 (3H, m).
Compound 241：1H-NMR (400MHz, CDCl3) δ=6.38~6.40 (ppm) (2H, m), 6.54~6.56 (1H, D), 6.68~6.70 (1H, m), 6.86~6.88 (1H, m), 7.07~7.09 (2H, m), 7.15~7.19 (3H, m), 7.27~ 7.29 (2H, m), 7.31~7.38 (5H, m), 7.40~7.44 (3H, m), 7.50~7.56 (6H, m), 7.61~7.66 (3H, M), 7.71~7.76 (4H, m), 7.80~7.82 (1H, m), 7.86~7.90 (3H, m).
Compound 245：1H-NMR (400MHz, CDCl3) δ=6.38~6.40 (ppm) (1H, m), 6.54~6.56 (1H, D), 6.68~6.70 (1H, m), 6.85~6.88 (2H, m), 7.07~7.09 (2H, m), 7.15~7.19 (3H, m), 7.27~ 7.29 (2H, m), 7.31~7.38 (5H, m), 7.40~7.44 (3H, m), 7.50~7.56 (5H, m), 7.61~7.63 (1H, M), 7.74~7.76 (1H, m), 7.85~7.89 (4H, m), 7.99~8.01 (1H, d).
Compound 250：1H-NMR (400MHz, CDCl3) δ=1.72 (ppm) (6H, s), 6.38~6.40 (2H, m), 6.54~6.56 (1H, d), 6.68~6.70 (1H, m), 6.86~6.88 (1H, m), 7.07~7.09 (3H, m), 7.15~ 7.19 (3H, m), 7.27~7.29 (2H, m), 7.32~7.41 (8H, m), 7.50~7.57 (7H, m), 7.62~7.66 (2H, M), 7.74~7.77 (2H, m), 7.86~7.90 (2H, m).
Compound 137：1H-NMR (400MHz, CDCl3) δ=6.38~6.40 (ppm) (1H, m), 6.54~6.56 (1H, D), 6.68~6.70 (1H, m), 6.85~6.87 (2H, m), 7.07~7.09 (2H, m), 7.15~7.19 (3H, m), 7.26~ 7.29 (3H, m), 7.35~7.41 (4H, m), 7.50~7.58 (10H, m), 7.74~7.87 (3H, m), 7.97~7.99 (1H, M), 8.19~8.21 (2H, d), 8.41~8.46 (3H, m).
Compound 258：δ=8.10~8.10 (1H, m) 1H-NMR (300MHz, DMSO) (ppm), 7.08~7.98 (2H, M), 7.82~7.90 (7H, m), 7.69~7.69 (2H, m), 7.27~7.57 (20H, m), 7.08~8.03 (4H, m), 6.91 ~6.91 (1H, m).
Compound 275：δ=1.69~1.69 (12H, s) 1H-NMR (300MHz, DMSO) (ppm), 8.22~8.22 (1H, D), 8.00~8.08 (3H, m) 7.86~7.90 (3H, m), 7.68~7.75 (3H, m), 7.28~7.55 (17H, m), 7.16~ 7.16 (1H, d), 6.97~6.97 (1H, d).
Compound 294：δ=1.69~1.69 (300MHz, DMSO) (ppm) 1H-NMR (12H, s) 8.18~8.18 (1H, D), 8.12~8.12 (2H, m), 7.86~7.99 (6H, m), 7.68~7.75 (4H, m), 7.28~7.55 (15H, m), 7.16 ~7.16 (1H, m).
Compound 373：δ=1.69~1.69 (6H, s) 1H-NMR (300MHz, DMSO) (ppm), 8.03~8.03 (2H, M), 7.90~7.90 (1H, m), 7.75~7.82 (8H, m), 7.65~7.65 (1H, m), 7.37~7.55 (17H, m), 7.28 ~7.28 (1H, m), 6.91~6.91 (1H, m).
Compound 377：δ=8.55~8.55 (1H, m) 1H-NMR (300MHz, DMSO) (ppm), 8.45~8.45 (1H, M), 8.31~8.31 (1H, d), 7.91~7.94 (3H, m), 7.84~7.84 (1H, d), 7.74~7.75 (6H, m), 7.35~ 7.62 (22H, m), 7.16~7.16 (1H, m).
Compound 395：δ=8.55~8.55 (2H, m) 1H-NMR (300MHz, DMSO) (ppm), 7.55~7.55 (2H, M), 8.11~8.11 (2H, m), 7.75~7.77 (10H, m), 7.37~7.55 (32H, m).
Compound 401：δ=1.69~1.69 (6H, s) 1H-NMR (300MHz, DMSO) (ppm), 8.00~8.03 (3H, M), 7.68~7.86 (13H, m), 7.33~7.55 (30H, m), 7.16~7.16 (1H, m), 6.91~6.91 (1H, m).
Compound 409：δ=8.03~8.03 (4H, m) 1H-NMR (300MHz, DMSO) (ppm), 7.75~7.82 (14H, M), 7.37~7.55 (28H, m), 6.91~6.91 (2H, m).
Compound 412：δ=8.62~8.62 (1H, d) 1H-NMR (300MHz, DMSO) (ppm), 8.22~8.24 (2H, M) 8.03~8.03 (2H, m), 7.74~7.82 (12H, m), 7.37~7.62 (33H, m), 7.25~7.27 (2H, m), 6.91 ~6.91 (1H, m).
Compound 416：1H-NMR (400MHz, CDCl3) δ=1.72~1.72 (ppm) (12H, s), 6.58~6.69 (10H, d), 6.75~6.75 (2H, s), 7.41~7.41 (4H, m), 7.51~7.54 (24H, m), 7.62~7.64 (4H, m), 7.77~7.77 (2H, s), 7.82~7.88 (4H, m), 7.93~7.93 (2H, d).
Compound 423：1H-NMR (400MHz, CDCl3) δ=6.69~6.71 (ppm) (8H, d), 7.07~7.15 (2H, S), 7.32~7.36 (2H, s), 7.38~7.40 (6H, d), 7.51~7.54 (26H, m), 7.66~7.69 (1H, m), 7.89 ~7.98 (2H, d), 8.45~8.47 (1H, m).
Compound 426：1H-NMR (400MHz, CDCl3) δ=6.34~6.37 (ppm) (1H, d), 6.69~6.69 (8H, D), 6.86~6.89 (1H, d), 7.41~7.54 (30H, m), 7.66~7.69 (1H, m), 7.65~7.68 (1H, s), 7.71 ~7.73 (3H, m), 7.81~7.86 (2H, m), 8.00~8.03 (2H, m)
Compound 434：1H-NMR (400MHz, CDCl3) δ=6.39~6.41 (ppm) (1H, d), 6.69~6.69 (8H, D), 6.86~6.89 (1H, d), 7.07~7.10 (1H, t), 7.41~7.54 (30H, m), 7.81~7.85 (3H, m), 8.20 ~8.41 (2H, d).
Compound 437：1H-NMR (400MHz, CDCl3) δ=1.72~1.75 (ppm) (6H, s), 6.45~6.54 (2H, D), 6.69~6.71 (8H, d), 7.38~7.54 (35H, m), 7.66~7.69 (1H, d), 7.87~7.89 (2H, t).
Compound 440：1H-NMR (400MHz, CDCl3) δ=1.72~1.75 (ppm) (6H, s), 6.54~6.57 (1H, D), 6.69~6.71 (8H, d), 6.92~6.95 (1H, d), 7.28~7.31 (1H, t), 7.32~7.54 (34H, m), 7.87 ~7.90 (1H, d), 7.98~8.01 (1H, m), 8.45~8.47 (1H, m).
Compound 441：1H-NMR (400MHz, CDCl3) δ=1.72~1.75 (ppm) (6H, s), 6.45~6.47 (1H, D), 6.57~6.60 (1H, d), 6.69~6.71 (8H, d), 7.32~7.54 (35H, m), 7.66~7.69 (1H, d), 7.87 ~7.89 (2H, m).
Compound 442：1H-NMR (400MHz, CDCl3) δ=1.72~1.75 (ppm) (6H, s), 6.54~6.57 (1H, D), 6.69~6.71 (8H, d), 6.92~6.95 (1H, d), 7.28~7.31 (1H, t), 7.38~7.51 (34H, m), 7.87 ~7.90 (1H, d), 7.98~8.01 (1H, m), 8.45~8.47 (1H, m).
Compound 444：1H-NMR (400MHz, CDCl3) δ=6.39~6.41 (ppm) (1H, d), 6.69~6.71 (8H, D), 6.75~6.77 (2H, d), 7.38~7.51 (37H, m), 7.75~7.77 (2H, d), 7.95~8.00 (2H, m), 8.18 ~8.21 (1H, d).
Embodiment 1：Manufacture organic luminescent device
It first uses distilled water and then there is tin indium oxide (ITO) electrode (first of about 1500 angstroms of thickness with methanol supersound washing Electrode, anode) glass substrate after, washed glass substrate is dried, plasma cleaning system is moved on to, then uses Oxygen plasma cleans 5min.Then the glass substrate is loaded into vacuum deposition device.
To there are about 1000 angstroms of thickness to be formed in the ITO electrode of compound 2-TNATA vacuum depositions to the glass substrate The HIL of degree forms the HTL with about 200 angstroms of thickness in 1 vacuum deposition to hole injection layer of compound for providing preparation example.
By compound ADN and DPAVBi (dopant) with 98：2 weight ratio be co-deposited on the hole transporting zone with Form the EML with about 300 angstroms of thickness.
Then, by Alq3Vacuum deposition is on the EML to form the ETL with about 250 angstroms of thickness.Then, LiF is sunk Product forms the EIL with about 5 angstroms of thickness on ETL, and by Al be deposited on the EIL up to about 1000 thickness to form the Two electrodes (cathode) thus complete the manufacture of organic luminescent device.
Embodiment 2-92：Manufacture organic luminescent device
Embodiment 2 manufactures organic luminescent device to embodiment 92 using method same as Example 1, the difference is that The compound 1 in 1 compound represented alternative embodiment 1 of table is respectively adopted.
Comparative example 1-5
Comparative example 1-5 is carried out using method similar to Example 1, the difference is that using the substance replacementization in table 1 It closes object 1 and manufactures organic luminescent device.
Test case
It is measured using current-voltage source meter (Keithley 2400) and Minolta CS-1000A spectroradiometers real Apply driving voltage, emission effciency and the service life of the organic luminescent device in example and comparative example.As a result it is shown in the following table 1.
(1) measurement relative to the current density change of voltage change
By using current-voltage source meter (Keithley 2400) while so that voltage is increased to about 10V from 0 volt (V) Measure and flow through the current value of each of the organic luminescent device, then by the area of itself divided by corresponding luminescent device with Obtain current density.
(2) measurement relative to the brightness change of voltage change
It is surveyed while so that voltage is increased to about 10V from about 0V by using Minolta CS-1000A spectroradiometers Measure the brightness of the organic luminescent device.
(3) measurement of emission effciency
Based on organic light emission described in current density, voltage and the brightness calculation obtained by measurement (1) and (2) described above Device is in 50 milliamps per square centimeter of (mA/cm2) certain current density under current efficiency.
(4) measurement in service life
Keep 5000cd/m2Brightness (cd/m2), and measure the time that current efficiency (cd/A) is decreased to 50%.
Table 1
The organic electroluminescence device tool formed by the organic compound of the present invention is can be seen that by the data in table 1 There are low driving voltage and obviously high compared with the prior art service life, current efficiency and brightness.
The preferred embodiment of the present invention has been described above in detail, and still, the present invention is not limited thereto.In the skill of the present invention In art conception range, technical scheme of the present invention can be carried out a variety of simple variants, including each technical characteristic with it is any its His suitable method is combined, and it should also be regarded as the disclosure of the present invention for these simple variants and combination, belongs to Protection scope of the present invention.

Claims (10)

1. a kind of organic compound, which has structure shown in formula (1),
Wherein, A and B be each independently O, S,
By R1、R2、R3And R4In the group of composition any one for structure shown in formula (Y) group, by R1、R2、R3And R4In it is surplus Excess-three and R5、R6、R7And R8Any one in the group of composition is the group of structure shown in formula (Z), and R1、R2、R3、R4、 R5、R6、R7And R8In residue six be H；
In formula (Y), R9And R10For H；Or in formula (Y), R9And R10Form substituted five-membered ring together, described substituted five Membered ring so that formula (Y) is the group of structure shown in formula (Y1) or formula (Y2), in formula (Y1), R13And R14It is each independently C1-4 Alkyl or phenyl；
In formula (Z), R11And R12It is H；Or in formula (Z), R11And R12In any one be structure shown in formula (Y) Group, and another is H.
2. compound according to claim 1, wherein in formula (Y), R9And R10For H；Or in formula (Y), R9And R10 Substituted five-membered ring is formed together, the substituted five-membered ring so that formula (Y) is the group of structure shown in formula (Y1) or formula (Y2), In formula (Y1), R13And R14It is each independently C1-4Alkyl；
In formula (Z), R11And R12It is H；Or in formula (Z), R11And R12In any one be structure shown in formula (Y3) Group, and another is H,
3. compound according to claim 1, wherein by R1、R2、R3And R4Any one in the group of composition is formula (Y11) or the group of structure shown in formula (Y12), in formula (Y11) and formula (Y12), R9And R10For H；Or
In formula (Y11) and formula (Y12), R9And R10Substituted five-membered ring is formed together, and the substituted five-membered ring makes formula (Y11) it is that the group or the substituted five-membered ring of structure shown in formula (Y111) or formula (Y112) so that formula (Y12) is formula (Y121) or the group of structure shown in formula (Y122)；
R13And R14It is each independently methyl or phenyl.
4. compound according to claim 3, wherein in formula (Y12), R9And R10Substituted five-membered ring is formed together, The substituted five-membered ring so that formula (Y12) is the group of structure shown in formula (Y122).
5. according to the compound described in any one of claim 1-3, wherein R13And R14It is each independently methyl or second Base.
6. compound according to claim 1, wherein the compound be structure as shown below compound in one kind or It is two or more：
7. application of the organic compound described in any one of claim 1-6 in organic electroluminescence device.
8. a kind of Organic Electricity of one or more of organic compound containing described in any one of claim 1-6 Electroluminescence device.
9. organic electroluminescence device according to claim 8, wherein the organic compound is present in the organic electroluminescence In at least one of hole transmission layer, luminescent layer and electronic barrier layer of luminescent device.
10. organic electroluminescence device according to claim 8 or claim 9, wherein the organic electroluminescence device include according to The secondary substrate being stacked, anode, hole injection layer, hole transmission layer, optional electronic barrier layer, luminescent layer, optional sky Cave barrier layer, electron transfer layer, electron injecting layer and cathode.
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CN108117543A (en) * 2016-11-29 2018-06-05 东进世美肯株式会社 Compounds and the organic electroluminescence device for including it
CN109988134A (en) * 2017-12-29 2019-07-09 东进世美肯株式会社 Compounds and organic luminescent device comprising it
CN109988134B (en) * 2017-12-29 2024-04-02 东进世美肯株式会社 Novel compound and organic light emitting device comprising the same
US20190341552A1 (en) * 2018-05-07 2019-11-07 Shanghai Nichem Fine Chemical Co., Ltd. Compound and organic electronic device using the same
US10937968B2 (en) * 2018-05-07 2021-03-02 Shanghai Nichem Fine Chemical Co., Ltd. Compound and organic electronic device using the same
CN110526887A (en) * 2018-05-23 2019-12-03 上海嵘彩光电材料有限公司 Compound and its organic electronic device
CN111138393B (en) * 2018-11-02 2023-04-07 昱镭光电科技股份有限公司 Arylamine compound and organic electroluminescent device using the same
CN111138393A (en) * 2018-11-02 2020-05-12 昱镭光电科技股份有限公司 Arylamine compound and organic electroluminescent device using the same
CN113056462A (en) * 2018-12-11 2021-06-29 Lt素材株式会社 Heterocyclic compound, organic light-emitting element comprising same, method for producing same, and composition for organic layer of organic light-emitting element
JP2022519980A (en) * 2018-12-11 2022-03-28 エルティー・マテリアルズ・カンパニー・リミテッド Heterocyclic compound, organic light emitting device containing the same, method for producing the same, and composition for an organic layer.
WO2020122576A1 (en) * 2018-12-11 2020-06-18 엘티소재주식회사 Heterocyclic compound, organic light-emitting device comprising same, method for manufacturing same, and composition for organic material layer
CN110669040A (en) * 2019-09-26 2020-01-10 上海天马有机发光显示技术有限公司 Compound, display panel and display device
CN113135881A (en) * 2020-01-17 2021-07-20 江苏三月光电科技有限公司 Triarylamine organic compound containing dibenzofuran and application thereof
CN113135881B (en) * 2020-01-17 2023-04-07 江苏三月科技股份有限公司 Triarylamine organic compound containing dibenzofuran and application thereof
WO2021261977A1 (en) * 2020-06-26 2021-12-30 주식회사 엘지화학 Organic light-emitting device

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