CN104804727A - Phenanthroimidazole derivative based luminescent material and application of material in electroluminescent device - Google Patents
Phenanthroimidazole derivative based luminescent material and application of material in electroluminescent device Download PDFInfo
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- CN104804727A CN104804727A CN201510141204.1A CN201510141204A CN104804727A CN 104804727 A CN104804727 A CN 104804727A CN 201510141204 A CN201510141204 A CN 201510141204A CN 104804727 A CN104804727 A CN 104804727A
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- 239000000463 material Substances 0.000 title claims abstract description 52
- GZPPANJXLZUWHT-UHFFFAOYSA-N 1h-naphtho[2,1-e]benzimidazole Chemical class C1=CC2=CC=CC=C2C2=C1C(N=CN1)=C1C=C2 GZPPANJXLZUWHT-UHFFFAOYSA-N 0.000 title abstract description 9
- 238000005401 electroluminescence Methods 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000003851 azoles Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 6
- 238000005286 illumination Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 264
- 238000003786 synthesis reaction Methods 0.000 description 258
- 230000015572 biosynthetic process Effects 0.000 description 256
- 239000000843 powder Substances 0.000 description 134
- 229940125904 compound 1 Drugs 0.000 description 133
- 239000000470 constituent Substances 0.000 description 130
- 238000004949 mass spectrometry Methods 0.000 description 130
- 238000005259 measurement Methods 0.000 description 130
- 150000001875 compounds Chemical class 0.000 description 93
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 31
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 31
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 31
- QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 28
- 238000000034 method Methods 0.000 description 19
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- 230000000903 blocking effect Effects 0.000 description 16
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- 230000027756 respiratory electron transport chain Effects 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- 238000002347 injection Methods 0.000 description 15
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 0 CC=C([C@@](N(C)c1c2c3cc(*)c(*)cc3c3cc(*)c(*)cc13)N2c1ccc(C2N(C3=CC=C=C3)c3c(cc(*)c(*)c4)c4c(cc(*)c(*)c4)c4c3N2C)cc1)C=C* Chemical compound CC=C([C@@](N(C)c1c2c3cc(*)c(*)cc3c3cc(*)c(*)cc13)N2c1ccc(C2N(C3=CC=C=C3)c3c(cc(*)c(*)c4)c4c(cc(*)c(*)c4)c4c3N2C)cc1)C=C* 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 10-hydroxy benzo quinoline compound Chemical class 0.000 description 3
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- 238000001194 electroluminescence spectrum Methods 0.000 description 3
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- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
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- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention provides a phenanthroimidazole derivative based luminescent material. The material can be taken as a luminescent material or a main material for preparing an organic electroluminescence device. Two phenanthroimidazole groups in each molecule of the material are asymmetrically connected together through a benzene ring, and the whole molecule does not have any symmetry; one phenanthroimidazole group is connected with the benzene ring in the middle through a C-C bond, and the other phenanthroimidazole group is connected with the benzene ring in the middle through an N-C bond. The phenanthroimidazole derivative can be directly prepared to form a luminescent layer to obtain a blue light electroluminescent device, and can be taken as the main material to be doped with a red, yellow or green light phosphorescence luminescent material for preparing a red, yellow or green light electroluminescent device. The device can be used in the application fields of panel display, illumination, light sources and the like.
Description
Technical field
The invention belongs to technical field of organic electroluminescence, be specifically related to class phenanthro-imdazole derivatives luminescent material and the application in electroluminescent device thereof.
Background technology
The people such as Pope report organic electroluminescent phenomenon the earliest in earlier 1960s, and they observed the blue light that anthracene sends when anthracene single crystal both sides apply the high pressure of four hectovolts.But because monocrystalline is difficult to growth, device drive voltage very high (400 ~ 2000V), the technique that they adopt almost does not have practical use.Until 1987, the people such as the C.W.Tang of Kodak company of the U.S. adopt ultrathin membrane technology using the good aromatic amine of hole transport effect as hole transmission layer, using the aluminum complex of oxine as luminescent layer, using tin indium oxide (ITO) film and metal alloy as anode and negative electrode, prepare luminescent device.This device obtains brightness up to 1000cd/m under 10V driving voltage
2green emission, the efficiency of device is 1.5lm/W (see C.W.TangandS.A.VanSlyke, Appl.Phys.Lett., 1987,51,913).This breakthrough makes organic electroluminescent research be able to worldwide in depth carry out rapidly.
Continue people's Late Cambrian Alq such as C.W.Tang
3after having good electroluminescent properties, people use oxine and derivative thereof and Al in succession
3+, Zn
2+, Ga
3+, Be
2+etc. having synthesized a series of complex electroluminescent material, these materials major part jaundice green glows, some blue light-emitting (see U.S.Pat.No.4,720,432; U.S.Pat.No.4,539,507; U.S.Pat.No.5,151,629; Y.Hamadaetal., Jpn.J.Appl.Phys., Part2., 1992,32, L514; M.Matsumuraetal., Jpn.J.Appl.Phys., 1996,35,5357; P.E.Burrowsetal., J.Appl.Phys., 1996,79,7991).The Sano of Sanyo company of Japan etc., at U.S.Pat.5, have prepared the blue-light device of better performances with Schiff 's base-Zn complex as luminescent layer in 432,014.It should be noted that the Hamada etc. of Japanese Sanyo company synthesizes 10-hydroxy benzo quinoline compound, its electroluminescent properties has exceeded Alq
3(Y.Hamadaetal., Chem.Lett., 1993,905).
Nineteen ninety, the people such as the Burroughes of univ cambridge uk are with polyphenylene ethylene (PPV) for the first high molecule electroluminescent device prepared by luminescent material, and the anode of device and negative electrode are respectively ITO and metallic aluminium, after the voltage applying 14V, device sends visible ray, maximum quantum efficiency is 0.05% (see J.H.Burroughes, D.D.C.Bradley, A.R.Brownetal., Nature, 1990,347,539).
The people such as the Forrest of Princeton university in 1998 study discovery, use organic luminescent device prepared by general organic materials or employing fluorescence dye doping techniques, due to the quantum mechanics transition rule constraint by spin conservation, its maximum luminous internal quantum efficiency is 25%.Phosphorescent coloring octaethylporphyrin platinum (PtOEP) is doped in main body luminescent material by they, preparing external quantum efficiency is 4%, internal quantum efficiency reaches the luminescent device of 23%, thus the frontier opening electrophosphorescence is (see M.A.Baldo, D.F.O'Brienetal., Nature, 1998,395,151).
The application of novel material in organic electroluminescence device promotes electroluminescent technology constantly improve and enter the required means of practical stage.In recent years, the exploitation of people to novel material has dropped into huge financial resources and energy, the material of a large amount of excellent property make organic electroluminescent achieve some breakthroughs (see U.S.Pat.No.5,150,006; 5,141,671; 5,073,446; 5,061,569; 5,059,862; 5,059,861; 5,047,687; 4,950,950; 5,104,740; 5,227,252; 5,256,945; 5,069,975; 5,122,711; 5,554,450; 5,683,823; 5,593,788; 5,645,948; 5,451,343; 5,623,080; 5,395,862).
In recent years, show huge application prospect along with at total colouring and solid-state white lighting field, organic electroluminescent technology is obtained in scientific research circle and industrial community and studies widely and pay close attention to.Organic micromolecular photoelectric material is used for exploitation as high performance material because of advantages such as its structure are clear and definite, be easy to modification, purification processing is simple by a large amount of.At present, luminous luminescent material and the material of main part that can meet industrial requirement are still less.Phenanthro-glyoxaline compound has the good thermostability of larger rigid plane Gu Jia ﹑ and higher fluorescence quantum efficiency, has synthesis Jian mono-﹑ product Shuai Gao ﹑ purification simultaneously and is easy to feature, therefore get more and more people's extensive concerning.
Summary of the invention
The object of the present invention is to provide phenanthro-imdazole derivatives luminescent material and preparing the application in organic electroluminescence device.
The outstanding feature of such phenanthro-imdazole derivatives is that two phenanthro-imidazole groups are asymmetricly linked together by a phenyl ring, and whole molecule is without any symmetry.In this quasi-molecule, one of them phenanthro-imidazole group is connected with the phenyl ring of centre by C-C key, and another one phenanthro-imidazole group is connected with middle phenyl ring by N-C key, and compound formula involved in the present invention is as follows:
Wherein R
1and R
2can be identical or different, can be H, the straight or branched alkyl containing 1-10 carbochain, the straight or branched alkoxyl group containing 1-10 carbochain, aromatic base, heterocyclic aromatic base;
R
3can be H, F, Cl, the straight or branched alkyl containing 1-10 carbochain, the straight or branched alkoxyl group containing 1-10 carbochain, aromatic base, heterocyclic aromatic base;
R
4and R
5can be identical or different, can be H, the straight or branched alkyl containing 1-10 carbochain, the straight or branched alkoxyl group containing 1-10 carbochain, aromatic base, heterocyclic aromatic base;
R
6can be H, F, Cl, the straight or branched alkyl containing 1-10 carbochain, straight or branched alkoxyl group, triphenylamine base and the derivative thereof containing 1-10 carbochain, hexichol amido and derivative, card azoles base and derivative thereof, N-phenyl card azoles base and derivative thereof.
Compou nd synthesis route general formula involved in the present invention is as follows:
According to above-mentioned building-up reactions general formula, compound involved in the present invention can be synthesized under similar reaction conditions.
The two phenanthro-imdazole derivatives (1-130) of the representativeness arrived involved in the present invention is as follows:
Accompanying drawing explanation
Fig. 1: apply EL device structure schematic diagram prepared by material of the present invention.
Fig. 2: the EL spectra figure applying compound 1 of the present invention preparation.
Fig. 3: the EL spectra figure applying material 77 of the present invention preparation.
Fig. 4: the EL spectra figure applying material 61 of the present invention preparation.
The structure of electroluminescent device prepared by the present invention as shown in Figure 1, each component names is: transparent glass or other transparent substrate 1, attachment ITO (indium tin oxide) anode 2 on a transparent substrate, NPB (N, N'-bis-(1-naphthyl)-N, N'-phenylbenzene-1, 1'-biphenyl-4, 4'-diamines) hole transmission layer 3, TCTA (4, 4', 4 "-three (9-carbazyl) triphenylamine) hole blocking layer 4, (two phenanthro-imdazole derivatives directly can be prepared into luminescent layer and obtain blue light electroluminescent device the luminescent layer 5 of material of the present invention, also can as material of main part and red, yellow or green phosphorescent luminescent material doping is prepared red, Huang or green glow electroluminescent device, the quality doping content of phosphorescent light-emitting materials is 5 ~ 10%), three (phenylbenzimidazol) benzene (TPBI) electron transfer layer 6, LiF electron injecting layer 7, metal A l be as negative electrode 8.Electroluminescent device of the present invention can be used for preparing display of organic electroluminescence or organize EL lighting source.
The structure of the phosphorescent light-emitting materials used is shown below:
NPB and TPBI structural formula is as follows:
Embodiment
Embodiment 1: compound PPI-NO
2synthesis:
By phenanthrenequione (12mmol), paranitrobenzaldehyde (12mmol), aniline (32mmol), ammonium acetate (62.5mmol), acetic acid (50mL) adds in there-necked flask, N
2under protection; in oil bath 123 DEG C of reflux 12 hours. stopped reaction; reaction mixture is poured in distilled water; agitation and filtration, gained grey filter cake uses water, Glacial acetic acid successively; washing with alcohol; obtain pale powder after oven dry, be then separated (silica gel, methylene dichloride) with column chromatography method and obtain white powder target product.
Involved in the present invention other contains the PPI-NO of various substituted radical
2the synthetic method of derivative is identical, according to above-mentioned reaction conditions, can be synthesized obtain by corresponding phenanthrenequione derivative, anils and benzaldehyde derivative.
Embodiment 2: compound PPI-NH
2synthesis:
By A (2mmol), 80% hydrazine hydrate (2mmol), 10%Pd/C (0.02mmol), ethanol (30mL) adds in there-necked flask, N
2under protection, in oil bath 80 DEG C of reflux 12h.Stopped reaction, filtered by reaction mixture, washed with dichloromethane filter cake, filtrate is spin-dried for, and obtains white powder target product.
Involved in the present invention other contains the PPI-NH of various substituted radical
2the synthetic method of derivative is identical, can according to above-mentioned reaction conditions, by corresponding PPI-NO
2derivative synthesis obtains.
Embodiment 3: the synthesis of compound 1:
By phenanthrenequione (0.42g, 2mmol), phenyl aldehyde (0.21g, 2mmol), compound H H (4-H)-NH
2(0.77g, 2mmol), ammonium acetate (0.39g, 5mmol), acetic acid (10mL) adds in there-necked flask, N
2under protection; in oil bath 123 DEG C of reflux 12h stopped reaction; reaction mixture is poured in distilled water; agitation and filtration; gained grey filter cake uses water, Glacial acetic acid, washing with alcohol successively, obtains pale powder after oven dry, is then separated (silica gel with column chromatography method; methylene dichloride) obtain white powder target product (0.95g, productive rate 72%).The molion quality that mass spectroscopy is determined is: 662.17 (calculated value is: 662.25); Theoretical elemental content (%) C
48h
30n
4: C, 86.98; H, 4.56; N, 8.45, actual measurement constituent content (%): C, 86.89; H, 4.61; N, 8.48.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Other target compound involved in the present invention can utilize the PPI-NH containing various substituted radical
2derivative obtains to being synthesized by corresponding phenanthrenequione derivative and benzaldehyde derivative.
Embodiment 4: the synthesis of compound 2:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 2 (1.08g, productive rate 80%), the molion quality that mass spectroscopy is determined is: 676.18 (calculated value is: 676.26); Theoretical elemental content (%) C
49h
32n
4: C, 86.96; H, 4.77; N, 8.28; Actual measurement constituent content (%): C, 86.91; H, 4.79; N, 8.29.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 5: the synthesis of compound 3:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 3 (1.16g, productive rate 84%), the molion quality that mass spectroscopy is determined is: 690.05 (calculated value is: 690.28); Theoretical elemental content (%) C
50h
34n
4: C, 86.93; H, 4.96; N, 8.11; Actual measurement constituent content (%): C, 86.73; H, 5.10; N, 8.16.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 6: the synthesis of compound 4:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 4 (1.10g, productive rate 78%), the molion quality that mass spectroscopy is determined is: 704.08 (calculated value is: 704.29); Theoretical elemental content (%) C
51h
36n
4: C, 86.90; H, 5.15; N, 7.95; Actual measurement constituent content (%): C, 86.79; H, 5.19; N, 8.02.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 7: the synthesis of compound 5:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 5 (1.07g, productive rate 76%), the molion quality that mass spectroscopy is determined is: 704.13 (calculated value is: 704.29); Theoretical elemental content (%) C
51h
36n
4: C, 86.90; H, 5.15; N, 7.95; Actual measurement constituent content (%): C, 86.75; H, 5.20; N, 8.04.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 8: the synthesis of compound 6:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 6 (1.08g, productive rate 75%), the molion quality that mass spectroscopy is determined is: 718.15 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.95; H, 5.36; N, 7.89.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 9: the synthesis of compound 7:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 7 (1.08g, productive rate 75%), the molion quality that mass spectroscopy is determined is: 718.19 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.73; H, 5.40; N, 7.86.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 10: the synthesis of compound 8:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 3 (0.96g, productive rate 75%), the molion quality that mass spectroscopy is determined is: 718.11 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.91; H, 5.30; N, 7.77.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 11: the synthesis of compound 9:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 9 (1.19g, productive rate 88%), the molion quality that mass spectroscopy is determined is: 676.05 (calculated value is: 676.26); Theoretical elemental content (%) C
49h
32n
4: C, 86.96; H, 4.77; N, 8.28; Actual measurement constituent content (%): C, 86.82; H, 4.82; N, 8.36.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 12: the synthesis of compound 10:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 10 (1.15g, productive rate 83%), the molion quality that mass spectroscopy is determined is: 690.11 (calculated value is: 690.28); Theoretical elemental content (%) C
50h
34n
4: C, 86.93; H, 4.96; N, 8.11; Actual measurement constituent content (%): C, 86.78; H, 5.01; N, 8.21.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 13: the synthesis of compound 11:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 11 (1.16g, productive rate 82%), the molion quality that mass spectroscopy is determined is: 704.15 (calculated value is: 704.29); Theoretical elemental content (%) C
51h
36n
4: C, 86.90; H, 5.15; N, 7.95; Actual measurement constituent content (%): C, 87.05; H, 5.09; N, 7.85.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 14: the synthesis of compound 12:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 12 (1.13g, productive rate 80%), the molion quality that mass spectroscopy is determined is: 704.11 (calculated value is: 704.29); Theoretical elemental content (%) C
51h
36n
4: C, 86.90; H, 5.15; N, 7.95; Actual measurement constituent content (%): C, 86.85; H, 5.25; N, 7.90.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 15: the synthesis of compound 13:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 13 (1.15g, productive rate 80%), the molion quality that mass spectroscopy is determined is: 718.20 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.75; H, 5.39; N, 7.85.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 16: the synthesis of compound 14:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 14 (1.08g, productive rate 75%), the molion quality that mass spectroscopy is determined is: 718.18 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.99; H, 5.30; N, 7.70.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 17: the synthesis of compound 15:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 15 (1.12g, productive rate 78%), the molion quality that mass spectroscopy is determined is: 718.15 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.75; H, 5.39; N, 7.85.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 18: the synthesis of compound 16:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 16 (1.04g, productive rate 75%), the molion quality that mass spectroscopy is determined is: 690.13 (calculated value is: 690.28); Theoretical elemental content (%) C
50h
34n
4: C, 86.93; H, 4.96; N, 8.11; Actual measurement constituent content (%): C, 87.12; H, 4.87; N, 8.00.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 19: the synthesis of compound 17:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 17 (1.03g, productive rate 72%), the molion quality that mass spectroscopy is determined is: 708.18 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 87.02; H, 5.27; N, 7.71.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 20: the synthesis of compound 18:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 18 (0.97g, productive rate 65%), the molion quality that mass spectroscopy is determined is: 746.21 (calculated value is: 746.34); Theoretical elemental content (%) C
54h
42n
4: C, 86.83; H, 5.67; N, 7.50; Actual measurement constituent content (%): C, 86.72; H, 5.71; N, 7.57.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 21: the synthesis of compound 19:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 19 (0.97g, productive rate 65%), the molion quality that mass spectroscopy is determined is: 746.18 (calculated value is: 746.34); Theoretical elemental content (%) C
54h
42n
4: C, 86.83; H, 5.67; N, 7.50; Actual measurement constituent content (%): C, 86.93; H, 5.56; N, 7.41.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 22: the synthesis of compound 20
According to the synthesis of compound 1, step is identical, and obtain white powder compound 20 (0.93g, productive rate 60%), the molion quality that mass spectroscopy is determined is: 774.21 (calculated value is: 774.37); Theoretical elemental content (%) C
56h
46n
4: C, 86.79; H, 5.98; N, 7.23; Actual measurement constituent content (%): C, 86.65; H, 6.02; N, 7.32.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 23: the synthesis of compound 21:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 21 (0.96g, productive rate 62%), the molion quality that mass spectroscopy is determined is: 774.29 (calculated value is: 774.37); Theoretical elemental content (%) C
56h
46n
4: C, 86.79; H, 5.98; N, 7.23; Actual measurement constituent content (%): C, 86.69; H, 6.02; N, 7.28.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 24: the synthesis of compound 22:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 22 (0.93g, productive rate 60%), the molion quality that mass spectroscopy is determined is: 774.26 (calculated value is: 774.37); Theoretical elemental content (%) C
56h
46n
4: C, 86.79; H, 5.98; N, 7.23; Actual measurement constituent content (%): C, 86.71; H, 6.08; N, 7.21.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 25: the synthesis of compound 23:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 23 (1.11g, productive rate 82%), the molion quality that mass spectroscopy is determined is: 676.11 (calculated value is: 676.26); Theoretical elemental content (%) C
49h
32n
4: C, 86.96; H, 4.77; N, 8.28; Actual measurement constituent content (%): C, 87.11; H, 4.70; N, 8.19.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 26: the synthesis of compound 24:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 24 (1.19g, productive rate 86%), the molion quality that mass spectroscopy is determined is: 690.13 (calculated value is: 690.28); Theoretical elemental content (%) C
50h
34n
4: C, 86.93; H, 4.96; N, 8.11; Actual measurement constituent content (%): C, 87.08; H, 4.90; N, 8.01.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 27: the synthesis of compound 25:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 25 (1.20g, productive rate 85%), the molion quality that mass spectroscopy is determined is: 704.19 (calculated value is: 704.29); Theoretical elemental content (%) C
51h
36n
4: C, 86.90; H, 5.15; N, 7.95; Actual measurement constituent content (%): C, 86.78; H, 5.20; N, 8.01.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 28: the synthesis of compound 26:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 26 (1.20g, productive rate 85%), the molion quality that mass spectroscopy is determined is: 704.19 (calculated value is: 704.29); Theoretical elemental content (%) C
51h
36n
4: C, 86.90; H, 5.15; N, 7.95; Actual measurement constituent content (%): C, 87.08; H, 5.07; N, 7.85.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 29: the synthesis of compound 27:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 27 (1.18g, productive rate 82%), the molion quality that mass spectroscopy is determined is: 718.21 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.75; H, 5.39; N, 7.86.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 30: the synthesis of compound 28:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 28 (1.15g, productive rate 80%), the molion quality that mass spectroscopy is determined is: 718.18 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.72; H, 5.38; N, 7.90.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 31: the synthesis of compound 29:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 29 (1.11g, productive rate 82%), the molion quality that mass spectroscopy is determined is: 676.18 (calculated value is: 676.26); Theoretical elemental content (%) C
49h
32n
4: C, 86.96; H, 4.77; N, 8.28; Actual measurement constituent content (%): C, 87.08; H, 4.72; N, 8.20.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 32: the synthesis of compound 30:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 30 (1.10g, productive rate 80%), the molion quality that mass spectroscopy is determined is: 690.19 (calculated value is: 690.28); Theoretical elemental content (%) C
50h
34n
4: C, 86.93; H, 4.96; N, 8.11; Actual measurement constituent content (%): C, 86.98; H, 4.78; N, 8.23.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 33: the synthesis of compound 31:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 31 (1.20g, productive rate 85%), the molion quality that mass spectroscopy is determined is: 704.22 (calculated value is: 704.29); Theoretical elemental content (%) C
51h
36n
4: C, 86.90; H, 5.15; N, 7.95; Actual measurement constituent content (%): C, 87.10; H, 5.05; N, 7.85.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 34: the synthesis of compound 32:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 32 (1.11g, productive rate 79%), the molion quality that mass spectroscopy is determined is: 704.19 (calculated value is: 704.29); Theoretical elemental content (%) C
51h
36n
4: C, 86.90; H, 5.15; N, 7.95; Actual measurement constituent content (%): C, 87.08; H, 5.07; N, 7.85.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 35: the synthesis of compound 33:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 33 (1.15g, productive rate 80%), the molion quality that mass spectroscopy is determined is: 718.18 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.78; H, 5.37; N, 7.84.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 36: the synthesis of compound 34:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 34 (1.12g, productive rate 78%), the molion quality that mass spectroscopy is determined is: 718.15 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.99; H, 5.28; N, 7.72.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 37: the synthesis of compound 35:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 35 (1.15g, productive rate 80%), the molion quality that mass spectroscopy is determined is: 718.19 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.99; H, 5.28; N, 7.72.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 38: the synthesis of compound 36:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 36 (1.13g, productive rate 82%), the molion quality that mass spectroscopy is determined is: 690.18 (calculated value is: 690.28); Theoretical elemental content (%) C
50h
34n
4: C, 86.93; H, 4.96; N, 8.11; Actual measurement constituent content (%): C, 87.05; H, 4.90; N, 8.05.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 39: the synthesis of compound 37:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 37 (1.08g, productive rate 75%), the molion quality that mass spectroscopy is determined is: 718.20 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.82; H, 5.30; N, 7.88.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 40: the synthesis of compound 38:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 38 (1.07g, productive rate 72%), the molion quality that mass spectroscopy is determined is: 746.22 (calculated value is: 746.34); Theoretical elemental content (%) C
54h
42n
4: C, 86.83; H, 5.67; N, 7.50; Actual measurement constituent content (%): C, 86.95; H, 5.60; N, 7.43.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 41: the synthesis of compound 39:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 39 (1.12g, productive rate 72%), the molion quality that mass spectroscopy is determined is: 774.28 (calculated value is: 774.37); Theoretical elemental content (%) C
56h
46n
4: C, 86.79; H, 5.98; N, 7.23; Actual measurement constituent content (%): C, 86.82; H, 5.90; N, 7.27.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 42: the synthesis of compound 40:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 40 (1.12g, productive rate 75%), the molion quality that mass spectroscopy is determined is: 746.22 (calculated value is: 746.34); Theoretical elemental content (%) C
54h
42n
4: C, 86.83; H, 5.67; N, 7.50; Actual measurement constituent content (%): C, 86.85; H, 5.72; N, 7.43.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 43: the synthesis of compound 41:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 41 (1.12g, productive rate 72%), the molion quality that mass spectroscopy is determined is: 774.25 (calculated value is: 774.37); Theoretical elemental content (%) C
56h
46n
4: C, 86.79; H, 5.98; N, 7.23; Actual measurement constituent content (%): C, 86.88; H, 5.87; N, 7.23.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 44: the synthesis of compound 42:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 42 (1.05g, productive rate 68%), the molion quality that mass spectroscopy is determined is: 774.29 (calculated value is: 774.37); Theoretical elemental content (%) C
56h
46n
4: C, 86.79; H, 5.98; N, 7.23; Actual measurement constituent content (%): C, 86.75; H, 5.92; N, 7.33.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 45: the synthesis of compound 43:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 43 (0.94g, productive rate 68%), the molion quality that mass spectroscopy is determined is: 690.19 (calculated value is: 690.28); Theoretical elemental content (%) C
50h
34n
4: C, 86.93; H, 4.96; N, 8.11; Actual measurement constituent content (%): C, 87.11; H, 4.88; N, 8.00.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 46: the synthesis of compound 44:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 44 (0.95g, productive rate 66%), the molion quality that mass spectroscopy is determined is: 718.18 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.76; H, 5.38; N, 7.84.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 47: the synthesis of compound 45:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 46 (1.04g, productive rate 70%), the molion quality that mass spectroscopy is determined is: 746.23 (calculated value is: 746.34); Theoretical elemental content (%) C
54h
42n
4: C, 86.83; H, 5.67; N, 7.50; Actual measurement constituent content (%): C, 86.95; H, 5.62; N, 7.43.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 48: the synthesis of compound 46:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 45 (0.96g, productive rate 62%), the molion quality that mass spectroscopy is determined is: 774.21 (calculated value is: 774.37); Theoretical elemental content (%) C
56h
46n
4: C, 86.79; H, 5.98; N, 7.23; Actual measurement constituent content (%): C, 86.95; H, 5.90; N, 7.15.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 49: the synthesis of compound 47:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 47 (0.94g, productive rate 68%), the molion quality that mass spectroscopy is determined is: 690.22 (calculated value is: 690.28); Theoretical elemental content (%) C
50h
34n
4: C, 86.93; H, 4.96; N, 8.11; Actual measurement constituent content (%): C, 87.11; H, 4.88; N, 8.00.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 50: the synthesis of compound 48:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 48 (0.95g, productive rate 66%), the molion quality that mass spectroscopy is determined is: 718.19 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.78; H, 5.38; N, 7.82.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 51: the synthesis of compound 49:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 49 (1.04g, productive rate 70%), the molion quality that mass spectroscopy is determined is: 746.28 (calculated value is: 746.34); Theoretical elemental content (%) C
54h
42n
4: C, 86.83; H, 5.67; N, 7.50; Actual measurement constituent content (%): C, 86.99; H, 5.61; N, 7.40.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 52: the synthesis of compound 50:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 50 (0.96g, productive rate 62%), the molion quality that mass spectroscopy is determined is: 774.25 (calculated value is: 774.37); Theoretical elemental content (%) C
56h
46n
4: C, 86.79; H, 5.98; N, 7.23; Actual measurement constituent content (%): C, 86.92; H, 5.95; N, 7.12.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 53: the synthesis of compound 51:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 51 (0.94g, productive rate 68%), the molion quality that mass spectroscopy is determined is: 690.20 (calculated value is: 690.28); Theoretical elemental content (%) C
50h
34n
4: C, 86.93; H, 4.96; N, 8.11; Actual measurement constituent content (%): C, 87.10; H, 4.86; N, 8.02.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 54: the synthesis of compound 52:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 52 (0.95g, productive rate 66%), the molion quality that mass spectroscopy is determined is: 718.15 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.72; H, 5.39; N, 7.87.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 55: the synthesis of compound 53:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 53 (0.94g, productive rate 68%), the molion quality that mass spectroscopy is determined is: 690.12 (calculated value is: 690.28); Theoretical elemental content (%) C
50h
34n
4: C, 86.93; H, 4.96; N, 8.11; Actual measurement constituent content (%): C, 87.06; H, 4.84; N, 8.09.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 56: the synthesis of compound 54:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 54 (0.83g, productive rate 58%), the molion quality that mass spectroscopy is determined is: 718.12 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.76; H, 5.33; N, 7.89.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 57: the synthesis of compound 55:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 55 (0.83g, productive rate 58%), the molion quality that mass spectroscopy is determined is: 718.18 (calculated value is: 718.31); Theoretical elemental content (%) C
52h
38n
4: C, 86.88; H, 5.33; N, 7.79; Actual measurement constituent content (%): C, 86.70; H, 5.35; N, 7.93.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 58: the synthesis of compound 56:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 55 (0.93g, productive rate 60%), the molion quality that mass spectroscopy is determined is: 774.19 (calculated value is: 774.37); Theoretical elemental content (%) C
56h
46n
4: C, 86.79; H, 5.98; N, 7.23; Actual measurement constituent content (%): C, 86.90; H, 5.95; N, 7.13.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 59: the synthesis of compound 57:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 57 (1.09g, productive rate 79%), the molion quality that mass spectroscopy is determined is: 690.01 (calculated value is: 690.28); Theoretical elemental content (%) C
60h
39n
5: C, 86.93; H, 4.96; N, 8.11; Actual measurement constituent content (%): C, 86.65; H, 5.08; N, 8.26.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 60: the synthesis of compound 58:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 58 (1.04g, productive rate 75%), the molion quality that mass spectroscopy is determined is: 690.03 (calculated value is: 690.28); Theoretical elemental content (%) C
60h
39n
5: C, 86.93; H, 4.96; N, 8.11; Actual measurement constituent content (%): C, 86.69; H, 5.09; N, 8.21.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 61: the synthesis of compound 59:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 59 (1.15g, productive rate 74%), the molion quality that mass spectroscopy is determined is: 774.12 (calculated value is: 774.37); Theoretical elemental content (%) C
60h
39n
5: C, 86.79; H, 5.98; N, 7.23; Actual measurement constituent content (%): C, 86.52; H, 6.03; N, 7.35.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 62: the synthesis of compound 60:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 60 (1.12g, productive rate 72%), the molion quality that mass spectroscopy is determined is: 774.16 (calculated value is: 774.37); Theoretical elemental content (%) C
60h
39n
5: C, 86.79; H, 5.98; N, 7.23; Actual measurement constituent content (%): C, 86.88; H, 5.79; N, 7.32.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 63: the synthesis of compound 61:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 61 (1.39g, productive rate 84%), the molion quality that mass spectroscopy is determined is: 827.12 (calculated value is: 827.30); Theoretical elemental content (%) C
60h
37n
5: C, 87.04; H, 4.50; N, 8.46; Actual measurement constituent content (%): C, 87.25; H, 4.39; N, 8.34.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 64: the synthesis of compound 62:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 62 (1.36g, productive rate 81%), the molion quality that mass spectroscopy is determined is: 841.28 (calculated value is: 841.32); Theoretical elemental content (%) C
61h
39n
5: C, 87.01; H, 4.67; N, 8.32; Actual measurement constituent content (%): C, 87.15; H, 4.58; N, 8.26.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 65: the synthesis of compound 63:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 63 (1.41g, productive rate 85%), the molion quality that mass spectroscopy is determined is: 829.23 (calculated value is: 829.32); Theoretical elemental content (%) C
60h
39n
5: C, 86.83; H, 4.74; N, 8.44; Actual measurement constituent content (%): C, 86.95; H, 4.68; N, 8.36.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 66: the synthesis of compound 64:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 64 (1.41g, productive rate 85%), the molion quality that mass spectroscopy is determined is: 843.29 (calculated value is: 843.34); Theoretical elemental content (%) C
61h
41n
5: C, 86.81; H, 4.90; N, 8.30; Actual measurement constituent content (%): C, 86.75; H, 4.99; N, 8.25.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 67: the synthesis of compound 65:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 65 (1.36g, productive rate 81%), the molion quality that mass spectroscopy is determined is: 883.27 (calculated value is: 883.37); Theoretical elemental content (%) C
64h
45n
5: C, 86.95; H, 5.13; N, 7.92; Actual measurement constituent content (%): C, 86.87; H, 5.16; N, 7.97.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 68: the synthesis of compound 66:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 66 (1.41g, productive rate 85%), the molion quality that mass spectroscopy is determined is: 885.31 (calculated value is: 885.38); Theoretical elemental content (%) C
64h
47n
5: C, 86.75; H, 5.35; N, 7.90; Actual measurement constituent content (%): C, 86.58; H, 5.41; N, 8.01.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 69: the synthesis of compound 67:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 67 (1.27g, productive rate 74%), the molion quality that mass spectroscopy is determined is: 857.12 (calculated value is: 857.35); Theoretical elemental content (%) C
60h
39n
5: C, 86.79; H, 5.05; N, 8.16; Actual measurement constituent content (%): C, 86.58; H, 5.20; N, 8.22.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 70: the synthesis of compound 68:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 68 (1.17g, productive rate 68%), the molion quality that mass spectroscopy is determined is: 857.04 (calculated value is: 857.35); Theoretical elemental content (%) C
60h
39n
5: C, 86.79; H, 5.05; N, 8.16; Actual measurement constituent content (%): C, 86.58; H, 5.12; N, 8.29.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 71: the synthesis of compound 69:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 69 (1.03g, productive rate 60%), the molion quality that mass spectroscopy is determined is: 855.29 (calculated value is: 855.34); Theoretical elemental content (%) C
62h
41n
5: C, 86.99; H, 4.83; N, 8.18; Actual measurement constituent content (%): C, 86.88; H, 4.88; N, 8.22.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 72: the synthesis of compound 70:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 70 (1.03g, productive rate 60%), the molion quality that mass spectroscopy is determined is: 855.26 (calculated value is: 855.34); Theoretical elemental content (%) C
62h
41n
5: C, 86.99; H, 4.83; N, 8.18; Actual measurement constituent content (%): C, 86.85; H, 4.86; N, 8.28.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 73: the synthesis of compound 71:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 71 (1.17g, productive rate 62%), the molion quality that mass spectroscopy is determined is: 941.28 (calculated value is: 941.45); Theoretical elemental content (%) C
60h
39n
5: C, 86.68; H, 5.88; N, 7.43; Actual measurement constituent content (%): C, 86.81; H, 5.84; N, 7.34.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 74: the synthesis of compound 72:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 72 (1.22g, productive rate 65%), the molion quality that mass spectroscopy is determined is: 941.23 (calculated value is: 941.45); Theoretical elemental content (%) C
60h
39n
5: C, 86.68; H, 5.88; N, 7.43; Actual measurement constituent content (%): C, 86.38; H, 5.99; N, 7.62.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 75: the synthesis of compound 73:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 73 (1.41g, productive rate 75%), the molion quality that mass spectroscopy is determined is: 939.35 (calculated value is: 939.43); Theoretical elemental content (%) C
68h
53n
5: C, 86.87; H, 5.68; N, 7.45; Actual measurement constituent content (%): C, 86.75; H, 5.72; N, 7.53.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 76: the synthesis of compound 74:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 74 (1.35g, productive rate 71%), the molion quality that mass spectroscopy is determined is: 953.38 (calculated value is: 953.45); Theoretical elemental content (%) C
69h
55n
5: C, 86.85; H, 5.81; N, 7.34; Actual measurement constituent content (%): C, 86.88; H, 5.75; N, 7.36.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 77: the synthesis of compound 75:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 75 (1.05g, productive rate 62%), the molion quality that mass spectroscopy is determined is: 843.12 (calculated value is: 843.34); Theoretical elemental content (%) C
61h
41n
5: C, 86.81; H, 4.90; N, 8.30; Actual measurement constituent content (%): C, 86.78; H, 4.82; N, 8.40.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 78: the synthesis of compound 76:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 76 (0.99g, productive rate 59%), the molion quality that mass spectroscopy is determined is: 841.18 (calculated value is: 841.32); Theoretical elemental content (%) C
61h
39n
5: C, 87.01; H, 4.67; N, 8.32; Actual measurement constituent content (%): C, 86.88; H, 4.70; N, 8.41.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 79: the synthesis of compound 77:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 77 (1.47g, productive rate 81%), the molion quality that mass spectroscopy is determined is: 905.22 (calculated value is: 905.35); Theoretical elemental content (%) C
60h
43n
5: C, 87.49; H, 4.78; N, 7.73; Actual measurement constituent content (%): C, 87.41; H, 4.81; N, 7.76.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 80: the synthesis of compound 78:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 78 (1.35g, productive rate 75%), the molion quality that mass spectroscopy is determined is: 902.68 (calculated value is: 903.34); Theoretical elemental content (%) C
66h
41n
5: C, 87.68; H, 4.57; N, 7.75; Actual measurement constituent content (%): C, 87.56; H, 4.61; N, 7.81.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 81: the synthesis of compound 79:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 79 (0.99g, productive rate 59%), the molion quality that mass spectroscopy is determined is: 919.18 (calculated value is: 919.37); Theoretical elemental content (%) C
67h
45n
5: C, 87.46; H, 4.93; N, 7.61; Actual measurement constituent content (%): C, 87.58; H, 4.88; N, 7.52.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 82: the synthesis of compound 80:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 80 (1.06g, productive rate 58%), the molion quality that mass spectroscopy is determined is: 917.26 (calculated value is: 917.35); Theoretical elemental content (%) C
67h
43n
5: C, 87.65; H, 4.72; N, 7.63; Actual measurement constituent content (%): C, 87.72; H, 4.68; N, 7.59.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 83: the synthesis of compound 81:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 81 (1.32g, productive rate 72%), the molion quality that mass spectroscopy is determined is: 912.78 (calculated value is: 917.35); Theoretical elemental content (%) C
67h
43n
5: C, 87.65; H, 4.72; N, 7.63; Actual measurement constituent content (%): C, 87.48; H, 4.81; N, 7.68.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 84: the synthesis of compound 82:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 82 (1.47g, productive rate 81%), the molion quality that mass spectroscopy is determined is: 919.15 (calculated value is: 919.37); Theoretical elemental content (%) C
67h
45n
5: C, 87.46; H, 4.93; N, 7.61; Actual measurement constituent content (%): C, 87.39; H, 5.01; N, 7.58.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 85: the synthesis of compound 83:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 83 (1.44g, productive rate 75%), the molion quality that mass spectroscopy is determined is: 958.88 (calculated value is: 959.40); Theoretical elemental content (%) C
70h
49n
5: C, 87.56; H, 5.14; N, 7.29; Actual measurement constituent content (%): C, 87.72; H, 4.06; N, 7.18.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 86: the synthesis of compound 84:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 84 (1.47g, productive rate 81%), the molion quality that mass spectroscopy is determined is: 919.15 (calculated value is: 919.37); Theoretical elemental content (%) C
67h
45n
5: C, 87.46; H, 4.93; N, 7.61; Actual measurement constituent content (%): C, 87.39; H, 5.01; N, 7.58.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 87: the synthesis of compound 85:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 85 (1.41g, productive rate 85%), the molion quality that mass spectroscopy is determined is: 829.20 (calculated value is: 829.32); Theoretical elemental content (%) C
60h
39n
5: C, 86.83; H, 4.74; N, 8.44; Actual measurement constituent content (%): C, 86.98; H, 4.69; N, 8.31.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 88: the synthesis of compound 86:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 86 (1.16g, productive rate 70%), the molion quality that mass spectroscopy is determined is: 827.15 (calculated value is: 827.30); Theoretical elemental content (%) C
60h
37n
5: C, 87.04; H, 4.50; N, 8.46; Actual measurement constituent content (%): C, 87.18; H, 4.42; N, 8.40.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 89: the synthesis of compound 87:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 87 (0.99g, productive rate 59%), the molion quality that mass spectroscopy is determined is: 841.18 (calculated value is: 841.32); Theoretical elemental content (%) C
61h
39n
5: C, 87.01; H, 4.67; N, 8.32; Actual measurement constituent content (%): C, 86.88; H, 4.70; N, 8.41.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 90: the synthesis of compound 88:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 88 (1.01g, productive rate 60%), the molion quality that mass spectroscopy is determined is: 843.22 (calculated value is: 843.34); Theoretical elemental content (%) C
61h
41n
5: C, 86.81; H, 4.90; N, 8.30; Actual measurement constituent content (%): C, 86.89; H, 4.80; N, 8.30.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 91: the synthesis of compound 89:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 89 (1.01g, productive rate 60%), the molion quality that mass spectroscopy is determined is: 843.25 (calculated value is: 843.34); Theoretical elemental content (%) C
61h
41n
5: C, 86.81; H, 4.90; N, 8.30; Actual measurement constituent content (%): C, 86.88; H, 4.85; N, 8.26.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 92: the synthesis of compound 90:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 90 (0.99g, productive rate 59%), the molion quality that mass spectroscopy is determined is: 841.21 (calculated value is: 841.32); Theoretical elemental content (%) C
61h
39n
5: C, 87.01; H, 4.67; N, 8.32; Actual measurement constituent content (%): C, 86.82; H, 4.72; N, 8.45.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 93: the synthesis of compound 91:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 91 (1.16g, productive rate 70%), the molion quality that mass spectroscopy is determined is: 829.20 (calculated value is: 829.32); Theoretical elemental content (%) C
60h
39n
5: C, 86.83; H, 4.74; N, 8.44; Actual measurement constituent content (%): C, 86.70; H, 4.80; N, 8.50.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 94: the synthesis of compound 92:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 92 (1.19g, productive rate 72%), the molion quality that mass spectroscopy is determined is: 827.21 (calculated value is: 827.30); Theoretical elemental content (%) C
60h
37n
5: C, 87.04; H, 4.50; N, 8.46; Actual measurement constituent content (%): C, 86.89; H, 4.55; N, 8.56.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 95: the synthesis of compound 93:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 93 (1.10g, productive rate 65%), the molion quality that mass spectroscopy is determined is: 843.19 (calculated value is: 843.34); Theoretical elemental content (%) C
61h
41n
5: C, 86.81; H, 4.90; N, 8.30; Actual measurement constituent content (%): C, 87.01; H, 4.80; N, 8.18.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 96: the synthesis of compound 94:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 94 (1.06g, productive rate 63%), the molion quality that mass spectroscopy is determined is: 841.15 (calculated value is: 841.32); Theoretical elemental content (%) C
61h
39n
5: C, 87.01; H, 4.67; N, 8.32; Actual measurement constituent content (%): C, 87.05; H, 4.70; N, 8.25.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 97: the synthesis of compound 95:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 95 (1.10g, productive rate 65%), the molion quality that mass spectroscopy is determined is: 843.17 (calculated value is: 843.34); Theoretical elemental content (%) C
61h
41n
5: C, 86.81; H, 4.90; N, 8.30; Actual measurement constituent content (%): C, 87.03; H, 4.82; N, 8.14.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 98: the synthesis of compound 96:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 96 (1.06g, productive rate 63%), the molion quality that mass spectroscopy is determined is: 841.12 (calculated value is: 841.32); Theoretical elemental content (%) C
61h
39n
5: C, 87.01; H, 4.67; N, 8.32; Actual measurement constituent content (%): C, 87.09; H, 4.60; N, 8.30.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 99: the synthesis of compound 97:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 97 (1.05g, productive rate 58%), the molion quality that mass spectroscopy is determined is: 905.23 (calculated value is: 905.35); Theoretical elemental content (%) C
66h
43n
5: C, 87.49; H, 4.78; N, 7.73; Actual measurement constituent content (%): C, 87.62; H, 4.75; N, 7.62.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 100: the synthesis of compound 98:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 98 (1.08g, productive rate 60%), the molion quality that mass spectroscopy is determined is: 903.25 (calculated value is: 903.34); Theoretical elemental content (%) C
66h
41n
5: C, 87.68; H, 4.57; N, 7.75; Actual measurement constituent content (%): C, 87.52; H, 4.65; N, 7.82.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 101: the synthesis of compound 99:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 99 (0.92g, productive rate 50%), the molion quality that mass spectroscopy is determined is: 919.24 (calculated value is: 919.37); Theoretical elemental content (%) C
67h
45n
5: C, 87.46; H, 4.93; N, 7.61; Actual measurement constituent content (%): C, 87.49; H, 4.96; N, 7.55.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 102: the synthesis of compound 100:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 100 (0.95g, productive rate 52%), the molion quality that mass spectroscopy is determined is: 917.27 (calculated value is: 917.35); Theoretical elemental content (%) C
67h
43n
5: C, 87.65; H, 4.72; N, 7.63; Actual measurement constituent content (%): C, 87.58; H, 4.69; N, 7.73.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 103: the synthesis of compound 101:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 101 (0.92g, productive rate 50%), the molion quality that mass spectroscopy is determined is: 919.28 (calculated value is: 919.37); Theoretical elemental content (%) C
67h
45n
5: C, 87.46; H, 4.93; N, 7.61; Actual measurement constituent content (%): C, 87.52; H, 4.98; N, 7.50.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 104: the synthesis of compound 102:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 102 (0.95g, productive rate 52%), the molion quality that mass spectroscopy is determined is: 917.21 (calculated value is: 917.35); Theoretical elemental content (%) C
67h
43n
5: C, 87.65; H, 4.72; N, 7.63; Actual measurement constituent content (%): C, 87.54; H, 4.74; N, 7.71.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 105: the synthesis of compound 103:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 103 (1.06g, productive rate 63%), the molion quality that mass spectroscopy is determined is: 841.16 (calculated value is: 841.32); Theoretical elemental content (%) C
61h
39n
5: C, 87.01; H, 4.67; N, 8.32; Actual measurement constituent content (%): C, 87.05; H, 4.66; N, 8.28.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 106: the synthesis of compound 104:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 104 (1.19g, productive rate 72%), the molion quality that mass spectroscopy is determined is: 827.20 (calculated value is: 827.30); Theoretical elemental content (%) C
60h
37n
5: C, 87.04; H, 4.50; N, 8.46; Actual measurement constituent content (%): C, 86.86; H, 4.59; N, 8.55.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 107: the synthesis of compound 105:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 105 (1.16g, productive rate 70%), the molion quality that mass spectroscopy is determined is: 829.18 (calculated value is: 829.32); Theoretical elemental content (%) C
60h
39n
5: C, 86.83; H, 4.74; N, 8.44; Actual measurement constituent content (%): C, 86.74; H, 4.82; N, 8.41.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 108: the synthesis of compound 106:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 106 (1.10g, productive rate 65%), the molion quality that mass spectroscopy is determined is: 843.19 (calculated value is: 843.34); Theoretical elemental content (%) C
61h
41n
5: C, 86.81; H, 4.90; N, 8.30; Actual measurement constituent content (%): C, 87.00; H, 4.88; N, 8.11.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 109: the synthesis of compound 107:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 107 (1.03g, productive rate 61%), the molion quality that mass spectroscopy is determined is: 845.16 (calculated value is: 845.30); Theoretical elemental content (%) C
60h
36fN
5: C, 85.19; H, 4.29; F, 2.25; N, 8.28; Actual measurement constituent content (%): C, 85.26; H, 4.22; F, 2.29; N, 8.22.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 110: the synthesis of compound 108:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 108 (1.07g, productive rate 63%), the molion quality that mass spectroscopy is determined is: 847.19 (calculated value is: 847.31); Theoretical elemental content (%) C
60h
38fN
5: C, 84.98; H, 4.52; F, 2.24; N, 8.26; Actual measurement constituent content (%): C, 84.85; H, 4.55; F, 2.29; N, 8.30.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 111: the synthesis of compound 109:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 109 (1.09g, productive rate 63%), the molion quality that mass spectroscopy is determined is: 865.15 (calculated value is: 865.30); Theoretical elemental content (%) C
60h
37f
2n
5: C, 83.22; H, 4.31; F, 4.39; N, 8.09; Actual measurement constituent content (%): C, 83.18; H, 4.38; F, 4.36; N, 8.16.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 112: the synthesis of compound 110:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 110 (1.05g, productive rate 61%), the molion quality that mass spectroscopy is determined is: 863.18 (calculated value is: 863.29); Theoretical elemental content (%) C
60h
35f
2n
5: C, 83.41; H, 4.08; F, 4.40; N, 8.11; Actual measurement constituent content (%): C, 83.28; H, 4.13; F, 4.42; N, 8.17.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 113: the synthesis of compound 111:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 111 (1.07g, productive rate 58%), the molion quality that mass spectroscopy is determined is: 923.15 (calculated value is: 923.34); Theoretical elemental content (%) C
66h
42fN
5: C, 85.78; H, 4.58; F, 2.06; N, 7.58; Actual measurement constituent content (%): C, 85.71; H, 4.53; F, 2.09; N, 7.66.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 114: the synthesis of compound 112:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 112 (0.96g, productive rate 52%), the molion quality that mass spectroscopy is determined is: 921.08 (calculated value is: 921.33); Theoretical elemental content (%) C
66h
40fN
5: C, 85.97; H, 4.37; F, 2.06; N, 7.60; Actual measurement constituent content (%): C, 85.92; H, 4.31; F, 2.09; N, 7.68.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 115: the synthesis of compound 113:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 113 (1.09g, productive rate 58%), the molion quality that mass spectroscopy is determined is: 941.28 (calculated value is: 941.33); Theoretical elemental content (%) C
66h
41f
2n
5: C, 84.15; H, 4.39; F, 4.03; N, 7.43; Actual measurement constituent content (%): C, 83.98; H, 4.46; F, 4.06; N, 7.50.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 116: the synthesis of compound 114:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 114 (0.98g, productive rate 52%), the molion quality that mass spectroscopy is determined is: 939.18 (calculated value is: 939.32); Theoretical elemental content (%) C
66h
39f
2n
5: C, 84.33; H, 4.18; F, 4.04; N, 7.45; Actual measurement constituent content (%): C, 84.38; H, 4.26; F, 4.01; N, 7.35.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 117: the synthesis of compound 115:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 115 (1.00g, productive rate 59%), the molion quality that mass spectroscopy is determined is: 845.16 (calculated value is: 845.30); Theoretical elemental content (%) C
60h
36fN
5: C, 85.19; H, 4.29; F, 2.25; N, 8.28; Actual measurement constituent content (%): C, 85.25; H, 4.23; F, 2.35; N, 8.16.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 118: the synthesis of compound 116:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 116 (1.03g, productive rate 61%), the molion quality that mass spectroscopy is determined is: 847.19 (calculated value is: 847.31); Theoretical elemental content (%) C
60h
38fN
5: C, 84.98; H, 4.52; F, 2.24; N, 8.26; Actual measurement constituent content (%): C, 85.05; H, 4.56; F, 2.15; N, 8.23.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 119: the synthesis of compound 117:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 117 (1.12g, productive rate 65%), the molion quality that mass spectroscopy is determined is: 865.21 (calculated value is: 865.30); Theoretical elemental content (%) C
60h
37f
2n
5: C, 83.22; H, 4.31; F, 4.39; N, 8.09; Actual measurement constituent content (%): C, 83.09; H, 4.36; F, 2.49; N, 8.05.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 120: the synthesis of compound 118:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 118 (1.04g, productive rate 60%), the molion quality that mass spectroscopy is determined is: 863.15 (calculated value is: 863.29); Theoretical elemental content (%) C
60h
35f
2n
5: C, 83.41; H, 4.08; F, 4.40; N, 8.11; Actual measurement constituent content (%): C, 83.49; H, 4.11; F, 4.35; N, 8.05.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 121: the synthesis of compound 119:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 119 (0.96g, productive rate 52%), the molion quality that mass spectroscopy is determined is: 923.29 (calculated value is: 923.34); Theoretical elemental content (%) C
66h
42fN
5: C, 85.78; H, 4.58; F, 2.06; N, 7.58; Actual measurement constituent content (%): C, 85.75; H, 4.51; F, 2.12; N, 7.62.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 122: the synthesis of compound 120:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 120 (1.01g, productive rate 55%), the molion quality that mass spectroscopy is determined is: 921.21 (calculated value is: 921.33); Theoretical elemental content (%) C
66h
40fN
5: C, 85.97; H, 4.37; F, 2.06; N, 7.60; Actual measurement constituent content (%): C, 85.85; H, 4.41; F, 2.08; N, 7.65.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 123: the synthesis of compound 121:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 121 (0.90g, productive rate 48%), the molion quality that mass spectroscopy is determined is: 939.24 (calculated value is: 939.32); Theoretical elemental content (%) C
66h
39f
2n
5: C, 84.33; H, 4.18; F, 4.04; N, 7.45; Actual measurement constituent content (%): C, C, 84.39; H, 4.23; F, 4.00; N, 7.38.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 124: the synthesis of compound 122:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 122 (0.90g, productive rate 48%), the molion quality that mass spectroscopy is determined is: 941.19 (calculated value is: 941.31); Theoretical elemental content (%) C
66h
41f
2n
5: C, 84.15; H, 4.39; F, 4.03; N, 7.43; Actual measurement constituent content (%): C, 84.25; H, 4.33; F, 4.07; N, 7.34.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 125: the synthesis of compound 123:
According to the synthesis of compound 1, step is identical obtains white powder compound 123 (0.86g, productive rate 51%), and the molion quality that mass spectroscopy is determined is: 847.18 (calculated value is: 847.31); Theoretical elemental content (%) C
60h
38fN
5: C, 84.98; H, 4.52; F, 2.24; N, 8.26; Actual measurement constituent content (%): C, 84.85; H, 4.59; F, 2.20; N, 8.36.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 126: the synthesis of compound 124:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 124 (1.22g, productive rate 72%), the molion quality that mass spectroscopy is determined is: 845.20 (calculated value is: 845.30); Theoretical elemental content (%) C
60h
36fN
5: C, 85.19; H, 4.29; F, 2.25; N, 8.28; Actual measurement constituent content (%): C, 85.25; H, 4.21; F, 2.19; N, 8.35.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 127: the synthesis of compound 125:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 125 (1.12g, productive rate 65%), the molion quality that mass spectroscopy is determined is: 863.18 (calculated value is: 863.29); Theoretical elemental content (%) C
60h
35f
2n
5: C, 83.41; H, 4.08; F, 4.40; N, 8.11; Actual measurement constituent content (%): C, 83.49; H, 4.13; F, 4.34; N, 8.04.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 128: the synthesis of compound 126:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 126 (1.18g, productive rate 68%), the molion quality that mass spectroscopy is determined is: 865.21 (calculated value is: 865.30); Theoretical elemental content (%) C
60h
37f
2n
5: C, 83.22; H, 4.31; F, 4.39; N, 8.09; Actual measurement constituent content (%): C, 83.29; H, 4.37; F, 4.33; N, 8.00.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 129: the synthesis of compound 127:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 127 (1.03g, productive rate 61%), the molion quality that mass spectroscopy is determined is: 847.22 (calculated value is: 847.31); Theoretical elemental content (%) C
60h
38fN
5: C, 84.98; H, 4.52; F, 2.24; N, 8.26; Actual measurement constituent content (%): C, 85.01; H, 4.52; F, 2.18; N, 8.28.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 130: the synthesis of compound 128:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 128 (1.00g, productive rate 59%), the molion quality that mass spectroscopy is determined is: 845.15 (calculated value is: 845.30); Theoretical elemental content (%) C
60h
36fN
5: C, 85.19; H, 4.29; F, 2.25; N, 8.28; Actual measurement constituent content (%): C, 85.21; H, 4.20; F, 2.37; N, 8.21.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 131: the synthesis of compound 129:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 129 (1.12g, productive rate 65%), the molion quality that mass spectroscopy is determined is: 865.16 (calculated value is: 865.30); Theoretical elemental content (%) C
60h
37f
2n
5: C, 83.22; H, 4.31; F, 4.39; N, 8.09; Actual measurement constituent content (%): C, 83.01; H, 4.39; F, 2.42; N, 8.17.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 132: the synthesis of compound 130:
According to the synthesis of compound 1, step is identical, and obtain white powder compound 130 (1.04g, productive rate 60%), the molion quality that mass spectroscopy is determined is: 863.18 (calculated value is: 863.29); Theoretical elemental content (%) C
60h
35f
2n
5: C, 83.41; H, 4.08; F, 4.40; N, 8.11; Actual measurement constituent content (%): C, 83.43; H, 4.17; F, 4.31; N, 8.09.Above-mentioned analytical results shows, the product of acquisition is the product estimated.
Embodiment 133: luminescent device [ITO/NPB/TCTA/ compound 1/TPBI/LiF/Al]
Evaporation hole transmission layer NPB (50nm) successively on the glass substrate being coated with ito anode, hole blocking layer TCTA (5nm), luminescent layer is compound 1 (20nm) prepared by embodiment 3, electron transfer layer TPBI (20nm), electron injection material LiF
al negative electrode
in evaporate process, keep pressure to be 5 × 10
-6pa.This device cut-in voltage is 3.3V, power efficiency 3.64lm/W, and brightness can reach 16130cd/m
2.
Embodiment 134: luminescent device [ITO/NPB/TCTA/ compound 77/TPBI/LiF/Al]
Evaporation hole transmission layer NPB (50nm) successively on the glass substrate being coated with ito anode, hole blocking layer TCTA (5nm), luminescent layer is compound 77 (20nm) prepared by embodiment 79, electron transfer layer TPBI (20nm), electron injection material LiF
al negative electrode
in evaporate process, keep pressure to be 5 × 10
-6pa.This device cut-in voltage is 3.2V, power efficiency 5.48lm/W, and brightness can reach 13950cd/m
2.
Embodiment 135: luminescent device [ITO/NPB/TCTA/ compound 61/TPBI/LiF/Al]
Evaporation hole transmission layer NPB (50nm) successively on the glass substrate being coated with ito anode, hole blocking layer TCTA (5nm), luminescent layer is compound 61 (20nm) prepared by embodiment 63, electron transfer layer TPBI (20nm), electron injection material LiF
al negative electrode
in evaporate process, keep pressure to be 5 × 10
-6pa.This device cut-in voltage is 3.4V, power efficiency 4.46lm/W, and brightness can reach 13820cd/m
2.
Embodiment 136: luminescent device [ITO/NPB/TCTA/ compound 61:Ir-1 (8%)/TPBI/LiF/Al]
Evaporation hole transmission layer NPB (50nm) successively on the glass substrate being coated with ito anode, hole blocking layer TCTA (5nm), luminescent layer is that compound 61 prepared by embodiment 63 adulterates 8%Ir-1 (20nm), electron transfer layer TPBI (20nm), electron injection material LiF
al negative electrode
luminescent layer doping content is weight percentage.In evaporate process, keep pressure to be 5 × 10
-6pa.This device cut-in voltage is 3.0V, power efficiency 55.8lm/W, and brightness can reach 68530cd/m
2.
Embodiment 137: luminescent device [ITO/NPB/TCTA/ compound 61:Ir-2 (8%)/TPBI/LiF/Al]
Evaporation hole transmission layer NPB (50nm) successively on the glass substrate being coated with ito anode, hole blocking layer TCTA (5nm), luminescent layer is that compound 61 prepared by embodiment 63 adulterates 8%Ir-2 (20nm), electron transfer layer TPBI (20nm), electron injection material LiF
al negative electrode
luminescent layer doping content is weight percentage.In evaporate process, keep pressure to be 5 × 10
-6pa.This device cut-in voltage is 2.9V, power efficiency 58.6lm/W, and brightness can reach 82510cd/m
2.
Embodiment 138: luminescent device [ITO/NPB/TCTA/ compound 61:Ir-3 (8%)/TPBI/LiF/Al]
Evaporation hole transmission layer NPB (50nm) successively on the glass substrate being coated with ito anode, hole blocking layer TCTA (5nm), luminescent layer is that compound 61 prepared by embodiment 63 adulterates 8%Ir-3 (20nm), electron transfer layer TPBI (20nm), electron injection material LiF
al negative electrode
luminescent layer doping content is weight percentage.In evaporate process, keep pressure to be 5 × 10
-6pa.This device cut-in voltage is 2.7V, power efficiency 20.8lm/W, and brightness can reach 36540cd/m
2.
Embodiment 139: luminescent device [ITO/NPB/TCTA/ compound 61:Ir-4 (8%)/TPBI/LiF/Al]
Evaporation hole transmission layer NPB (50nm) successively on the glass substrate being coated with ito anode, hole blocking layer TCTA (5nm), luminescent layer is that compound 61 prepared by embodiment 63 adulterates 8%Ir-4 (20nm), electron transfer layer TPBI (20nm), electron injection material LiF
al negative electrode
luminescent layer doping content is weight percentage.In evaporate process, keep pressure to be 5 × 10
-6pa.This device cut-in voltage is 3.1V, power efficiency 50.1lm/W, and brightness can reach 67490cd/m
2.
Embodiment 140: luminescent device [ITO/NPB/TCTA/ compound 61:Ir-5 (8%)/TPBI/LiF/Al]
Evaporation hole transmission layer NPB (50nm) successively on the glass substrate being coated with ito anode, hole blocking layer TCTA (5nm), luminescent layer is that compound 61 prepared by embodiment 63 adulterates 8%Ir-5 (20nm), electron transfer layer TPBI (20nm), electron injection material LiF
al negative electrode
luminescent layer doping content is weight percentage.In evaporate process, keep pressure to be 5 × 10
-6pa.This device cut-in voltage is 3.0V, power efficiency 53.1lm/W, and brightness can reach 59740cd/m
2.
Embodiment 141: luminescent device [ITO/NPB/TCTA/ compound 61:Ir-6 (8%)/TPBI/LiF/Al]
Evaporation hole transmission layer NPB (50nm) successively on the glass substrate being coated with ito anode, hole blocking layer TCTA (5nm), luminescent layer is that compound 61 prepared by embodiment 63 adulterates 8%Ir-6 (20nm), electron transfer layer TPBI (20nm), electron injection material LiF
al negative electrode
luminescent layer doping content is weight percentage.In evaporate process, keep pressure to be 5 × 10
-6pa.This device cut-in voltage is 3.0V, power efficiency 49.5lm/W, and brightness can reach 60830cd/m
2.
Embodiment 142: luminescent device [ITO/NPB/TCTA/ compound 61:Ir-7 (8%)/TPBI/LiF/Al]
Evaporation hole transmission layer NPB (50nm) successively on the glass substrate being coated with ito anode, hole blocking layer TCTA (5nm), luminescent layer is that compound 61 prepared by embodiment 63 adulterates 8%Ir-7 (20nm), electron transfer layer TPBI (20nm), electron injection material LiF
al negative electrode
luminescent layer doping content is weight percentage.In evaporate process, keep pressure to be 5 × 10
-6pa.This device cut-in voltage is 2.9V, power efficiency 53.2lm/W, and brightness can reach 67430cd/m
2.
Embodiment 143: luminescent device [ITO/NPB/TCTA/ compound 61:Ir-8 (8%)/TPBI/LiF/Al]
Evaporation hole transmission layer NPB (50nm) successively on the glass substrate being coated with ito anode, hole blocking layer TCTA (5nm), luminescent layer is that compound 61 prepared by embodiment 63 adulterates 8%Ir-8 (20nm), electron transfer layer TPBI (20nm), electron injection material LiF
al negative electrode
luminescent layer doping content is weight percentage.In evaporate process, keep pressure to be 5 × 10
-6pa.This device cut-in voltage is 3.0V, power efficiency 50.4lm/W, and brightness can reach 59780cd/m
2.
Embodiment 144: luminescent device [ITO/NPB/TCTA/ compound 61:Ir-9 (8%)/TPBI/LiF/Al]
Evaporation hole transmission layer NPB (50nm) successively on the glass substrate being coated with ito anode, hole blocking layer TCTA (5nm), luminescent layer is that compound 61 prepared by embodiment 63 adulterates 8%Ir-9 (20nm), electron transfer layer TPBI (20nm), electron injection material LiF
al negative electrode
luminescent layer doping content is weight percentage.In evaporate process, keep pressure to be 5 × 10
-6pa.This device cut-in voltage is 3.1V, power efficiency 54.3lm/W, and brightness can reach 63740cd/m
2.
Embodiment 145: luminescent device [ITO/NPB/TCTA/ compound 61:Ir-10 (8%)/TPBI/LiF/Al]
Evaporation hole transmission layer NPB (50nm) successively on the glass substrate being coated with ito anode, hole blocking layer TCTA (5nm), luminescent layer is that compound 61 prepared by embodiment 63 adulterates 10%Ir-10 (20nm), electron transfer layer TPBI (20nm), electron injection material LiF
al negative electrode
luminescent layer doping content is weight percentage.In evaporate process, keep pressure to be 5 × 10
-6pa.This device cut-in voltage is 3.1V, power efficiency 55.6lm/W, and brightness can reach 61760cd/m
2.
Embodiment 146: luminescent device [ITO/NPB/TCTA/ compound 61:Ir-11 (8%)/TPBI/LiF/Al]
Evaporation hole transmission layer NPB (50nm) successively on the glass substrate being coated with ito anode, hole blocking layer TCTA (5nm), luminescent layer is that compound 61 prepared by embodiment 63 adulterates 10%Ir-11 (20nm), electron transfer layer TPBI (20nm), electron injection material LiF
al negative electrode
luminescent layer doping content is weight percentage.In evaporate process, keep pressure to be 5 × 10
-6pa.This device cut-in voltage is 3.1V, power efficiency 60.3lm/W, and brightness can reach 71460cd/m
2.
Embodiment 147: luminescent device [ITO/NPB/TCTA/ compound 61:Ir-12 (8%)/TPBI/LiF/Al]
Evaporation hole transmission layer NPB (50nm) successively on the glass substrate being coated with ito anode, hole blocking layer TCTA (5nm), luminescent layer is that compound 61 prepared by embodiment 63 adulterates 10%Ir-12 (20nm), electron transfer layer TPBI (20nm), electron injection material LiF
al negative electrode
luminescent layer doping content is weight percentage.In evaporate process, keep pressure to be 5 × 10
-6pa.This device cut-in voltage is 3.1V, power efficiency 50.3lm/W, and brightness can reach 59270cd/m
2.
Claims (6)
1. a class phenanthro-imdazole derivatives luminescent material, its general structure is as follows:
Wherein, R
1and R
2identical or different, be H, the straight or branched alkyl containing 1-10 carbochain, straight or branched alkoxyl group, aromatic base or the heterocyclic aromatic base containing 1-10 carbochain;
R
3h, F, Cl, the straight or branched alkyl containing 1-10 carbochain, straight or branched alkoxyl group, aromatic base or the heterocyclic aromatic base containing 1-10 carbochain;
R
4and R
5identical or different, be H, the straight or branched alkyl containing 1-10 carbochain, straight or branched alkoxyl group, aromatic base or the heterocyclic aromatic base containing 1-10 carbochain;
R
6h, F, Cl, the straight or branched alkyl containing 1-10 carbochain, straight or branched alkoxyl group, triphenylamine base and the derivative thereof containing 1-10 carbochain, hexichol amido and derivative, card azoles base and derivative thereof or N-phenyl card azoles base and derivative thereof.
2. phenanthro-imdazole derivatives luminescent material as claimed in claim 1, shown in one of its concrete structure formula is following:
3. an organic electroluminescence device, is characterized in that: by the phenanthro-imdazole derivatives luminescent material described in claim 1 or 2 as luminescent layer.
4. an organic electroluminescence device, is characterized in that: to be adulterated as material of main part and phosphorescent light-emitting materials by the phenanthro-imdazole derivatives luminescent material described in claim 1 or 2 and prepare luminescent layer.
5. a kind of organic electroluminescence device as claimed in claim 4, is characterized in that: shown in one of the structural formula of phosphorescent light-emitting materials is following,
6. the organic electroluminescence device as described in claim 3 or 4 or 5, is characterized in that: this electroluminescent device is for the preparation of display of organic electroluminescence or organize EL lighting source.
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| CN105777649A (en) * | 2016-03-30 | 2016-07-20 | 吉林大学 | Aggregation-induced emissive material of triphenylethenyl-substituted phenanthroimidazole derivatives and application of aggregation-induced emissive material in preparation of organic electroluminescence device |
| CN108912053A (en) * | 2018-06-29 | 2018-11-30 | 吉林大学 | A kind of luminous organic material with distortion molecular structure and its application in organic electroluminescence device |
| CN115850187A (en) * | 2023-02-21 | 2023-03-28 | 季华实验室 | Organic electroluminescent material based on dibenzenesulfenimidazole derivative, preparation method and application thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105777649A (en) * | 2016-03-30 | 2016-07-20 | 吉林大学 | Aggregation-induced emissive material of triphenylethenyl-substituted phenanthroimidazole derivatives and application of aggregation-induced emissive material in preparation of organic electroluminescence device |
| CN105777649B (en) * | 2016-03-30 | 2018-07-06 | 吉林大学 | The gathering induced luminescence material of triphenylethylene base substitution phenanthro- imdazole derivatives and its application in organic electroluminescence device is prepared |
| CN108912053A (en) * | 2018-06-29 | 2018-11-30 | 吉林大学 | A kind of luminous organic material with distortion molecular structure and its application in organic electroluminescence device |
| CN115850187A (en) * | 2023-02-21 | 2023-03-28 | 季华实验室 | Organic electroluminescent material based on dibenzenesulfenimidazole derivative, preparation method and application thereof |
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