CN103130824A - Method of synthetizing benzpyrole [3, 2-b] carbazoleand in high-yield mode and application of benzpyrole [3, 2-b] carbazoleand in organic solar cells - Google Patents
Method of synthetizing benzpyrole [3, 2-b] carbazoleand in high-yield mode and application of benzpyrole [3, 2-b] carbazoleand in organic solar cells Download PDFInfo
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Abstract
The invention discloses a preparation method of synthetizing benzpyrole [3, 2-b] carbazole and ramification of the benzpyrole [3, 2-b] carbazole in a high-yield mode and application of the benzpyrole [3, 2-b] carbazole and the ramification of the benzpyrole [3,2-b] carbazole. The product structure of the benzpyrole [3, 2-b] carbazole is expressed in the first formula, and the synthetizing technology is expressed in the second formula. The first technology condition is strongly acidic buffer solution, and the second technology condition is strong alkaline media. R represents an alkyl unit on a chemical compound main body and is in a structure of ethyl, alkyl thiophene, alkyl fluorene, n-octyl, isooctyl, a sulfhydryl group or a naphthenic base. X is in a structure of fluorine, chlorine, bromine, iodine, and the like, and also can be in a structure of boric acid ester, alkyl tin, alkyl magnesium or alkyl copper. Through the synthetizing technology of synthetizing benzpyrole [3, 2-b] carbazole, products expressed in the first formula can be obtained in a high yield mode. The high-yield synthetized benzpyrole [3, 2-b] carbazole has wide application prospects in photoelectric functional devices, especially in polymer solar cells, organic field effect tubes, and organic light-emitting diodes.
Description
Technical field
Due to the needs to the renewable energy utilization of cheapness, increasing researcher has turned to sight in the field of efficient, cheap photovoltaic device.The advantage that organic photovoltaic system take polymkeric substance as the basis has cheapness, easily prepares than inorganic semiconductor material, simultaneously, the potential advantages of organic photovoltaic devices are that it can prepare large-area flexible device, and this is that inorganic semiconductor material is beyond one's reach.In the last few years, the photoelectric transformation efficiency of organic photovoltaic devices was constantly soaring, had reached at present 5-9%.But in the report of just present organic solar batteries, the polymkeric substance novel material is the effective way of the efficient organic photovoltaic devices of preparation.
Background technology
The new polymers of carbazole constantly occurs, and performance is excellent aspect the raising of organic solar batteries efficient.Except the carbazole of small segment, the carbazole of condensed ring has the structure of similar pentacene, high electroconductibility.Chemically can realize that the polymkeric substance of different target is synthetic in a plurality of positions functionalization, two Fischer ring closure reaction synthesis of indole [3,2-b] carbazole is the general method of class, but the method severe reaction conditions, reaction mechanism is very complicated, the target product productive rate at present report only have 10-26%.The conjugation material of extensive synthetic planarity is the basis of realizing organic optoelectronic device, finds a kind of synthesis technique of simple and effective high yield particularly important.Technique of the present invention can be brought up to more than 51% by 10-26% by simple and effective productive rate with indoles [3,2-b] carbazole, and separates simple.
Summary of the invention
The purpose of this invention is to provide the method for a kind of high yield synthesis of indole [3,2-b] carbazole and the application in organic solar batteries thereof
Compound provided by the present invention, structure is suc as formula shown in I.
Synthesis technique such as formula III, wherein, processing condition 1 are strongly-acid buffered soln; Processing condition 2 are strongly basic medium.Alkyl unit on R representation compound main body is ethyl, alkylthrophene, alkyl fluorenes, n-octyl, iso-octyl, sulfydryl or cycloalkyl structure; X is fluorine, chlorine, bromine, iodine class formation; X also can be the structure of boric acid fat or tin alkyl, alkyl magnesium, alkyl copper, can high yield obtain the product shown in formula I by synthesis technique of the present invention, at the photoelectric functional device, particularly on polymer solar battery, organic field effect effect pipe aspect, the Organic Light Emitting Diode aspect has broad application prospects.
Preferably, compou nd synthesis method of the present invention is the reaction conditions shown in formula II.
Wherein, the preparation method of the compound of formula II structure is in dehydrated alcohol, adds the para-bromophenyl-hydrazine hydrochloride, adds in N2 gas under the aqueous solution room temperature of sodium-acetate to stir, and adds acetic acid in reaction solution, is heated to 50 ℃, splashes into Isosorbide-5-Nitrae-cyclohexanedione, filters.Leach product.Add glacial acetic acid after leaching the thing drying, the vitriol oil, anhydrous sodium acetate is heated to 60 ℃, reacts 10 minutes, and the deionized water cancellation is filtered, and leaches to obtain the formula III products collection efficiency greater than 51% after the thing anhydrous methanol is purified.
Preferably, compound of the present invention is the structure of formula III.
Perhaps, be the compound of formula IV structure,
Here the compound of formula III synthetic as follows:
1) 2,8-two bromo indoles [3,2-b] carbazole, sodium hydride, DMF reacted 30 minutes, added bromo-iso-octane reaction 24 hours.Add deionized water, use dichloromethane extraction, the mixture that obtains after drying separates through silica gel chromatographic column.Get yellow needle-like crystal, yield 83%.
2) yellow needle-like crystal is added, Potassium ethanoate connects boric acid alcohol ester frequently, DMF, Isosorbide-5-Nitrae-dioxane.Add Pd (dppf)
2Cl
2, reacted three days, add entry, dichloromethane extraction, vacuum is revolved the steaming evaporate to dryness, and the mixture that obtains separates through silica gel chromatographic column.Get pale yellow powder, yield 96%.
Here the synthetic polymer of formula V is as follows:
1) with 2,8-two (4,4,5,5-tetramethyl--1,3,2-dioxy borine)-5.11-diisooctyl indoles [3,2-b] carbazole, 4,7-two (5-bromo thiophene-2-yl)-5,6-two (alkoxyl group)-[1,2,5]-diazosulfide, 4,9-two (5-bromo thiophene-2-yl)-6,7 dialkyl group-[1,2,5] thiadiazoles [3,4-g] quinoline is in reaction 24-48 hour at 100-120 ℃ of temperature under tetrakis triphenylphosphine palladium catalysis, obtains the block conjugated polymer of formula V structure.
Another object of the present invention is to provide the application of block conjugated polymer of the present invention in organic solar batteries.
Polymer application of the present invention when the organic solar batteries, can be carried out: as follows with polymkeric substance and C
60And derivative or other the material mixing that can be used as electron acceptor(EA), add dissolution with solvents, prepare the film of one deck homogeneous by spin coating or other modes on the ITO conductive glass, then steam the mode of crossing by vacuum and prepare metal electrode on polymkeric substance, can obtain the polymer organic solar cell.
The present invention has improved the productive rate of indoles [3,2-b] carbazole, and the acceptor diazosulfide carries out side group and modifies, the block conjugated polymer that obtains has improved solvability on the one hand, reduce simultaneously the steric hindrance of alkyl chain, improved the crystal properties, thereby obtained very high organic solar batteries efficient.So polymkeric substance provided by the invention will have wide practical use in solar cell.
Description of drawings
Fig. 1 is the ultraviolet-visible absorption spectroscopy figure of embodiment 3 polymkeric substance;
Fig. 2 is the voltage-to-current curve of embodiment 4 devices.
Embodiment
Embodiment 1, preparation 2,8-two (4,4,5,5-tetramethyl--1,3,2-dioxy borine)-5.11-di-n-octyl indoles [3,2-b] carbazole are the important module during polymkeric substance synthesizes, and its preparation feedback formula is as follows:
Specifically describe as follows:
Step 1) in the 200mL dehydrated alcohol, add 30.62g (137mmol) para-bromophenyl-hydrazine hydrochloride to stir 10 minutes, the aqueous solution 100mL (the 34g sodium acetate, anhydrous is dissolved in the 100mL deionized water) that adds sodium-acetate after displacement N2 gas, stirred 20 minutes under room temperature, add 50mL acetic acid in reaction solution, be heated to 50 ℃, splashed into the solution of Isosorbide-5-Nitrae-cyclohexanedione (1): 7.67g (68.4mmol) by the constant voltage dropper and be dissolved in the 100mL dehydrated alcohol.Reacted 1 hour stopped reaction after dripping off at 50 ℃.Cool to 0 ℃ of after product and separate out, filter.Leaching thing repeatedly washs with deionized water.Naturally dry in air, get yellow powder 31.2g.Yield is in 90% left and right.
Step 2) at the 120mL glacial acetic acid, the 30mL vitriol oil adds in anhydrous sodium acetate 5g, after being cooled to 0 ℃, add several times phenylhydrazone 26.7g obtained in the previous step, stirred 10 minutes, remove ice-water bath, be heated rapidly to 60 ℃ after 15 minutes, react and naturally be down to room temperature in 10 minutes.Add deionized water 200mL to stir after 10 minutes and filter, leach thing and add the 200mL anhydrous methanol to reflux 10 minutes, slightly cold, heat filtering.With anhydrous methanol washing leaching cake repeatedly.Get pale yellow powder 13g.Yield 51%.
Step 3) 2,8-two bromo indoles [3,2-b] carbazole, 2.0g (4.83mmol), sodium hydride 1.2g (48.3mmol) is after excluding air displacement N2 gas, add dry DMF 50mL with the 50mL disposable syringe, stirred 30 minutes, and added n-octane bromide 4.6g (24mmol) with the 20mL disposable syringe in reaction system, stirring at room 24 hours.Add deionized water 100mL, divide three extractions with methylene dichloride 150mL, merge organic phase, steaming reduces pressure on instrument evaporates organic solvent through revolving after anhydrous sodium sulfate drying, and the mixture that obtains separates through silica gel chromatographic column.Sherwood oil: methylene dichloride (10: 1) is as elutriant.Get yellow needle-like crystal 2.27g, yield 73.7%.
Step 4) add 2,8-, two bromo-5.11-di-n-octyl indoles [3,2-b] carbazoles, 1.0g (1.57mmol), Potassium ethanoate (0.44g, 0.45mmol) connects boric acid alcohol ester (1.0g, 3.94mmol) frequently; DMF 20mL, Isosorbide-5-Nitrae-dioxane 40mL.Through the degassed nitrogen that fills of arm, add Pd (dppf) 2Cl2,100mg, 1-3%equ, bar up cock airtight be heated to 80 ℃ the reaction three days, add 150mL water, use the 50mL dichloromethane extraction, the organic phase that extracts three times is once removed DMF with the reextraction of 50mL water, after anhydrous sodium sulfate drying at every turn, vacuum is revolved the steaming evaporate to dryness, and the mixture that obtains separates through silica gel chromatographic column.Petrol ether/ethyl acetate (10/1) is crossed silicagel column, gets pale yellow powder 0.77g, yield 67%.
The compound of embodiment 2, preparation formula II structure
The compound structure of formula II structure is 2,8-two (4,4,5,5-tetramethyl--1,3,2-dioxy borine)-5.11-diisooctyl indoles [3,2-b] carbazole
Its preparation structural formula is as follows:
Step 1) 2,8-two bromo indoles [3,2-b] carbazole, 2.0g (4.83mmol), sodium hydride 1.2g (48.3mmol) is after excluding air displacement N2 gas, add dry DMF 50mL with the 50mL disposable syringe, stirred 30 minutes, and added bromo-iso-octane 4.6g (24mmol) with the 20mL disposable syringe in reaction system, stirring at room 24 hours.Add deionized water 100mL, divide three extractions with methylene dichloride 150mL, merge organic phase, steaming reduces pressure on instrument evaporates organic solvent through revolving after anhydrous sodium sulfate drying, and the mixture that obtains separates through silica gel chromatographic column.Sherwood oil: methylene dichloride (10: 1) is as elutriant.Get yellow needle-like crystal 2.5g, yield 83%.
Step 2) add 2,8-, the two just different basic indoles of bromo-5.11-two [3,2-b] carbazoles, 1.0g (1.57mmol), Potassium ethanoate (0.44g, 0.45mmol) connects boric acid alcohol ester (1.0g, 3.94mmol) frequently; DMF 20mL, Isosorbide-5-Nitrae-dioxane 40mL.Through the degassed nitrogen that fills of arm, add Pd (dppf) 2Cl2,100mg, 1-3%equ, bar up cock airtight be heated to 80 ℃ the reaction three days, add 150mL water, use the 50mL dichloromethane extraction, the organic phase that extracts three times is once removed DMF with the reextraction of 50mL water, after anhydrous sodium sulfate drying at every turn, vacuum is revolved the steaming evaporate to dryness, and the mixture that obtains separates through silica gel chromatographic column.Petrol ether/ethyl acetate (10/1) is crossed silicagel column, gets pale yellow powder 1.1g, yield 96%.
The block conjugated polymer of embodiment 3, preparation formula III structure
The binary conjugated polymers of formula III structure is to have 2,8-, two bromo-5.11-di-n-octyl indoles [3,2-b] carbazoles, 4,7-two (5-bromo thiophene-2-methylene radical)-5,6-two octane Oxy-1s, 3, the copolymer of 5-diazosulfide, its preparation feedback formula is as follows:
with 4 of 1mmol, 7-two (5-bromo thiophene-2-methylene radical)-5, 6-two octane Oxy-1s, 3, the 5-diazosulfide, 2 of 1mmol, 8-two (4, 4, 5, 5-tetramethyl--1, 3, 2-dioxy borine)-5.11-diisooctyl indoles [3, 2-b] carbazole, the sodium bicarbonate of 10mmol joins the tetrahydrofuran (THF) of 50ml, in the mixed solvent of the toluene of 10ml and the water of 10ml, the catalyzer tetrakis triphenylphosphine palladium that adds 0.1mmol under nitrogen protection, after heating reflux reaction three days, be cooled to room temperature, after trichloromethane, the acetone sedimentation is three times, obtain the block conjugated polymer formula III.
Embodiment 4, the organic solar batteries of preparation take conjugated polymers of the present invention as active layer material
The ultraviolet-visible absorption spectroscopy of the described ternary block conjugated polymer of embodiment 3 respectively as shown in Figure 1, from the absorption spectrum as can be known, polymkeric substance has wide absorption peak in the visible region, this is very helpful to polymer solar battery is provided to sun Optical Absorption, can be used for the making of polymer solar battery.
3mg formula III block conjugated polymer (embodiment 3 preparations) and 12mg[6,6]-phenyl-C
61-methyl-butyrate (being called for short PCBM) mixes, add the dissolving of 0.6ml orthodichlorobenzene, preparing the approximately thick film of 100nm of one deck by the spin coating mode on the ITO of PEDOT:PSS modified conductive glass, then steam the mode of crossing by vacuum and prepare metal electrode with aluminium on polymkeric substance, obtain solar cell.
We adopt following condition the test of device:
(freely open up the xenon source that scientific ﹠ technical corporation buys from Beijing, do not add filter plate, proofread and correct with the irradiatometer that the Beijing Normal University optical instrument factory buys, light intensity is 100mW/cm to simulated solar irradiation
2) under, performance of devices shows as short-circuit current=9.24 mA/cm
2Open circuit voltage=0.72V; Packing factor=0.38; Effciency of energy transfer=2.59%.Under equal test condition, the device efficiency of nonheat-treated poly-(3-hexyl thiophene) is 1.59%.
Claims (10)
1. the synthesis technique of the condensed ring carbazole of a formula I structure,
Wherein, processing condition 1 are strongly-acid buffered soln; Processing condition 2 are strongly basic medium.Alkyl unit on R representation compound main body is ethyl, alkylthrophene, alkyl fluorenes, n-octyl, iso-octyl, sulfydryl or cycloalkyl structure; X is fluorine, chlorine, bromine, iodine class formation; X also can for the structure of boric acid fat or tin alkyl, alkyl magnesium, alkyl copper, can high yield obtain the product shown in formula I by synthesis technique of the present invention.
2. synthesis technique according to claim 1, it is characterized in that: described target product synthesis condition is the reaction conditions of formula II,
Here, X is the halogen atoms such as chlorine, bromine, iodine, and processing condition one are the Lewis acids such as the vitriol oil, concentrated hydrochloric acid, acetic acid, zinc chloride.
3. synthesis technique according to claim 1, it is characterized in that: described target product synthesis condition is the reaction conditions of formula III,
Here, processing condition two are anhydrous sodium acetate, anhydrous acetic acid potassium, sodium hydroxide, potassium hydroxide, ammonium chloride, ammonium acetate etc.
4. compound according to claim 1, it is characterized in that: described reaction is the reaction conditions of formula IV.
Here, R is that carbonatoms is the saturated alkyl of 1-32, and X is the halogen atoms such as chlorine, bromine, iodine.
Reaction conditions 3 is strong basic reagent: sodium hydride, sodium hydroxide, sodium carbonate, potassium hydride KH, potassium hydroxide, salt of wormwood.
5. the preparation method of compound claimed in claim 2, be with glacial acetic acid, the vitriol oil, and the derivative of anhydrous sodium acetate and phenylhydrazine obtains 2,8-dihalo--5,11-dihydro-indoles [3,2-b] carbazole ten minutes high yields of 50-60 ℃ of reaction.
6. the preparation method of the described compound of claim 3, with glacial acetic acid, the vitriol oil, the derivative of anhydrous sodium acetate and phenylhydrazine obtains 2 ten minutes high yields of 50-60 ℃ of reaction, 8-dihalo--5,11-dihydro-indoles [3,2-b] carbazole, the crude product that obtains reflux and filter in the anhydrous methanol of heat, ethanol equal solvent is removed impurity and is obtained highly purified condensed ring carbazole.
7. claim 4 an alkylating compounds process for production thereof, be with 2,8-dihalo--5, and 11-dihydro-indoles [3,2-b] carbazole is with strong basic reagent sodium hydride, sodium hydroxide, sodium carbonate, potassium hydride KH, potassium hydroxide, salt of wormwood etc.With haloalkane reaction 24-48 hour, obtain the compound of formula IV structure.
8. preparation method according to claim 1 is characterized in that: described 2, and 8-dihalo--5,11-dihydro-indoles [3,2-b] carbazole is prepared by following steps:
1) in nitrogen, the para-bromophenyl-hydrazine hydrochloride is dissolved in the ethanolic soln of aqueous sodium acetate solution, and obtains the derivative of the two phenylhydrazines of Isosorbide-5-Nitrae hexamethylene after Isosorbide-5-Nitrae cyclohexanedione reacting by heating;
2) derivative of the two phenylhydrazines of Isosorbide-5-Nitrae hexamethylene is joined in the vitriol oil/acetic acid/acidic buffer media such as sodium acetate return stirring in nitrogen, then slowly add deionized water cancellation reaction, reaction obtains, and 2,8-dihalo--5,11-dihydro-indoles [3,2-b] carbazole crude product.
3) with 2,8-dihalo--5,11-dihydro-indoles [3,2-b] carbazole crude product.Slowly added in anhydrous methanol reflux 2-4 hour, 40-50 ℃ of filtration.It is pure 2 that the filtering thing is, 8-dihalo--5,11-dihydro-indoles [3,2-b] carbazole.
4) with 2,8-dihalo--5,11-dihydro-indoles [3,2-b] add the N that is dissolved with strong basic reagent sodium hydride, sodium hydroxide, sodium carbonate, potassium hydride KH, potassium hydroxide, salt of wormwood etc. under the carbazole room temperature, in the solution of dinethylformamide or dimethyl sulfoxide (DMSO), reaction obtained 2 in 10-48 hour with haloalkane, 8-dihalo--5,11-dialkyl group-indoles [3,2-b] carbazole.
5) with 2,8-dihalo--5,11-dialkyl group-indoles [3,2-b] boric acid fat is 1 under nitrogen with even for carbazole, and under the catalysis of 1 '-two Diphenyl phosphino ferrocene Palladous chloride methylene dichloride, 70-100 ℃ of reaction obtained 2 in 24-72 hour, 8-diboron hexahydride-5,11-dialkyl group-indoles [3,2-b] carbazole.
9. the application of the described compound of claim 1 in conjugated polymers is synthetic.
10. application according to claim 6 is characterized in that: the photoelectric functional device is polymer solar battery or semiconduction organic optoelectronic material.
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| CN103626792A (en) * | 2013-11-27 | 2014-03-12 | 山西大学 | Arylboron-containing indolo[3,2-b]carbazole compound, and preparation and application thereof |
| CN105810829A (en) * | 2016-05-06 | 2016-07-27 | 南昌航空大学 | Preparation method of indole and diazosulfide based hybrid solar cell |
| CN106478635A (en) * | 2016-08-25 | 2017-03-08 | 西安欧得光电材料有限公司 | A kind of green synthesis method of electroluminescent organic material indole carbazole compound |
| CN110741028A (en) * | 2017-06-01 | 2020-01-31 | 住友化学株式会社 | Method for producing polymer compound |
| CN111138453A (en) * | 2020-01-08 | 2020-05-12 | 河南师范大学 | Synthetic method and application of organic semiconductor material intermediate |
| CN113461692A (en) * | 2021-05-31 | 2021-10-01 | 贵州大学 | Synthetic method of indolocarbazole derivative and preparation method of long-afterglow material of indolocarbazole derivative |
| CN114853763A (en) * | 2022-03-23 | 2022-08-05 | 大连理工大学 | D-pi-A compound and application thereof in perovskite solar cell passivation |
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| CN103626792A (en) * | 2013-11-27 | 2014-03-12 | 山西大学 | Arylboron-containing indolo[3,2-b]carbazole compound, and preparation and application thereof |
| CN103626792B (en) * | 2013-11-27 | 2015-10-21 | 山西大学 | A kind of indoles [3,2-b] carbazole compound containing aryl boron and Synthesis and applications thereof |
| CN105810829A (en) * | 2016-05-06 | 2016-07-27 | 南昌航空大学 | Preparation method of indole and diazosulfide based hybrid solar cell |
| CN106478635A (en) * | 2016-08-25 | 2017-03-08 | 西安欧得光电材料有限公司 | A kind of green synthesis method of electroluminescent organic material indole carbazole compound |
| CN106478635B (en) * | 2016-08-25 | 2018-09-25 | 西安欧得光电材料有限公司 | A kind of green synthesis method of electroluminescent organic material indole carbazole compound |
| CN110741028A (en) * | 2017-06-01 | 2020-01-31 | 住友化学株式会社 | Method for producing polymer compound |
| CN110741028B (en) * | 2017-06-01 | 2022-05-03 | 住友化学株式会社 | Method for producing polymer compound |
| CN111138453A (en) * | 2020-01-08 | 2020-05-12 | 河南师范大学 | Synthetic method and application of organic semiconductor material intermediate |
| CN111138453B (en) * | 2020-01-08 | 2021-10-26 | 河南师范大学 | Synthetic method and application of organic semiconductor material intermediate |
| CN113461692A (en) * | 2021-05-31 | 2021-10-01 | 贵州大学 | Synthetic method of indolocarbazole derivative and preparation method of long-afterglow material of indolocarbazole derivative |
| CN114853763A (en) * | 2022-03-23 | 2022-08-05 | 大连理工大学 | D-pi-A compound and application thereof in perovskite solar cell passivation |
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Application publication date: 20130605 |