CN102603542A - Saccharide-modified triphenylamine organic hole transport material for all-solid-state quantum dot dye-sensitized solar cell - Google Patents
Saccharide-modified triphenylamine organic hole transport material for all-solid-state quantum dot dye-sensitized solar cell Download PDFInfo
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- Y02E10/542—Dye sensitized solar cells
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Abstract
The invention discloses a saccharide-modified triphenylamine organic hole transport material for an all-solid-state quantum dot dye-sensitized solar cell. The saccharide-modified triphenylamine organic hole transport material is characterized in that: in the organic hole transport material, triphenylamine is taken as a parent substance; a saccharide compound is introduced into any one or any two or three of positions a, b and c of triphenylamine for modifying; and the saccharide compound can be any one of glyceraldehyde, erythrose, threose, ribose, arabinose, xylose, lyxose, allose, altrose, glucose, seminose, gulose, idose, galactose and talose. A solar cell prepared with a technology disclosed by the invention has a good effect.
Description
[technical field]: the invention belongs to technical field of solar batteries, especially relate to the application of triphenylamine organic hole transport material in all solid state quantum dot sensitized solar cell that one type of carbohydrate is modified.
[background technology]: quantum dot sensitized solar cell adopts the inorganic quantum dot in narrow with crack, and (quantum dots, QDs) material such as CdSe, CdS etc. are adsorbed on inorganic semiconductor such as the titanium oxide in wide with crack and make as the light anode.The inorganic quanta point material in this narrow with crack has following advantage: 1) controllable adjustment can be realized through changing the particulate size in the with crack of QDs, and then can regulate and control the spectral response range of QDs, to reach the coupling good with solar spectrum; 2) QDs has high molar extinction coefficient, can improve the utilization ratio of sunshine; 3) quantum dot sensitized solar cell can utilize thermoelectron to produce a plurality of electron-hole pairs, therefore has higher theoretical conversion efficient (44%).
Ionogen generally is redox couple to be dissolved in the specific solvent prepare as the important composition material of quantum dot sensitized solar cell.In the work of battery, through transmitting the regeneration that electronics is realized QDs to QDs, and make battery accomplish a complete circulation through accept electronics at photocathode.Therefore, electrolytical performance has fundamental influence to the efficient of quantum dot sensitized solar cell.The best ionogen of result of use is to be many sulphur ionogen of solvent with water at present.Yet the problem that this ionogen of making solvent with water inevitably can exist volatilization to reveal has had a strong impact on the stability of battery, is difficult to satisfy the needs of practical application.Adopt the organic hole transport material to replace liquid electrolyte can be assembled into all solid state quantum dot sensitized solar cell, can solve the volatilization leakage problem of liquid electrolyte.The organic hole transport material of report has only one kind of spiro-OMeDAT at present; Also be from dye sensitization solar battery, to lend; Be not well positioned to meet the needs of quantum dot sensitized solar cell; So efficient very low (being far smaller than 1%), organic hole transport material ionogen also is not developed out efficiently.
The organic hole transport material that is used for quantum dot sensitized solar cell should have: the hole mobility that (1) is higher; (2) contact between organic hole transport material and the porous titanium dioxide film will be got well; 3) electronics and the dark reaction between the hole in the hole mobile material that are injected in the titanium dioxide film are little.Triphenylamine has higher hole mobility as the p-N-type semiconductorN, is very potential one type of organic hole transport material.The electronics and the dark reaction between the hole in the hole mobile material that how to improve the contact of triphenylamine molecule and poriferous titanium dioxide film and suppress in the titanium dioxide film are the problems of needing solution badly.
Based on this; This patent has been introduced saccharide compound on the triphenylamine parent; Utilize hydroxyl and the effect of poriferous titanium dioxide film on the sugar, make this sugar-modified triphenylamine to be adsorbed on preferably on the poriferous titanium dioxide film, increased the contact of itself and poriferous titanium dioxide film; This effect simultaneously also can the better inhibited dark reaction, has obtained good effect.Patent and document to having announced are retrieved, and do not find associated viscera.Patent of the present invention has obvious practicability, novelty and novelty.
[summary of the invention]: the present invention makes full use of the characteristic that hydroxyl can adsorb on titanium dioxide film; Utilize saccharide compound that triphenylamine is modified; Thereby obtained the verivate of a series of triphenylamines, and it has been used in the quantum dot sensitized solar cell, obtained good effect.Utilizing the interactional notion of organic molecule and inorganic semiconductor to design quantum dot sensitization solar battery electrolyte is the place of the new meaning of this invention.In addition, a series of triphenylamine derivatives that in patent of the present invention, prepare are to be applied in all solid state quantum dot sensitized solar cell as the organic hole transport material for the first time, and the result compares with existing result and also has advance.
[technical scheme of the present invention]:
Exist unsettled hydroxyl on the surface of titanium dioxide nano material, therefore can form hydrogen bond with the hydroxyl in the sugar; The surface of titanium dioxide nano material also has the undersaturated titanium atom of a large amount of coordinations in addition, they be very easy to sugared hydroxyl in oxygen combine, form co-ordination bond.This hydrogen bond and co-ordination bond acting in conjunction can make that the contact performance between sugar-modified triphenylamine and the porous titanium dioxide film greatly improves, and help improving the performance of battery.On the other hand, the dark reaction between the electronics of injection titanium oxide and the hole of hole mobile material is carried out through the undersaturated titanium atom of coordination, and this coordination can reduce the number of surface state greatly, suppresses the generation of dark reaction.
The synthetic schemes of described triphenylamine organic hole transport material: the carbohydrate that this patent adopted is poly-hydroxy aldehyde, utilizes the Wittig reaction of the phosphorus ylide reagent (4-6) of aldehyde radical and triphen amido, through two keys corresponding carbohydrate is incorporated on the triphenylamine.Therefore, the synthetic the first step is the phosphorus ylide reagent (4-6) of preparation triphen amido.
Phosphorus ylide reagent (4-6) the preparation process of triphen amido: with substituted triphenylamine of iodomethyl (1-3) and triphenyl phosphorus reaction; Obtain quaternary alkylphosphonium salt, then quaternary alkylphosphonium salt that obtains and highly basic are reacted the phosphorus ylide reagent (4-6) that obtains corresponding triphen amido under nitrogen protection.
With the phosphorus ylide reagent (4-6) of the triphen amido that obtains and any one reaction of Glycerose, erythrose, threose, ribose, pectinose, wood sugar, Lay threose, allose, altrose, glucose, seminose, gulose, idose, semi-lactosi and talose accordingly, just obtained corresponding sugar-modified triphenylamine (7-9).
The assembling process of described all solid state quantum dot sensitized solar cell is following:
1) adopt the method for silk screen printing that titania slurry is printed on the conductive glass (10); Number of times control thickness through printing; With printed titanium dioxide film high-temperature calcination, removing the organism in the slurry, and improve the contact tightness degree between the titania nanoparticles; 2) titanium dioxide film (11) after the calcining immerses the aqueous solution of halfcystine; Use acetone then; Put into the toluene solution of CdSe quantum dot at last; CdSe quantum dot (12) is adsorbed on obtains light anode, 3 on the titanium dioxide electrodes) synthetic organic hole transport material (13) is dissolved in volatile acetonitrile, methylene dichloride, any one solvent of ethanol, concentration is 0.01～0.5mol/L; 4) method of above-mentioned solution with spin coating dripped on the light anode, so that organic hole transport material solution is better immersed in the light anode, and the volatilization of accelerated solvent; 5) containing steaming gold on the light anode of organic hole transport material,, obtain complete all solid state quantum dot sensitized solar cell as counter electrode (14).
The all solid state quantum dot sensitized solar cell of said material assembling reached～electricity conversion of 1-2%.
Said one type of triphenylamine organic hole transport material that is used for the carbohydrate modification of all solid state quantum dot sensitized solar cell; It is characterized in that described organic hole transport material is parent with the triphenylamine, in arbitrary position of a of triphenylamine, b, c position or any two positions or three positions introduce saccharide compound simultaneously and modify.
Described one type of triphenylamine organic hole transport material that is used for the carbohydrate modification of all solid state quantum dot sensitized solar cell is characterized in that described saccharide compound can be any one of Glycerose, erythrose, threose, ribose, pectinose, wood sugar, Lay threose, allose, altrose, glucose, seminose, gulose, idose, semi-lactosi and talose.
Described one type of triphenylamine organic hole transport material that is used for the carbohydrate modification of all solid state quantum dot sensitized solar cell; It is characterized in that all solid state quantum dot sensitized solar cell is to assemble through following step: at first the organic hole transport material is dissolved in acetonitrile, methylene dichloride, any one solvent of ethanol, is made into the dilute solution that concentration is 0.01～0.5mol/L; Method through spin coating drips in the light anode of quantum dot sensitized solar cell then, lets solvent evaporates; At last golden counter electrode is evaporated on the above-mentioned light anode that contains the organic hole transport material.
[advantage of the present invention and effect]: patent of the present invention provides one type of triphenylamine organic hole transport material that is used for the carbohydrate modification of all solid state quantum dot sensitized solar cell; It has the following advantages and beneficial effect: 1) triphenylamine is as the p-N-type semiconductorN; Having higher hole mobility, is very potential one type of organic hole transport material.The electronics and the dark reaction between the hole in the hole mobile material that how to improve the contact of triphenylamine molecule and poriferous titanium dioxide film and suppress in the titanium dioxide film are the problems of needing solution badly.2) this patent has been introduced saccharide compound on the triphenylamine parent; Utilize hydroxyl and the effect of poriferous titanium dioxide film on the sugar; Make this sugar-modified triphenylamine can be adsorbed on the poriferous titanium dioxide film preferably; Increased the contact of itself and poriferous titanium dioxide film, this effect simultaneously also can the better inhibited dark reaction, has obtained good effect.
[description of drawings]:
Fig. 1 is the building-up process of the phosphorus ylide reagent of triphen amido.
Fig. 2 is the building-up process of organic hole transport material
Fig. 3 is based on the structural representation of all solid state quantum dot sensitized solar cell of organic hole transport material.
[embodiment]:
Below in conjunction with embodiment content of the present invention is further specified, but protection domain of the present invention is not limited only to following examples, everyly belongs to the technical scheme that content of the present invention is equal to, all belong to the protection domain of this patent.
The 0.01mol triphenyl phosphorus is dissolved in the 200mL THF, then the substituted triphenylamine of 0.01mol iodomethyl (1) is dripped slowly in above-mentioned solution, stirring at room 24 hours is washed the deposition that obtains drying with ether.Then dried solid is dissolved in the 200mL THF, nitrogen protection adds the NaH of 0.02mol down, and stirring at room 20 hours obtains phosphorus ylide (4).5mmol is dissolved in the 20mL THF with phosphorus ylide (4); Any one of the corresponding Glycerose of adding 5mmol, erythrose, threose, ribose, pectinose, wood sugar, Lay threose, allose, altrose, glucose, seminose, gulose, idose, semi-lactosi and talose, stirring at room 48 hours.After reaction stops reaction solution being poured in the water and wash, and extract organic product with anhydrous diethyl ether, the organic phase that obtains use anhydrous sodium sulfate drying, and rotary evaporation is except that desolvating.The solid that obtains separates purification (is eluent with the sherwood oil) with column chromatography, obtains pure sugar-modified triphenylamine organic hole transport material (7), and productive rate is 50～75%.
The 0.02mol triphenyl phosphorus is dissolved in the 200mL THF, then the dibasic triphenylamine of 0.01mol iodomethyl (2) is dripped slowly in above-mentioned solution, stirring at room 24 hours is washed the deposition that obtains drying with ether.Then dried solid is dissolved in the 200mL THF, nitrogen protection adds the NaH of 0.04mol down, and stirring at room 20 hours obtains phosphorus ylide (5).5mmol is dissolved in the 20mL THF with phosphorus ylide (5); Any one of the corresponding Glycerose of adding 10mmol, erythrose, threose, ribose, pectinose, wood sugar, Lay threose, allose, altrose, glucose, seminose, gulose, idose, semi-lactosi and talose, stirring at room 48 hours.After reaction stops reaction solution being poured in the water and wash, and extract organic product with anhydrous diethyl ether, the organic phase that obtains use anhydrous sodium sulfate drying, and rotary evaporation is except that desolvating.The solid that obtains separates purification (is eluent with the sherwood oil) with column chromatography, obtains pure sugar-modified triphenylamine organic hole transport material (8), and productive rate is 45～60%.
The 0.03mol triphenyl phosphorus is dissolved in the 200mL THF, then the trisubstituted triphenylamine of 0.01mol iodomethyl (3) is dripped slowly in above-mentioned solution, stirring at room 24 hours is washed the deposition that obtains drying with ether.Then with the resolution of precipitate that obtains in the 200mL THF, nitrogen protection adds down the NaH of 0.06mol, stirring at room 20 hours obtains phosphorus ylide (6).5mmol is dissolved in the 20mL THF with phosphorus ylide (6); Any one of the corresponding Glycerose of adding 15mmol, erythrose, threose, ribose, pectinose, wood sugar, Lay threose, allose, altrose, glucose, seminose, gulose, idose, semi-lactosi and talose, stirring at room 48 hours.After reaction stops reaction solution being poured in the water and wash, and extract organic product with anhydrous diethyl ether, the organic phase that obtains use anhydrous sodium sulfate drying, and rotary evaporation is except that desolvating.The solid that obtains separates purification (is eluent with the sherwood oil) with column chromatography, obtains pure sugar-modified triphenylamine organic hole transport material (9), and productive rate is 40～52%.
The assembling of all solid state quantum dot sensitized solar cell:
1) adopt the method for silk screen printing that titania slurry is printed on the conductive glass (10), the prescription of titania slurry is: 0.26g TKK 021 and 0.95g titania nanoparticles (P25) are dispersed in the 5mL Terpineol 350.Print 1 layer, obtain the titanium dioxide film of 2 micron thick,, removing the organism in the slurry, and improve the contact tightness degree between the titania nanoparticles 450 ℃ of printed titanium oxide calcining half a hour; 2) titanium dioxide film for preparing (11) immerses the aqueous solution of halfcystine, 70 ℃ of held 1 hour, uses acetone then.Put into the toluene solution of CdSe quantum dot at last, 24 hours, obtain the titanium dioxide electrodes of quantum dot (12) sensitization, i.e. the light anode; 3) with synthetic organic hole transport material (13), the monobasic triphenylamine of glucose is dissolved in the acetonitrile, and concentration is 0.25mol/L; 4) method of above-mentioned solution with spin coating dripped on the light anode, so that organic hole transport material solution is better immersed in the light anode, and the volatilization of accelerated solvent; 5) treat that solvent evaporates is dried, containing steaming gold on the light anode of organic hole transport material, as counter electrode (14), the thickness of gold is 100nm, obtains complete all solid state quantum dot sensitized solar cell.The electricity conversion of battery is 1.3%.
Other organic hole transport material is done ionogen, and the process of assembling all solid state quantum dot sensitized solar cell is identical with above-mentioned process, and corresponding efficient sees the following form.
Sugar-modified triphenylamine is assembled into the efficient table of battery
| One replaces | Two replace | Three replace | |
| Glycerose | 1.3％ | 1.4％ | 1.3％ |
| Erythrose | 1.6％ | 1.1％ | 1.7％ |
| Threose | 1.6％ | 1.5％ | 1.4％ |
| Ribose | 1.4％ | 1.4％ | 1.2％ |
| Pectinose | 1.8％ | 1.9％ | 1.7％ |
| Wood sugar | 1.8％ | 1.9％ | 1.8％ |
| The Lay threose | 1.4％ | 1.8％ | 1.5％ |
| Allose | 1.8％ | 1.4％ | 1.7％ |
| Altrose | 1.4％ | 1.8％ | 1.9％ |
| Glucose | 1.3％ | 1.5％ | 1.8％ |
| Seminose | 1.4 | 1.5％ | 1.7％ |
| Gulose | 1.4％ | 1.1％ | 1.2％ |
| Idose | 1.7％ | 1.5％ | 1.5％ |
| Semi-lactosi | 1.7％ | 1.8％ | 1.2％ |
| Talose | 1.4％ | 1.5％ | 1.7％ |
Claims (3)
1. one type of triphenylamine organic hole transport material that the carbohydrate that is used for all solid state quantum dot sensitized solar cell is modified; It is characterized in that described organic hole transport material is parent with the triphenylamine, in arbitrary position of a of triphenylamine, b, c position or any two positions or three positions introduce saccharide compound simultaneously and modify.
2. one type of triphenylamine organic hole transport material that is used for the carbohydrate modification of all solid state quantum dot sensitized solar cell according to claim 1 is characterized in that described saccharide compound can be any one of Glycerose, erythrose, threose, ribose, pectinose, wood sugar, Lay threose, allose, altrose, glucose, seminose, gulose, idose, semi-lactosi and talose.
3. according to claim 1 and 2 described one type of triphenylamine organic hole transport material that are used for the carbohydrate modification of all solid state quantum dot sensitized solar cell; It is characterized in that all solid state quantum dot sensitized solar cell is to assemble through following step: at first the organic hole transport material is dissolved in acetonitrile, methylene dichloride, any one solvent of ethanol, is made into the dilute solution that concentration is 0.01～0.5mol/L; Method through spin coating drips in the light anode of quantum dot sensitized solar cell then, lets solvent evaporates; At last golden counter electrode is evaporated on the above-mentioned light anode that contains the organic hole transport material.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102938329A (en) * | 2012-10-29 | 2013-02-20 | 东莞电子科技大学电子信息工程研究院 | Inorganic sensitizing dye-sensitized solar cell and preparation method thereof |
| CN104319100A (en) * | 2014-11-07 | 2015-01-28 | 河北联合大学 | Double-charge organic hole-transport material for fully-solid-state quantum dot sensitized solar cell |
| CN104319101A (en) * | 2014-11-07 | 2015-01-28 | 河北联合大学 | Azobenzene double-charge organic hole-transport material used for all-solid-state quantum dot sensitized solar cell |
| CN106486289A (en) * | 2016-12-12 | 2017-03-08 | 河北工业大学 | A kind of POSS modifies the preparation method of CdTe quantum sensitization solar battery |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN104319101A (en) * | 2014-11-07 | 2015-01-28 | 河北联合大学 | Azobenzene double-charge organic hole-transport material used for all-solid-state quantum dot sensitized solar cell |
| CN104319100B (en) * | 2014-11-07 | 2017-05-24 | 河北联合大学 | Double-charge organic hole-transport material for solar cell |
| CN104319101B (en) * | 2014-11-07 | 2017-10-10 | 华北理工大学 | One class azobenzene double charge organic hole transport material used for solar batteries |
| CN106486289A (en) * | 2016-12-12 | 2017-03-08 | 河北工业大学 | A kind of POSS modifies the preparation method of CdTe quantum sensitization solar battery |
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Inventor after: Li Chunsheng Inventor after: Sun Yan Inventor after: Shi Jifu Inventor after: Zhang Shaoyan Inventor after: Yao Weixue Inventor after: Song Dawei Inventor after: Ma Xuegang Inventor after: Wang Yaozu Inventor after: Wang Lina Inventor before: Li Chunsheng Inventor before: Sun Yan Inventor before: Shi Jifu Inventor before: Wang Yaozu Inventor before: Wang Lina Inventor before: Ma Xuegang |
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Free format text: CORRECT: INVENTOR; FROM: LI CHUNSHENG SUN YAN SHI JIFU WANG YAOZU WANG LINA MA XUEGANG TO: LI CHUNSHENG SUN YAN SHI JIFU ZHANG SHAOYAN YAO WEIXUE SONG DAWEI MA XUEGANG WANG YAOZU WANG LINA |
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Granted publication date: 20131120 Termination date: 20190302 |
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| CF01 | Termination of patent right due to non-payment of annual fee |