CN100348593C - Uniformpoly thiophene derivative and its preparation method and uses - Google Patents
Uniformpoly thiophene derivative and its preparation method and uses Download PDFInfo
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- CN100348593C CN100348593C CNB2005100368584A CN200510036858A CN100348593C CN 100348593 C CN100348593 C CN 100348593C CN B2005100368584 A CNB2005100368584 A CN B2005100368584A CN 200510036858 A CN200510036858 A CN 200510036858A CN 100348593 C CN100348593 C CN 100348593C
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Abstract
The present invention relates to an oligomerization thiophene derivative, a preparation method thereof and the application thereof. The oligomerization thiophene derivative is 5-carboxaldehyde-2, 2': 5', 2'-trithiofuran which comprises the preparation method that 1, with the protection of N2, N, N-dimethylformamide is added in a reaction bottle, oxyphosphoryl trichloride is slowly dropped in the bottle, and the mixture is stirred for reaction; 2, 2, 2': 5', 2'-trithiofuran is added, the mixture is heated, distilled water is added after the reaction, and then brown flocculent precipitates are obtained; coarse products are obtained via vacuum filtration, and silicon gel columns are used for separating. The solar battery devices prepared by the oligomerization thiophene derivative can obtain 2.25 V of open circuit voltage and 1.81 mA/cm<2> of short circuit current under the light irradiation condition of 78.2 mW/cm<2> simulated sunlight, fill factor is 48.3%, and photoelectric conversion efficiency is 2.52%.
Description
Technical field
The present invention relates to organic polymer photoelectric material technical field, be specifically related to a kind of Uniformpoly thiophene derivative; The invention still further relates to the preparation method of described Uniformpoly thiophene derivative; The invention still further relates to the application of described Uniformpoly thiophene derivative in the preparation solar cell device.
Background technology
The high purity Uniformpoly thiophene that the polymerization degree and polymerization position can be controlled, have definite molecular weight is not only " model " compound of research Polythiophene, self also is that a kind of πDian Zi with excellent light, electrical property is a conjugated compound.Because its excellent light, electrical property in recent years, are used as functional organic material and research and develop.Up to the present, according to the research and development target of Uniformpoly thiophene, design, synthesized various Uniformpoly thiophene derivatives as the photoelectric information functional organic materials.These Uniformpoly thiophene derivatives mainly are used to the research of following several respects: (1) studies the relation of the electric conductivity of resulting ion free radical salt with conjugate length by electrochemical doping.Result of study shows, improves the conjugate length of Uniformpoly thiophene, and electric conductivity also will improve thereupon.For example, the electric conductivity of 6 aggressiveness (6T) of thiophene is 10
0-10
-1Scm
-1, and the electric conductivity of 12 aggressiveness (4Oc12T) of thiophene reaches 10Scm
-1(2) the research and development Uniformpoly thiophene is as the photoelectric characteristic of photoelectric conversion material.Result of study demonstrates, and Uniformpoly thiophene is a kind of very excellent p N-type semiconductorN material.(3) the research Uniformpoly thiophene is as the characteristics of luminescence of electroluminescent organic material.
Though Uniformpoly thiophene has been studied as electro-conductive material, photoelectric conversion material, electroluminescent material etc., at present about Uniformpoly thiophene as photoelectric conversion material, its photoelectric transformation efficiency is also lower, does not reach 2%.Just because of this reason, thereby limited the application of Uniformpoly thiophene as photoelectric conversion material.
Summary of the invention
The objective of the invention is to problem, a kind of Uniformpoly thiophene derivative of preparing the high photoelectric device of photoelectric transformation efficiency is provided at the prior art existence;
The present invention also aims to provide the preparation method of described Uniformpoly thiophene derivative.
The present invention also aims to provide the application of described Uniformpoly thiophene derivative in the preparation solar cell device.
The title of Uniformpoly thiophene derivative of the present invention be 5-carboxaldehyde radicals-2,2 ': 5 ', 2 " three thiophene (be called for short 3T-CHO) have the molecular formula of following structure:
Its physical parameter is as follows:
Mass spectrum: m/z 276 (M
+);
Proton nmr spectra: δ (ppm)=9.35 (s, 1H), 7.13 (m, 4H), 7.01 (s, 1H), 6.88 (s, 1H), 6.72 (s, 1H); Infrared spectra: (KBr method, cm
-1): 1650 (v
C=O).
The preparation method of Uniformpoly thiophene derivative of the present invention comprises the steps:
The first step, at N
2Protection under, in reaction flask, add N, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus (POCl then
3), stirred 1-4 hour;
Second step, add 2,2 ': 5 ', 2 " three thiophene (3T) reacts 1-5 hour, were heated to 75-85 ℃ then, reacts after 12-16 hour, and adding distilled water must the brown flocks; Vacuum filtration obtains crude product, separates with silicagel column then, promptly gets the pure products of 3T-CHO.
It can be chloroform that silicagel column separates the washing fluid that adopts.
Preparation 5-carboxaldehyde radicals-2,2 ': 5 ', 2 " reaction process of three thiophene (being called for short 3T-CHO) can be expressed as follows:
The method that Uniformpoly thiophene derivative of the present invention is used to prepare solar cell device comprises the steps:
The method of the first step, employing vacuum evaporation goes up evaporation one deck Uniformpoly thiophene derivative (3T-CHO) at conductive glass (ITO), and the thickness of 3T-CHO is 140-150nm;
The method of second step, employing vacuum evaporation, evaporation one deck 3,4,9 on 3T-CHO, 10-perylene tetracarboxylic acid dianhydride (PCH), the thickness of PCH are 130-140nm;
The method of the 3rd step, employing vacuum evaporation, 3,4,9,10-perylene tetracarboxylic acid dianhydride (PCH) is gone up evaporation layer of metal aluminium, and the thickness of aluminium is 110-120nm;
The solar cell device for preparing has following physical parameter:
Open circuit voltage: 2.23-2.25V; Short-circuit current: 1.79-1.81mA/cm
2Packing factor: 48.1-48.3%; Photoelectric transformation efficiency: 2.45-2.52%.
The present invention has following advantage and beneficial effect:
1, provides a kind of novel Uniformpoly thiophene derivative (being called for short 3T-CHO), can be used for as solar cell material;
2, utilize the prepared solar cell device of described novel Uniformpoly thiophene derivative (being called for short 3T-CHO), have high packing factor and photoelectric transformation efficiency, be respectively 48.3% and 2.52%.
3, utilize described novel Uniformpoly thiophene derivative (being called for short 3T-CHO), the preparation method of solar cell device is provided;
Description of drawings
Fig. 1 is the current-voltage curve figure that utilizes the solar cell device of Uniformpoly thiophene derivative preparation of the present invention.
Embodiment
Embodiment 1
5-carboxaldehyde radicals-2,2 ': 5 ', the 2 " preparations of three thiophene (being called for short 3T-CHO)
The first step, at N
2Protection under, in reaction flask, add N, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus (POCl then
3), stirring at room 1 hour;
Second step, the first step reaction be after 1 hour, add 2,2 ': 5 ', 2 " three thiophene (3T) reacts 1 hour, were heated to 75-85 ℃ then, reacts after 12 hours, and adding distilled water gets the brown flocks; Vacuum filtration obtains crude product, separates with silicagel column then, promptly gets the pure products of 3T-CHO.
The preparation of solar cell device:
The method of the first step, employing vacuum evaporation goes up evaporation one deck 3T-CHO at conductive glass (ITO), and the thickness of 3T-CHO is 143nm;
The method of second step, employing vacuum evaporation, evaporation one deck 3,4,9 on 3T-CHO, 10-perylene tetracarboxylic acid dianhydride (PCH), the thickness of PCH are 135nm;
The method of the 3rd step, employing vacuum evaporation, evaporation layer of metal aluminium on PCH, the thickness of aluminium is 112nm.
The open circuit voltage of the solar cell device for preparing as shown in Figure 1: 2.25V; Short-circuit current: 1.81mA/cm
2Packing factor: 48.3%; Photoelectric transformation efficiency: 2.52%.
The first step, at N
2Protection under, in reaction flask, add N, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus (POCl then
3), stirring at room 2 hours;
Second step, the first step reaction be after 2 hours, add 2,2 ': 5 ', 2 " three thiophene (3T) reacts 3 hours, were heated to 75-85 ℃ then, reacts after 15 hours, and adding distilled water gets the brown flocks; Vacuum filtration obtains crude product, separates with silicagel column then, promptly gets the pure products of 3T-CHO.
The preparation of solar cell device:
The method of the first step, employing vacuum evaporation goes up evaporation one deck 3T-CHO at conductive glass (ITO), and the thickness of 3T-CHO is 146nm;
The method of second step, employing vacuum evaporation, evaporation one deck 3,4,9 on 3T-CHO, 10-perylene tetracarboxylic acid dianhydride (PCH), the thickness of PCH are 138nm;
The method of the 3rd step, employing vacuum evaporation, evaporation layer of metal aluminium on PCH, the thickness of aluminium is 116nm;
The open circuit voltage of the solar cell device for preparing: 2.24V; Short-circuit current: 1.80mA/cm
2Packing factor: 48.2%; Photoelectric transformation efficiency: 2.48%.
Embodiment 3
5-carboxaldehyde radicals-2,2 ': 5 ', the 2 " preparations of three thiophene (being called for short 3T-CHO)
The first step, at N
2Protection under, in reaction flask, add N, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus (POCl then
3), stirring at room 4 hours;
Second step, the first step reaction be after 4 hours, add 2,2 ': 5 ', 2 " three thiophene (3T) reacts 5 hours, were heated to 75-85 ℃ then, reacts after 16 hours, and adding distilled water gets the brown flocks; Vacuum filtration obtains crude product, separates with silicagel column then, promptly gets the pure products of 3T-CHO.
The preparation of solar cell device:
The method of the first step, employing vacuum evaporation goes up evaporation one deck 3T-CHO at conductive glass (ITO), and the thickness of 3T-CHO is 150nm;
The method of second step, employing vacuum evaporation, evaporation one deck 3,4,9 on 3T-CHO, 10-perylene tetracarboxylic acid dianhydride (PCH), the thickness of PCH are 140nm;
The method of the 3rd step, employing vacuum evaporation, evaporation layer of metal aluminium on PCH, the thickness of aluminium is 120nm;
The open circuit voltage of the solar cell device for preparing: 2.23V; Short-circuit current: 1.79mA/cm
2Packing factor: 48.1%; Photoelectric transformation efficiency: 2.45%.
Claims (2)
1, a kind of preparation method of Uniformpoly thiophene derivative Uniformpoly thiophene derivative is characterized in that comprising the steps:
The first step, at N
2Protection under, in reaction flask, add N, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus, stirring at room 1-4 hour then;
Second step, add 2,2 ': 5 ', 2 " three thiophene reacts 1-5 hour, were heated to 75-85 ℃ then, reacts after 12-16 hour, and adding distilled water must the brown flocks; Vacuum filtration obtains crude product, separates with silicagel column then;
Obtain 5-carboxaldehyde radicals-2,2 ': 5 ', 2 " three thiophene have the molecular formula of following structure:
2, method according to claim 1 is characterized in that the washing fluid that adopts when silicagel column separates is a chloroform.
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| CNB2005100368584A CN100348593C (en) | 2005-08-30 | 2005-08-30 | Uniformpoly thiophene derivative and its preparation method and uses |
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| CN1730478A CN1730478A (en) | 2006-02-08 |
| CN100348593C true CN100348593C (en) | 2007-11-14 |
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| CN102329299B (en) * | 2011-07-11 | 2013-10-30 | 华南理工大学 | Star-shaped oligothiophene derivative, preparation method and application thereof |
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Non-Patent Citations (3)
| Title |
|---|
| Functionalised poly(terthiophenes). A.K.Burrell et al..Synthetic Metals,Vol.135.136. 2003 * |
| Optical properties of furanic and thiophenic ethane-1,2-dionesA combined experimental and theoretical sttudy. Synthetic Metals,Vol.138. 2003 * |
| Singlet oxygen photosensitizing properities of bithiophene andterthiophene derivatives. R. Boch et al..Journal of Photochemistry and photobiology A:Chemistry,Vol.93. 1996 * |
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