CN101367790B - Quick preparation method for oligomerization thiophene derivant and uses thereof - Google Patents
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Abstract
The present invention relates to a rapid preparation method of oligomerized thiophen derivatives, and an application thereof. The oligomerized thiophen derivatives are 5, 5''-bisformaldehyde radical-2,2':5',2''-terthienyl, 5,5''- bisformaldehyde radical-2,2':5',2'':5'',2''- tetrathiophene and 5,5''''- bisformaldehyde radical-2,2':5',2'':5'',2'':5'',2''-pentathiophene. The rapid preparation method comprises the following steps: with the N2 protection, N, N-dimethyl formamide is added into a reaction bottle, phospho-rylchloride is slowly dropped into the bottle, a certain temperature is controlled, and the reaction is performed through stirring the mixture in a microwave device, terthienyl, tetrathiophene or pentathiophene is added into the reaction solution, and the reaction solution is stirred continuously; distilled water is added, and the brown flocculent sedimentation can be produced; the crude product can be acquired through vacuum pumping and filtration, and is then separated through a chromatographic column, and the oligomerized thiophen derivatives can be used for assembling flexible organic photovoltaic devices.
Description
Technical field
The present invention relates to organic polymer photovaltaic material technical field, be specifically related to the fast preparation method of Uniformpoly thiophene derivative; The invention still further relates to the application of said Uniformpoly thiophene derivative in the flexible organic photovoltaic devices of preparation.
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 photoelectric information functional property organic materials.These Uniformpoly thiophene derivatives mainly are used to the research of following several respects: the relation of the electric conductivity of resulting ion radical salt with conjugate length studied through electrochemical doping in (1).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 type, semiconductor material.(3) the research Uniformpoly thiophene is as the characteristics of luminescence of electroluminescent organic material.
Uniformpoly thiophene is being carried out on the basis of broad research as electro-conductive material, photoelectric conversion material, electroluminescent material etc., also synthesized many Uniformpoly thiophene derivatives simultaneously, but the time of the required cost of building-up process is being long.In addition, the present organic photovoltaic devices of studying is to be substrate with rigid conductive glass mostly, does not have flexibility, can't compete with inorganic photovoltaic device.Just because of above-mentioned reason, utilize fast preparation method synthetic Uniformpoly thiophene derivative as the organic photovoltaic material, the research of carrying out flexible organic photovoltaic devices has very large meaning.
Summary of the invention
The objective of the invention is problem, a kind of fast preparation method of Uniformpoly thiophene derivative is provided to the prior art existence.
The present invention also aims to provide the application of said Uniformpoly thiophene derivative in the flexible organic photovoltaic devices of preparation.
Uniformpoly thiophene derivative of the present invention comprises 5,5 " two carboxaldehyde radicals-2,2 ': 5 ', 2 " three thiophene (OHC-3T-CHO), 5; 5 " '-two carboxaldehyde radicals-2,2 ': 5 ', 2 ": 5 ", 2 " ＇-four thiophene (OHC-4T-CHO) and 5; 5 " "-two thienyls-2,2 ': 5 ', 2 ": 5 "; 2 " ': 5 " ＇, 2 " "-five thiophene (OHC-5T-CHO) have following molecular structure:
The preparation method of Uniformpoly thiophene derivative of the present invention comprises the steps:
The first step is at N
2Protection under, in reaction flask, add N, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus then, in microwave device, control reaction temperature is 45 ℃, stirring reaction 20-25 minute;
Second step, in above-mentioned reaction solution, add 2,2 ': 5 ', 2 " three thiophene, 2,2 ': 5 ', 2 ": 5 ", 2 " ＇-four thiophene or 2,2 ': 5 ', 2 ": 5 ", 2 " ': 5 " ＇, 2 " "-five thiophene, control reaction temperature is 65 ℃, stirring reaction 30-40 minute;
The 3rd goes on foot, and reaction finishes the back and adds zero(ppm) water, gets the brown flocks;
In the 4th step, vacuum filtration obtains crude product, separates with chromatogram then.Obtain 5,5 " two carboxaldehyde radicals-2,2 ': 5 ', 2 " three thiophene (OHC-3T-CHO), 5,5 " '-two carboxaldehyde radicals-2; 2 ': 5 ', 2 ": 5 ", 2 " ＇-four thiophene (OHC-4T-CHO) or 5,5 " "-two thienyls-2; 2 ': 5 ', 2 ": 5 ", 2 " ': 5 " ', 2 " "-five thiophene (OHC-5T-CHO).
As preferred version, the first step and second being reflected in the microwave device of step are carried out.
In the 4th step, the preferred toluene of washing fluid that chromatographic separation adopts.
The reaction process for preparing Uniformpoly thiophene derivative of the present invention can be expressed as follows:
The method that Uniformpoly thiophene derivative of the present invention is used to prepare flexible organic photovoltaic devices comprises the steps:
The method of the first step, employing vacuum evaporation, the described Uniformpoly thiophene derivative of vapor deposition one deck claim 1 on the conductive polyester film, its thickness is 140-150nm;
The method of second step, employing vacuum evaporation, vapor deposition one deck 3,4,9 on Uniformpoly thiophene derivative, 10-perylene tetracarboxylic acid dianhydride, its thickness are 130-140nm;
The method of the 3rd step, employing vacuum evaporation, 3,4,9, vapor deposition layer of metal aluminium on the 10-perylene tetracarboxylic acid dianhydride, the thickness of aluminium is 110-120nm.
The solar cell device for preparing has following physical parameter:
At 78.2mW/cm
2Under the light conditions of simulated solar irradiation, utilize the flexible organic photovoltaic devices of OHC-3T-CHO assembling, can obtain the photoelectric transformation efficiency of open circuit voltage and the 1.00-1.04% of 1.07-1.12V; Utilize the flexible organic photovoltaic devices of OHC-4T-CHO assembling, can obtain the photoelectric transformation efficiency of open circuit voltage and the 1.03-1.07% of 1.27-1.31V; Utilize the flexible organic photovoltaic devices of OHC-5T-CHO assembling, can obtain the photoelectric transformation efficiency of open circuit voltage and the 1.08-1.12% of 1.78-1.82V.
The present invention compared with prior art has following advantage and beneficial effect:
1, a kind of quick preparation Uniformpoly thiophene derivative method of (being called for short OHC-3T-CHO, OHC-4T-CHO and OHC-5T-CHO) is provided, OHC-3T-CHO, OHC-4T-CHO and OHC-5T-CHO can be used for as flexible organic photovoltaic battery material;
2, utilize said Uniformpoly thiophene derivative (being called for short OHC-3T-CHO, OHC-4T-CHO and OHC-5T-CHO), flexible organic photovoltaic battery preparation of devices method is provided;
Embodiment
Embodiment 15,5 " two carboxaldehyde radicals-2,2 ': 5 ', the 2 " preparations of three thiophene (OHC-3T-CHO)
The first step is at N
2Protection under, in reaction flask, add N, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus then, in microwave device, control reaction temperature is 45 ℃, stirring reaction 20 minutes;
Second step, in above-mentioned reaction solution, add 2,2 ': 5 ', 2 " three thiophene (3T), in microwave device, control reaction temperature is 65 ℃, stirring reaction 30 minutes;
The 3rd goes on foot, and reaction finishes the back and adds zero(ppm) water, gets the brown flocks; Vacuum filtration obtains crude product, separates with chromatogram then.
The assembling of flexible organic photovoltaic devices:
The method of the first step, employing vacuum evaporation, the described Uniformpoly thiophene derivative of vapor deposition one deck claim 1 on the conductive polyester film, its thickness is 142nm;
The method of second step, employing vacuum evaporation, vapor deposition one deck 3,4,9 on Uniformpoly thiophene derivative, 10-perylene tetracarboxylic acid dianhydride, its thickness are 133nm;
The method of the 3rd step, employing vacuum evaporation, 3,4,9, vapor deposition layer of metal aluminium on the 10-perylene tetracarboxylic acid dianhydride, the thickness of aluminium is 113nm.
The open circuit voltage of obtained flexible organic photovoltaic devices: 1.07V; Photoelectric transformation efficiency: 1.00%.
Embodiment 25,5 ＂-two carboxaldehyde radicals-2,2 ': 5 ', the 2 " preparations of three thiophene (OHC-3T-CHO)
The first step under the protection of N2, adds N in reaction flask, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus then, and in microwave device, control reaction temperature is 45 ℃, stirring reaction 23 minutes;
Second step, in above-mentioned reaction solution, add 2,2 ': 5 ', 2 " three thiophene (3T), in microwave device, control reaction temperature is 65 ℃, stirring reaction 35 minutes;
The 3rd goes on foot, and reaction finishes the back and adds zero(ppm) water, gets the brown flocks; Vacuum filtration obtains crude product, separates with chromatogram then.
The assembling of flexible organic photovoltaic devices:
The method of the first step, employing vacuum evaporation, the described Uniformpoly thiophene derivative of vapor deposition one deck claim 1 on the conductive polyester film, its thickness is 146nm;
The method of second step, employing vacuum evaporation, vapor deposition one deck 3,4,9 on Uniformpoly thiophene derivative, 10-perylene tetracarboxylic acid dianhydride, its thickness are 135nm;
The method of the 3rd step, employing vacuum evaporation, 3,4,9, vapor deposition layer of metal aluminium on the 10-perylene tetracarboxylic acid dianhydride, the thickness of aluminium is 115nm.
The open circuit voltage of obtained flexible organic photovoltaic devices: 1.09V; Photoelectric transformation efficiency: 1.02%.
Embodiment 35,5 " two carboxaldehyde radicals-2,2 ': 5 ', the 2 " preparations of three thiophene (OHC-3T-CHO)
The first step under the protection of N2, adds N in reaction flask, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus then, and in microwave device, control reaction temperature is 45 ℃, stirring reaction 25 minutes;
Second step, in above-mentioned reaction solution, add 2,2 ': 5 ', 2 " three thiophene (3T), in microwave device, control reaction temperature is 65 ℃, stirring reaction 40 minutes;
The 3rd goes on foot, and reaction finishes the back and adds zero(ppm) water, gets the brown flocks; Vacuum filtration obtains crude product, separates with chromatogram then.
The assembling of flexible organic photovoltaic devices:
The method of the first step, employing vacuum evaporation, the described Uniformpoly thiophene derivative of vapor deposition one deck claim 1 on the conductive polyester film, its thickness is 140nm;
The method of second step, employing vacuum evaporation, vapor deposition one deck 3,4,9 on Uniformpoly thiophene derivative, 10-perylene tetracarboxylic acid dianhydride, its thickness are 135nm;
The method of the 3rd step, employing vacuum evaporation, 3,4,9, vapor deposition layer of metal aluminium on the 10-perylene tetracarboxylic acid dianhydride, the thickness of aluminium is 120nm.
The open circuit voltage of obtained flexible organic photovoltaic devices: 1.12V; Photoelectric transformation efficiency: 1.04%.
Embodiment 45,5 " ＇-two carboxaldehyde radicals-2,2 ': 5 ', 2 ": 5 ", the 2 " preparations of ＇-four thiophene (OHC-4T-CHO)
The first step is at N
2Protection under, in reaction flask, add N, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus then, in microwave device, control reaction temperature is 45 ℃, stirring reaction 23 minutes;
Second step, in above-mentioned reaction solution, add 2,2 ': 5 ', 2 ": 5 ", 2 " ＇-four thiophene (4T), in microwave device, control reaction temperature is 65 ℃, stirring reaction 32 minutes;
The 3rd goes on foot, and reaction finishes the back and adds zero(ppm) water, gets the brown flocks; Vacuum filtration obtains crude product, separates with chromatogram then.
The assembling of flexible organic photovoltaic devices:
The method of the first step, employing vacuum evaporation, the described Uniformpoly thiophene derivative of vapor deposition one deck claim 1 on the conductive polyester film, its thickness is 145nm;
The method of second step, employing vacuum evaporation, vapor deposition one deck 3,4,9 on Uniformpoly thiophene derivative, 10-perylene tetracarboxylic acid dianhydride, its thickness are 134nm;
The method of the 3rd step, employing vacuum evaporation, 3,4,9, vapor deposition layer of metal aluminium on the 10-perylene tetracarboxylic acid dianhydride, the thickness of aluminium is 112nm.
The open circuit voltage of obtained flexible organic photovoltaic devices: 1.27V; Photoelectric transformation efficiency: 1.03%.
Embodiment 55,5 " ＇-two carboxaldehyde radicals-2,2 ': 5 ', 2 ": 5 ", the 2 " preparations of ＇-four thiophene (OHC-4T-CHO)
The first step is at N
2Protection under, in reaction flask, add N, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus then, in microwave device, control reaction temperature is 45 ℃, stirring reaction 24 minutes;
Second step, in above-mentioned reaction solution, add 2,2 ': 5 ', 2 ": 5 ", 2 " ＇-four thiophene (4T), in microwave device, control reaction temperature is 65 ℃, stirring reaction 35 minutes;
The 3rd goes on foot, and reaction finishes the back and adds zero(ppm) water, gets the brown flocks; Vacuum filtration obtains crude product, separates with chromatogram then.
The assembling of flexible organic photovoltaic devices:
The method of the first step, employing vacuum evaporation, the described Uniformpoly thiophene derivative of vapor deposition one deck claim 1 on the conductive polyester film, its thickness is 146nm;
The method of second step, employing vacuum evaporation, vapor deposition one deck 3,4,9 on Uniformpoly thiophene derivative, 10-perylene tetracarboxylic acid dianhydride, its thickness are 137nm;
The method of the 3rd step, employing vacuum evaporation, 3,4,9, vapor deposition layer of metal aluminium on the 10-perylene tetracarboxylic acid dianhydride, the thickness of aluminium is 113nm.
The open circuit voltage of obtained flexible organic photovoltaic devices: 1.29V; Photoelectric transformation efficiency: 1.05%.
Embodiment 65,5 " '-two carboxaldehyde radicals-2,2 ': 5 ', 2 ": 5 ", the 2 " preparations of ＇-four thiophene (OHC-4T-CHO)
The first step is at N
2Protection under, in reaction flask, add N, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus then, in microwave device, control reaction temperature is 45 ℃, stirring reaction 25 minutes;
Second step, in above-mentioned reaction solution, add 2,2 ': 5 ', 2 ": 5 ", 2 " ＇-four thiophene (4T), in microwave device, control reaction temperature is 65 ℃, stirring reaction 38 minutes;
The 3rd goes on foot, and reaction finishes the back and adds zero(ppm) water, gets the brown flocks; Vacuum filtration obtains crude product, separates with chromatogram then.
The assembling of flexible organic photovoltaic devices:
The method of the first step, employing vacuum evaporation, the described Uniformpoly thiophene derivative of vapor deposition one deck claim 1 on the conductive polyester film, its thickness is 148nm;
The method of second step, employing vacuum evaporation, vapor deposition one deck 3,4,9 on Uniformpoly thiophene derivative, 10-perylene tetracarboxylic acid dianhydride, its thickness are 133nm;
The method of the 3rd step, employing vacuum evaporation, 3,4,9, vapor deposition layer of metal aluminium on the 10-perylene tetracarboxylic acid dianhydride, the thickness of aluminium is 117nm.
The open circuit voltage of obtained flexible organic photovoltaic devices: 1.31V; Photoelectric transformation efficiency: 1.07%.Embodiment 75,5 " "-two thienyls-2,2 ': 5 ', 2 ": 5 ", 2 " ＇: 5 " ＇, the preparation of 2 " "-five thiophene (OHC-5T-CHO)
The first step is at N
2Protection under, in reaction flask, add N, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus then, in microwave device, control reaction temperature is 45 ℃, stirring reaction 25 minutes;
Second step, in above-mentioned reaction solution, add 2,2 ': 5 ', 2 ": 5 ", 2 " ＇: 5 " ＇, 2 " "-five thiophene (5T), in microwave device, control reaction temperature is 65 ℃, stirring reaction 36 minutes;
The 3rd goes on foot, and reaction finishes the back and adds zero(ppm) water, gets the brown flocks; Vacuum filtration obtains crude product, separates with chromatogram then.
The assembling of flexible organic photovoltaic devices:
The method of the first step, employing vacuum evaporation, the described Uniformpoly thiophene derivative of vapor deposition one deck claim 1 on the conductive polyester film, its thickness is 145nm;
The method of second step, employing vacuum evaporation, vapor deposition one deck 3,4,9 on Uniformpoly thiophene derivative, 10-perylene tetracarboxylic acid dianhydride, its thickness are 134nm;
The method of the 3rd step, employing vacuum evaporation, 3,4,9, vapor deposition layer of metal aluminium on the 10-perylene tetracarboxylic acid dianhydride, the thickness of aluminium is 112nm.
The open circuit voltage of obtained flexible organic photovoltaic devices: 1.78V; Photoelectric transformation efficiency: 1.08%.
Embodiment 85,5 ＂ ＂-two thienyls-2,2 ': 5 ', 2 ＂: 5 ＂, 2 ＂ ＇: 5 ＂ ＇, the preparation of 2 ＂ ＂-five thiophene (OHC-5T-CHO)
The first step is at N
2Protection under, in reaction flask, add N, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus then, in microwave device, control reaction temperature is 45 ℃, stirring reaction 22 minutes;
Second step, in above-mentioned reaction solution, add 2,2 ': 5 ', 2 ": 5 ", 2 " ＇: 5 " ＇, 2 " "-five thiophene (5T), in microwave device, control reaction temperature is 65 ℃, stirring reaction 40 minutes;
The 3rd goes on foot, and reaction finishes the back and adds zero(ppm) water, gets the brown flocks; Vacuum filtration obtains crude product, separates with chromatogram then.
The assembling of flexible organic photovoltaic devices:
The method of the first step, employing vacuum evaporation, the described Uniformpoly thiophene derivative of vapor deposition one deck claim 1 on the conductive polyester film, its thickness is 150nm;
The method of second step, employing vacuum evaporation, vapor deposition one deck 3,4,9 on Uniformpoly thiophene derivative, 10-perylene tetracarboxylic acid dianhydride, its thickness are 140nm;
The method of the 3rd step, employing vacuum evaporation, 3,4,9, vapor deposition layer of metal aluminium on the 10-perylene tetracarboxylic acid dianhydride, the thickness of aluminium is 120nm.
The open circuit voltage of obtained flexible organic photovoltaic devices: 1.80V; Photoelectric transformation efficiency: 1.10%.
Embodiment 95,5 ＂ ＂-two thienyls-2,2 ': 5 ', 2 ": 5 ", 2 " ＇: 5 " ＇, the preparation of 2 " "-five thiophene (OHC-5T-CHO)
The first step is at N
2Protection under, in reaction flask, add N, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus then, in microwave device, control reaction temperature is 45 ℃, stirring reaction 24 minutes;
Second step, in above-mentioned reaction solution, add 2,2 ': 5 ', 2 ": 5 ", 2 " ＇: 5 " ＇, 2 " "-five thiophene (5T), in microwave device, control reaction temperature is 65 ℃, stirring reaction 33 minutes;
The 3rd goes on foot, and reaction finishes the back and adds zero(ppm) water, gets the brown flocks; Vacuum filtration obtains crude product, separates with chromatogram then.
The assembling of flexible organic photovoltaic devices:
The method of the first step, employing vacuum evaporation, the described Uniformpoly thiophene derivative of vapor deposition one deck claim 1 on the conductive polyester film, its thickness is 148nm;
The method of second step, employing vacuum evaporation, vapor deposition one deck 3,4,9 on Uniformpoly thiophene derivative, 10-perylene tetracarboxylic acid dianhydride, its thickness are 136nm;
The method of the 3rd step, employing vacuum evaporation, 3,4,9, vapor deposition layer of metal aluminium on the 10-perylene tetracarboxylic acid dianhydride, the thickness of aluminium is 117nm.
The open circuit voltage of obtained flexible organic photovoltaic devices: 1.82V; Photoelectric transformation efficiency: 1.12%.
Claims (2)
1. the preparation method of a Uniformpoly thiophene derivative is characterized in that comprising the steps:
The first step is at N
2Protection under, in reaction flask, add N, dinethylformamide slowly is added dropwise to tri-chlorination oxygen phosphorus then, control reaction temperature is 45 ℃, stirring reaction 20-25 minute;
Second step, in above-mentioned reaction solution, add 2,2 ': 5 ', 2 " three thiophene, 2,2 ': 5 ', 2 ": 5 ", 2 " '-four thiophene or 2,2 ': 5 ', 2 ": 5 ", 2 " ': 5 " ', 2 " "-five thiophene, control reaction temperature is 65 ℃, stirring reaction 30-40 minute;
The 3rd goes on foot, and reaction finishes the back and adds zero(ppm) water, gets the brown flocks;
In the 4th step, vacuum filtration obtains crude product, separates with chromatogram then, obtains 5; 5 " two carboxaldehyde radicals-2,2 ': 5 ', 2 " three thiophene, 5,5 " '-two carboxaldehyde radicals-2; 2 ': 5 ', 2 ": 5 ", 2 " '-four thiophene or 5,5 " "-two carboxaldehyde radicals-2; 2 ': 5 ', 2 ": 5 ", 2 " ': 5 " ', 2 " "-five thiophene;
The first step and being reflected in the microwave device in second step are carried out.
2. method according to claim 1 is characterized in that the washing fluid that said chromatographic separation adopts is a toluene in the 4th step.
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Non-Patent Citations (3)
| Title |
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| M. Melucci等.Solution-Phase Microwave-Assisted Synthesis of Unsubstituted and Modified α-Quinque- and Sexithiophenes.《J. Org. Chem.》.2004,第69卷(第14期),第4821、4823-4824页. * |
| Vladimir Lukes.Structure, electronic and optical characterization of oligothiophenes.《Synthetic Metals》.2007,第157卷770-778. * |
| VladimirLukes.Structure electronic and optical characterization of oligothiophenes.《Synthetic Metals》.2007 |
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