CN100999588A - High order polythiophene film and preparation process thereof - Google Patents
High order polythiophene film and preparation process thereof Download PDFInfo
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- CN100999588A CN100999588A CN 200610131641 CN200610131641A CN100999588A CN 100999588 A CN100999588 A CN 100999588A CN 200610131641 CN200610131641 CN 200610131641 CN 200610131641 A CN200610131641 A CN 200610131641A CN 100999588 A CN100999588 A CN 100999588A
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Abstract
The present invention relates to one kind of highly ordered polythiophene film and its making process. The highly ordered polythiophene film is made with soluble polythiophene material, preferably soluble poly-3-alkyl thiophene and exhibits highly ordered crystalline state with polythiophene molecule main chain perpendicular to the base direction. It is prepared through preparing CS2 solution of soluble polythiophene and slow volatilization of the solvent to film directly. The highly ordered polythiophene film has crystal thickness in the direction perpendicular to the base greater than 16 nm and high carrier mobility in the said direction. The highly ordered polythiophene film may be used in solar cell, photoelectronic detector, semiconductor memory, FET and other electronic devices.
Description
Technical field
The present invention relates to a kind of high order polythiophene film and preparation method thereof, be specifically related to a kind of Polythiophene molecular backbone chain perpendicular to crystallization high order polythiophene film of substrate orientation and preparation method thereof.
Background technology
The organic polymer electron device because of its low cost, flexibility, the common concern that plurality of advantages is subjected to people such as be easy to process.The film that is made by the soluble poly thiophene is a kind of polymer thin-film material with outstanding photoelectric functional.Replace by 3 of Polythiophene being carried out alkyl, improved the solubility of Polythiophene in organic solvent greatly, make it be suitable for preparing film with the method for solution film forming.This class mainly includes machine solar cell and organic field-effect tube based on the electron device of soluble poly thiophene film.For these devices, the mobility of charge carrier rate is an important indicator, particularly how to control the carrier mobility of specific direction in the film, makes the key point of high-performance organic polymer electron device especially.The H.Sirringhaus of univ cambridge uk's Cavendish laboratory and R.H.Friend professor show with other professor's joint study of Holland, in the soluble poly thiophene film with the traditional method preparation, the Polythiophene molecular backbone chain only lies low with respect to the conformation of substrate in film, and (Nature 1999 with edge-on two kinds of orientation forms, 401,685).The crystalline region size of these two kinds of conformations on the direction of vertical substrate often has only 3-5nm (J.Polym.Sci.PartB:Polym.Phys.1993,31,735/J.Phys.Chem.B2006,110,15763), so small orderly crystalline region thickness has seriously reduced the mobility of current carrier in this direction.And how to make main polymer chain in its film with perpendicular to substrate direction growth, obtain to have continuous height zone in order, thereby make at the high order polythiophene film that has high carrier mobility perpendicular to the substrate direction in this direction, do not appear in the newspapers as yet.
Summary of the invention
One of the object of the invention provides a kind of high order polythiophene film, is to be made of soluble poly thiophene material; Polythiophene presents high orderly crystal form in this film, and the Polythiophene molecular backbone chain is perpendicular to the substrate orientations.Described soluble poly thiophene material, preferred soluble poly (3-alkyl) thiophene, molecular structural formula is as follows:
R=C in the formula
mH
2m+ 1, m represents substituting group alkyl chain length, m=4-12; More preferably alkyl chain length is poly-(3-alkyl) thiophene of m=4 or 6, promptly poly-(3-butyl) thiophene or poly-(3-hexyl) thiophene;
Polythiophene presents the preferred high orderly spherocrystal attitude of high orderly crystal form in described this film.
Two of the object of the invention provides a kind of preparation method of high order polythiophene film.In this film according to method preparation provided by the present invention, the Polythiophene molecular backbone chain is arranged perpendicular to substrate, form described high order thin film two kinds of methods are arranged: 1, the dithiocarbonic anhydride solution of soluble poly thiophene, by the direct film forming of the slow volatilization of solvent, film is made of the Polythiophene of the orderly compact arranged spherocrystal of height; 2, the soluble poly thiophene is handled under dithiocarbonic anhydride atmosphere then with other solvent film forming, the crystallization of Polythiophene molecular backbone chain takes place in the film reset, and is reassembled into compact arranged spherulitic crystal structure from traditional whisker form, thereby obtains high order polythiophene film.
The step and the condition of method of the present invention are as follows:
(1). is concentration dithiocarbonic anhydride, chloroform, chlorobenzene, dichloro benzene,toluene,xylene or the tetrahydrofuran solution of the soluble poly thiophene of 5-20 mg/ml, spin coating at room temperature, blade coating or printing, vapor away solvent, obtain film, this film was left standstill under the dithiocarbonic anhydride atmosphere of 0.50-0.98 times of saturation vapour pressure 20 minutes-24 hours, obtain a kind of high order polythiophene film.
Described soluble poly thiophene material, preferred soluble poly (3-alkyl) thiophene, molecular structural formula is as follows:
R=C in the formula
mH
2m+ 1, m represents substituting group alkyl chain length, m=4-12; More preferably alkyl chain length is poly-(3-alkyl) thiophene of m=4 or 6, promptly poly-(3-butyl) thiophene or poly-(3-hexyl) thiophene.
Described soluble poly thiophene is preferred, and more preferably alkyl chain length is poly-(3-alkyl) thiophene of m=4 or 6, promptly poly-(3-butyl) thiophene or poly-(3-hexyl) thiophene.
(2). at room temperature, be concentration the dithiocarbonic anhydride solution of the soluble poly thiophene of 5-20 mg/ml, directly spin coating in the dithiocarbonic anhydride atmosphere of 0.50-0.98 times of saturation vapour pressure, blade coating or printing obtain a kind of high order polythiophene film.
Described soluble poly thiophene material, preferred soluble poly (3-alkyl) thiophene, molecular structural formula is as follows:
R=C in the formula
mH
2m+ 1, m represents substituting group alkyl chain length, m=4-12; More preferably alkyl chain length is poly-(3-alkyl) thiophene of m=4 or 6, promptly poly-(3-butyl) thiophene or poly-(3-hexyl) thiophene.
The evaporation rate of the solvent dithiocarbonic anhydride of method (2) can film need not aftertreatment than obviously slowing down under natural atmosphere.Obtain at last and the same a kind of high order polythiophene film of method (1), the Polythiophene molecular backbone chain is perpendicular to substrate in this high order thin film.
As depicted in figs. 1 and 2, the transmission electron microscopy of the prepared a kind of high order polythiophene film of the present invention and original position selected area electron diffraction result of study show that the Polythiophene molecular backbone chain is perpendicular to film substrate in resulting a kind of high order polythiophene film.
The present invention is to provide the high order polythiophene film of a kind of Polythiophene molecular backbone chain perpendicular to substrate orientation, have the orderly zone of continuous height on perpendicular to the matrix direction in this film and yardstick controlled, obtain high carrier mobility thereby make on this direction.Its preparation method is to be base material with the soluble poly thiophene, the Polythiophene molecular backbone chain is arranged perpendicular to substrate in the film that obtains, improve the crystallization degree of order on the vertical substrate direction greatly, its crystal thickness on this direction by original 3 to 5 nanometers bring up to that the present invention realizes greater than 16 nanometers, this can improve the carrier mobility on the vertical substrate direction.Film of the present invention can be applied to electron devices such as organic polymer solar cell, photodetector, semiconductor memory and field effect transistor.
Description of drawings
Fig. 1 is the transmission electron microscope light field photo according to poly-(3-butyl) thiophene film of embodiment 7 described condition preparations.
Fig. 2 is by corresponding to being marked the corresponding electron-diffraction diagram in constituency among Fig. 1.Point diffraction has carried out indexing according to Miller indices among Fig. 2.As can be seen from the figure: film is made of compact arranged spherocrystal platelet, and these platelets are along the growth of crystalline b axle, i.e. pi-pi stacked direction.Survey electron beam [001] zone axis in the sample crystal, just the main polymer chain in the film sample is perpendicular to substrate grown.
Embodiment
Embodiment 1: be concentration the dithiocarbonic anhydride solution of poly-(3-butyl) thiophene of 5 mg/ml, spin coating at ambient temperature vapors away solvent, obtains film, this film was left standstill 20 minutes under the dithiocarbonic anhydride atmosphere of 0.98 times of saturation vapour pressure, obtain a kind of high order polythiophene film.
Embodiment 2: adopt to scrape and paint film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 1.
Embodiment 3: adopt to be printed as film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 1.
Embodiment 4: be concentration the dichlorobenzene solution of poly-(3-butyl) thiophene of 20 mg/ml, spin coating at ambient temperature vapors away solvent, obtains film, with this film under the dithiocarbonic anhydride atmosphere of 0.50 times of saturation vapour pressure 24 hours, obtain a kind of high order polythiophene film.
Embodiment 5: adopt to scrape and paint film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 4.
Embodiment 6: adopt to be printed as film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 4.
Embodiment 7: be concentration the chlorobenzene solution of poly-(3-butyl) thiophene of 10 mg/ml, spin coating at ambient temperature vapors away solvent, obtains film, this film was left standstill 3 hours under the dithiocarbonic anhydride atmosphere of 0.90 times of saturation vapour pressure, obtain a kind of high order polythiophene film.
Embodiment 8: adopt to scrape and paint film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 7.
Embodiment 9: adopt to be printed as film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 7.
Embodiment 10: be concentration the toluene solution of poly-(3-butyl) thiophene of 10 mg/ml, spin coating at ambient temperature vapors away solvent, obtains film, this film was left standstill 3 hours under the dithiocarbonic anhydride atmosphere of 0.90 times of saturation vapour pressure, obtain a kind of high order polythiophene film.
Embodiment 11: adopt to scrape and paint film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 10.
Embodiment 12: adopt to be printed as film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 10.
Embodiment 13: be concentration the chloroformic solution of poly-(3-butyl) thiophene of 5 mg/ml, spin coating at ambient temperature vapors away solvent, obtains film, this film was left standstill 20 minutes under the dithiocarbonic anhydride atmosphere of 0.98 times of saturation vapour pressure, obtain a kind of high order polythiophene film.
Embodiment 14: adopt to scrape and paint film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 13.
Embodiment 15: adopt to be printed as film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 13.
Embodiment 16: be concentration the xylene solution of poly-(3-butyl) thiophene of 15 mg/ml, spin coating at ambient temperature vapors away solvent, obtains film, this film was left standstill 5 hours under the dithiocarbonic anhydride atmosphere of 0.80 times of saturation vapour pressure, obtain a kind of high order polythiophene film.
Embodiment 17: adopt to scrape and paint film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 16.
Embodiment 18: adopt to be printed as film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 16.
Embodiment 19: be concentration the tetrahydrofuran solution of poly-(3-butyl) thiophene of 8 mg/ml, spin coating at ambient temperature vapors away solvent, obtains film, this film was left standstill 12 hours under the dithiocarbonic anhydride atmosphere of 0.70 times of saturation vapour pressure, obtain a kind of high order polythiophene film.
Embodiment 20: adopt to scrape and paint film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 19.
Embodiment 21: adopt to be printed as film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 19.
Embodiment 22: be concentration the chlorobenzene solution of poly-(3-hexyl) thiophene of 10 mg/ml, spin coating at ambient temperature vapors away solvent, obtains film, this film was left standstill 2 hours under the dithiocarbonic anhydride atmosphere of 0.90 times of saturation vapour pressure, obtain a kind of high order polythiophene film.
Embodiment 23: adopt to scrape and paint film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 22.
Embodiment 24: adopt to be printed as film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 22.
Embodiment 25: is concentration the dithiocarbonic anhydride solution of poly-(3-butyl) thiophene of 5 mg/ml, and directly spin coating in the dithiocarbonic anhydride atmosphere of 0.98 times of saturation vapour pressure vapors away solvent, obtains a kind of high order polythiophene film.
Embodiment 26: adopt to scrape and paint film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 25.
Embodiment 27: adopt to be printed as film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 25.
Embodiment 28: is concentration the dithiocarbonic anhydride solution of poly-(3-butyl) thiophene of 10 mg/ml, and directly spin coating in the dithiocarbonic anhydride atmosphere of 0.8 times of saturation vapour pressure vapors away solvent, obtains a kind of high order polythiophene film.
Embodiment 29: adopt to scrape and paint film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 28.
Embodiment 30: adopt to be printed as film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 28.
Embodiment 31: is concentration the dithiocarbonic anhydride solution of poly-(3-butyl) thiophene of 20 mg/ml, and directly spin coating in the dithiocarbonic anhydride atmosphere of 0.5 times of saturation vapour pressure vapors away solvent, obtains a kind of high order polythiophene film.
Embodiment 32: adopt to scrape and paint film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 31.
Embodiment 33: adopt to be printed as film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 31.
Embodiment 34: is concentration the dithiocarbonic anhydride solution of poly-(3-hexyl) thiophene of 10 mg/ml, and directly spin coating in the dithiocarbonic anhydride atmosphere of 0.80 times of saturation vapour pressure vapors away solvent, obtains a kind of high order polythiophene film.
Embodiment 35: adopt to scrape and paint film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 34.
Embodiment 36: adopt to be printed as film.Remaining condition and step obtain a kind of high order polythiophene film with embodiment 34.
Claims (10)
1. a high order polythiophene film is to be made of soluble poly thiophene material, it is characterized in that, Polythiophene presents high orderly crystal form in this film, and the Polythiophene molecular backbone chain is perpendicular to the substrate orientations.
2. a kind of high order polythiophene film as claimed in claim 1 is characterized in that, described soluble poly thiophene material, and preferred soluble poly (3-alkyl) thiophene, its molecular structural formula is as follows:
In the formula, R=C
mH
2m+1, m represents substituting group alkyl chain length, m=4-12.
3. a kind of high order polythiophene film as claimed in claim 2 is characterized in that, described soluble poly (3-alkyl) thiophene, and more preferably alkyl chain length is poly-(3-butyl) thiophene or poly-(3-hexyl) thiophene of m=4 or m=6.
4. a kind of high order polythiophene film as claimed in claim 1 is characterized in that, Polythiophene presents the preferred high orderly spherocrystal attitude of high orderly crystal form in described this film.
5. the preparation method of a kind of high order polythiophene film as claimed in claim 1, it is characterized in that, step and condition are as follows: the dithiocarbonic anhydride of the soluble poly thiophene of 5-20 mg/ml, chloroform, chlorobenzene, dichloro benzene,toluene,xylene or tetrahydrofuran solution, at room temperature become film, scrape and paint film or be printed as film through spin coating, after solvent evaporates is complete, this film was left standstill under the dithiocarbonic anhydride atmosphere of 0.50-0.98 times of saturation vapour pressure 20 minutes-24 hours, obtain a kind of high order polythiophene film.
6. the preparation method of a kind of high order polythiophene film as claimed in claim 1, it is characterized in that, step and condition are as follows: at room temperature, is concentration the dithiocarbonic anhydride solution of the soluble poly thiophene of 5-20 mg/ml, directly spin coating becomes film, scrapes and paint film or be printed as film in the dithiocarbonic anhydride atmosphere of 0.50-0.98 times of saturation vapour pressure, obtains a kind of high order polythiophene film.
7. the preparation method of a kind of high order polythiophene film as claimed in claim 5 is characterized in that, described preferred soluble poly (3-alkyl) thiophene, and its molecular structural formula is as follows:
In the formula, R=C
mH
2m+1, m represents substituting group alkyl chain length, m=4-12.
8. the preparation method of a kind of high order polythiophene film as claimed in claim 6 is characterized in that, described preferred soluble poly (3-alkyl) thiophene, and its molecular structural formula is as follows:
In the formula, R=C
mH
2m+1, m represents substituting group alkyl chain length, m=4-12.
9. the preparation method of a kind of high order polythiophene film as claimed in claim 7 is characterized in that, described soluble poly (3-alkyl) thiophene, and more preferably alkyl chain length is poly-(3-butyl) thiophene or poly-(3-hexyl) thiophene of m=4 or 6.
10. the preparation method of a kind of high order polythiophene film as claimed in claim 8 is characterized in that, described soluble poly (3-alkyl) thiophene, and more preferably alkyl chain length is poly-(3-butyl) thiophene or poly-(3-hexyl) thiophene of m=4 or 6.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN100533806C (en) * | 2007-08-21 | 2009-08-26 | 中国科学院长春应用化学研究所 | Process for producing polymer solar battery |
| CN102117890A (en) * | 2011-01-26 | 2011-07-06 | 福建农林大学 | Preparation method of organic/polymer solar battery and magnetizing equipment thereof |
| CN102786703A (en) * | 2012-07-20 | 2012-11-21 | 中国科学院长春应用化学研究所 | Method for preparing poly(3-hexylthiophene) (P3HT) oriented ordered film through solution deposition |
| CN102969462A (en) * | 2012-12-05 | 2013-03-13 | 中国科学院长春应用化学研究所 | Preparation method of multi-grade sequentially-arrayed sequential heterojunctions of donor material |
| CN105749979A (en) * | 2016-04-11 | 2016-07-13 | 郑州大学 | Pd-heterocyclic aromatic hydrocarbons Schiff base electrochemically polymerized-self-assembled-doped thin film and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1129353A (en) * | 1995-02-16 | 1996-08-21 | 南京大学 | High-intensive conducting polythiophene thin film, thin-film diode and making method thereof |
| JP2001196664A (en) * | 2000-01-12 | 2001-07-19 | Japan Science & Technology Corp | Thin film material for generation and transfer of optical carrier of photoelectric conversion element comprising stereoregularity polythiophene derivative |
| DE60216257T2 (en) * | 2001-04-17 | 2007-06-14 | Matsushita Electric Industrial Co., Ltd., Kadoma | Conductive organic thin film, process for its manufacture, as well as electric and electrical cables that make use of it |
| US7262264B2 (en) * | 2005-01-12 | 2007-08-28 | Honeywell International Inc. | Halogenated thiophene monomer for the preparation of regioregular polythiophenes |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN100533806C (en) * | 2007-08-21 | 2009-08-26 | 中国科学院长春应用化学研究所 | Process for producing polymer solar battery |
| CN102117890A (en) * | 2011-01-26 | 2011-07-06 | 福建农林大学 | Preparation method of organic/polymer solar battery and magnetizing equipment thereof |
| CN102117890B (en) * | 2011-01-26 | 2012-09-19 | 福建农林大学 | Preparation method of organic/polymer solar battery and magnetizing equipment thereof |
| CN102786703A (en) * | 2012-07-20 | 2012-11-21 | 中国科学院长春应用化学研究所 | Method for preparing poly(3-hexylthiophene) (P3HT) oriented ordered film through solution deposition |
| CN102786703B (en) * | 2012-07-20 | 2015-10-21 | 中国科学院长春应用化学研究所 | The method of the poly-3-hexyl thiophene ordered orientation film of a kind of solution deposition preparation |
| CN102969462A (en) * | 2012-12-05 | 2013-03-13 | 中国科学院长春应用化学研究所 | Preparation method of multi-grade sequentially-arrayed sequential heterojunctions of donor material |
| CN105749979A (en) * | 2016-04-11 | 2016-07-13 | 郑州大学 | Pd-heterocyclic aromatic hydrocarbons Schiff base electrochemically polymerized-self-assembled-doped thin film and preparation method thereof |
| CN105749979B (en) * | 2016-04-11 | 2017-08-01 | 郑州大学 | Pd heterocyclic arene class schiff bases electrochemical polymerization self assembly doping films and preparation method thereof |
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