CN100519634C - Conjugated polymer and nano-particle composite thin film and its production - Google Patents
Conjugated polymer and nano-particle composite thin film and its production Download PDFInfo
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- CN100519634C CN100519634C CNB2007100553974A CN200710055397A CN100519634C CN 100519634 C CN100519634 C CN 100519634C CN B2007100553974 A CNB2007100553974 A CN B2007100553974A CN 200710055397 A CN200710055397 A CN 200710055397A CN 100519634 C CN100519634 C CN 100519634C
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- conjugated polymers
- laminated film
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- 229920000547 conjugated polymer Polymers 0.000 title claims abstract description 38
- 239000002105 nanoparticle Substances 0.000 title claims description 9
- 239000002131 composite material Substances 0.000 title abstract 2
- 239000010409 thin film Substances 0.000 title abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 35
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 22
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 13
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000011159 matrix material Substances 0.000 claims description 5
- 238000004528 spin coating Methods 0.000 claims description 5
- -1 poly phenylenevinylene Polymers 0.000 claims description 4
- 229920000553 poly(phenylenevinylene) Polymers 0.000 claims description 4
- 229920002098 polyfluorene Polymers 0.000 claims description 4
- 229920000123 polythiophene Polymers 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 230000005669 field effect Effects 0.000 abstract description 2
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 239000002159 nanocrystal Substances 0.000 abstract 2
- 230000002776 aggregation Effects 0.000 abstract 1
- 238000004220 aggregation Methods 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000003446 memory effect Effects 0.000 abstract 1
- 229920000620 organic polymer Polymers 0.000 abstract 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 46
- 229930192474 thiophene Natural products 0.000 description 23
- 238000004627 transmission electron microscopy Methods 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 238000002524 electron diffraction data Methods 0.000 description 4
- 238000002003 electron diffraction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920000291 Poly(9,9-dioctylfluorene) Polymers 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000004098 selected area electron diffraction Methods 0.000 description 1
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Abstract
A composite thin-film consists of conjugated polymer and carbon 60 nano-crystal. The Carbon 60 nano-crystal distributes uniformly and the diameter is between 10-100nm. It has excellent dispersion effect and no aggregation. It can be used for organic polymer solar battery, super-conductive device, photoelectric detector, semi-conductor memory and field-effect tube.
Description
Technical field
The present invention relates to laminated film of a kind of conjugated polymers and nanoparticle and preparation method thereof.
Background technology
The laminated film of conjugated polymers and nanoparticle has important use to be worth, the laminated film of conjugated polymers and soccerballene carbon 60 for example, because it has photoelectric response characteristic (Science1995,270,1789-1791), add polymeric film peculiar flexibility, be easy to process and plurality of advantages such as low cost and be subjected to people's common concern.But, require these carbon 60 in film, to exist with nano level (tens nanometers) crystalline structure formation in order to obtain good device performance.Yet because carbon 60 relatively poor dissolving power and easy crystallinity thereof in usual vehicle are difficult to its crystallization behavior and crystalline pattern that obtains in film of control.Therefore conjugated polymers and diameter do not have report as yet less than the even one dimension C-60 nanocrystalline laminated film of 100 nanometers.But this film is at organic semiconductor material, and fields such as photoelectric device, superconduction and magneticsubstance have very wide application prospect.
Summary of the invention
One of the object of the invention provides the laminated film of a kind of conjugated polymers and nanoparticle.Described laminated film is conjugated polymers and one dimension C-60 nanocrystalline laminated film; Constituting the conjugated polymers of this laminated film and the quality proportioning of carbon 60 is 2:8-8:2; The one dimension C-60 nanocrystalline is dispersed in the conjugated polymers laminated film matrix; The diameter of described one dimension C-60 nanocrystalline is 10-100nm;
Described conjugated polymers is: can be dissolved in dithiocarbonic anhydride, toluene, chlorobenzene or orthodichlorobenzene altogether with carbon 60, and can prepare the conjugated polymers that does not have the even original laminated film that big area is separated; The preferred soluble poly thiophene of described conjugated polymers, soluble poly phenylenevinylene or soluble poly fluorenes.
Two of the object of the invention provides a kind of preparation method of conjugated polymers laminated film, and its step and condition are as follows:
Is the quality proportioning that conjugated polymers and the carbon 60 of 2:8-8:2 is dissolved in dithiocarbonic anhydride, toluene, chlorobenzene or the orthodichlorobenzene solvent, and obtaining total concn is the solution of the polymkeric substance/carbon 60 of 10-30 mg/ml; The spin coating at room temperature of this solution, blade coating or printing, vapor away solvent, obtain conjugated polymers and carbon 60 original laminated films; Under the normal temperature this film is placed in the container, rate of pressure rise with 0.01-1.0 times of saturated dithiocarbonic anhydride vapour pressures of per second boosts, in the solvent atmosphere of 0.83-0.98 times of saturation vapour pressure, left standstill 2 seconds-18 hours, and obtained conjugated polymers and the nanocrystalline laminated film of one dimension C-60 nanocrystalline.
Described conjugated polymers is: can be dissolved in dithiocarbonic anhydride, toluene, chlorobenzene or orthodichlorobenzene altogether with carbon 60, and can prepare the conjugated polymers that does not have the even original laminated film that big area is separated; The preferred soluble poly thiophene of described conjugated polymers, soluble poly phenylenevinylene or soluble poly fluorenes.
As shown in drawings, the transmission electron microscopy of conjugated polymers of the present invention and one dimension C-60 nanocrystalline laminated film and original position selected area electron diffraction result of study show, C-60 nanocrystalline is that one-dimensional crystal with nanoscale exists in the resulting laminated film, and be dispersed in the conjugated polymers matrix, the diameter of one dimension C-60 nanocrystalline is 10-100nm.
The present invention is to provide conjugated polymers and one dimension C-60 nanocrystalline laminated film, the diameter of one dimension C-60 nanocrystalline is 10-100nm in this film, is dispersed in the conjugated polymers matrix, thereby reaches two-phase microphase-separated and carbon 60 crystallizations simultaneously.This class conjugated polymers/one dimension C-60 nanocrystalline matrix material has in fields such as photoelectron, superconduction, field effect transistor widely to be used.
Description of drawings
Fig. 1 is the transmission electron microscopy picture according to poly-(3-hexyl) thiophene/carbon 60 laminated films of high-regularity of embodiment 14 described condition preparations.
Fig. 2 is that electron diffraction shows carbon 60 crystallization, corresponding to the nano bar-shape structure in the bright field image according to the transmission electron microscopy picture and the electron diffraction pattern thereof of poly-(3-hexyl) thiophene/carbon 60 laminated films of high-regularity of embodiment 9 described condition preparations.
Fig. 3 is that arrow is represented carbon 60 crystal growth directions according to the transmission electron microscopy picture and the electron diffraction pattern thereof of poly-(3-hexyl) thiophene/carbon 60 laminated films of high-regularity of embodiment 5 described condition preparations.
Fig. 4 be according to the described conditions preparation of embodiment 16 poly-(2-methoxyl group-5-(3 ', 7 '-dimethyl oxygen in last of the ten Heavenly stems base))-1, the transmission electron microscopy picture and the electron diffraction pattern thereof of 4-phenylene ethylene/carbon 60 laminated films, electron diffraction shows carbon 60 crystallization, corresponding to the nano bar-shape structure in the bright field image.
Fig. 5 is that electron diffraction shows carbon 60 crystallization, corresponding to the nano bar-shape structure in the bright field image according to the transmission electron microscopy picture and the electron diffraction pattern thereof of poly-(9,9 '-dioctyl fluorene)/carbon 60 laminated films of the described conditions preparation of embodiment 17.
Embodiment
Embodiment 1: is the quality proportioning that poly-(3-butyl) thiophene of high-regularity and the carbon 60 of 1:1 is dissolved in the dithiocarbonic anhydride solvent, obtain total concn and be 10 mg/ml the dithiocarbonic anhydride solution of poly-(3-butyl) thiophene/carbon 60 of high-regularity, the spin coating at ambient temperature of this solution, vapor away the dithiocarbonic anhydride solvent, obtain polymkeric substance and carbon 60 laminated films; At room temperature, this laminated film is raised to the rate of pressure rise of 1.0 times of dithiocarbonic anhydride saturation vapour pressures of per second under the atmosphere of 0.98 times of dithiocarbonic anhydride saturation vapour pressure and left standstill 18 hours, obtain poly-(3-butyl) thiophene of a kind of high-regularity and one dimension C-60 nanocrystalline laminated film, wherein the mean diameter of one dimension C-60 nanocrystalline is 100nm.
Embodiment 2: adopt to scrape and paint film.Remaining condition and step obtain poly-(3-butyl) thiophene of a kind of high-regularity and one dimension C-60 nanocrystalline laminated film with embodiment 1, and wherein the mean diameter of one dimension C-60 nanocrystalline is 100nm.
Embodiment 3: adopt to be printed as film.Remaining condition and step obtain poly-(3-butyl) thiophene of a kind of high-regularity and one dimension C-60 nanocrystalline laminated film with embodiment 1, and wherein the mean diameter of one dimension C-60 nanocrystalline is 100nm.
Embodiment 4: rate of pressure rise is 0.01 times of vapour pressure of per second, and remaining condition and step obtain poly-(3-butyl) thiophene of a kind of high-regularity and one dimension C-60 nanocrystalline laminated film with embodiment 1, and wherein the mean diameter of one dimension C-60 nanocrystalline is 100nm.
Embodiment 5: is the quality proportioning that poly-(3-hexyl) thiophene of high-regularity and the carbon 60 of 1:1 is dissolved in the orthodichlorobenzene solvent, obtain total concn and be 10 mg/ml the o-dichlorobenzene solution of poly-(3-butyl) thiophene/carbon 60 of high-regularity, the spin coating at ambient temperature of this solution, vapor away the orthodichlorobenzene solvent, obtain polymkeric substance and carbon 60 laminated films; At room temperature, this laminated film is raised to the rate of pressure rise of 1.0 times of dithiocarbonic anhydride saturation vapour pressures of per second under the atmosphere of 0.96 times of dithiocarbonic anhydride saturation vapour pressure and left standstill 30 seconds, obtain poly-(3-hexyl) thiophene of a kind of high-regularity and one dimension C-60 nanocrystalline laminated film, wherein the mean diameter of one dimension C-60 nanocrystalline is 100nm.
Embodiment 6: adopting composition of raw materials is poly-(3-hexyl) thiophene/C60 (quality proportioning 8:2) of high-regularity.Remaining condition and step obtain poly-(3-hexyl) thiophene of a kind of high-regularity and one dimension C-60 nanocrystalline laminated film with embodiment 5, and wherein the mean diameter of one dimension C-60 nanocrystalline is 100nm.
Embodiment 7: adopting composition of raw materials is poly-(3-hexyl) thiophene/C60 (quality proportioning 2:8) of high-regularity.Remaining condition and step obtain poly-(3-hexyl) thiophene of a kind of high-regularity and one dimension C-60 nanocrystalline laminated film with embodiment 5, and wherein the mean diameter of one dimension C-60 nanocrystalline is 100nm.
Embodiment 8: rate of pressure rise is 0.1 times of vapour pressure of per second, and remaining condition and step obtain poly-(3-hexyl) thiophene of a kind of high-regularity and one dimension C-60 nanocrystalline laminated film with embodiment 5, and wherein the mean diameter of one dimension C-60 nanocrystalline is 100nm.
Embodiment 9: the dithiocarbonic anhydride vapour pressure is 0.83 times of saturation vapour pressure, time of repose is 5 seconds, remaining condition and step obtain poly-(3-hexyl) thiophene of a kind of high-regularity and one dimension C-60 nanocrystalline laminated film with embodiment 5, and wherein the mean diameter of one dimension C-60 nanocrystalline is 10nm.
Embodiment 10: film time of repose in dithiocarbonic anhydride atmosphere is 2 seconds, remaining condition and step are with embodiment 5, obtain poly-(3-hexyl) thiophene of a kind of high-regularity and one dimension C-60 nanocrystalline laminated film, wherein the mean diameter of one dimension C-60 nanocrystalline is 40nm.
Embodiment 11: film storage period in dithiocarbonic anhydride atmosphere is 10 seconds, remaining condition and step are with embodiment 5, obtain poly-(3-hexyl) thiophene of a kind of high-regularity and one dimension C-60 nanocrystalline laminated film, wherein the mean diameter of one dimension C-60 nanocrystalline is 70nm.
Embodiment 12: material solution is a toluene solution, and remaining condition and step obtain poly-(3-hexyl) thiophene of a kind of high-regularity and one dimension C-60 nanocrystalline laminated film with embodiment 5, and wherein the mean diameter of one dimension C-60 nanocrystalline is 100nm.
Embodiment 13: material solution is a chlorobenzene solution, and remaining condition and step obtain poly-(3-hexyl) thiophene of a kind of high-regularity and one dimension C-60 nanocrystalline laminated film with embodiment 5, and wherein the mean diameter of one dimension C-60 nanocrystalline is 100nm.
Embodiment 14: rate of pressure rise is 0.1 times of vapour pressure of per second, and remaining condition and step obtain poly-(3-hexyl) thiophene of a kind of high-regularity and one dimension C-60 nanocrystalline laminated film with embodiment 9, and wherein the mean diameter of one dimension C-60 nanocrystalline is 10nm.
Embodiment 15: is the quality proportioning being dissolved in the orthodichlorobenzene solvent with carbon 60 of 1:1, obtain total concn and be 10 mg/ml poly-(2-methoxyl group-5-(3 ', 7 '-dimethyl oxygen in last of the ten Heavenly stems base))-1, the o-dichlorobenzene solution of 4-phenylene ethylene/carbon 60, the spin coating at ambient temperature of this solution, vapor away the orthodichlorobenzene solvent, gathered (2-methoxyl group-5-(3 ', 7 '-dimethyl oxygen in last of the ten Heavenly stems base))-1,4-phenylene ethylene and carbon 60 laminated films; At room temperature, this laminated film is raised to the rate of pressure rise of 1.0 times of dithiocarbonic anhydride saturation vapour pressures of per second under the atmosphere of 0.98 times of dithiocarbonic anhydride saturation vapour pressure and left standstill 5 seconds, obtain a kind of poly-(2-methoxyl group-5-(3 ', 7 '-dimethyl oxygen in last of the ten Heavenly stems base))-1,4-phenylene ethylene and one dimension C-60 nanocrystalline laminated film, wherein the mean diameter of one dimension C-60 nanocrystalline is 40nm.
Embodiment 16: dithiocarbonic anhydride solvent atmosphere vapour pressure is 0.83 times of saturated dithiocarbonic anhydride vapour pressure, remaining condition and step are with embodiment 14, obtain a kind of poly-(2-methoxyl group-5-(3 ', 7 '-dimethyl oxygen in last of the ten Heavenly stems base))-1,4-phenylene ethylene and one dimension C-60 nanocrystalline laminated film, wherein the mean diameter of one dimension C-60 nanocrystalline is 10nm.
Embodiment 17: solution is poly-(9 of total concn 20 mg/ml, 9 '-dioctyl fluorene)/o-dichlorobenzene solution of carbon 60 (quality proportioning 1:1), remaining condition and step are with embodiment 15, obtain a kind of poly-(9,9 '-dioctyl fluorene) and one dimension C-60 nanocrystalline laminated film, wherein the mean diameter of one dimension C-60 nanocrystalline is 10nm.
Claims (3)
1. the laminated film of conjugated polymers and nanoparticle is characterized in that described laminated film is conjugated polymers and one dimension C-60 nanocrystalline laminated film; Constituting the conjugated polymers of this laminated film and the quality proportioning of carbon 60 is 2:8-8:2; The one dimension C-60 nanocrystalline is dispersed in the conjugated polymers laminated film matrix;
Described conjugated polymers is soluble poly thiophene, soluble poly phenylenevinylene or soluble poly fluorenes.
2. the laminated film of a kind of conjugated polymers as claimed in claim 1 and nanoparticle is characterized in that, the diameter of described one dimension C-60 nanocrystalline is 10-100nm.
3. the preparation method of the laminated film of a kind of conjugated polymers as claimed in claim 1 and nanoparticle is characterized in that step and condition are as follows:
Is the quality proportioning that conjugated polymers and the carbon 60 of 2:8-8:2 is dissolved in dithiocarbonic anhydride, toluene, chlorobenzene or the orthodichlorobenzene solvent, and obtaining total concn is the solution of the conjugated polymers/carbon 60 of 10-30 mg/ml; The spin coating at room temperature of this solution, blade coating or printing, vapor away solvent, obtain conjugated polymers and carbon 60 original laminated films; Under the normal temperature this film is placed in the container, rate of pressure rise with 0.01-1.0 times of saturated dithiocarbonic anhydride vapour pressures of per second boosts, in the dithiocarbonic anhydride solvent atmosphere of 0.83-0.98 times of saturation vapour pressure, left standstill 2 seconds-18 hours, and obtained the laminated film of a kind of conjugated polymers and nanoparticle;
Described conjugated polymers is soluble poly thiophene, soluble poly phenylenevinylene or soluble poly fluorenes.
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| CN100519634C true CN100519634C (en) | 2009-07-29 |
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| CN101494255B (en) * | 2009-03-05 | 2010-06-02 | 中国科学院长春应用化学研究所 | Preparation method for thin-film solar cell based on narrowband gap conjugated polymer |
| CN102702550B (en) * | 2012-06-11 | 2013-09-04 | 合肥工业大学 | Preparation method for transparent organic and inorganic hybridization heterojunction material |
| CN110804196B (en) * | 2019-12-10 | 2022-04-08 | 中国科学院合肥物质科学研究院 | Method for preparing polymer-carbon nano composite material oriented film by means of strong magnetic field |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1155167A (en) * | 1996-01-16 | 1997-07-23 | 南京大学 | Polythiophene-conductive-fiber composite film and making method and usage thereof |
| WO2003090285A1 (en) * | 2002-04-16 | 2003-10-30 | The Regent Of The University Of California | High-performance and low-cost plastic solar cells |
| CN1687175A (en) * | 2005-04-07 | 2005-10-26 | 徐良衡 | Disperse system of nano composition colloid of polythiophene, and preparation method |
| CN1841573A (en) * | 2005-03-31 | 2006-10-04 | Tdk株式会社 | Transparent conductor |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1155167A (en) * | 1996-01-16 | 1997-07-23 | 南京大学 | Polythiophene-conductive-fiber composite film and making method and usage thereof |
| WO2003090285A1 (en) * | 2002-04-16 | 2003-10-30 | The Regent Of The University Of California | High-performance and low-cost plastic solar cells |
| CN1841573A (en) * | 2005-03-31 | 2006-10-04 | Tdk株式会社 | Transparent conductor |
| CN1687175A (en) * | 2005-04-07 | 2005-10-26 | 徐良衡 | Disperse system of nano composition colloid of polythiophene, and preparation method |
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