CN105842302B - A kind of solwution method prepares method and the application of porous organic semiconductor thin-film - Google Patents
A kind of solwution method prepares method and the application of porous organic semiconductor thin-film Download PDFInfo
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- CN105842302B CN105842302B CN201610229122.7A CN201610229122A CN105842302B CN 105842302 B CN105842302 B CN 105842302B CN 201610229122 A CN201610229122 A CN 201610229122A CN 105842302 B CN105842302 B CN 105842302B
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/02—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating impedance
- G01N27/04—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating impedance by investigating resistance
- G01N27/12—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating impedance by investigating resistance of a solid body in dependence upon absorption of a fluid; of a solid body in dependence upon reaction with a fluid, for detecting components in the fluid
- G01N27/125—Composition of the body, e.g. the composition of its sensitive layer
- G01N27/126—Composition of the body, e.g. the composition of its sensitive layer comprising organic polymers
Abstract
The invention discloses the method and its application that a kind of solwution method prepares porous organic semiconductor thin-film, it is characterised in that：In organic solvent by the organic semiconductor of high molecular weight and the dissolving of the oligomer of low molecular weight, blend solution is obtained；Blend solution is spin-coated in substrate by solution spin-coating method and forms blend film, after then using suitable solvent to remove the oligomer dissolving of low molecular weight in blend film, that is, obtains porous organic semiconductor thin-film.The present invention prepares porous membrane by solwution method, and method is simple, reproducible, and the requirement to equipment and process conditions is relatively low, is suitable for the preparation of most of semiconducting polymer porous membrane.The porous organic semiconductor thin-film of gained of the invention can be used in vapor phase sensor, by providing a kind of effective gas dispensing passage, be remarkably improved detection result of the organic semiconducting materials to corresponding analyte gas.
Description
Technical field
The invention belongs to organic semiconductor thin-film and devices fields, and in particular to a kind of to prepare porous organic semiconductor thin-film
New method and its application in chemical vapor sensors.
Background technology
A kind of organic compound thin film material of the conductivity between organic insulator and organic conductor is known as organic half
Conductor thin film is mainly used in organic field effect tube (OFET), organic photovoltaic cell (OSC), Organic Light Emitting Diode
(OLED) and the active layer of the devices such as organic sensor (Organic Sensor).Wherein, porous organic with porous structure
Semiconductive thin film is applied to because that can significantly increase vapor detection ability in chemical vapor sensors.
The pattern of organic semiconductor thin-film largely decides the performance of device with micro-structure, and prepared by tradition organic partly leads
The method of body thin film includes vacuum vapour deposition, spin coating solution method, ink-jet printing, dip-coating method and the method for silk-screen printing,
The different semiconductive thin films that these methods are formed have respective advantageous feature.Wherein, the system of porous organic semiconductor thin-film
It is standby to be realized at present by the technological design of vapor deposition and a series of complex.Therefore, one kind is developed simply and easily to prepare
The method of porous organic semiconductor thin-film is come to promote the development in chemical sensitisation field be particularly critical.
Invention content
The present invention is to avoid above-mentioned existing deficiencies in the technology, provides a kind of more convenient solwution method
The method for preparing porous organic semiconductor thin-film, it is more simple and effective in order to be provided for structure high-performance chemical vapor phase sensor
Approach.
The present invention solves technical problem, adopts the following technical scheme that：
The method that solwution method of the present invention prepares porous organic semiconductor thin-film, feature are：By the organic of high molecular weight
Semiconductor and the dissolving of the oligomer of low molecular weight in organic solvent, obtain blend solution；It will be blended by solution spin-coating method molten
Liquid, which is spin-coated in substrate, forms blend film, and suitable solvent is then used to remove the oligomer dissolving of low molecular weight in blend film
After going, that is, obtain porous organic semiconductor thin-film；
The organic semiconductor of the high molecular weight is polythiophene class polymer semiconductor, bioxindol polymer and its derivative
Series semiconductor or pyrrolo-pyrrole-dione polymer and its derivative series semiconductor；The organic of the high molecular weight partly leads
Shown in the general structure of body such as formula (1)
The oligomer of the low molecular weight is structural formula polyester quasi-oligomer or structural formula such as formula (3) as shown in formula (2)
Shown in polysiloxanes quasi-oligomer；R in formula (2)1、R2It is independently selected from alkyl group or phenyl ring；R in formula (3)1、R2Respectively
It is selected from alkyl group from independent；
The suitable solvent refers to the oligomer that can dissolve low molecular weight and the organic semi-conductor of insoluble high molecular weight
Solvent, such as acetone or ethyl acetate.
When the organic semiconductor of the high molecular weight is polythiophene class polymer semiconductor, the structure of A and B in formula (1)
Formula is all as shown in formula (4), and R is alkyls side chain in formula, and R is respectively independent in the structural formula of A and B；
When the organic semiconductor of the high molecular weight is bioxindol polymer and its derivative series semiconductor, formula (1)
Shown in the structural formula of middle A such as formula (5) or formula (6), structural formula such as formula (7), formula (8), the formula (9) of B is shown, and R is alkyl in formula (7)
Class side chain；
When the organic semiconductor of the high molecular weight is pyrrolo-pyrrole-dione polymer and its derivative series semiconductor
When, in formula (1) shown in the structural formula such as formula (10) or formula (11) of A, structural formula such as formula (12), formula (13), formula (14) or the formula of B
(15) shown in；
When the oligomer of the low molecular weight is polyester quasi-oligomer, shown in structural formula such as formula (16) or (17)；
When the oligomer of the low molecular weight is polysiloxanes quasi-oligomer, shown in structural formula such as formula (18) or (19)；
In the blend solution, a concentration of 1~10mg/mL of organic semi-conductor of the high molecular weight；Described low point
A concentration of 1~10mg/mL of the oligomer of son amount.
The organic solvent is the one kind that can dissolve the organic semiconductor of high molecular weight and the oligomer of low molecular weight simultaneously
Mixing of solvent or multi-solvents, such as chloroform, chlorobenzene, dichloro-benzenes etc..
The porous organic semiconductor thin-film of the present invention, is the blend film for being initially formed blending, is then reused suitable molten
Agent removes oligomer so that organic semiconductor, which is mutually formed by film, generates hole, to obtain with porous structure
Organic semiconductor thin-film, and the size in hole can regulate and control according to the ratio of two-phase substance in blend solution.
Invention further provides pass through the porous organic semiconductor thin-film prepared by the above method.
The present invention also provides application of the above-mentioned porous organic semiconductor thin-film in vapor phase sensor.By porous organic half
Active layer of the conductor thin film as vapor phase sensor, porous structure can effectively enhance the phase of gas or steam and channel region
Interaction improves the detectability of device, obtains high-performance vapor phase sensor part.Compared with nonporous film device, gas molecule in space
This process for reaching device channel layer is spread from semiconductive thin film, porous membrane spreads arrival channel layer for gas molecule and provides
A kind of more effective and more direct mode or path, generate therewith faster, stronger interaction, to improving senser element
The sensing capabilities parameter such as detectable limit, sensitivity, response time and recovery time, be effectively improved the property of gas chemistry sensor
Energy.
According to the difference of characteristic of semiconductor, porous organic semiconductor thin-film is used in vapor phase sensor, detection can be enhanced
Gas or steam can be nitrogen dioxide, nitric oxide, sulfur dioxide, ammonia, phosgene, dimethyl suflfate, methane, ethane, second
The common toxic and harmful gas such as alkene, hydrogen cyanide, hydrogen sulfide and nitrobenzene, methanol, chloroform, chlorobenzene, ethyl acetate, dichloromethane,
The common organic vapor such as n-hexane, tetrahydrofuran.
Compared with the existing method for preparing porous organic semiconductor thin-film, beneficial effects of the present invention are embodied in：
1, the present invention prepares porous membrane by solwution method, and method is simple, reproducible, relative to traditional evaporation coating method
Speech, the requirement to equipment and process conditions is relatively low, easily operated, and suitable for the system of most of semiconducting polymer porous membrane
It is standby, solve the problems, such as that semiconducting polymer is not suitable for evaporation process；
2, the oligomer of low molecular weight used in the present invention is all industrial relatively conventional plasticizer, lubricant etc.
Material, it is of low cost, derive from a wealth of sources, it can be produced in enormous quantities.
3, when preparing porous organic semiconductor thin-film, the amount ratio by changing two components in blend solution is the present invention
The size of controllable product mesoporous also can get non-porous film, side when by the way that the dosage of oligomer in blend solution being adjusted to relatively low
Method is easy.
4, the present invention prepared by porous organic semiconductor thin-film when for vapor phase sensor, have by providing one kind
The gas dispensing passage of effect is remarkably improved detection result of the organic semiconducting materials to corresponding analyte gas.
Description of the drawings
Fig. 1 is the molecular formula of PBIBDF-BT in the embodiment of the present invention 1；
Fig. 2 is the flow diagram of porous organic semiconductor film preparation in the embodiment of the present invention 1；
Fig. 3 is the embodiment of the present invention 1 with the atomic force microscope images of gained PBIBDF-BT films under different PBA contents
(AFM), wherein (a) is PBA contents when being 0wt.% gained film, (b) when be PBA contents being 20wt.% obtained by film, (c)
Gained film when for PBA contents being 40wt.%；
Fig. 4 is the embodiment of the present invention 2 with the atomic force microscope images of gained PBIBDF-BT films under different silicone oils
(AFM), wherein (a) is silicone oil when being 0wt.% gained film, (b) when be silicone oil being 10wt.% obtained by film,
(c) gained film when be silicone oil being 20wt.%；
Fig. 5 is the molecular formula of PIID-BT in the embodiment of the present invention 3；
Fig. 6 is the atomic force microscope images (AFM) of the 3 porous PIID-BT films of gained of the embodiment of the present invention；
Fig. 7 is the molecular formula of PBTPBF-DBT in the embodiment of the present invention 4；
Fig. 8 is the atomic force microscope images (AFM) of the 4 porous PBTPBF-DBT films of gained of the embodiment of the present invention；
Fig. 9 is the molecular formula of polythiophene class semi-conducting material in the embodiment of the present invention 5；
Figure 10 is pyrrolo-pyrrole-dione (DPP) polymer and its derivative series semiconductor in the embodiment of the present invention 6
Molecular formula；
Figure 11 is porous PBIBDF-BT films NH3Sensor structure schematic diagram；
Figure 12 is porous PBIBDF-BT thin-film devices figure compared with the sensing capabilities of non-porous PBIBDF-BT thin-film devices,
In (a) be multi-aperture device sensing repeat linearity curve, (b) be non-porous device sensing repeat linearity curve.
Specific implementation mode
Embodiment 1
The present embodiment is with bioxindol polymerisomer derivative PBIBDF-BT (structural formula such as Fig. 1) for high molecular weight
Organic semiconductor (its weight average molecular weight be 58852), with polyadipate (Isosorbide-5-Nitrae) butanediol ester (PBA) (structural formula such as formula (16)
It is shown) oligomer (its weight average molecular weight be 2000) as the low molecular weight being blended, in the SiO of Cytop modifications2It is made in substrate
Standby porous PBIBDF-BT films.
As shown in Fig. 2, the preparation process of the porous PBIBDF-BT films of the present embodiment is as follows：
To carry 300nm SiO2The heavy doping silicon chip of layer uses acetone, ethyl alcohol, deionized water to clean successively as substrate
15min reuses ozone treatment 15min.Then, in substrate with the rotating speed spin coating Cytop solution about 1min of 3000r/min,
180 DEG C of heating 15min in thermal station are placed it in again, obtain the SiO of Cytop modifications2Substrate.
By 60wt.%：The ratio of 40wt.% weighs PBIBDF-BT and PBA, keep total concentration of solutes be 5mg/mL by its
It is dissolved in chloroform (CF) solvent, is uniformly mixed using stirrer, obtain the blend solution of PBIBDF-BT and PBA.Then exist
Blend solution is spin-coated on in the glove box full of nitrogen with the rotating speed of 4000r/min the SiO of Cytop modifications2In substrate, to
Form the blend film of PBIBDF-BT and PBA；Blend film is finally impregnated into 15min in acetone, to remove PBA components, i.e.,
Obtain porous PBIBDF-BT films.
To be compared, PBA contents in blend solution are adjusted to 0,20wt.%, two kinds are obtained by same steps
PBIBDF-BT films.The AFM surface topography maps of non-porous PBIBDF-BT films and porous PBIBDF-BT films obtained by the present embodiment
Respectively as shown in Fig. 3 (a), Fig. 3 (b) and Fig. 3 (c), as can be seen from the figure：When PBA contents are 0%, one kind can be obtained
Non-porous smooth continuous film.When PBA contents increase to 20% and 40%, it is thin to form a kind of porous organic semiconductor
Film.Therefore, porous membrane structure can be obtained by PBIBDF and PBA being blended by addition.
Embodiment 2
The present embodiment is to be with bioxindol polymerisomer derivative PBIBDF-BT (its weight average molecular weight is 55200)
The organic semiconductor of high molecular weight, with dimethyl silicone polymer (abbreviation silicone oil, shown in structural formula such as formula (18)) as blending
Low molecular weight oligomer (its weight average molecular weight be 3000), in the silicon base that octadecyl trichlorosilane alkane (OTS) is modified
It prepares porous PBIBDF-BT films, and regulates and controls the pore size in perforated membrane by adjusting the content of oligomer.Specific steps
It is as follows：
Silicon base is placed in H2SO4/H2O2(volume ratio 7:3) substrate, is then placed in by 150 DEG C of cleanings in mixed solution
It drips in the 20mL dry toluenes for having 0.05mL OTS and impregnates 20min, the OTS decorative layers for keeping one layer of its surface self-organization hydrophobic obtain
Obtain the silicon base of OTS modifications.
PBIBDF-BT and silicone oil are pressed into 100wt.% respectively：0wt.%, 90wt.%：10wt.%, 80wt.%：
20wt.% weighs weight, and it is that 5mg/mL is dissolved in chloroform (CF) solvent to keep solute concentration, is stirred using stirrer mixed
Close uniform, the blend solution of acquisition PBIBDF-BT and silicone oil.Then turned with 4000r/min in the glove box full of nitrogen
Blend solution is spin-coated on substrate by speed, to form the blend film of PBIBDF-BT and silicone oil.Finally blend film is immersed in
15min in acetone obtains PBIBDF-BT films, is named as sample 1, sample 2, sample 3 successively to remove silicone oil component.
Fig. 4 is the AFM surface topography maps of each sample obtained by the present embodiment, (a) in figure, (b), (c) be corresponding in turn to sample 1,
Sample 2, sample 3.It can be seen from the figure that by the way that silicone oil is added, the PBIBDF-BT films with porous structure can be obtained.
And with the increase of silicone oil, the size in hole becomes larger.
Embodiment 3
The present embodiment prepares porous organic semiconductor thin-film by 1 identical mode of embodiment, differs only in PBIBDF-
BT is substituted for PIID-BT polymer (its molecular formula such as Fig. 5, weight average molecular weight 65560), obtains porous PIID-BT films.
The AFM of porous PIID-BT films obtained by the present embodiment schemes as shown in fig. 6, as can be seen from the figure foring porous
Film.
Embodiment 4
The present embodiment prepares porous organic semiconductor thin-film by 1 identical mode of embodiment, differs only in PBIBDF-
BT is substituted for PBTPBF-DBT polymer (its molecular formula such as Fig. 7, weight average molecular weight 70565), obtains porous PBTPBF-
DBT films.
The AFM of porous PBTPBF-DBT films obtained by the present embodiment schemes as shown in figure 8, as can be seen from the figure foring more
Pore membrane.
Embodiment 5
The present embodiment prepares porous organic semiconductor thin-film by 1 identical mode of embodiment, differs only in PBIBDF-
BT is substituted for polythiophene class semi-conducting material (its molecular formula such as Fig. 9, weight average molecular weight 65660), prepares porous organic half
Conductor thin film.
Through characterization, film has porous structure obtained by the present embodiment.
Embodiment 6
The present embodiment prepares porous organic semiconductor thin-film by 1 identical mode of embodiment, differs only in PBIBDF-
BT be substituted for pyrrolo-pyrrole-dione (DPP) polymer and its derivative series semiconductor (its molecular formula such as Figure 10, it is heavy to divide equally
Son amount is 75349), to prepare porous organic semiconductor thin-film.
Through characterization, film has porous structure obtained by the present embodiment.
Embodiment 7
The present embodiment is in the 1 non-porous PBIBDF-BT films of gained of embodiment and porous PBIBDF-BT films on the basis of system
Standby organic thin film transistor device, and test it and be applied to two kinds of film performances in ammonia sensing as chemical vapor sensors
Comparison.It is as follows：
Distinguish plated with gold source and drain electricity on non-porous PBIBDF-BT films and porous PBIBDF-BT films using metal mask plate
Pole, raceway groove is 150 μm a length of, ditch road width is 800 μm.Then it is tested using semi-conductor test instrument.
Figure 11 is porous PBIBDF-BT films as NH3The structural schematic diagram of the bottom gate top contact transistor of senser element.
Sensing curve of the device in real-time detection corresponding to porous PBIBDF-BT films and non-porous PBIBDF-BT films is respectively such as
Shown in Figure 12 (a) and Figure 12 (b).Multi-aperture device shows excellent repeatability and stability as can be seen from Fig., and responds
Speed is a kind of high performance ammonia gas sensor part.In addition, the sensitivity of multi-aperture device, response time, recovery time are all
Significantly it is better than non-porous device.Therefore, the porous structure in device can effectively enhance the sensing capabilities of device.
Claims (7)
1. a kind of method that solwution method prepares porous organic semiconductor thin-film, it is characterised in that：Organic by high molecular weight partly leads
Body and the dissolving of the oligomer of low molecular weight in organic solvent, obtain blend solution；Blend solution is revolved by solution spin-coating method
It is coated in substrate and forms blend film, then use suitable solvent to dissolve the oligomer of low molecular weight in blend film and remove
Afterwards, that is, porous organic semiconductor thin-film is obtained；
The organic semiconductor of the high molecular weight is polythiophene class polymer semiconductor, bioxindol polymer and its derivative series
Semiconductor or pyrrolo-pyrrole-dione polymer and its derivative series semiconductor；The organic semi-conductor of the high molecular weight
Shown in general structure such as formula (1)
The oligomer of the low molecular weight is shown in structural formula polyester quasi-oligomer or structural formula such as formula (3) as shown in formula (2)
Polysiloxanes quasi-oligomer；R in formula (2)1、R2It is independently selected from alkyl group or phenyl ring；R in formula (3)1、R2Respectively solely
Vertical is selected from alkyl group；
The suitable solvent refers to that the organic semi-conductor for the oligomer and insoluble high molecular weight that can dissolve low molecular weight is molten
Agent；
The structural formula of A and B is all when the organic semiconductor of the high molecular weight is polythiophene class polymer semiconductor, in formula (1)
As shown in formula (4), R is alkyls side chain in formula, and R is respectively independent in the structural formula of A and B；
When the organic semiconductor of the high molecular weight is bioxindol polymer and its derivative series semiconductor, A in formula (1)
Shown in structural formula such as formula (5) or formula (6), structural formula such as formula (7), formula (8), the formula (9) of B is shown, and R is alkyls side in formula (7)
Chain；
When the organic semiconductor of the high molecular weight is pyrrolo-pyrrole-dione polymer and its derivative series semiconductor, formula
(1) structural formula of A such as formula (10) or formula (11) are shown in, structural formula such as formula (12), formula (13), formula (14) or formula (15) institute of B
Show；
2. according to the method described in claim 1, it is characterized in that：When the oligomer of the low molecular weight is polyester quasi-oligomer
When, shown in structural formula such as formula (16) or (17)；
When the oligomer of the low molecular weight is polysiloxanes quasi-oligomer, shown in structural formula such as formula (18) or (19)；
3. according to the method described in claim 1, it is characterized in that：In the blend solution, the high molecular weight it is organic
A concentration of 1~10mg/mL of semiconductor；A concentration of 1~10mg/mL of the oligomer of the low molecular weight.
4. according to the method described in claim 1, it is characterized in that：The organic solvent is that can dissolve having for high molecular weight simultaneously
The mixing of a kind of solvent or multi-solvents of machine semiconductor and the oligomer of low molecular weight.
5. according to the method described in claim 1, it is characterized in that：The suitable solvent is acetone or ethyl acetate.
6. the porous organic semiconductor thin-film prepared by a kind of any one of Claims 1 to 5 the method.
7. the application of porous organic semiconductor thin-film described in a kind of claim 6, it is characterised in that：In vapor phase sensor.
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| CN107192755B (en) * | 2017-05-23 | 2019-08-30 | 合肥工业大学 | A kind of preparation method of ultrathin membrane and the organic field effect tube sensor based on it |
| CN108963080B (en) * | 2018-07-07 | 2020-05-26 | 河南大学 | Preparation method of porous organic semiconductor film |
| CN109137123B (en) * | 2018-08-14 | 2020-12-22 | 郑州大学 | Method for preparing polycarbazole derivative nanofiber |
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