CN101645487A - Light-sensing organic field-effect transistor and preparation method thereof - Google Patents

Light-sensing organic field-effect transistor and preparation method thereof Download PDF

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CN101645487A
CN101645487A CN200910080767A CN200910080767A CN101645487A CN 101645487 A CN101645487 A CN 101645487A CN 200910080767 A CN200910080767 A CN 200910080767A CN 200910080767 A CN200910080767 A CN 200910080767A CN 101645487 A CN101645487 A CN 101645487A
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thiophene
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于贵
郭云龙
杜春燕
蒋士冬
狄重安
闫寿科
刘云圻
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Abstract

The invention discloses a light-sensing organic field-effect transistor and a preparation method thereof. The transistor comprises a substrate, a grid electrode arranged on the substrate and an insulating layer arranged on the grid electrode; the transistor further comprises a self-assembled monomolecular-modified layer and a source electrode, a drain electrode and at least one organic semiconductor compound single crystal wire positioned on the self-assembled monomolecular layer. The self-assembled monomolecular layer comprises materials of octadecyltrichlorosilane, octacyltrichlorosilane, phenyltrichlorosilane and the like; and the preferential organic semiconductor compound is 6-methyl-anthracene [2,3-b] benzo-[d] thiophene. The length of the organic semiconductor compound single crystal is 80-300 microns, and the diameter is 1-10 microns. The preparation method provided by the invention has simple prepration process and low cost, and the prepared organic field-effect transistor hasvery high response on a low-energy light source with the energy of 10-90 microwatts per square centimeter, high mobility, high photosensitivity and high ratio of light current to dark current.

Description

A kind of light-sensing organic field-effect transistor and preparation method thereof
Technical field
The present invention relates to the organic field effect tube field of sensing technologies, particularly relate to a kind of light-sensing organic field-effect transistor and preparation method thereof.
Background technology
Development along with organic electronic, organic field effect tube (organic field-effect transistors, be called for short OFETs) with its lightweight, easy flexibility and unique advantage with low cost, and in drives, aspect wide application prospect such as fast-response probe are attracting people's sight.In numerous OFETs research, the light sensing OFETs (organic phototransistors (OPTs)) with OFETs switch performance and the effect of light sensing is a very promising class photoelectric device.Trace it to its cause, OPTs has own unique advantage: identical light sensitivity principles but has better signal amplifying function; It is structurally than junction field effect transistor easier integrated on a large scale (Y.-Y.Noh, D.-Y.Kim, and K.Yase, J.Appl.Phys.2005,98,074505; Y.Liang, G.F.Dong, Y.Hu, L.D.Wang, and Y.Qiu, Appl.Phys.Lett.2005,86,132101).
In recent years, people are synthetic and developed multiple high performance light sensation organic semiconducting materials, and it is integrated in the organic effect device, Development of Materials has promoted the research of OPTs greatly, and for example: poly-(9, the 9-dioctyl fluorene is di-thiophene, 2 altogether, the research of 5-two-biphenyl-4-thienothiophene and perfluor CuPc OPTs (M.C.Hamilton et al.IEEE Trans.Electron Devices, 2004,51,877; Y.-Y.Noh, D.-Y.Kim, Y.Yoshida, K.Yase, B.-J.Jung, E.Lim, and H.-K.Shim, Appl.Phys.Lett.2005,86,043501; Q.X.Tang, L.Q.Li, Y.B.Song, Y.L.Liu, H.X.Li, W.Xu, Y.Q.Liu, W.P.Hu, and D.B.Zhu, Adv.Mater.2007,19,2624).Go out the enough good organic semiconducting materials of photosensitive property but these researchs are also untapped, and device is to have relatively high expectations (energy is greater than 1 milliwatt) of light source.Up to people such as M.Y.Cho to star- shaped molecule 1,2,4,5-four (5-n-hexyl [2,2 '] di-thiophene-5-vinyl)-benzene and 1,2,4, the application and development of 5-four (5-n-hexyl [2,2 '] connection three thiophene-5-vinyl)-benzene just makes the index of OPTs except that carrier transport speed reach the level (M.Y.Cho that compares favourably with unformed silicon PTs, S.J.Kim, Y.D.Han, D.H.Park, K.H.Kim, D.H.Choi, and J.Joo, Adv.Funct.Mater.2008,18,2905).Yet above-mentioned research does not really reach the level that every important indicator and unformed silicon PTs compare favourably, and traces it to its cause, and is owing to lack semi-conductive exploitation of high light sensation and the application study deficiency of different state of aggregations in device.Therefore, develop high performance photonasty semi-conducting material and utilize appropriate state of aggregation fabricate devices, high performance OPTs has crucial Research Significance and commercial value for preparation.
Summary of the invention
The purpose of this invention is to provide a kind of smooth sensing organic field effect transistor and preparation method thereof.
Light-sensing organic field-effect transistor provided by the invention, its structural representation as shown in Figure 3, as seen from the figure, this transistor is a upper electrode arrangement, comprises substrate 1, is positioned at the gate electrode 2 on the substrate and is positioned at insulating barrier on the gate electrode;
Wherein, organic field effect tube also comprises and is positioned at the self assembled monolayer on the insulating barrier and is positioned at source electrode 5, drain electrode 6 and at least one organic semiconductor compound single crystal 4 on the self assembled monolayer, and 3 indications are insulating barrier and are positioned at self assembled monolayer on the insulating barrier among the figure.
In this transistor, the material that constitutes substrate is the backing material of various routines, can buy from commercial channels to obtain, as glass, pottery, polymer or silicon chip; The material that constitutes gate electrode also is various common gate material, as metal, alloy and metal oxide; Wherein, metal can be gold, silver, aluminium or copper etc., and alloy is albronze or aluminium silver alloy, and metal oxide is a tin indium oxide.The material that constitutes insulating barrier is silicon dioxide, silicon nitride or polymer.
The material that constitutes self assembled monolayer is octadecyl chlorosilane, eight alkylchlorosilanes, phenyl chlorosilane or trichlorosilane; Organic semiconductor monocrystal is between source electrode and drain electrode.
The material of formation source electrode and drain electrode is metal, alloy, metal oxide, conducting polymer or conduction micromolecular compound.Wherein, metal can be gold, silver, aluminium or copper etc.; Alloy is albronze or aluminium silver alloy; Metal oxide is a tin indium oxide; Conducting polymer is polyaniline, polythiophene, gathers 3, the complex compound of 4-enedioxy thiophene and poly styrene sulfonate (PEDOT/PSS) or 7,7,8, and the 8-four cyano is to the compound of methylene benzoquinones and tetrathiafulvalene.
Above-mentioned organic semiconductor compound is anthracene [2,3-b] benzos [d] thiophene of anthracene [2,3-b] benzo [d] thiophene or replacement, and substituting group is methyl, ethyl or phenyl, preferred 6-methyl-anthracene [2,3-b] benzos [d] thiophene.The length of this organic semiconductor compound single crystal is the 80-300 micron, and diameter is the 1-10 micron.The thickness of substrate is the 300-800 micron, preferred 400-500 micron; The thickness of gate electrode is because of preparation technology's difference, and thickness can be different, can be the 0.01-500 micron, preferred 400-500 micron; The thickness of insulating barrier is the 100-500 nanometer, preferred 300-500 nanometer.
The method of the above-mentioned light-sensing organic field-effect transistor of preparation provided by the invention comprises the steps:
1) on substrate, prepares gate electrode;
2) on the gate electrode that step 1) obtains, prepare insulating barrier;
3) with step 2) substrate that has insulating barrier that obtains and in octadecyl chlorosilane, eight alkylchlorosilanes, phenyl chlorosilane or the trichlorosilane any one, heat treated under vacuum condition obtains the self-composed monomolecular decorative layer;
4) in the saturated solution of organic semiconductor compound, add poor solvent, described organic semiconductor compound is self-assembled into organic semiconductor compound single crystal, and at least one described organic semiconductor compound single crystal placed on the self-composed monomolecular decorative layer that described step 3) obtains;
5) preparation source electrode and drain electrode obtain light-sensing organic field-effect transistor provided by the invention;
Wherein, source electrode and drain electrode are positioned at the two ends of organic semiconductor compound single crystal.
In above-mentioned preparation method's the step 1), gate electrode can be bought from commercial channels and obtain, and also can be prepared according to the preparation method of routine, and (vacuum degree is 10 as vacuum thermal evaporation -4-10 -7Pascal, evaporation rate is 1-10 dust/second), (vacuum degree is 10 to electron beam evaporation -4-10 -7Pascal, evaporation rate is 1-10 dust/second), (vacuum degree is 10 to magnetron sputtering -4-10 -7Pascal, sputtering rate is 1-10 dust/second) or the chemical vapour deposition technique that strengthens of plasma (vacuum degree is 10 -3-10 -5Pascal, the crystallizing field temperature is the 300-500 degree);
Step 2) in, insulating barrier is that the preparation method according to routine is prepared, and (vacuum degree is 10 as air thermal oxidation (temperature 900-1200 degree), electron beam evaporation -4-10 -7Pascal, evaporation rate is 1-10 dust/second) or magnetron sputtering (vacuum degree is 10 -4-10 -7Pascal, sputtering rate is 1-10 dust/second);
In the step 3), vacuum degree is 10-0.1 Pascal, and the temperature during heat treated is 120-150 ℃, and be 1-4 hour heating time; Before blend step, can be earlier with step 2) substrate that has insulating barrier that obtains cleans with deionized water, ethanol and acetone and dry successively.
In the step 4), organic semiconductor compound is preferably 6-methyl-anthracene [2,3-b] benzos [d] thiophene; In the saturated solution of this organic semiconductor compound, solvent is carrene, chloroform or toluene, and poor solvent is ethanol or methyl alcohol; The self assembly time is 0.1-10 hour.
In the step 5), source electrode and drain electrode are that the preparation method according to routine is prepared, and (vacuum degree is 10 as vacuum thermal evaporation -3-10 -5Pascal, evaporation rate is 1-10 dust/second), (vacuum degree is 10 to electron beam evaporation -4-10 -7Pascal, evaporation rate is 1-10 dust/second) or Method of printing.Wherein, this Method of printing adopts organic material private print equipment, and print speed is 2 meter per seconds, and precision is about 5 microns, and printable material comprises metal nanoparticle, solubility organic polymer and micromolecular semiconductor and electric conducting material etc.
In addition, [2, the 3-b] benzos of 6-methyl-anthracene shown in the used formula I of the present invention [d] thiophene compound is prepared as follows:
1) 3-(3-R base-6-carboxyl-benzoyl) the dibenzothiophenes compound shown in phthalic anhydride generation friedel-crafts acylation production (III) structural formula of the replacement shown in dibenzothiophenes and formula (II) structural formula;
2) the 6-R base-9 shown in the 3-shown in formula (III) structural formula (3-R base-6-carboxyl-benzoyl) dibenzothiophenes compound generation self friedel-crafts acylation production (IV) structural formula, 10-diketone-anthracene [2,3-b] benzos [d] thiophene;
3) the 6-R base-9 shown in formula (IV) structural formula, 10-diketone-anthracene [2,3-b] benzos [d] thiophene are reduced compound 6-R base-anthracene [2,3-b] benzos [d] thiophene shown in the formula of obtaining (I);
Wherein, the structural formula of formula (II), formula (III), formula (IV) is as follows respectively:
Figure A20091008076700081
Formula (II) formula (III) formula (IV)
Wherein, the R base is a methyl.
In the step 1), the reaction dissolvent of friedel-crafts acylation is a carrene, and catalyst is an alchlor.The mol ratio of the phthalic anhydride of the replacement shown in dibenzothiophenes and the formula (II) is 1.1: 1 in the step 1).
Step 2) in, the reaction dissolvent of friedel-crafts acylation is an o-dichlorohenzene, and catalyst is alchlor and phosphorus pentachloride.
In the step 3), the solvent of reduction reaction is an oxolane; Reducing agent is alchlor and Lithium Aluminium Hydride.
The method for preparing light-sensing organic field-effect transistor provided by the invention, preparation technology is simple, and cost is low.The organic field effect tube for preparing to energy between the low energy light source between every square centimeter of 10~90 microwatt, high response is just arranged, has high photoelectric properties parameter: high mobility, the ratio of high luminous sensitivity and high photoelectric current and dark current has good application prospects in the photosensitive semiconductor device field.
Description of drawings
Fig. 1 is the preparation flow schematic diagram of the embodiment of the invention 1 used organic semiconductor micron single crystal wire.
Fig. 2 a, Fig. 2 b and Fig. 2 c are respectively stereoscan photograph, transmission electron microscope light field pattern and the transmission electron microscope diffraction pattern of organic semiconductor micron monocrystalline in the embodiment of the invention 1.
Fig. 3 a is the structural representation of smooth sensing organic field effect transistor provided by the invention; Fig. 3 b, Fig. 3 c are respectively this transistorized light microscope and atomic force microscope characterizes.
Fig. 4 a is the curve of output of OPTs under no optical condition that the embodiment of the invention 1 prepares, and Fig. 4 b is the transfer curve of this OPTs under no optical condition.
The contrast of the OPTs that Fig. 5 prepares for the embodiment of the invention 1 transfer curve under transfer curve under the effect of low-yield white light (30 microwatt/square centimeter) and no optical condition.
The OPTs light sensation performance parameter that Fig. 6 prepares for the embodiment of the invention 1 is with the situation of change of gate voltage.
Embodiment
The invention will be further described below in conjunction with specific embodiment, but the present invention is not limited to following examples.
Among the present invention, the photoelectricity performance of organic photoinduction micron single-crystal field effect transistor is measured under atmospheric environment and room temperature condition.
Earlier micron devices is carried out basic output and shifts property detection under no optical condition, draw electric property (Y.Liang, G.F.Dong such as saturation region mobility, Y.Hu, L.D.Wang, and Y.Qiu, Low-voltagepentacene thin-film transistors with Ta 2O 5Gate insulators and their reversiblelight-induced threshold voltage shift Appl.Phys.Lett.2005,86,132101.).
And then under low-yield white light conditions, test its transfer characteristic, compare the difference of its electric property.Calculate by following formula:
The luminous power that is applied on light sensation susceptibility=(electric current-transistor under the transistor illumination condition does not have the electric current under the optical condition)/micron monocrystalline;
Photoelectric current/dark current=(electric current-transistor under the transistor illumination condition does not have the electric current under the optical condition)/transistor does not have the electric current under the optical condition.
The ratio (M.C.Hamilton eta1.Thin-Film Organic Polymer Phototransistors, IEEE Trans.Electron Devices, 2004,51,877) of photoinduction susceptibility that calculates by above-mentioned formula and photoelectric current and dark current.
Embodiment 1
Present embodiment prepares light-sensing organic field-effect transistor according to following step:
1) used substrate layer is a monocrystalline silicon piece, and this silicon wafer thickness is the 400-500 micron, and gate electrode is that (as nitrogen element or P elements, doping content is every cubic metre 1~9 * 10 to highly doped silicon 20), gate electrode thickness is about 400~500 microns;
2) prepare insulating barrier according to silicon thermal oxidation method (Wang Yongzhen, Gong Guoquan, Cui Jingzhong, the preparation of silica membrane and application, vacuum and low temperature, 2003,9,228) on gate electrode, the material that constitutes insulating barrier is a silicon dioxide; Wherein, the temperature of thermal oxidation is 900-1200 ℃, and thickness of insulating layer is 500 nanometers;
3) with step 2) substrate that deposits insulating barrier that obtains with deionized water, ethanol, acetone ultrasonic cleaning after oven for drying, put into a culture dish with the octadecyl trichlorosilane together with substrate then, put into baking oven, be evacuated to 0.1 Pascal, being heated to 120 degree handled after 3 hours, naturally cool to room temperature, obtain self assembled monolayer;
4) with the 6-methyl-anthracene [2 shown in the formula I, 3-b] benzo [d] thiophene powder is dissolved in the good solvent carrene, being made into 1 milliliter of saturated solution adds in the measuring cup, add 2 milliliters of poor solvent ethanol then, make it slowly be self-assembled into a micron single crystal wire (about 24 hours of self assembly time), as shown in Figure 1, gained micro wire length is at the hundreds of micron, width be between the 1-8 micron and transmission to characterize point diffraction obvious, as shown in Figure 2, then with capillary transfer to the self-composed monomolecular decorative layer of step 3) gained substrate, 6-methyl-anthracene [2,3-b] benzos [d] thiophene micron monocrystalline of selecting 2 microns is as semiconductor.
Figure A20091008076700091
5) with 30 microns spun golds as mask, be 5 * 10 in vacuum degree -4Under the handkerchief, prepare 50 nm of gold,, obtain light-sensing organic field-effect transistor provided by the invention as source electrode and drain electrode with the speed of per second 1 dust;
The photoelectricity performance of this organic photoinduction micron single-crystal field effect transistor is measured under atmospheric environment and room temperature condition.
Earlier property detection is exported and shifted to this transistor device, draw mobility and be square every volt per metre of 1.66 centimetres, on-off ratio is 10 6, shown in Fig. 4 a and Fig. 4 b, wherein, Fig. 4 a is the curve of output of OPTs under no optical condition, Fig. 4 b is the transfer curve of this OPTs under no optical condition.
And then in its transfer characteristic of the following test of low-yield white light conditions (30 microwatt/square centimeter), the difference that compares its electric property, as shown in Figure 5, by the formula meter: the luminous power that is applied on light sensation susceptibility=(electric current-transistor under the transistor illumination condition does not have the electric current under the optical condition)/micron monocrystalline, ratio=(electric current-transistor under the transistor illumination condition does not have the electric current under the optical condition)/transistor of photoelectric current and dark current does not have the electric current (as shown in Figure 6) under the optical condition.The surface area of being accepted light by crystal is: 2 microns * 30 microns=60 square microns; It is 12000 amperes/watt that calculating can draw the highest lightsensitivity, and photoelectric current/dark current=6000.Every important performance characteristic can compare favourably with amorphous silicon light sensation transistor.
In addition, used 6-methyl-anthracene [2,3-b] benzos [d] thiophene (compound Me-ABT) in the present embodiment step 4) is prepared as follows:
1) 3-(3-methyl-6-carboxyl-benzoyl) dibenzothiophenes is synthetic
Under the nitrogen protection; in the 250ml there-necked flask, add 100ml carrene and 4g (30mmol) alchlor; add 1.7g (10mmol) 4-methylphthalic acid acid anhydride then; this mixed liquor is in stirring at room after 1 hour; drip 10ml dibenzothiophenes (2g with dropping funel; dichloromethane solution 11mmol); dropwise; stirred overnight at room temperature is poured in the mixed solution of 40ml frozen water and 60ml hydrochloric acid (the quality percentage composition is 37%) dichloromethane extraction into; merge organic facies; dried over mgso is spin-dried for solvent and obtains orange colour solid 3-(3-methyl-6-carboxyl-benzoyl) dibenzothiophenes 2.9g, productive rate 80%.
The structural characterization data are as follows:
Mass spectrum: [MS (EI)] m/z:346 (M +).
Nucleus magnetic hydrogen spectrum: 1H-NMR (400MHz, CDCl 3) δ (ppm): 2.34 (s, 3H), 7.50-7.52 (m, 2H), 7.67-7.71 (m, 2H), 7.87 (s, 1H), 7.98-8.02 (m, 2H), 8.08 (s, 1H), 8.27 (s, 1H), 8.55 (s, 1H), 11.55 (s, 1H).
2) 6-methyl-9,10-diketone-anthracene [2,3-b] benzos [d] thiophene synthetic
Under the nitrogen protection; in the 100ml there-necked flask, add the 30ml o-dichlorohenzene; 2g (5.8mmol) 3-(3-methyl-6-carboxyl-benzoyl) dibenzothiophenes; alchlor (1.15g; 8.67mmol); (1.8g, 8.67mmol) (phosphorus pentachloride is mainly used in the catalytic reaction dehydration) added thermal response 12 hours at 100 ℃ to phosphorus pentachloride.Reactant liquor is chilled to room temperature, in the hydrochloric acid ice water mixed liquid of impouring 300ml (wherein, the volumn concentration of the hydrochloric acid of 37% (mass ratio) is 40%), filters, and collects solid.The gained solid is crossed post with toluene, gets pistac solid 6-methyl-9,10-diketone-anthracene [2,3-b] benzos [d] thiophene 1.3g, and productive rate is 68.6%.
The structural characterization data are as follows:
Mass spectrum: [MS (EI)] m/z:328 (M +).
Nucleus magnetic hydrogen spectrum: 1H-NMR (400MHz, CDCl 3) δ (ppm): 2.34 (s, 3H), 7.50-7.52 (m, 3H), 7.59 (s, 1H), 7.76 (s, 1H), 7.98 (m, 1H), 8.35-8.40 (m, 3H).
3) 6-methyl-anthracene [2,3-b] benzos [d] thiophene is synthetic
Under the nitrogen protection; in the there-necked flask of 250ml, add the dry oxolane that gets of 100ml; ice bath is cooled to zero degree; add 0.455g (12mmol) Lithium Aluminium Hydride and 1.6g (12mmol) alchlor respectively; after the stirring at room 30 minutes; divide and add 1g (3mmol) 6-methyl-9 for three times; 10-diketone-anthracene [2; 3-b] benzo [d] thiophene, reflux two hours is after the cooling; pour in frozen water and the hydrochloric acid mixture; filtering-depositing, toluene recrystallization get yellow solid (compound MeABT) 0.447g, and productive rate is 49.2%.
The structural characterization data are as follows:
Mass spectrum: [MS (EI)] m/z:298 (M +).
Nucleus magnetic hydrogen spectrum: 1H-NMR (400MHz, CDCl 3) δ (ppm): 2.45 (s, 3H), 7.30-7.33 (d, 1H), 7.45-7.52 (m, 2H), 7.78-7.79 (m, 2H), 7.93-7.95 (m, 1H), 8.27-8.28 (m, 1H), 8.40 (s, 1H), 8.45 (s, 1H), 8.54 (s, 1H), 8.76 (s, 1H).
Elementary analysis: molecular formula: C 21H 14S; Theoretical value: C, 84.53; H, 4.73; Measured value: C, 84.62; H, 4.99.
Embodiment 2
According to embodiment 1 identical preparation method, only change the good solvent in the step 4) into chloroform, poor solvent is a methyl alcohol, with the foregoing description 1 identical preparation condition under obtain light-sensing organic field-effect transistor, this transistorized pattern and device performance are identical with embodiment 1.
Embodiment 3
According to embodiment 1 identical preparation method, only change the good solvent in the step 4) into toluene, poor solvent is a methyl alcohol, with the foregoing description 1 identical preparation condition under obtain light-sensing organic field-effect transistor, this transistorized pattern and device performance are identical with embodiment 1.

Claims (12)

1, a kind of light-sensing organic field-effect transistor comprises substrate, is positioned at the gate electrode on the described substrate and is positioned at insulating barrier on the described gate electrode; It is characterized in that: described organic field effect tube also comprises and is positioned at the self assembled monolayer on the described insulating barrier and is positioned at source electrode, drain electrode and at least one organic semiconductor compound single crystal on the described self assembled monolayer;
The material of described formation self assembled monolayer is octadecyl trichlorosilane, eight alkyl trichlorosilanes, phenyl trichlorosilane etc.;
Described organic semiconductor monocrystal is between described source electrode and drain electrode.
2, transistor according to claim 1 is characterized in that: the material of described formation source electrode and drain electrode is metal, alloy, metal oxide, conducting polymer or conduction micromolecular compound;
Described organic semiconductor compound is anthracene [2,3-b] benzos [d] thiophene of anthracene [2,3-b] benzo [d] thiophene or replacement, and in the anthracene of described replacement [2,3-b] benzos [d] thiophene, substituting group is methyl, ethyl or phenyl.
3, transistor according to claim 2 is characterized in that: described metal is gold, silver, aluminium or copper;
Described alloy is albronze or aluminium silver alloy;
Described metal oxide is a tin indium oxide;
Described conducting polymer is polyaniline or polythiophene;
Described conduction micromolecular compound is 7,7,8, and the 8-four cyano is to the compound of methylene benzoquinones and tetrathiafulvalene;
Described organic semiconductor compound is [2, the 3-b] benzos of 6-methyl-anthracene shown in the formula I [d] thiophene;
(formula I).
4, according to the arbitrary described transistor of claim 1-3, it is characterized in that: the length of described organic semiconductor compound single crystal is the 80-300 micron, and diameter is the 1-10 micron.
5, method according to claim 3 is characterized in that: described 6-methyl-anthracene [2,3-b] benzos [d] thiophene is prepared as follows:
1) the compound generation friedel-crafts acylation shown in dibenzothiophenes and the formula II structural formula generates the compound shown in the formula III structural formula;
2) compound shown in the generation of the compound shown in the formula III structural formula self the friedel-crafts acylation production IV structural formula;
3) compound shown in the formula IV structural formula is reduced and obtains the compound shown in the formula I;
The structural formula of described formula II, formula III, formula IV is as follows respectively:
(formula II) (formula III) (formula IV)
Wherein, R is a methyl.
6, method according to claim 5 is characterized in that: in the described step 1), the reaction dissolvent of described friedel-crafts acylation is a carrene, and catalyst is an alchlor; The mol ratio of the compound shown in described dibenzothiophenes and the formula II structural formula 1.1: 1;
Described step 2) in, the reaction dissolvent of described friedel-crafts acylation is an o-dichlorohenzene, and catalyst is alchlor and phosphorus pentachloride;
In the described step 3), the solvent of described reduction reaction is an oxolane; Reducing agent is alchlor and Lithium Aluminium Hydride.
7, according to the arbitrary described method of claim 1-6, it is characterized in that: the thickness of described substrate is the 300-800 micron, preferred 400-500 micron; The thickness of described gate electrode is the 0.01-500 micron, preferred 400-500 micron; The thickness of described insulating barrier is the 100-500 nanometer, preferred 300-500 nanometer.
8, a kind of method for preparing the described light-sensing organic field-effect transistor of claim 1 comprises the steps:
1) on substrate, prepares gate electrode;
2) on the gate electrode that described step 1) obtains, prepare insulating barrier;
3) with described step 2) any one or any two kinds in the substrate that has insulating barrier that obtains and octadecyl trichlorosilane, eight alkyl trichlorosilanes, the phenyl trichlorosilane, heat treated under vacuum condition obtains the self-composed monomolecular decorative layer;
4) in the saturated solution of organic semiconductor compound, add poor solvent, described organic semiconductor compound is self-assembled into organic semiconductor compound single crystal, and at least one described organic semiconductor compound single crystal placed on the self assembled monolayer that described step 3) obtains;
5) preparation source electrode and drain electrode obtain described light-sensing organic field-effect transistor;
Wherein, described source electrode and drain electrode are positioned at the two ends of described organic semiconductor compound single crystal.
9, method according to claim 8 is characterized in that: in the described step 3), vacuum degree is 0.1-10 Pascal, and the temperature during heat treated is 60-150 ℃, and be 0.2-6 hour heating time;
In the described step 4), organic semiconductor compound is anthracene [2,3-b] benzos [d] thiophene of anthracene [2,3-b] benzo [d] thiophene or replacement, and in the anthracene of described replacement [2,3-b] benzos [d] thiophene, substituting group is methyl, ethyl or phenyl;
In the saturated solution of described organic semiconductor compound, solvent is carrene, chloroform or toluene, and described poor solvent is ethanol or methyl alcohol.
10, according to Claim 8 or 9 described methods, it is characterized in that: in the described step 1), the material that constitutes substrate is glass, pottery, polymer or silicon chip; Described gate electrode is selected from metal, alloy and metal oxide;
Described metal is gold, silver, aluminium or copper, and described alloy is albronze or aluminium silver alloy, and described metal oxide is a tin indium oxide;
Described step 2) in, the material that constitutes insulating barrier is silicon dioxide or silicon nitride;
In the described step 4), the self assembly time is 0.1-10 hour;
In the described step 5), the material that constitutes source electrode and drain electrode is metal, alloy, metal oxide, conducting polymer or conduction micromolecular compound.
11, according to Claim 8 arbitrary-10 described method is characterized in that: in the described step 1), the preparation method of gate electrode is the chemical vapour deposition technique that vacuum thermal evaporation, electron beam evaporation, magnetron sputtering or plasma strengthen;
Described step 2) in, the preparation method of described insulating barrier is air thermal oxidation, electron beam evaporation or magnetron sputtering;
In the described step 3), before the blend step, earlier with described step 2) substrate that has insulating barrier that obtains cleans with deionized water, ethanol and acetone and dry successively;
In the described step 5), the preparation method of source electrode and drain electrode is vacuum thermal evaporation, electron beam evaporation or printing.
12, method according to claim 11 is characterized in that:
In the described step 1), the vacuum degree of vacuum thermal evaporation is 10 -5-10 -3Pascal, evaporation rate is 1-10 dust/second; The vacuum degree of electron beam evaporation is 10 -7-10 -4Pascal, evaporation rate is 1-10 dust/second; The vacuum degree of magnetron sputtering is 10 -7-10 -4Pascal, sputtering rate is 1-10 dust/second; The vacuum degree of the chemical vapour deposition technique that plasma strengthens is 10 -5-10 -3Pascal, the crystallizing field temperature is the 300-500 degree;
Described step 2) in, the temperature of air thermal oxidation is 900-1200 ℃, and the vacuum degree of electron beam evaporation is 10 -7-10 -4Pascal, evaporation rate is 1-10 dust/second; The vacuum degree of magnetron sputtering is 10 -7-10 -4Pascal, sputtering rate is 1-10 dust/second;
In the described step 5), the vacuum degree of hot evaporation is 10 -5-10 -3Pascal, evaporation rate is 1-10 dust/second; The vacuum degree of electron beam evaporation is 10 -7-10 -4Pascal, evaporation rate is 1-10 dust/second; In the Method of printing, print speed is 2 meter per seconds, and precision is 5 microns.
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