CN101353352B - Hexa-thiophen and derivatives thereof, preparation and use thereof - Google Patents
Hexa-thiophen and derivatives thereof, preparation and use thereof Download PDFInfo
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- CN101353352B CN101353352B CN2008102222171A CN200810222217A CN101353352B CN 101353352 B CN101353352 B CN 101353352B CN 2008102222171 A CN2008102222171 A CN 2008102222171A CN 200810222217 A CN200810222217 A CN 200810222217A CN 101353352 B CN101353352 B CN 101353352B
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Abstract
The invention discloses hexthiophene, the derivative thereof, and the preparation method and application of the hexthiophene and the derivative. The structural formula of the hexthiophene derivative is represented by Formula (I), wherein, R represents H, alkyl or aryl. The invention also provides a method for preparing the compound of the Formula (I). The invention has the advantages that the syntheticroute is simple and effective, both the migration rate and the on-off ratio of OFET prepared by using the hexthiophene of the invention as the organic semi-conductor layer are very high ( the max of Mu is 0.06cm<2> /V question mark s,, the on-off ratio is10<5> ), and the hexthiophene and hexthiophene derivative have favorable application prospect in the OFET.
Description
Technical field
The present invention relates to hexa-thiophen and derivative thereof and their preparation method and application.
Background technology
From 1986 first organic field effect tube (OFET) be in the news since (Tsumura, A.; Koezuka, H.; Ando, T.Appl.Phys.Lett, 1986,49,1210), OFET has obtained significant progress.The advantage of organic field effect tube is: preparation technology is simple, cost is low, in light weight and snappiness good, can be used for aspects such as smart card, electronic trademark, Electronic Paper, storer, transmitter and Active Matrix Display, is the key components of organic optoelectronic device and circuit.
Thiophenes is the important organic semiconductor material of a class.(α-nT) and derivative thereof have been widely applied to (Katz, H.E. in the organic field effect tube to α-Lian thiophene; Laquindanum, J.G.; Lovinger, A.J.Chem.Mater.1998,10,633.Ong, B.S.; Wu, Y.; LiuP.; Gardner, S.Adv.Mater.2005,17,1141), still, be easy to bending owing to connect the thiophene molecule, be difficult for forming the plane, thereby influence band gap (Videlot-Ackermann, the C. of molecule; Ackermann, J.; Brisset, H.; Kawamura, K.; Yoshimoto, N.; Raynal, P.; El Kassmi, A.; Fages, F.J.Am.Chem.Soc.2005,127,16346.Katz, H.E.; Bao, Z.; Gilat, S.L.Acc.Chem.Res.2001,34,359).Increase the overlapping electron coupling that helps between adjacent molecule of π-track, thereby improve carrier mobility.With respect to connecting thiophene, condensed ring thiophene has better Orbital Overlap, takes aspectant π-pi accumulation mode easilier, thereby helps obtaining high carrier mobility.In recent years, condensed ring and two thiophene and and the derivative of three thiophene in organic field effect tube, obtained widespread use (MurphyA.R.; Fr é chet, J.M.J.Chem.Rev.2007,107,1066).The pentacene molecule is herring-bone and piles up (herringbone stacking) in single crystal structure, intermolecular C-H-π effect is to charge transfer contribution big (Mattheus, C.C.; De Wijs, G.A.; De Groot, R.A.; Palstra, T.T.M.J.Am.Chem.Soc.2003,125,6323), yet pentacene is very unstable in air, has seriously restricted its preparation technology and practical application.And five thiophene the molecular structure that is similar to pentacene is arranged, but higher stability is arranged, with and its mobility of Thin Film Transistor (TFT) of five thiophene preparation be 0.045cm
2/ Vs, on-off ratio are 10
3, (Xiao, K.; Liu, Y.; Qi, T.; Zhang, W.; Wang, F.; Gao, J.; Qiu, W.; Ma, Y.; Cui, G.; Chen, S.; Zhan, X.; Yu, G.; Qin, J.; Hu, W.; Zhu, D.J.Am.Chem.Soc.2005,127,13281).
Summary of the invention
The purpose of this invention is to provide hexa-thiophen and derivative thereof and their preparation method.
Hexa-thiophen provided by the present invention and derivative thereof, structure be as the formula (1):
Formula (I)
Wherein, R is hydrogen, alkyl or aryl.
The method of compound shown in the preparation formula provided by the present invention (I) may further comprise the steps:
1) anhydrous ether solution with 3,6-dibromo and two thiophene is cooled to-10～-20 ℃, adds the hexane solution of n-Butyl Lithium, reacts 1-1.5 hour, obtains mixed system a;
2) under-10～-20 ℃, the anhydrous ether solution of Compound I I is added among the described mixed system a, reacted 1-1.5 hour, room temperature reaction 12～15 hours, obtain compound III then;
3) anhydrous ether solution of preparation compound III is cooled to 0～-10 ℃, adds the hexane solution of n-Butyl Lithium, react 2-3 hour, then room temperature reaction 2～5 hours, obtains the solution b of adularescent precipitation generation;
4) anhydrous ether solution with anhydrous cupric chloride is cooled to 0～-10 ℃, obtains brown solution c, and described solution b is added among the described solution c, carries out the oxidation coupling reaction, and obtaining with the hexa-thiophen is formula (I) compound of nuclear;
Wherein, the structural formula of Compound I I, compound III is as follows:
Formula (II) formula (III)
Wherein, R is hydrogen, alkyl or aryl.
Described method comprises that also the compound that step 4) is obtained uses methyl alcohol successively, washing with acetone, the step of purifying with the distillation of gradient subliming furnace again.
Wherein, the concentration of 3,6-dibromo and two thiophene is 0.03～0.1mmol/ml in the anhydrous ether solution of described 3,6-dibromo and two thiophene.The concentration of n-Butyl Lithium is 1.6～2.5mol/L in the hexane solution of described n-Butyl Lithium.The concentration of anhydrous cupric chloride is 0.3～0.5mmol/ml in the anhydrous ether solution of described anhydrous cupric chloride.
The mol ratio of 3,6-dibromo and two thiophene and n-Butyl Lithium is 1 in the described step 1): (2-2.5).
The mol ratio of compound III and n-Butyl Lithium is 1 in the described step 3): (4-5).
Another object of the present invention provides the hexa-thiophen shown in the formula (I) and the purposes of derivative thereof.
The purposes of compound shown in the formula provided by the present invention (I) is the application of this compound in the preparation organic field effect tube.
The invention has the advantages that:
1, synthetic route is simple, effective, and synthetic cost is low;
2, HTA is linear big pi-conjugated molecule, has the inflexible two dimensional structure, can be used for preparing the OFET device of high mobility;
3, has higher thermostability (decomposition temperature is greater than 320 ℃);
4, have lower HOMO energy level and (approximately-5.06eV),, help obtaining the OFET device of high on-off ratio stable in the air the stability height of oxygen.
5, be that all very high (μ is up to 0.06cm for the mobility of OFET of organic semiconductor layer preparation and on-off ratio with hexa-thiophen of the present invention
2/ Vs, on-off ratio are 10
5), good prospects for application is arranged in OFET.
Description of drawings
Fig. 1 is the synthetic route chart of hexa-thiophen.
Fig. 2 is embodiment 1 a hexa-thiophen thermogravimetric analysis curve.
Fig. 3 is the ultra-violet absorption spectrum and the fluorescence spectrum of embodiment 1 hexa-thiophen solution.
Fig. 4 is the ultra-violet absorption spectrum of embodiment 1 hexa-thiophen film.
Fig. 5 is the cyclic voltammetry curve of embodiment 1 hexa-thiophen.
Fig. 6 is for being the structural representation of the organic field effect tube of organic layer with embodiment 1 hexa-thiophen.
Fig. 7 is for being the output curve diagram of the organic field effect tube of organic layer with embodiment 1 hexa-thiophen.
Fig. 8 is for being the transition curve figure of the organic field effect tube of organic layer with embodiment 1 hexa-thiophen.
Embodiment
Synthetic (in the formula (I), R is the compound of H) of embodiment 1, hexa-thiophen
3,6-dibromo and two thiophene and two (3-sulphur thiophene) (R is the compound of hydrogen in the formula (II)) synthetic method see reference document (Fuller, L.S.; Iddon, B.; Smith.K.A.J.Chem.Soc., Perkin Trans.11997,3465.Lumbroso, H.; Catel, J.M.; Le Coustumer, G.; Andrieu, C.G.J.Mol.Struct.1999,513,201.)
Synthesizing of two (3-sulphur thiophene):
The anhydrous ether solution of 3-bromothiophene of 0.5～1mmol/ml is cooled under-55～-78 ℃, adds 1.6～2.5mol L
-1The hexane solution of n-Butyl Lithium reacted 1～1.5 hour, added elemental sulfur, reacted 1～1.5 hour again, added six hydrated iron potassium cyanide, and the oxidation coupling obtains two (3-sulphur thiophene).
The synthetic method of the synthetic reference two (3-sulphur thiophene) of two (2-alkyl-4-sulphur thiophene) only needs 3-bromothiophene is replaced with 2-alkyl-4-bromothiophene.
The synthetic method of the synthetic reference two (3-sulphur thiophene) of two (2-aryl-4-sulphur thiophene) only needs 3-bromothiophene is replaced with 2-aryl-4-bromothiophene.
1) 3,6-two-(3-sulphur thiophene) and two thiophene (formula (III) in R be the compound of hydrogen) synthetic
Under the nitrogen protection, in the 250ml there-necked flask, add 3,6-dibromo and two thiophene 2.98g (10.0mmol), anhydrous ether solution 100mL, be cooled to-10～-20 ℃, drip 2.5mol L
-1The hexane solution 8mL (20mmol) of n-Butyl Lithium reacted 1 hour, obtained the mixed system a that the adularescent precipitation generates.Under the nitrogen protection; in another 250ml there-necked flask, add two (3-sulphur thiophene) 4.60g (20mmol); anhydrous diethyl ether 50mL obtains the anhydrous ether solution of two (3-sulphur thiophene), is cooled to-10～-20 ℃; slowly be added dropwise among the mixed system a; reacted 1.5 hours, reaction solution reacted 12 hours to room temperature again; rotate solvent evaporated then, use 2.0mol L
-1Aqueous hydrochloric acid/methylene dichloride (volume ratio 1:1) extraction (300ml * 2); Merge organic phase, anhydrous magnesium sulfate drying.Rotary evaporation in vacuo is removed organic solvent, and crude product is purified (leacheate-sherwood oil) through silica gel column chromatography, collects R
fBe 0.2 component, obtain white solid 3,6-two-(3-sulphur thiophene) and two thiophene (3.12mg, productive rate 82%).
3,6-two-(3-sulphur thiophene) and two thiophene structural characterization data as follows:
Mass spectrum: MS m/z368 (M
+, 100).
Ultimate analysis: molecular formula: C
14H
8S
6Theoretical value: C, 45.62; H, 2.19. measured value: C, 45.66; H, 2.26.
Nucleus magnetic hydrogen spectrum:
1H NMR (CDCl
3, 400MHz): δ=7.01-7.02ppm (d, 2H, J=4.0Hz), 7.30-7.31ppm (d, 6H, J=4.0Hz).
Nuclear-magnetism carbon spectrum:
13CNMR (CDCl
3) δ
C123.9 (s), 126.5 (s), 126.6 (s), 127.9 (s), 128.6 (s), 130.3 (s), 140.5 (s).
2) hexa-thiophen (HTA) is synthetic
Under the nitrogen protection, add 3,6-two-(3-sulphur thiophene) and two thiophene 2g (5.5mmol) of step 1) preparation in the 250ml there-necked flask, anhydrous diethyl ether 100mL is cooled to-10 ℃, drips 2.5mol L
-1The hexane solution 10mL (25mmol) of n-Butyl Lithium reacted 2 hours.Reaction solution reacted 2 hours to room temperature again, obtained the solution b that the adularescent precipitation generates.
Under the nitrogen protection, in another 250ml there-necked flask, add anhydrous cupric chloride 3.38g (25mmol), anhydrous diethyl ether 50mL; be cooled under-10 ℃, reacted 1 hour, obtain brown solution c; sedimentary solution b slowly is added dropwise among the brown solution c with adularescent, reacts 1 hour.Reaction solution rises to room temperature and reacted 12 hours again.Rotate solvent evaporated then, use 2.0mol L
-1Aqueous hydrochloric acid washing (60ml * 3); Obtain pale brown look solid.Thick product is used methyl alcohol successively, and washing with acetone is purified three times with the distillation of gradient subliming furnace again.Obtain lurid hexa-thiophen (HTA) (120mg, productive rate 6.0%) at last.
The structural characterization data of hexa-thiophen are as follows:
Mass spectrum: HRMS (MALDI) m/z[C
14H
4S
6] theoretical value: 363.8637, measured value: 363.8639.
Ultimate analysis: molecular formula: C
14H
4S
6Theoretical value: C, 46.12; H, 1.11. measured value: C, 46.04; H, 1.39.
Nucleus magnetic hydrogen spectrum:
1H NMR (p-Cl
2Ph, 300MHz, 380k), δ
H=7.16-7.18 (2H, d, J=6.0); 7.11-1.13 (2H, d, J=6.0).
Adopt identical synthesis technique, with 2-alkyl-4-bromothiophene or 2-aryl-4-bromothiophene after the butyl lithiumation, obtain two (2-alkyl-4-sulphur thiophene) or two (2-aryl-4-sulphur thiophene) through Tripotassium iron hexacyanide oxidation coupling again, respectively with 3,6-dibromo and two thiophene react, and can obtain accordingly based on alkyl replace or aryl replace the organic effect material of hexa-thiophen for nuclear.
The thermodynamic property of embodiment 2, hexa-thiophen, spectral quality, electrochemical properties and field-effect transistor character
1) thermodynamic property
Fig. 2 is a hexa-thiophen TGA-DTA curve, and as seen from the figure, hexa-thiophen demonstrates good thermostability, and decomposition temperature is about 320 ℃.
2) tetrahydrofuran solution of hexa-thiophen and and the ultra-violet absorption spectrum and the fluorescence spectrum of film
The film of hexa-thiophen is near 10 in vacuum tightness
-4Under the Pa, the film (thickness 50nm) that the hexa-thiophen evaporation is made to the quartz plate.
As shown in Figure 3, the ultraviolet maximum absorption peak position of hexa-thiophen in solution is about 312nm, and fluorescence emission maximum peak position is about 415nm; As shown in Figure 4, the film ultraviolet maximum absorption peak position of hexa-thiophen is 353nm, and optical band gap is 2.82eV.
3) electrochemical properties of hexa-thiophen
Fig. 5 is the cyclic voltammetry curve of hexa-thiophen.Electrolyzer adopts three electrode test systems, in vacuum tightness near 10
-4Under the Pa, make film (thickness 10nm) as working electrode on the sheet glass that the hexa-thiophen evaporation is modified to tin indium oxide (ITO), Ag/AgCl is as reference electrode, and platinum filament is as counter electrode, Bu
4NPF
6(0.1M) as supporting electrolyte.The condition of cyclic voltammetric is: sweep limit is 0～1.8V (vs.Ag/AgCl), and scanning speed is 50mV/s.
Electro-chemical test shows its initial oxidation current potential about 0.86, and the HOMO of calculating (highest occupied molecular orbital energy level) is-5.06eV to show that hexa-thiophen has very high oxidative stability.
4) the field-effect transistor character of hexa-thiophen
The preparation of organic field effect tube: adopt highly doped silicon chip (Si) as substrate, the thick silicon-dioxide of 470nm is as insulation layer, and source electrode (S), drain electrode (D) all use gold (Au) as electrode, hexa-thiophen in vacuum tightness near 10
-4Evaporation is modified on the titanium dioxide silicon chip of (OTS) to the octadecyl trichlorosilane under the Pa, and steaming degree thickness is approximately 50nm.The structural representation of organic field effect tube is seen Fig. 6.
At room temperature use Hewlett-Packard (HP) 4140B semi-conductor test instrument to measure the electrical property of prepared organic field effect tube (OFET).Two key parameters of the performance of decision OFET are: the on-off ratio (I of mobility of charge carrier rate (μ) and device
On/ I
Off).Mobility is meant: under unit electric field, (unit is cm to the average drift velocity of current carrier
2/Vs), it has reflected hole or the transfer ability of electronics in semi-conductor under electric field.On-off ratio is defined as: under certain grid voltage, and the ratio of the electric current of transistor under " opening " state and " pass " state, it has reflected the quality of devices switch performance.For a high performance field-effect transistor, its mobility and on-off ratio should be high as much as possible.
Fig. 7 has provided prepared field-effect transistor at different grid voltage V
G(0V ,-20V ,-40V ,-60V ,-80V ,-curve of output under 100V).Shown good linear section and saturation region, illustrated that the OFET device of hexa-thiophen has good field-effect regulation and control performance.
Fig. 8 is the transition curve of prepared field-effect transistor.Can obtain the mobility and the on-off ratio of field-effect transistor by figure.
Carrier mobility can be drawn by Equation for Calculating:
I
DS=(W/2L) C
iμ (V
G-V
T)
2(saturation region, V
DS=V
G-V
T)
Wherein, I
DSBe drain current, μ is a carrier mobility, V
GBe grid voltage, V
TBe threshold voltage, W is channel width (W=3mm), and L is channel length (L=0.05mm), C
iBe isolator electric capacity (C
i=7.5 * 10
-9F/cm
2).Utilize (I
DS, sat)
1/2To V
GMapping, and do linear regression, the slope of the tropic is extrapolated carrier mobility (μ) thus, tries to achieve V by the section of the tropic and X-axis
TMobility can calculate according to the slope of formula from transition curve.I
DS＝(W/2L)C
iμ(V
G-V
T)
2。
On-off ratio can be drawn by the maximum value of the figure right side source-drain current ratio with minimum value.
We are that organic layer has been made a lot of organic field effect tube devices with synthetic new compound among the present invention, and in these devices, wherein the highest mobility can reach 0.06cm
2/ Vs, on-off ratio are 10
5
Experimental result shows that hexa-thiophen is good organic field effect tube material.Good device performance is given the credit to the present invention's design philosophy originally, with six single thiophene condensed ring together, can enlarge the conjugated system of molecule like this, has obtained high performance OFET material.This material that the invention is not restricted to be reported is that the substitution compound of centronucleus is of a great variety with the hexa-thiophen, and the synthetic method that the present invention provides is simple, effectively.This will make bigger contribution to the screening based on the field-effect material of hexa-thiophen and derivative thereof.
Claims (7)
1. the method for compound shown in the preparation formula (I) may further comprise the steps:
1) with 3, the anhydrous ether solution of 6-dibromo and two thiophene is cooled to-10～-20 ℃, adds the hexane solution of n-Butyl Lithium, and reaction 1～1.5h forms mixed system a;
2) under-10～-20 ℃, the anhydrous ether solution of Compound I I is added among the described mixed system a, reaction 1-1.5h at room temperature reaction 12～15h, obtains compound III then;
3) anhydrous ether solution of preparation compound III is cooled to 0～-10 ℃, adds the hexane solution of n-Butyl Lithium, and reaction 2～3h then at room temperature reaction 2～5h, obtains the solution b that the adularescent precipitation generates;
4) anhydrous ether solution with anhydrous cupric chloride is cooled to 0～-10 ℃, obtains brown solution c, and described solution b is added among the described solution c, carries out the oxidation coupling reaction, obtains the compound shown in the formula (I);
Wherein, the structural formula of the compound shown in the formula (I), Compound I I, compound III is as follows:
Formula (I)
Compound I I compound III
Wherein, R is H.
2. method according to claim 1 is characterized in that: described method comprises that also the compound that step 4) is obtained uses methyl alcohol successively, washing with acetone, the step of purifying with the distillation of gradient subliming furnace again.
3. method according to claim 1 and 2 is characterized in that: described 3, in the anhydrous ether solution of 6-dibromo and two thiophene 3, the concentration of 6-dibromo and two thiophene is 0.03～0.1mmol/ml.
4. method according to claim 1 and 2 is characterized in that: the concentration of n-Butyl Lithium is 1.6～2.5mol/L in the hexane solution of described n-Butyl Lithium.
5. method according to claim 1 and 2 is characterized in that: in the described step 1) 3, the mol ratio of 6-dibromo and two thiophene and n-Butyl Lithium is 1: (2-2.5).
6. method according to claim 1 and 2 is characterized in that: the mol ratio of compound III and n-Butyl Lithium is 1 in the described step 3): (4-5).
7. method according to claim 1 and 2 is characterized in that: the concentration of anhydrous cupric chloride is 0.3～0.5mmol/ml in the anhydrous ether solution of described anhydrous cupric chloride.
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| JP2012167057A (en) * | 2011-02-15 | 2012-09-06 | Sumitomo Chemical Co Ltd | Compound, method for producing the same, thin film comprising the compound, and organic transistor comprising the thin film |
| JP6364878B2 (en) * | 2014-03-31 | 2018-08-01 | 東ソー株式会社 | Organic thin film transistor |
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