CN101161656B - Dibenzo tetrathiafulvalene tetracarbonyl imide derivative and preparation method and uses thereof - Google Patents
Dibenzo tetrathiafulvalene tetracarbonyl imide derivative and preparation method and uses thereof Download PDFInfo
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Abstract
A kind of dibenzo tetrathiafulvalene tetracarbonyl imide derivative, structure are as follows:
, R is alkyl in formula. Preparation method are as follows: A) 4,Bis- chloro-phthalic anhydride of 5- and amine with molar ratio 1: 1.5-3 in propionic acid in 140-160 DEG C reflux 2-4 hours; B) product of step A preparation with benzyl mercaptan with molar ratio 1: 2-3, react 10-16 hours in dimethyl acetamide in the presence of excessive K2CO3 by 60-80 DEG C of heating; C) the product of step B preparation debenzylation in dry toluene in the presence of excessive AlCl3,It is reacted at 70-90 DEG C 2-5 hours with carbonyl dimidazoles,4,The molar ratio of phthalimide and carbonyl dimidazoles that bis- benzylthio of 5- replaces is 1: 1-3; D) product of step C preparation flows back in toluene/triethyl phosphite mixed liquor of molar ratio 2-3/1,Carry out itself coupling reaction 10-14 hours,Cold filtration,Obtain target product.
Description
Technical field
The present invention relates to a kind of organic semiconductor material, relate in particular to a kind of dibenzo tetrathiafulvalene tetracarbonyl imide derivative.
The invention still further relates to the preparation method of above-mentioned organic semiconductor material.
The invention still further relates to the application of above-mentioned organic semiconductor material in organic field effect tube.
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.It has a lot of particular performances, thereby more and more is subject to people's attention.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.Under the size of the inorganic FET situation near the miniaturization natural limit, organic OFET has demonstrated great development and application prospect.
In recent years, tetrathiafulvalene (TTF) derivative has obtained widespread use (Mas-Torrent, M. in organic field effect tube; Rovira, C.J.Mater.Chem.2006,16,433.).Single-crystal field effect transistor mobility based on two thieno-TTF reaches 1.4cm
2/ Vs (Mas-Torrent, M.; Durkut, M.; Hadley, P.; Ribas, X.; Rovira, C.J.Am.Chem.Soc.2004,126,984.), with 3, the film F ET device of 4-dichloro-quinoxaline-pyrazine and TTF preparation demonstrates 0.64cm
2High mobility (the Naraso. of/Vs; Nishida, J.; Kumaki, D.; Tokito, S.; Yamashita, Y.J.Am.Chem.Soc.2006,128,9598.).Yet most OFET devices based on the TTF derivative demonstrate relatively poor performance, as: lower on-off ratio (＜10
3); Under the zero volt grid voltage bigger electric current is arranged, can not effectively turn-off; Lack saturation currnet etc. in the curve of output.Introduce aromatic ring on the TTF skeleton, especially the aromatic ring of electron deficiency can effectively reduce the electron donation of molecule and the electricity of molecule aggregates and lead, and improves the stability of material to oxygen, thereby obtains high performance thin-film device (Naraso.; Nishida, J.; Ando, S.; Yamaguchi, J.; Itaka, K.; Koinuma, H.; Tada, H.; Tokito, S.; Yamashita, Y.J.Am.Chem.Soc.2005,127,10142.Naraso.; Nishida, J.; Kumaki, D.; Tokito, S.; Yamashita, Y.J.Am.Chem.Soc.2006,128,9598.).Up to the present, as the pervasive synthetic route of the most shortage of the TTF derivative of field-effect transistor, the ability of deriving of compound is relatively poor, and synthetic difficulty is bigger.Therefore, in the field-effect transistor research field based on the TTF derivative, it is simple, pervasive to seek synthetic method, easily derive and TTF derivative that electron donation is moderate significant.Dicarbapentaborane imide group (DCI) has moderate electronic capability and the extremely strong chemically derived property of drawing, and therefore the DCI group is introduced in the TTF skeleton, is expected to obtain that class species are abundant, high performance organic semiconductor material.
Summary of the invention
The object of the present invention is to provide a kind of organic semiconductor material-dibenzo tetrathiafulvalene tetracarbonyl imide derivative (being abbreviated as dibenzo TTF four carbonyl acyl diimine derivatives).
Another purpose of the present invention is to provide the method for the above-mentioned organic semiconductor material of preparation.
For achieving the above object, dibenzo TTF four carbonyl diurethane imide derivatives provided by the invention, its structure is shown below
R is an alkyl in the formula.
The present invention prepares the method for dibenzo TTF four carbonyl diurethane imide derivatives, the steps include:
A) under the nitrogen protection, 4,5-two chloro-phthalic anhydrides and amine with mol ratio 1: 1.5-3 in propionic acid in 140-160 ℃ of backflow 2-4 hour, cooling removes desolvates, the product that obtains is 4,5-dichloro phthalimide derivative;
B) under the nitrogen protection, 4 of steps A preparation, 5-two chlorophthalimide and benzyl sulfhydrate with mol ratio 1: 2-3 at excessive K
2CO
3Exist down in N,N-DIMETHYLACETAMIDE 60-80 ℃ reacting by heating 10-16 hour, cold filtration, the product that obtains are 4, the phthalimide derivative that 5-two benzylthio-s replace;
C) under the nitrogen protection, 4 of step B preparation, the phthalic imidine that 5-two benzylthio-s replace is at excessive AlCl
3There is debenzylation in exsiccant toluene down, reacted 2-5 hour down in 70-90 ℃ with carbonyl dimidazoles, 4, the phthalic imidine that 5-two benzylthio-s replace and the mol ratio of carbonyl dimidazoles are 1: 1-3, cooling removes and desolvates, the product that obtains is for containing imido benzo 1,3-dithio-2-ketone compound;
D) step C preparation contain imido benzo 1,3-dithio-2-ketone compound refluxes in toluene/triethyl-phosphite mixed solution of mol ratio 2-3/1, carry out self coupling reaction 10-14 hour, cold filtration obtains target product.
Described method, wherein the described amine of steps A is aliphatic amide.
Described method, wherein the amine of steps A is n-Butyl Amine 99, normal hexyl Amine, octylame or positive amino dodecane etc.
Described method, wherein product recrystallization in methyl alcohol of obtaining of steps A.
Described method, wherein the product that obtains of step B is in methyl alcohol backflow 20-40 minute, heat filtering, hot methanol washing, vacuum-drying.
Described method, wherein the product that obtains of step C is purified through silica gel column chromatography, and leacheate is 6: 1 a petrol ether/ethyl acetate mixed solution of volume ratio.
Described method, wherein the cooling among the step D is to separate out solid phase prod in the reaction solution impouring frozen water.
Dibenzo TTF four carbonyl diurethane imide derivatives provided by the invention have high mobility and good conjugacy, and have characterized the molecular structure that respectively goes on foot precursor raw material with ultimate analysis, mass spectrum (EIMS), proton nmr spectra, carbon-13 nmr spectra; With ultimate analysis, mass spectrum (EIMS and HRMS), infrared spectrum characterization two instantiation compounds 1 of dibenzo TTF four carbonyl diurethane imide derivatives and 2 molecular structure.Studied the photophysical property of compound 1 and 2 with ultra-violet absorption spectrum.Studied the electrochemical properties of compound 1 and 2 with cyclic voltammetry.Studied the thermodynamic property of two compounds with differential thermal-difference weight analysis (DTA-TGA).And be that organic semiconductor layer has been made transistor with it, good device performance shows that dibenzo TTF four carbonyl diurethane imide derivatives are the good semiconductor materials of a class.
The invention has the advantages that:
1. synthetic route is simple, effective; Raw material is business-like cheap products, and synthetic cost is low; And synthetic method has universality, can promote the use of the synthetic of other classes TTF derivative.
2. the four carbonyl diurethane imide derivatives of dibenzo TTF are linear big pi-conjugated molecules, have the inflexible two dimensional structure, are expected to prepare the OFET device of high mobility.
3. have lower HOMO energy level and (approximately-5.4eV),, help obtaining the OFET device of high on-off ratio stable in the air the stability height of oxygen.
4. has higher thermostability (decomposition temperature is approximately 460 ℃).
5. good prospects for application is arranged in OFET, and its mobility and on-off ratio are all very high, and (μ is up to 0.35cm
2/ Vs, on-off ratio is greater than 10
7).
Description of drawings
Fig. 1 is the film ultra-violet absorption spectrum of compound 1 and 2.
Fig. 2 is the cyclic voltammetry curve of compound 2.
Fig. 3 is thermogravimetric analysis (TGA) curve of compound 1 and 2.
Fig. 4 is the structural representation (the four carbonyl diurethane imide derivatives of dibenzo TTF, promptly DBTTFTCDI is organic layer) of organic field effect tube.
Fig. 5 is the curve of output of the field-effect transistor of compound 2.
Fig. 6 is the transition curve of the field-effect transistor of compound 2.
Embodiment
Shown below is the synthetic route of embodiment 1 and embodiment 2:
Embodiment 1, N, N '-dibutyl-dibenzo tetrathiafulvalene-2,3,6,7-four carbonyl diurethane imides (compound 1)
Under the nitrogen protection, in the 250ml there-necked flask, add 6.0g (28mmol) 4,5-two chloro-phthalic anhydrides, 4.1g (56mmol) n-Butyl Amine 99, the 100mL propionic acid was 140 ℃ of back flow reaction 3 hours.Reaction solution is chilled to room temperature, and decompression is revolved and desolvated, and recrystallization in methyl alcohol gets white crystalline solid (compound 3) 6.5g, productive rate 85.5%.
Mass spectrum: [MS (EI)] m/z:271 (M
+).
Ultimate analysis: molecular formula: C
12H
11Cl
2NO
2Theoretical value: C, 52.96H; 4.07; N, 5.15;
Measured value: C, 52.97; H, 4.13; N, 5.13.
Nucleus magnetic hydrogen spectrum:
1H-NMR (300MHz, CDCl
3) δ (ppm): 0.92-0.97 (t, J=7.30Hz, 3H), 1.31-1.39 (m, 2H), 1.65 (m, 2H), 3.65-3.70 (t, J=7.23Hz, 2H), 7.91 (s, 2H).
Nuclear-magnetism carbon spectrum:
13C-NMR (75MHz, CDCl
3) δ (ppm): 12.4,18.9,29.3,37.1,124.1,130.2,137.6,165.2 (CO).
Under the nitrogen protection, in the 100ml there-necked flask, add 3.0g (11mmol) compound 3,3.2g (25mmol) benzyl sulfhydrate, 4.5g K
2CO
3, the 50mL N,N-DIMETHYLACETAMIDE was 65 ℃ of reacting by heating 12 hours.Reaction solution is chilled to room temperature, in the impouring 300ml frozen water, filters.The gained solid refluxes half an hour in methyl alcohol, and the heat filter is with three times (20ml * 3) of hot methanol washing.Vacuum-drying gets faint yellow cotton-shaped solid (compound 5) 2.8g, productive rate 57%.
Mass spectrum: [MS (EI)] m/z:447 (M
+).
Ultimate analysis: molecular formula: C
26H
25NO
2S
2Theoretical value: C, 69.77; H, 5.63; N, 3.13;
Measured value: 69.36; H, 5.63; N, 3.23.
Nucleus magnetic hydrogen spectrum:
1H-NMR (300MHz, CDCl
3) δ (ppm): 0.91-0.96 (t, J=7.30Hz, 3H), 1.36 (m, 2H), 1.63 (m, 2H), 3.61-3.66 (t, J=7.22Hz, 2H), 4.24 (s, 4H), 7.30-7.37 (m, 10H), 7.62 (s, 2H).
Nuclear-magnetism carbon spectrum:
13C-NMR (75MHz, CDCl
3) δ (ppm): 12.5,18.9,29.5,36.8,36.8,120.0,126.7,127.7,127.9,128.0,134.1,142.8,166.9 (CO).
Under the nitrogen protection, in the there-necked flask of 250ml, with 1.5g (3.4mmol) compound 5 and 3.7g (27.2mmol) AlCl
3Room temperature reaction is 2 hours in the 80ml dry toluene.In reaction solution, add 1.1g (6.8mmol) carbonyl dimidazoles, in 80 ℃ of reacting by heating 3 hours.Decompression is revolved and is desolvated.Crude product is through silica gel column chromatography purification (leacheate-petrol ether/ethyl acetate 6: 1v/v), obtain white crystalline solid (compound 7) 0.65g, productive rate 65.3%.
Mass spectrum: [MS (EI)] m/z:293 (M
+).
Ultimate analysis: molecular formula: C
13H
11NO
3S
2Theoretical value: C, 53.22; H, 3.78; N, 4.77;
Measured value: C, 53.28; H, 3.79; N, 4.76.
Nucleus magnetic hydrogen spectrum:
1H-NMR (300MHz, CDCl
3) δ (ppm): 0.93-0.98 (t, J=7.26,3H), 1.33-1.40 (m, 2H), 1.67 (m, 2H), 3.68-3.72 (t, J=7.16,2H), 7.96 (s, 2H).
Nuclear-magnetism carbon spectrum:
13C-NMR (75MHz, CDCl
3) δ (ppm): 12.5,18.9,29.4,37.1,116.6,129.3,137.3,165.8 (CO, (CO)
2N), 186.1 (CO, SCOS).
Under the nitrogen protection, in the 50ml there-necked flask, add 0.325g (1.1mmol) compound 7,20mL toluene, 10ml triethyl-phosphite, back flow reaction 12 hours.Reaction solution is chilled to room temperature, filters, three times (30ml * 3) of hot chloroform washing, and vacuum-drying gets red solid (compound 1) 0.23g, productive rate 75.5%.Vacuum-sublimation gets the shiny red solid, is used for structural characterization.
Mass spectrum: [MS (EI)] m/z:554 (M
+). high resolution mass spectrum actual measurement: 554.0467. theory, C
26H
22N
2O
4S
4: 554.0462.
Ultimate analysis: molecular formula: C
26H
22N
2O
4S
4Theoretical value: C, 56.29; H, 4.00; N, 5.05;
Measured value: C, 56.09; H, 4.05; N, 4.86.
Infrared spectra: FT-IR (KBr, cm
-1) v3086,2963,2937,2873,1768,1709 (vs), 1592,1438,1395 (s), 1371,1312,1204,1058,915,877,744,596.
Compound 4 is synthetic with compound 3 among the embodiment 1, and amine adopts normal hexyl Amine (also can adopt octylame or positive amino dodecane etc.): productive rate 86.5%.
Mass spectrum: [MS (EI)] m/z:299 (M
+).
Ultimate analysis: molecular formula: C
14H
15Cl
2NO
2Theoretical value: C, 56.02; H, 5.04; N, 4.67;
Measured value: C, 56.04; H, 5.08; N, 4.63.
Nucleus magnetic hydrogen spectrum:
1H-NMR (300MHz, CDCl
3) δ (ppm): 0.85-0.89 (t, J=6.41Hz, 3H), 1.30 (s, 6H), 1.65 (m, 2H), 3.64-3.68 (t, J=7.26Hz, 2H), 7.90 (s, 2H).
Nuclear-magnetism carbon spectrum:
3C-NMR (75MHz, CDCl
3) δ (ppm): 12.8,21.3,25.3,27.3,30.2,37.4,124.1,130.2,137.6,165.2 (CO).
Compound 6 is synthetic with compound 5: productive rate 61%.
Mass spectrum: [MS (EI)] m/z:475 (M
+).
Ultimate analysis: molecular formula: C
28H
29NO
2S
2Theoretical value: C, 70.70; H, 6.15; N, 2.94;
Measured value: C, 70.57; H, 5.97; N, 3.01.
Nucleus magnetic hydrogen spectrum:
1H-NMR (300MHz, CDCl
3) δ (ppm): 0.86-0.90 (t, J=5.80Hz, 3H), 1.31 (s, 6H), 1.61-1.66 (m, 2H), 3.60-3.65 (t, J=7.20Hz, 2H), 4.24 (s, 4H), 7.30-7.37 (m, 10H), 7.62 (s, 2H).
Nuclear-magnetism carbon spectrum:
13C-NMR (75MHz, CDCl
3) δ (ppm): 12.9,21.4,25.4,27.4,30.2,36.8,37.0,119.9,126.7,127.7,127.9,128.0,134.1,142.7,166.9 (CO).
Compound 8 is synthetic with compound 7: productive rate 55%.
Mass spectrum: [MS (EI)] m/z:321 (M
+).
Ultimate analysis: molecular formula: C
15H
15NO
3S
2Theoretical value: C, 56.05; H, 4.70; N, 4.36;
Measured value: C, 55.87; H, 4.83; N, 4.15.
Nucleus magnetic hydrogen spectrum:
1H-NMR (300MHz, CDCl
3) δ (ppm): 0.86-0.90 (t, J=5.4Hz, 3H), 1.31 (s, 6H), 1.69 (m, 2H), 3.67-3.71 (t, J=7.12Hz, 2H), 7.96 (s, 2H).
Nuclear-magnetism carbon spectrum:
13C-NMR (75MHz, CDCl
3) δ (ppm): 12.9,21.4,25.4,27.3,30.2,37.3,116.6,129.3,137.3,165.8 (CO, (CO)
2N), 186.1 (CO, SCOS).
Mass spectrum: [MS (EI)] m/z:610 (M
+). high resolution mass spectrum actual measurement: 610.1083. theory, C
26H
22N
2O
4S
4: 610.1088.
Ultimate analysis: molecular formula: C
30H
30N
2O
4S
4Theoretical value: C, 58.99; H, 4.95; N, 4.59;
Measured value: C, 58.60; H, 4.87; N, 4.36.
Infrared spectra: FT-IR (KBr, cm
-1) v3085,2957,2929,2856,1769,1709 (vs), 1592,1438,1396 (s), 1372,1312,1206,1065,913,877,742,596.
Fig. 1 has provided the film ultra-violet absorption spectrum of compound 1 and 2, and their ultraviolet maximum absorption peak position is about 560nm, and optical band gap is 2.1eV.Fig. 2 has provided the circulation volt amine curve of compound 2.Electro-chemical test shows their initial oxidation current potential about 1.2V, and the HOMO energy level of Ji Suaning is-5.4eV thus.
Fig. 3 has provided the TGA-DTA curve of compound 1 and 2, and compound 1 and 2 demonstrates good thermostability, and decomposition temperature is about 460 ℃.
Fig. 4 has provided the structural representation of organic field effect tube, and as shown in the figure, as substrate, the thick silicon-dioxide of 480nm is as insulation layer with highly doped silicon chip in the present invention, source-drain electrode all use gold as the thick organic layer of electrode .50nm in vacuum tightness near 10
-4Evaporation is to silicon-dioxide under the Pa.At room temperature use Hewlett-Packard (HP) 4140B semi-conductor test instrument to measure its electrical property.
Fig. 5 and Fig. 6 have provided the curve of output and the transition curve of the field-effect transistor of compound 2 respectively.The present invention is that organic layer has been made a lot of organic field effect tube devices with the synthetic compound, and in these devices, wherein the highest mobility can reach 0.40cm
2/ Vs, on-off ratio is greater than 10
7All experimental results show that the dibenzo tetrathiafulvalene tetracarbonyl imide compounds is good organic field effect tube material.Good device performance is given the credit to design philosophy of the present invention, and dicarbapentaborane imide (DCI) group is introduced in the TTF skeleton, and the so promptly appropriate electron donation that has reduced molecule has enlarged the conjugated system of molecule again, has obtained high performance OFET material.Two materials of this that the invention is not restricted to be reported are that four carbonyl diurethane imide compounds of centronucleus are of a great variety with dibenzo TTF, 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 TTF derivative.
Claims (8)
1. dibenzo tetrathiafulvalene tetracarbonyl imide derivative, its structure is shown below
R is an alkyl in the formula.
2. prepare the method for the described dibenzo tetrathiafulvalene tetracarbonyl imide derivative of claim 1, the steps include:
A) under the nitrogen protection, 4,5-two chloro-phthalic anhydrides and amine with mol ratio 1: 1.5-3 in propionic acid in 140-160 ℃ of backflow 2-4 hour, cooling removes desolvates, the product that obtains is 4,5-dichloro phthalimide derivative;
B) under the nitrogen protection, 4 of steps A preparation, 5-dichloro phthalimide derivative and benzyl sulfhydrate with mol ratio 1: 2-3 at excessive K
2CO
3Exist down in N,N-DIMETHYLACETAMIDE 60-80 ℃ reacting by heating 10-16 hour, cold filtration, the product that obtains are 4, the phthalimide derivative that 5-two benzylthio-s replace;
C) under the nitrogen protection, 4 of step B preparation, the phthalimide derivative that 5-two benzylthio-s replace is at excessive AlCl
3There is debenzylation in exsiccant toluene down, reacted 2-5 hour down in 70-90 ℃ with carbonyl dimidazoles, 4, the phthalic imidine that 5-two benzylthio-s replace and the mol ratio of carbonyl dimidazoles are 1: 1-3, cooling removes and desolvates, the product that obtains is for containing imido benzo 1,3-dithio-2-ketone compound;
D) step C preparation contain imido benzo 1,3-dithio-2-ketone compound is at mol ratio 2-3: reflux in 1 toluene/triethyl-phosphite mixed solution, carry out self coupling reaction 10-14 hour, cold filtration obtains target product.
3. method as claimed in claim 2, wherein the amine of steps A is n-Butyl Amine 99, normal hexyl Amine, octylame or positive amino dodecane.
4. method as claimed in claim 2, wherein product recrystallization in methyl alcohol of obtaining of steps A.
5. method as claimed in claim 2, wherein the product that obtains of step B is in methyl alcohol backflow 20-40 minute, heat filtering, hot methanol washing, vacuum-drying.
6. method as claimed in claim 2, wherein the product that obtains of step C is purified through silica gel column chromatography, and leacheate is 6: 1 a petrol ether/ethyl acetate mixed solution of volume ratio.
7. method as claimed in claim 2, wherein the cooling among the step D is to separate out solid phase prod in the reaction solution impouring frozen water.
8. the described dibenzo tetrathiafulvalene tetracarbonyl imide derivative of claim 1 is as the application of organic layer in organic field effect tube.
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| 朱玉兰，杨艳杰等.四硫富瓦烯衍生物在有机光电功能材料方面的研究进展.有机化学25 10.2005,25(10),1167-1175. |
| 朱玉兰,杨艳杰等.四硫富瓦烯衍生物在有机光电功能材料方面的研究进展.有机化学25 10.2005,25(10),1167-1175. * |
| 沈永嘉，倪彩英等.二苯并四硫代富瓦烯类衍生物的合成和电化学行为.有机化学 4.1995,(4),394-398. |
| 沈永嘉,倪彩英等.二苯并四硫代富瓦烯类衍生物的合成和电化学行为.有机化学 4.1995,(4),394-398. * |
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