CN100341869C - Phenanthrene/thiophene hybridized high-mobility organic semiconductor and application thereof - Google Patents
Phenanthrene/thiophene hybridized high-mobility organic semiconductor and application thereof Download PDFInfo
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- CN100341869C CN100341869C CNB2005101190019A CN200510119001A CN100341869C CN 100341869 C CN100341869 C CN 100341869C CN B2005101190019 A CNB2005101190019 A CN B2005101190019A CN 200510119001 A CN200510119001 A CN 200510119001A CN 100341869 C CN100341869 C CN 100341869C
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Abstract
The present invention relates to a phenanthrene/thiophene hybridized high mobility organic semiconductor which can be used as a transmission layer and can be used for organic film transistors, and the present invention belongs to the technical field of photoelectron materials. The structure general formula of the phenanthrene/thiophene hybridized organic semiconductor with high mobility is shown as the right formula. The phenanthrene/thiophene hybridized organic semiconductor with high mobility provided by the present invention has the advantages of high thermal stability and high environmental stability; high purity products can be obtained by a vacuum sublimation method and have the characteristic of high mobility. The products have low solubility in organic solvents and can adopt a mature photoetching process in the process of device preparation, so the products can be used as a transmission layer and can be used in the organic film transistors, and the prepared devices are stable in the air.
Description
Technical field
The invention belongs to organic optoelectronic material technology field, relate to phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor and the application in OTFT thereof.
Technical background
In recent years, be that the OTFT (OTFTs) of transport layer has caused people's extensive concern with the organic semiconductor material.This device has potential and uses in flat pannel display driving circuit and low-cost memory cell (as identification card, commodity price label etc.).With traditional non-crystalline silicon (device of α-Si:H) compare have low cost, can realize big area cover, can with advantages such as flexible substrates is integrated.The Philips company of Holland has finished first research and development based on the active-matrix liquid-crystal displaying screen of OTFTs (Nature, 2001,414,599.) in the world, and organic semiconductor layer is Polythienylenevinylethermoelectric (PTV).
The performance index of OTFT device mainly are field-effect mobility (μ
FET) and current on/off ratio (I
On/ I
Off).The ideal organic semiconductor should have high mobility (＞0.1cm
2/ V.s) and low " pass " attitude electric current.The important point is that organic semiconductor should have good environmental stability in addition.
Acene class aromatic fused ring compound is the analog high mobility organic semi-conducting material the most widely of research at present, and the field causes mobility and reached non-crystalline silicon (0.1～1cm
2/ V.s) level.But they have narrower energy gap and higher the highest occupied molecular orbital(MO) (HOMO) energy level, and are easily oxidized and cause the device performance decay in air, have limited their range of application.Therefore, the stable high mobility organic semi-conducting material of preparation is one of important topic of organic optoelectronic research field.
In order to overcome the shortcoming of above-mentioned materials, it is a series of oligopolymers of structure primitive with the phenanthrene that the contriver provides, and its success is applied to OTFT device (Chinese patent application number: 200510016895.9), but its field of further improving material of still needing is caused mobility, and then improve the performance index of OTFTs device.
Summary of the invention
Consider that stability and oligomerized thiophen analog material that luxuriant and rich with fragrance compounds is good have good molecular interaction, one of purpose of the present invention provides phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor, and two of purpose of the present invention provides the purposes of phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor in OTFT.The present invention has further optimized the ionization potential of material when obtaining stable material, make the energy level coupling of gold electrode in phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor and the device better, and has further improved the mobility that causes of material.
Phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor provided by the invention has following general structure:
Wherein
Comprise following structure:
The preparation of phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor, implement according to following method:
1. contain the preparation of phenanthryl unit:
1) (application number: method 200510016895.9) prepares 2-iodine phenanthrene according to the Chinese patent application material;
2) preparation of phenanthrene-2-formaldehyde:
With 2-iodine phenanthrene is matching criterion, under argon shield 2-iodine phenanthrene is dissolved in the tetrahydrofuran (THF) of anhydrous, anaerobic, under-78 ℃, add the n-Butyl Lithium of 0.9-1.2 times of molar weight, stirs after 0.5-1 hour, the DMF of anhydrous, the anaerobic of 1-1.5 times of molar weight of adding, rise to room temperature, continue to stir 3-10 hour, pour in the big water gaging, use dichloromethane extraction, the saturated common salt water washing, anhydrous magnesium sulfate drying, rotary evaporation is removed solvent, carry out post and separate, obtain phenanthrene-2-formaldehyde;
3) preparation of phenanthrene-2-formic acid:
The preparation method is with 2), DMF anhydrous, anaerobic is replaced with dry CO
2
2. the preparation of thiophene nucleoid:
1) have the preparation of the thiophene nucleoid of structure (I):
According to literature method (J.Org.Chem.1995,60,6813-6819) can prepare 2-tributyl tinbase thiophene (n=1), 5,5 '-two (tributyl tinbase)-2,2 '-two thiophene (n=2) and 5,5 " two (tributyl tinbases)-2,2 ': 5 ', 2 " three thiophene (n=3).
2) have the preparation of the thiophene nucleoid of structure (II):
According to literature method (J.Am.Chem.Soc.1998,120,2206-2207) can prepare 2,2 '-two [3,2-b] and two thiophene (X=C; N=2); According to literature method (J.Chem.Soc., Perkin.Trans.1,1997,15,3465-3470) can prepare 2,5-two (tributyl tin)-[3,2-b] and two thiophene (X=C; N=1) and 5,5 '-two (tributyl tinbases)-2,2 '-two [3,2-b] and two thiophene (X=C; N=2);
3) have the preparation of the thiophene nucleoid of structure (III):
According to literature method (Adv.Mater.1997,9,36-39) can prepare 2,6-two (tributyl tinbase)-benzo [1,2-b:4,5-b '] two thiophene (X=C)
3. the preparation of phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor:
1) utilizes the method for Stille linked reaction to prepare and contain X=C in structure (I), the structure (II), phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor of X=C in n=1-2 and the structure (III).The preparation method is as follows: under argon shield, with the material of halogen-containing simple function group, contain the material and the Pd (PPh of two organic tin salt functional groups
3)
4Be (2-2.5) by the molar weight ratio: 1: (0.01-0.05) be dissolved in (concentration of reactants is at 0.05-0.3mol/L) among the DMF, 70-100 ℃ stir 12-48 hour after, cool to room temperature, filter the collecting precipitation thing, continuous water, ethanol, methylene dichloride, washing with acetone, vacuum-drying, obtain thick product, thick product is carried out twice vacuum-sublimation purifies, obtain containing X=C in structure (I), the structure (II), phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor of X=C in n=1-2 and the structure (III).
2) utilize the annulation preparation of phenanthrene-2-formaldehyde and rubeanic acid to contain X=N in the structure (II), phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor of n=1-2.The preparation method is as follows: be matching criterion with the rubeanic acid, phenanthrene-2-the formaldehyde of rubeanic acid and 2-3 times of molar weight is dissolved in the orthodichlorobenzene, after reflux 12-36 hour, cool to room temperature, with sedimentation and filtration, vacuum-drying obtains containing X=N in the structure (II), phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor of n=1-2 after vacuum-sublimation.
3) utilize phenanthrene-2-formic acid and 2, the 5-diaminostilbene, the annulation preparation of the dihydrochloride of 4-diphenyl sulfide fen contains the phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor of X=N in the structure (III).The preparation method is as follows: with 2, the 5-diaminostilbene, the dihydrochloride of 4-diphenyl sulfide fen is a matching criterion, in three mouthfuls of containers that excessive polyphosphoric acid (PPA) and tetramethylene sulfone are housed, add 2, the 5-diaminostilbene, the dihydrochloride of 4-diphenyl sulfide fen is in stirring at room after 24 hours, phenanthrene-2-the formic acid that adds 2-3 times of molar weight again, be warming up to 90 ℃ of reactions 5 hours, 145 ℃ were reacted 13 hours, and 170 ℃ were reacted 14 hours, 200 ℃ were reacted 1 hour, pour in the methyl alcohol after being cooled to room temperature, filtering-depositing is used weak ammonia and this throw out of water washing repeatedly, after the vacuum-drying, distillation is purified and is obtained containing the phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor of X=N in the structure (III).
With phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor of the present invention as shown in Figure 1 as the OTFT of charge transport layer preparation.
With heavily doped n type silicon chip is substrate 1 and gate electrode 2, is coated with the thick dielectric layer of 1500-3000 3 on it, and electric capacity is 10-30nF/cm
2, dielectric layer can optionally carry out chemical individual layer to be modified, and phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor is to adopt vacuum moulding machine to dielectric layer as charge transport layer 4, and vacuum tightness is (4.2-6.8) * 10
-4Pa, sedimentation rate is 0.1-10 /s, phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor is measured with crystal-vibration-chip as the thickness of charge transport layer 4 and is about 30-50nm, substrate is heated by the copper billet of temperature control in the deposition process, to realize different base reservoir temperatures, the gold of 20-40nm as source, drain electrode 5 through the mask plate hydatogenesis to organic semiconductor layer, the conducting channel breadth-length ratio (W/L) of the device of preparation is 9-60.In room temperature, carry out the test of electrical properties under the air conditions, by two cover Keithley, 236 instrument synchro measures, wherein 5,5 '-two (2-phenanthryl)-2,2 '-two thiophene (structure that meets n=2 in the structure (I)) are representative, and it causes mobility is 0.11cm
2/ V.s, current on/off ratio are 2 * 10
5(see figure 4), made is that the device (not lucifuge) in air of transport layer was preserved device performance no change (see figure 5) 1 month with phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor.
The electrochemical properties test result of phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor of the present invention:
The electrochemical properties of phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor is tested on the CHI660a electrochemical workstation, and organic solvent is an anhydrous acetonitrile, and supporting electrolyte is a tetrabutyl hexafluoro phosphonic acids amine (0.1mol/L), and working electrode is circular platinized platinum (0.6cm
2), phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor vacuum moulding machine is to platinized platinum, and platinum filament is a counter electrode, Ag/AgCl is a reference electrode, and sweep velocity is 80mV/s, and current potential is demarcated (in the acetonitrile with ferrocene, with respect to the Ag/AgCl reference electrode is 0.42V), HOMO energy level formula:
Calculate, the HOMO energy level that calculates gained is between-5.6--5.2eV, be lower than the HOMO energy level of thiophene six aggressiveness, being higher than with the phenanthrene is a series of oligopolymers of structure primitive, (5.2--5.4eV) be complementary with the work content of gold electrode, wherein the HOMO energy level that can get 5,5 '-two (2-phenanthryl)-2,2 '-two thiophene (structure that meets n=2 in the structure (I)) from cyclic voltammogram is-5.26eV (see figure 2).
The heat stability testing result of phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor of the present invention:
The thermostability of phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor is tested on Perkin-Elmer TGA 7 thermal gravimetric analyzers, condition is: heating rate is 10 ℃/min, nitrogen flow rate is 20ml/min, the result shows, the thermolysis starting temperature of phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor is higher than 400 ℃, wherein 5, the thermolysis starting temperature of 5 '-two (2-phenanthryl)-2,2 '-two thiophene (structure that meets n=2 in the structure (I)) is that 405 ℃ of (see figure 3)s are better than thiophene oligomers.
The field of phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor of the present invention causes the test result of mobility:
OTFT as shown in Figure 1 is in room temperature, carry out the test of electrical properties under the air conditions, by two cover Keithley, 236 instrument synchro measures, measuring result shows, the field of phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor causes a series of oligopolymers that mobility ratio is the structure primitive with the phenanthrene (application number: 200510016895.9) improve an order of magnitude, wherein to cause mobility be 0.11cm in the field of 5,5 '-two (2-phenanthryl)-2,2 '-two thiophene (structure that meets n=2 in the structure (I))
2/ V.s (see figure 4), made is that the device (not lucifuge) in air of transport layer was preserved device performance no change (see figure 5) 1 month with phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor.
Phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor of the present invention is compared with thiophene oligomers has high thermostability and environmental stability, can obtain high purity product by the method for vacuum-sublimation, and has characteristics such as high mobility, and it causes mobility is 0.11cm
2/ V.s, current on/off ratio are 2 * 10
5Because solvability is extremely low in organic solvent, can adopt matured photoetching process in the device preparation process, is applied in the OTFT as transport layer, and is stable in the air with the device of its preparation.
Description of drawings
1 of Fig. 1 represents substrate, and 2 represent grid, and 3 represent dielectric layer, and 4 represent phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor charge transport layer, and 5 represent source-drain electrode.This figure also is the specification digest accompanying drawing.
Fig. 2 is the cyclic voltammogram of 5,5 '-two (2-phenanthryl)-2,2 '-two thiophene (embodiment 3), therefrom can calculate the HOMO energy level to be-5.26eV.
Fig. 3 is the hot weightless picture of 5,5 '-two (2-phenanthryl)-2,2 '-two thiophene (embodiment 3) and six bithiophenes.
Fig. 4 is the transfer characteristic curve of the OTFT of 5,5 '-two (2-phenanthryl)-2,2 '-two thiophene (embodiment 3), and therefrom can calculating the field of material, to cause mobility be 0.11cm
2/ V.s, current on/off ratio are 2 * 10
5
Fig. 5 is that the OTFT (not lucifuge) in air of 5,5 '-two (2-phenanthryl)-2,2 '-two thiophene (embodiment 3) is preserved the I after 1 month
D-V
GCurve, device performance no change as can be known.
Embodiment
Synthesizing of embodiment 1:2-(2-phenanthryl) thiophene
Under argon shield, the 250ml round-bottomed flask that is connected on the biexhaust pipe is toasted three times with gaslight, add the 2-iodine phenanthrene of 7.69g (25.3mmol), the 2-of 8.58g (23.0mmol) (tributyl tinbase) thiophene, the Pd (PPh of 500mg-1g
3)
4, 80-150ml DMF, this reaction mixture 70-90 ℃ stir 5-10 hour after, cool to room temperature is poured in the 500ml water, extracts respectively three times with the 100ml dichloromethane extraction, merge organic phase, wash respectively three times with the 100ml saturated aqueous common salt, anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, the thick product that obtains is separated purification with column chromatography, sherwood oil is a leacheate, obtains 2-(2-phenanthryl) thiophene, productive rate 85%.
Synthesizing of embodiment 2:2-bromo-5-(2-phenanthryl) thiophene
In argon shield; under the lucifuge; 2-(2-phenanthryl) thiophene that in the 250ml there-necked flask, adds 4.79g (18.4mmol); the DMF 100-200ml that adding is crossed through the hydrolith drying treatment; under condition of ice bath, in 0.5-1 hour the gradation of 3.44g (19.3mmol) bromo-succinimide is added in the there-necked flask; under this temperature stirring reaction 1-2 hour; remove ice bath; continue at ambient temperature to stir 2-4 hour; add 500ml water to finish reaction; use the 200ml ether continuously; saturated hypo solution with 100ml washs respectively three times; the organic phase anhydrous magnesium sulfate drying, rotary evaporation removes and desolvates, and the thick product that obtains is used the mixing solutions recrystallization of sherwood oil and methylene dichloride; obtain 2-bromo-5-(2-phenanthryl) thiophene, productive rate 80%.
Embodiment 3:5,5 '-two (2-phenanthryl)-2,2 '-two thiophene synthetic
Under argon shield, the 250ml round-bottomed flask that is connected on the biexhaust pipe is toasted three times with gaslight, add the 2-iodine phenanthrene of 4.79g (15.7mmol); 5.32g (7.15mmol) 5; 5 '-two (tributyl tinbases)-2,2 '-two thiophene, the Pd (PPh of 110-420mg
3)
460-200ml DMF, this reaction mixture 70-100 ℃ stir 12-48 hour after, cool to room temperature, filter the collecting precipitation thing, continuous water, ethanol, methylene dichloride, washing with acetone, vacuum-drying is carried out twice vacuum-sublimation with thick product and is purified, obtain 5,5 '-two (2-phenanthryl)-2,2 '-two thiophene, productive rate 50%.
Embodiment 4:5,5 " two (2-phenanthryl)-2,2 ': 5 ', 2 " synthesizing of three thiophene
With 5,5 " two (tributyl tinbases)-2,2 ': 5 ', 2 " 5,5 '-two (tributyl tinbases)-2,2 '-two thiophene among the three thiophene replacement embodiment 3; Feed ratio, reaction conditions and treatment process obtain 5,5 with embodiment 3 " two (2-phenanthryl)-2,2 ': 5 ', 2 " three thiophene, productive rates 45%.
Embodiment 5:5,5 -two (2-phenanthryl)-2,2 ': 5 ', 2 ": 5 ", 2 -four thiophene synthetic
Under argon shield, the 250ml round-bottomed flask that is connected on the biexhaust pipe is toasted three times with gaslight, add 2-bromo-5-(2-phenanthryl) thiophene of 4.68g (13.8mmol); 4.29g (5.76mmol) 5; 5 '-two (tributyl tinbases)-2,2 '-two thiophene, the Pd (PPh of 80-300mg
3)
4, 100-250mlDMF, reaction conditions and treatment process obtain 5,5 -two (2-phenanthryl)-2,2 ' with embodiment 3: 5 ', 2 ": 5 ", 2 -four thiophene, productive rate 35%.
Embodiment 6:2,5-two (2-phenanthryl)-[3,2-b] are synthesizing of two thiophene also
Under argon shield, the 250ml round-bottomed flask that is connected on the biexhaust pipe is toasted three times with gaslight, add the 2-iodine phenanthrene of 2.60g (8.55mmol); 3.41g (4.75mmol) 2; 5-two (tributyl tin)-[3,2-b] and two thiophene, the Pd (PPh of 100-360mg
3)
4, 50-150ml DMF, reaction conditions and treatment process obtain 5,5 -two (2-phenanthryl)-2,2 ' with embodiment 3: 5 ', 2 ": 5 ", 2 -four thiophene, productive rate 55%.
Embodiment 7:5,5 '-two (2-phenanthryl)-2,2 '-two [3,2-b] be synthesizing of two thiophene also
With 5,5 '-two (tributyl tinbase)-2,2 '-two [3,2-b] and two thiophene replace 2 among the embodiment 6,5-two (tributyl tin)-[3,2-b] and two thiophene, feed ratio, reaction conditions and treatment process are with embodiment 6, obtain 5,5 '-two (2-phenanthryl)-2,2 '-two [3,2-b] and two thiophene, productive rate 45%.
Embodiment 8:2,5-two (2-phenanthryl)-1,3-thiazoles be synthesizing of [5,4-d]-1,3-thiazoles also
1.04g (8.61mmol) rubeanic acid and 3.38g (16.4mmol) phenanthrene-2-formaldehyde are dissolved in the 10-40ml orthodichlorobenzene, after reflux 12-36 hour, cool to room temperature, with sedimentation and filtration, vacuum-drying, after vacuum-sublimation, obtain 2,5-two (2-phenanthryl)-1,3-thiazoles is [5,4-d]-1 also, 3-thiazole, productive rate are 42%.
Embodiment 9:2,6-two (2-phenanthryl)-benzo [1,2-b:4,5-b '] two thiophene synthetic
Under argon shield, the 250mL round-bottomed flask that is connected on the biexhaust pipe is toasted three times with gaslight, add 2 of 4.86g (6.09mmol); 6-two (tributyl tinbase)-benzo [1,2-b:4,5-b '] two thiophene; 4.41g 2-iodine phenanthrene (14.5mmol), the Pd (PPh of 90-360mg
3)
4, 50-200mlDMF, reaction conditions and treatment process obtain 2 with embodiment 3,6-two (2-phenanthryl)-benzo [1,2-b:4,5-b '] two thiophene, productive rate 48%.
Embodiment 10:2,6-two (2-phenanthryl)-benzo [1,2-d:4,5-d '] dithiazole synthetic
In the 100ml there-necked flask that 22g polyphosphoric acid (PPA) and 10g tetramethylene sulfone are housed, add 2 of 1.08g (4.37mmol), the 5-diaminostilbene, the dihydrochloride of 4-diphenyl sulfide fen, in stirring at room after 24 hours, phenanthrene-2-the formic acid that adds 2.90g (13.0mmol) again is warming up to 90 ℃ of reactions 5 hours, and 145 ℃ were reacted 13 hours, 170 ℃ were reacted 14 hours, and 200 ℃ were reacted 1 hour.Pour in the methyl alcohol after being cooled to room temperature, filtering-depositing is used weak ammonia and water washing repeatedly, and after the vacuum-drying, distillation is purified, and obtains 2,6-two (2-phenanthryl)-benzo [1,2-d:4,5-d '] dithiazole, productive rate 45%.
Claims (2)
1, a kind of phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor is characterized in that, it has following general structure:
Wherein
Comprise following formula:
2, the purposes of a kind of phenanthrene/phenanthrene/thiophene hybridized high-mobility organic semiconductor as claimed in claim 1 is characterized in that: this organic semiconductor is used for OTFT as charge transport layer.
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| CN102675605B (en) * | 2012-05-16 | 2013-10-30 | 华南理工大学 | Soluble poly-6,9-phenanthrene thiophthene and preparation method and application thereof |
| CN104559286B (en) * | 2014-12-23 | 2016-09-07 | 东莞理工学院 | A kind of triphenylamine-boron fluoride complexing dimethyl pyrrole methine derivative organic dyestuff and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02216791A (en) * | 1989-02-17 | 1990-08-29 | Pioneer Electron Corp | Electric field luminous element |
| US20020177009A1 (en) * | 2001-02-22 | 2002-11-28 | Koichi Suzuki | Fused polynuclear compound and organic luminescence device |
| CN1546477A (en) * | 2003-12-04 | 2004-11-17 | 复旦大学 | Method for preparing electron transport / hole barrier material and its electro-glow parts |
| CN1638573A (en) * | 2004-01-06 | 2005-07-13 | Lg电子有限公司 | Organic electroluminescence device |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02216791A (en) * | 1989-02-17 | 1990-08-29 | Pioneer Electron Corp | Electric field luminous element |
| US20020177009A1 (en) * | 2001-02-22 | 2002-11-28 | Koichi Suzuki | Fused polynuclear compound and organic luminescence device |
| CN1546477A (en) * | 2003-12-04 | 2004-11-17 | 复旦大学 | Method for preparing electron transport / hole barrier material and its electro-glow parts |
| CN1638573A (en) * | 2004-01-06 | 2005-07-13 | Lg电子有限公司 | Organic electroluminescence device |
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