CN106565428B - A kind of aphthacene organic semiconducting materials and preparation method thereof - Google Patents
A kind of aphthacene organic semiconducting materials and preparation method thereof Download PDFInfo
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Abstract
The present invention discloses a kind of aphthacene organic semiconducting materials and preparation method thereof.Aphthacene organic semiconducting materials structural formula is as follows:R is one of following substituent group: R is the linear or branched alkyl group of C1-C40, the alkenyl of C2-C40, the alkynyl of C2-C40, the linear or branched alkyl group that the halogen of C1-C40 replaces, the alkenyl that the halogen of C2-C40 replaces, the alkynyl that the halogen of C2-C40 replaces, it is adjacent or or the contraposition alkyl that replaces the linear chain or branched chain of the C1-C40 of 2- phenyl to replace, the alkenyl or alkynyl of the linear chain or branched chain of C2-C40, the oxyalkyl that the linear chain or branched chain of C1-C40 replaces, it is adjacent or or contraposition replace 2- phenyl C2-C40 linear chain or branched chain alkenyl or alkynyl, it is adjacent or face or to fluorine cyclohexyl.Method preparation of the invention is simple, and obtains a series of aphthacene derivatives.The present invention modifies tetracene material, improves mobility, provides the foundation for the application of tetracene material.
Description
Technical field
The present invention relates to organic chemistry fileds more particularly to a kind of aphthacene organic semiconducting materials and preparation method thereof.
Background technique
Enter science and technology rapidly traditional inorganic semiconductor material, such as silicon, germanium, gallium nitride, GaAs etc.
Information age exhibits one's skill to the full in the information age of high speed.Although inorganic semiconductor material is shown much in development in science and technology
Superiority, still, inorganic semiconductor material also remains its limitation, and the type of material is relatively simple, preparation work
Some disadvantages such as skill is complicated, cost is relatively high greatly limit its development.With these disadvantages, organic semiconducting materials are met the tendency of
And it gives birth to.Organic semiconducting materials are a kind of materials with semiconductor property, in organic field effect tube (OTFT), Organic Electricity
Mutagens color (OEC), perovskite, has a wide range of applications in organic solar batteries (OPV) at Organic Light Emitting Diode (OLED).
Organic semiconducting materials have many advantages, such as that the processing is simple, cost is relatively low organic semiconducting materials, in addition organic semiconducting materials are also
Different energy level ranges, semiconductor material of different nature can be obtained by the fine tuning in structure.
There are carbon-carbon double bond structure, the P of two carbon atoms in organic semiconducting materials structureZTrack form bonding orbital and
Antibonding orbital is respectively formed HOMO (highest occupied molecular orbital) and LUMO (minimum occupied orbital), the HOMO in organic semiconductor
The valence band and conduction band being equivalent to lumo energy in inorganic semiconductor.After electronics is excited on LUMO by HOMO, HOMO is lacked
Hole, LUMO electron rich are electronically formed, the two forms electron-hole pair, and the property of energy level affects organic semiconducting materials
Various optical and electrical properties.
Summary of the invention
In view of above-mentioned deficiencies of the prior art, the purpose of the present invention is to provide a kind of aphthacene organic semiconducting materials and
Preparation method, it is intended to obtain the organic semiconducting materials of excellent performance.
Technical scheme is as follows:
A kind of aphthacene organic semiconducting materials, wherein its structural formula is as follows:
Wherein, R is one of following substituent group: R is the linear or branched alkyl group of C1-C40, the alkenyl of C2-C40, C2-
The alkynyl of C40, the linear or branched alkyl group that the halogen of C1-C40 replaces, the alkenyl that the halogen of C2-C40 replaces, the halogen of C2-C40
The alkynyl that element replaces, it is adjacent or the contraposition alkyl that replaces the linear chain or branched chain of the C1-C40 of 2- phenyl to replace, C2-C40's is straight
The alkenyl or alkynyl of chain or branch, the oxyalkyl that the linear chain or branched chain of C1-C40 replaces, it is adjacent or or contraposition replace 2- phenyl
The alkenyl or alkynyl of the linear chain or branched chain of C2-C40, it is adjacent face or or to fluorine cyclohexyl, alkoxy, phenyl, trifluoro methoxy
Base, trifluoromethylthio, it is adjacent or or to fluorine or Trifluoromethoxyphen-l, it is adjacent or or to fluorine or trifluoromethylthio phenyl, thiophene
Base, the alkyl that the linear chain or branched chain of the C1-C40 of 3 or 4 or 5 substitution 2- thienyls replaces, 2 or 4 or 5 substitution 3- thienyls
C1-C40 linear chain or branched chain replace alkyl, 3 or 4 or 5 substitution 2- furyl C1-C40 linear chain or branched chain replace
Alkyl, 2 or 4 or 5 substitution 3- furyl C1-C40 linear chain or branched chain replace alkyl, anthryl, naphthalene, fluorenyl, oxygen
Fluorenyl, dibenzothiophen base, carbazolyl.
A kind of preparation method of aphthacene organic semiconducting materials as described above, wherein comprising steps of
A, the bromo-derivative containing R substituent and magnesium powder are added in anhydrous tetrahydro furan solvent at room temperature, are put
It sets and is stirred at room temperature, after mixing evenly heating reaction, reflux obtains compound 1；
B, 2- bromo aphthacene, catalyst n iCl2(dppp) and anhydrous tetrahydro furan is placed in the appearance in nitrogen atmosphere
In device, it is stirred at room temperature uniformly, the anhydrous tetrahydrofuran solution of compound 1 is slowly dropped in container at room temperature, In
It is reacted overnight under heated reflux condition；After reaction, it if product is readily soluble, is successively quenched, extracts, merging organic phase, it is organic
Mutually washing for several times, obtains compound 2 after silica gel post separation；If product indissoluble, washs after filtering, purified by sublimed method
To compound 2.
The preparation method, wherein in the step A, in the step A, be heated to reflux under the conditions of 70-80 DEG C.
The preparation method, wherein in the step A, being heated to reflux the time is 12h.
The preparation method, wherein in the step B, in the step B, be heated to reflux under the conditions of 70-80 DEG C.
The preparation method, wherein in the step B, being heated to reflux the time is 12h.
The utility model has the advantages that method preparation of the invention is simple, and a series of aphthacene derivatives are obtained, to obtain difference
Type using aphthacene as the organic semiconducting materials of parent nucleus.The present invention modifies tetracene material, improves and four
The mobility of benzene material provides the foundation for the application of tetracene material.
Detailed description of the invention
Fig. 1 is aphthacene organic semiconductor compound synthetic method of the present invention.
Fig. 2 is the schematic diagram of organic semiconductor 2- phenyl aphthacene synthesis process in the embodiment of the present invention 1.
Fig. 3 is that organic effect crystalline substance is prepared based on organic semiconductor 2- phenyl aphthacene in the embodiment of the present invention 1
The transfer curve of body pipe.
Fig. 4 is that organic effect crystalline substance is prepared based on organic semiconductor 2- phenyl aphthacene in the embodiment of the present invention 1
The curve of output of body pipe.
Specific embodiment
The present invention provides a kind of aphthacene organic semiconducting materials and preparation method thereof, to make the purpose of the present invention, technology
Scheme and effect are clearer, clear, and the present invention is described in more detail below.It should be appreciated that described herein specific
Embodiment is only used to explain the present invention, is not intended to limit the present invention.
A kind of aphthacene organic semiconducting materials provided by the invention, structural formula are as follows:
Wherein, R is one of following substituent group: R is the linear or branched alkyl group of C1-C40, the alkenyl of C2-C40, C2-
The alkynyl of C40, the linear or branched alkyl group that the halogen of C1-C40 replaces, the alkenyl that the halogen of C2-C40 replaces, the halogen of C2-C40
The alkynyl that element replaces, it is adjacent or the contraposition alkyl that replaces the linear chain or branched chain of the C1-C40 of 2- phenyl to replace, C2-C40's is straight
The alkenyl or alkynyl of chain or branch, the oxyalkyl that the linear chain or branched chain of C1-C40 replaces, it is adjacent or or contraposition replace 2- phenyl
The alkenyl or alkynyl of the linear chain or branched chain of C2-C40, it is adjacent face or or to fluorine cyclohexyl, alkoxy, phenyl, trifluoro methoxy
Base, trifluoromethylthio, it is adjacent or or to fluorine or Trifluoromethoxyphen-l, it is adjacent or or to fluorine or trifluoromethylthio phenyl, thiophene
Base, the alkyl that the linear chain or branched chain of the C1-C40 of 3 or 4 or 5 substitution 2- thienyls replaces, 2 or 4 or 5 substitution 3- thienyls
C1-C40 linear chain or branched chain replace alkyl, 3 or 4 or 5 substitution 2- furyl C1-C40 linear chain or branched chain replace
Alkyl, 2 or 4 or 5 substitution 3- furyl C1-C40 linear chain or branched chain replace alkyl, anthryl, naphthalene, fluorenyl, oxygen
Fluorenyl, dibenzothiophen base, carbazolyl.
For example, aphthacene organic semiconducting materials of the invention can be following structure.
Aphthacene organic semiconducting materials of the invention are that R substituent is added on No. 2 positions of aphthacene, for adjusting
Save different optics, the electrical properties of semiconductor material.In the present invention, aphthacene is connected with a R substituent on No. 2 sites, passes through
Different substituent groups is added, band gap (band gap) size is made to change with institute at film morphology, absorbing wavelength moves,
Cause a series of performance change of material.
The present invention also provides a kind of preparation methods of aphthacene organic semiconducting materials as described above, as shown in Figure 1, its
Comprising steps of
S1, at room temperature by the bromo-derivative containing R substituent and the anhydrous tetrahydro furan solvent of magnesium powder, holding chamber
Temperature stirring, after mixing evenly heating reaction, reflux obtain compound 1；
S2,2- bromo aphthacene, catalyst n iCl2(dppp) and anhydrous tetrahydro furan is placed in the container of nitrogen atmosphere
In (such as three-necked flask), it is stirred at room temperature uniformly, the anhydrous tetrahydrofuran solution of compound 1 is transferred to constant pressure at room temperature
It in dropping funel, and is slowly dropped in three-necked flask, reaction is stayed overnight under reflux condition；After reaction, if product
It is readily soluble, then it is successively quenched, extracts, merging organic phase, organic phase is washed for several times, and compound 2 is obtained after silica gel post separation；If producing
Object indissoluble washs after then filtering, purifies to obtain compound 2 by sublimed method.
Further, it in the step S1, is heated to reflux under the conditions of 70-80 DEG C, during this, being heated to reflux the time is
12h。
Further, it in the step S2, is heated to reflux under the conditions of 70-80 DEG C, during this, being heated to reflux the time is
12h。
Performance the present invention also provides above-mentioned organic semiconducting materials as organic field effect tube semiconductor layer material
Test method is to prepare film on silicon wafer by vapour deposition method, then gold is deposited as electrode material first, obtains organic effect
Transistor device measures the transfer curve and curve of output of device by probe station.Organic effect crystalline substance is prepared on silicon wafer
Then body pipe measures the performance of device.
Specific manufacturing process is as follows, and by silicon wafer, each ultrasonic wave is clear in acetone, deionized water and isopropanol in succession first
It washes 30 minutes, after ultraviolet irradiation 15 minutes, using dry toluene as solvent, compound concentration is that eight alkyltrichlorosilanes of 0.1M are molten
Liquid, by silicon wafer, 60 DEG C of heating after twenty minutes, are cleaned silicon chip surface with toluene, are dried up with nitrogen gun in the solution.Divide on silicon wafer
The gold electrode that the semiconductor and thickness that other evaporation thickness is about 30nm are about 50nm, prepares organic field effect tube, and to it
Performance is measured.
Embodiment 1
S1, bromobenzene (2.54g, 16.2mmol) and magnesium powder (0.49g, 20.0mmol) addition will be contained at room temperature
In 250ml anhydrous tetrahydro furan solvent, placement is stirred at room temperature, and heats initiation reaction after mixing evenly, is heated to reflux 12h.Reaction
After complete, solution is down to room temperature, obtains phenyl-magnesium-bromide, is transferred in constant pressure funnel.
S2, by 2- bromo aphthacene (1.25g, 4.05mmol) and NiCl2(dppp)(2.20g,4.05×10-2Mmol) In
It is added under nitrogen protection in the three-necked flask equipped with 50mL anhydrous tetrahydro furan, stirs evenly, start that phenyl bromination is slowly added dropwise
The anhydrous tetrahydrofuran solution of magnesium, and system is heated to reflux, after reacting 12h, reaction system is down to room temperature and is gone out with water extraction.
Filtering, obtained solid are purified by sublimed method.Reaction principle is as shown in Figure 2.
Embodiment 2
Each ultrasonic cleaning 30 minutes in acetone, deionized water and isopropanol in succession by silicon wafer first, through ultraviolet irradiation
After 15 minutes, using dry toluene as solvent, compound concentration is the eight alkyltrichlorosilanes solution of 0.1M, by silicon wafer in the solution 60
DEG C heating after twenty minutes, clean silicon chip surface with toluene, dried up with nitrogen gun.Evaporation thickness is about 30nm's respectively on silicon wafer
The gold electrode that semiconductor and thickness are about 50nm, prepares organic field effect tube.
Embodiment 3
The device simulation result of 2- phenyl aphthacene is as follows:
Using gold electrode as source electrode and drain electrode, with probe station measurement device transfer curve and curve of output, transfer curve and
Curve of output measurement result difference is as shown in Figure 3 and Figure 4.The mobility data of measurement see the table below:
In conclusion method preparation of the invention is simple, and a series of aphthacene derivatives are obtained, to obtain difference
Type using aphthacene as the organic semiconducting materials of parent nucleus.The present invention modifies tetracene material, improves and four
The mobility of benzene material provides the foundation for the application of tetracene material.
It should be understood that the application of the present invention is not limited to the above for those of ordinary skills can
With improvement or transformation based on the above description, all these modifications and variations all should belong to the guarantor of appended claims of the present invention
Protect range.
Claims (5)
1. a kind of preparation method of aphthacene organic semiconducting materials, which is characterized in that the aphthacene organic semiconducting materials
Structure it is as follows:
Wherein, R is one of following substituent group: R is phenyl, it is adjacent or to fluorine or Trifluoromethoxyphen-l, it is adjacent or or
To fluorine or trifluoromethylthio phenyl, anthryl, naphthalene, fluorenyl, dibenzofuran base, dibenzothiophen base, carbazolyl, contraposition substitution alkyl phenyl；
The method includes the steps:
A, room temperature in the bromo-derivative containing R substituent and the anhydrous tetrahydro furan solvent of magnesium powder, will be placed at room temperature to stir
It mixes, after mixing evenly heating reaction, reflux obtains compound 1；
B, 2- bromo aphthacene, catalyst n iCl2(dppp) it is placed in the container in nitrogen atmosphere with anhydrous tetrahydro furan,
It is stirred at room temperature uniformly, the anhydrous tetrahydrofuran solution of compound 1 is slowly dropped in container at room temperature, is being heated back
It is reacted overnight under the conditions of stream；After reaction, it if product is readily soluble, is successively quenched, extracts, merging organic phase, organic phase washing
For several times, compound 2 is obtained after silica gel post separation；If product indissoluble, is washed after filtering, purify to obtain chemical combination by sublimed method
Object 2.
2. preparation method according to claim 1, which is characterized in that in the step A, in the step A, in 70-80
It is heated to reflux under the conditions of DEG C.
3. preparation method according to claim 1, which is characterized in that in the step A, being heated to reflux the time is 12h.
4. preparation method according to claim 1, which is characterized in that in the step B, in the step B, in 70-80
It is heated to reflux under the conditions of DEG C.
5. preparation method according to claim 1, which is characterized in that in the step B, being heated to reflux the time is 12h.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009176985A (en) * | 2008-01-25 | 2009-08-06 | Asahi Kasei Corp | New optical field effect transistor with organic semiconductor layer |
| CN103288583A (en) * | 2013-06-14 | 2013-09-11 | 中国科学院长春应用化学研究所 | Preparation method of 2,3,3'4'-tetramethyl biphenyl |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009176985A (en) * | 2008-01-25 | 2009-08-06 | Asahi Kasei Corp | New optical field effect transistor with organic semiconductor layer |
| CN103288583A (en) * | 2013-06-14 | 2013-09-11 | 中国科学院长春应用化学研究所 | Preparation method of 2,3,3'4'-tetramethyl biphenyl |
Non-Patent Citations (2)
| Title |
|---|
| Bond Dissociation Enthalpies of Large Aromatic Carbon-Centered Radicals;Karen Hemelsoet等;《J.Phys.Chem.A》;20081231(第112期);第13566-13573页 * |
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