CN106565428A - Tetracene organic semiconductor material and preparation method thereof - Google Patents
Tetracene organic semiconductor material and preparation method thereof Download PDFInfo
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- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
Abstract
The invention discloses a tetracene organic semiconductor material and a preparation method thereof. The structural formula of the tetracene organic semiconductor material is shown in the description; and in the formula, R is one of a C1-C40 linear or branched alkyl group, a C2-C40 alkenyl group, a C2-C40 alkynyl group, a C1-C40 halogen-substituted linear or branched alkyl group, a C2-C40 halogen-substituted alkenyl group, a C2-C40 halogen-substituted alkynyl group, an o- or m- or p-substituted 2-phenyl C1-C40 linear or branched chain substituted alkyl group, a C2-C40 linear or branched alkenyl or alkynyl group, a C1-C40 linear or branched chain substituted alkoxy group, an o- or m- or p-substituted 2-phenyl C2-C40 linear or branched alkenyl or alkynyl group, and an o- or m- or p-fluorocyclohexyl group. The method is simple, and allows a series of tetracene derivatives to be obtained. A tetracene material is modified, the mobility is improved, and foundation is provided for the application of the tetracene material.
Description
Technical field
The present invention relates to organic chemistry filed, more particularly to a kind of aphthacene organic semiconducting materials and preparation method thereof.
Background technology
For traditional inorganic semiconductor material, such as silicon, germanium, gallium nitride, GaAs etc. make science and technology rapidly enter
Information age, exhibit one's skill to the full in the information age of high speed.Although inorganic semiconductor material shows much in development in science and technology
Superiority, but, inorganic semiconductor material also remains its limitation, and the species of material is relatively simple, prepare work
Skill is complicated, cost is higher etc., and some shortcomings greatly limit its development.With these shortcomings, organic semiconducting materials meet the tendency of
And give birth to.Organic semiconducting materials are a kind of materials with semiconductor property, in organic field effect tube (OTFT), Organic Electricity
Have a wide range of applications in mutagens color (OEC), Organic Light Emitting Diode (OLED), perovskite, organic solar batteries (OPV).
Organic semiconducting materials have the advantages that processing is simple, the relatively low organic semiconducting materials of cost, and in addition organic semiconducting materials are also
Fine setting in structure can be passed through, different energy level scopes, semi-conducting material of different nature is obtained.
There are carbon-carbon double bond structure, the P of two carbon atoms in organic semiconducting materials structureZTrack define bonding orbital and
Antibonding orbital, i.e., form respectively HOMO (highest occupied molecular orbital) and LUMO (minimum occupied orbital), the HOMO in organic semiconductor
With lumo energy equivalent to the valence band and conduction band in inorganic semiconductor.After electronics is excited on LUMO by HOMO, HOMO lacks
Hole is electronically formed, LUMO electron riches, the two formation hole-electron pair, the property of energy level have impact on organic semiconducting materials
Various optical and electrical properties.
The content of the invention
In view of above-mentioned the deficiencies in the prior art, it is an object of the invention to provide a kind of aphthacene organic semiconducting materials and
Its preparation method, it is intended to obtain the organic semiconducting materials of premium properties.
Technical scheme is as follows：
A kind of aphthacene organic semiconducting materials, wherein, its structural formula is as follows：
Wherein, R is the one kind in following substituent group：R for C1-C40 straight or branched alkyl, the thiazolinyl of C2-C40, C2-
The alkynyl of C40, the straight or branched alkyl of the halogen substiuted of C1-C40, the thiazolinyl of the halogen substiuted of C2-C40, the halogen of C2-C40
The alkynyl that element replaces, it is adjacent or para-orientation 2- phenyl C1-C40 the alkyl that replaces of straight or branched, C2-C40's is straight
The alkenyl or alkynyl of chain or side chain, the oxyalkyl that the straight or branched of C1-C40 replaces, it is adjacent or or para-orientation 2- phenyl
The alkenyl or alkynyl of the straight or branched of C2-C40, it is adjacent face or or to fluorine cyclohexyl, alkoxyl, 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 of the straight or branched replacement of the C1-C40 of 3 or 4 or 5 replacement 2- thienyls, 2 or 4 or 5 replacement 3- thienyls
C1-C40 straight or branched replace alkyl, 3 or 4 or 5 replacement 2- furyls C1-C40 straight or branched replace
Alkyl, 2 or 4 or 5 replacement 3- furyls C1-C40 straight or branched replace alkyl, anthryl, naphthyl, fluorenyl, oxygen
Fluorenyl, dibenzothiophen base, carbazolyl.
A kind of preparation method of aphthacene organic semiconducting materials as above, wherein, including step：
A, the bromo-derivative containing R substituent and magnesium powder be added in anhydrous tetrahydro furan solvent at ambient temperature, put
Put and be stirred at room temperature, the post-heating that stirs reaction, backflow obtains compound 1；
B, 2- bromo aphthacenes, catalyst n iCl2And anhydrous tetrahydro furan is placed in the appearance in nitrogen atmosphere (dppp)
In device, it is stirred at room temperature uniformly, the anhydrous tetrahydrofuran solution of compound 1 is slowly dropped in container at ambient temperature,
React overnight under heated reflux condition；After reaction terminates, if product is readily soluble, it is quenched successively, extracts, merging organic faciess, it is organic
Mutually washing for several times, compound 2 is obtained Jing after silica gel post separation；If product indissoluble, wash after filtering, purified by sublimed method
To compound 2.
Described preparation method, wherein, in step A, in step A, it is heated to reflux under the conditions of 70-80 DEG C.
Described preparation method, wherein, in step A, the time is heated to reflux for 12h.
Described preparation method, wherein, in step B, in step B, it is heated to reflux under the conditions of 70-80 DEG C.
Described preparation method, wherein, in step B, the time is heated to reflux for 12h.
Beneficial effect：The method of the present invention is prepared simply, and obtains a series of aphthacene derivatives, so as to obtain difference
The organic semiconducting materials with aphthacene as parent nucleus of type.The present invention is modified tetracene material, is improve and four
The mobility of benzene material, is that the application of tetracene material provides the foundation.
Description of the drawings
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 building-up processes in the embodiment of the present invention 1.
Fig. 3 is that organic effect crystalline substance is prepared based on organic semiconductor 2- phenyl aphthacenes 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 aphthacenes 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 definite, and below the present invention is described in more detail.It should be appreciated that described herein concrete
Embodiment only to explain the present invention, is not intended to limit the present invention.
A kind of aphthacene organic semiconducting materials that the present invention is provided, its structural formula is as follows：
Wherein, R is the one kind in following substituent group：R for C1-C40 straight or branched alkyl, the thiazolinyl of C2-C40, C2-
The alkynyl of C40, the straight or branched alkyl of the halogen substiuted of C1-C40, the thiazolinyl of the halogen substiuted of C2-C40, the halogen of C2-C40
The alkynyl that element replaces, it is adjacent or para-orientation 2- phenyl C1-C40 the alkyl that replaces of straight or branched, C2-C40's is straight
The alkenyl or alkynyl of chain or side chain, the oxyalkyl that the straight or branched of C1-C40 replaces, it is adjacent or or para-orientation 2- phenyl
The alkenyl or alkynyl of the straight or branched of C2-C40, it is adjacent face or or to fluorine cyclohexyl, alkoxyl, 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 of the straight or branched replacement of the C1-C40 of 3 or 4 or 5 replacement 2- thienyls, 2 or 4 or 5 replacement 3- thienyls
C1-C40 straight or branched replace alkyl, 3 or 4 or 5 replacement 2- furyls C1-C40 straight or branched replace
Alkyl, 2 or 4 or 5 replacement 3- furyls C1-C40 straight or branched replace alkyl, anthryl, naphthyl, fluorenyl, oxygen
Fluorenyl, dibenzothiophen base, carbazolyl.
Illustrate, the aphthacene organic semiconducting materials of the present invention can be following structure.
The aphthacene organic semiconducting materials of the present invention, it is to add R substituent on No. 2 positions of aphthacene, for adjusting
Different optics, the electrical properties of section semi-conducting material.In the present invention, aphthacene is connected with a R substituent on No. 2 sites, passes through
Different substituent groups are added, make band gap (band gap) sizes and institute change into film morphology, absorbing wavelength is moved,
Cause a series of performance change of material.
The present invention also provides a kind of preparation method of aphthacene organic semiconducting materials as above, as shown in figure 1, its
Including step：
S1, at ambient temperature by the anhydrous tetrahydro furan solvent of the bromo-derivative containing R substituent and magnesium powder, holding chamber
Temperature stirring, the post-heating that stirs reaction, backflow obtains compound 1；
S2,2- bromo aphthacenes, catalyst n iCl2And anhydrous tetrahydro furan is placed in the container of nitrogen atmosphere (dppp)
In (such as there-necked flask), it is stirred at room temperature uniformly, at ambient temperature the anhydrous tetrahydrofuran solution of compound 1 is transferred to into constant pressure
In Dropping funnel, and it is slowly dropped in there-necked flask, reacts overnight under heated reflux condition；After reaction terminates, if product
It is readily soluble, then it is quenched successively, extracts, merges organic faciess, organic faciess are washed for several times, and compound 2 is obtained Jing after silica gel post separation；If producing
Thing indissoluble, then wash after filtering, and by sublimed method purification compound 2 is obtained.
Further, in step S1, it is heated to reflux under the conditions of 70-80 DEG C, during this, the time of being heated to reflux is
12h。
Further, in step S2, it is heated to reflux under the conditions of 70-80 DEG C, during this, the time of being heated to reflux is
12h。
The present invention also provides performance of the above-mentioned organic semiconducting materials as organic field effect tube semiconductor layer material
Method of testing, is that thin film, then gold evaporation are prepared on silicon chip as electrode material by vapour deposition method first, obtains organic effect
Transistor device, by probe station the transfer curve and curve of output of device are determined.Organic effect is prepared on silicon chip brilliant
Body pipe, then determines the performance of device.
Specific manufacturing process is as follows, and first by silicon chip, in succession each ultrasound wave is clear in acetone, deionized water and isopropanol
Wash 30 minutes, Jing after ultra-vioket radiation 15 minutes, with dry toluene as solvent, compound concentration is molten for eight alkyltrichlorosilanes of 0.1M
Liquid, by silicon chip in the solution 60 DEG C heating 20 minutes after, with toluene clean silicon chip surface, dried up with nitrogen gun.Divide on silicon chip
Other evaporation thickness is about the gold electrode that the quasiconductor and thickness of 30nm is 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) will be contained at ambient temperature add
In 250ml anhydrous tetrahydro furan solvents, placement is stirred at room temperature, and stir post-heating initiation reaction, is heated to reflux 12h.Reaction
After complete, solution is down to room temperature, obtains phenyl-magnesium-bromide, in being transferred to constant pressure funnel.
S2, by 2- bromo aphthacenes (1.25g, 4.05mmol) and NiCl2(dppp)(2.20g,4.05×10-2Mmol) exist
Nitrogen protection is lower to be added in the there-necked flask equipped with 50mL anhydrous tetrahydro furans, is stirred, and starts to be slowly added dropwise phenyl bromination
The anhydrous tetrahydrofuran solution of magnesium, and system is heated to reflux, after reaction 12h, reaction system is down to into room temperature and is gone out with water extraction.
Filter, gained solid is purified by sublimed method.Reaction principle is as shown in Figure 2.
Embodiment 2
First by silicon chip, in succession each ultrasound wave is cleaned 30 minutes in acetone, deionized water and isopropanol, Jing ultra-vioket radiation
After 15 minutes, with dry toluene as solvent, compound concentration for 0.1M eight alkyltrichlorosilanes solution, by silicon chip in the solution 60
DEG C heating 20 minutes after, with toluene clean silicon chip surface, dried up with nitrogen gun.Respectively evaporation thickness is about 30nm's on silicon chip
Quasiconductor and thickness are about the gold electrode of 50nm, prepare organic field effect tube.
Embodiment 3
The device simulation result of 2- phenyl aphthacenes is as follows：
With gold electrode as source electrode and drain electrode, with probe station the transfer curve and curve of output of device are determined, transfer curve and
Curve of output measurement result is respectively as shown in Figure 3 and Figure 4.The mobility data of measure see the table below：
In sum, the method for the present invention is prepared simply, and obtains a series of aphthacene derivatives, so as to obtain difference
The organic semiconducting materials with aphthacene as parent nucleus of type.The present invention is modified tetracene material, is improve and four
The mobility of benzene material, is that the application of tetracene material provides the foundation.
It should be appreciated that the application of the present invention is not limited to above-mentioned citing, and for those of ordinary skills, can
To be improved according to the above description or be converted, all these modifications and variations should all belong to the guarantor of claims of the present invention
Shield scope.
Claims (6)
1. a kind of aphthacene organic semiconducting materials, it is characterised in that its structural formula is as follows：
Wherein, R is the one kind in following substituent group：R for C1-C40 straight or branched alkyl, the thiazolinyl of C2-C40, C2-C40
Alkynyl, the straight or branched alkyl of the halogen substiuted of C1-C40, the thiazolinyl of the halogen substiuted of C2-C40, the halogen of C2-C40 takes
The alkynyl in generation, it is adjacent or para-orientation 2- phenyl C1-C40 the alkyl that replaces of straight or branched, the straight chain of C2-C40 or
The alkenyl or alkynyl of side chain, the oxyalkyl that the straight or branched of C1-C40 replaces, it is adjacent or or para-orientation 2- phenyl C2-
The alkenyl or alkynyl of the straight or branched of C40, it is adjacent face or or to fluorine cyclohexyl, alkoxyl, phenyl, trifluoromethoxy,
Trifluoromethylthio, it is adjacent or to fluorine or Trifluoromethoxyphen-l, it is adjacent or or to fluorine or trifluoromethylthio phenyl, thienyl, 3
Or the alkyl that the straight or branched of the C1-C40 of 4 or 5 replacement 2- thienyls replaces, the C1- of 2 or 4 or 5 replacement 3- thienyls
The alkyl that the straight or branched of C40 replaces, the alkane of the straight or branched replacement of the C1-C40 of 3 or 4 or 5 replacement 2- furyls
Base, the alkyl of the straight or branched replacement of the C1-C40 of 2 or 4 or 5 replacement 3- furyls, anthryl, naphthyl, fluorenyl, dibenzofuran base,
Dibenzothiophen base, carbazolyl.
2. a kind of preparation method of aphthacene organic semiconducting materials as claimed in claim 1, it is characterised in that including step
Suddenly：
A, at ambient temperature will in the anhydrous tetrahydro furan solvent of the bromo-derivative containing R substituent and magnesium powder, place room temperature stir
Mix, the post-heating that stirs reaction, backflow obtains compound 1；
B, 2- bromo aphthacenes, catalyst n iCl2(dppp) it is placed in the container of 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 ambient temperature, is heating back
React overnight under the conditions of stream；After reaction terminates, if product is readily soluble, it is quenched successively, extracts, merges organic faciess, organic faciess washing
For several times, compound 2 is obtained Jing after silica gel post separation；If product indissoluble, wash after filtering, chemical combination is obtained by sublimed method purification
Thing 2.
3. preparation method according to claim 2, it is characterised in that in step A, in step A, in 70-80
It is heated to reflux under the conditions of DEG C.
4. preparation method according to claim 2, it is characterised in that in step A, is heated to reflux the time for 12h.
5. preparation method according to claim 2, it is characterised in that in step B, in step B, in 70-80
It is heated to reflux under the conditions of DEG C.
6. preparation method according to claim 2, it is characterised in that in step B, is heated to reflux the time for 12h.
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Citations (3)
| 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 |
| US20090226822A1 (en) * | 2008-03-07 | 2009-09-10 | Kabushiki Kaisha Toshiba | Recording medium |
| 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 |
-
2016
- 2016-10-18 CN CN201610908604.5A patent/CN106565428B/en active Active
Patent Citations (3)
| 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 |
| US20090226822A1 (en) * | 2008-03-07 | 2009-09-10 | Kabushiki Kaisha Toshiba | Recording medium |
| 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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| Title |
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| B. A. HESS, JR等: "DIELS-ALDERREACTIVITYOFPOLYCYCL AROMATICHYDROCARBONS-5", 《TETRAHEDRON》 * |
| KAREN HEMELSOET等: "Bond Dissociation Enthalpies of Large Aromatic Carbon-Centered Radicals", 《J.PHYS.CHEM.A》 * |
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