CN113861388A - Melt-processable polymer material, and preparation method and application thereof - Google Patents
Melt-processable polymer material, and preparation method and application thereof Download PDFInfo
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- CN113861388A CN113861388A CN202110948260.1A CN202110948260A CN113861388A CN 113861388 A CN113861388 A CN 113861388A CN 202110948260 A CN202110948260 A CN 202110948260A CN 113861388 A CN113861388 A CN 113861388A
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- melt
- polymeric material
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- selenophene
- bithiophene
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- 239000002861 polymer material Substances 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 27
- 229920000642 polymer Polymers 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 239000000155 melt Substances 0.000 claims description 13
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 12
- 238000010128 melt processing Methods 0.000 claims description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 claims description 5
- 230000009471 action Effects 0.000 claims description 5
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 claims description 5
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 claims description 5
- 229930192474 thiophene Natural products 0.000 claims description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 2
- HFVIYAZBVIGNAN-UHFFFAOYSA-N 1,1-dibromodecane Chemical compound CCCCCCCCCC(Br)Br HFVIYAZBVIGNAN-UHFFFAOYSA-N 0.000 claims description 2
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 claims description 2
- SAWCWRKKWROPRB-UHFFFAOYSA-N 1,1-dibromohexane Chemical compound CCCCCC(Br)Br SAWCWRKKWROPRB-UHFFFAOYSA-N 0.000 claims description 2
- FSTKSTMFMLANPA-UHFFFAOYSA-N 1,1-dibromononane Chemical compound CCCCCCCCC(Br)Br FSTKSTMFMLANPA-UHFFFAOYSA-N 0.000 claims description 2
- STBMZSJLFYGOJU-UHFFFAOYSA-N 1,1-dibromooctane Chemical compound CCCCCCCC(Br)Br STBMZSJLFYGOJU-UHFFFAOYSA-N 0.000 claims description 2
- ATWLRNODAYAMQS-UHFFFAOYSA-N 1,1-dibromopropane Chemical compound CCC(Br)Br ATWLRNODAYAMQS-UHFFFAOYSA-N 0.000 claims description 2
- BXXWFOGWXLJPPA-UHFFFAOYSA-N 2,3-dibromobutane Chemical compound CC(Br)C(C)Br BXXWFOGWXLJPPA-UHFFFAOYSA-N 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- NTIGNJOEVBTPJJ-UHFFFAOYSA-N 3,3-dibromopentane Chemical compound CCC(Br)(Br)CC NTIGNJOEVBTPJJ-UHFFFAOYSA-N 0.000 claims description 2
- TZFKFDQPHRPMKH-UHFFFAOYSA-N 4,4-dibromoheptane Chemical compound CCCC(Br)(Br)CCC TZFKFDQPHRPMKH-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 1
- 238000002844 melting Methods 0.000 abstract description 6
- 230000008018 melting Effects 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 3
- 238000003672 processing method Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 238000005566 electron beam evaporation Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000001808 coupling effect Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- 229910017107 AlOx Inorganic materials 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- -1 dibromo alkane Chemical class 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000005294 ferromagnetic effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
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Abstract
The invention provides a melt-processable polymer material and a preparation method and application thereof. The structural general formula of the melt-processable polymer material is as follows:
Description
Technical Field
The invention relates to the technical field of spinning, in particular to a melt-processable polymer material and a preparation method and application thereof.
Background
Since the birth of spintronics at the end of the last 80 th century, people gradually realize that by utilizing the spin property of electrons, a new-generation microelectronic device with more convenient operation and control, stronger function, faster processing speed and lower energy consumption can be obtained, thereby realizing the leap development of the information age. The traditional spintronics material has stronger spin-orbit coupling effect, the spin relaxation time of electrons is short (nanosecond level), and the application of the traditional spintronics material in the aspect of spintronics is severely limited. The organic semiconductor material is mainly composed of light elements (H, C, N, O and the like) with lower atomic number, the spin-orbit coupling effect of the organic semiconductor material is weak, the spin relaxation time of electrons is very long (in the order of seconds), and the organic semiconductor material has great potential in the aspects of realizing high-efficiency spin transport and room-temperature spin control. At present, the development of high-efficiency spin transport materials has become the key point of the continuous development of organic spintronics, and is also the necessary premise for further realizing the electronic spin control and constructing a spin information operation processing type electronic device.
In the preparation of organic spin electronic devices, a thermal evaporation film forming method which is commonly adopted at present is utilized, and although a relatively pure active layer film can be prepared and a foreign spin scattering center is not easy to introduce, the method is not suitable for the organic semiconductor material which is processed by the mainstream solution method at present. The organic thin film prepared by the solution spin coating method generally has residual solvent and vacancies caused by solvent volatilization, and the defects tend to form spin scattering centers to weaken the spin transport capability of the material.
In view of this, the present invention is specifically set forth.
Disclosure of Invention
In view of the deficiencies of the prior art, it is an object of the present invention to provide a melt processable polymeric material. The polymer material has low melting point, is applied to the spinning electronics by a melt processing process for the first time, can reduce the defects caused by film formation by a solution method in the melt processing film formation process, and weakens the spin scattering. In addition, the polymer molecules are accelerated in the melt processing process, the aggregation state structure of the organic layer can be optimized, and the method has important scientific significance for realizing high-efficiency and long-distance spin transport.
It is another object of the present invention to provide a method for preparing said melt processable polymeric material.
It is a further object of the present invention to provide the use of said melt processable polymeric material.
The technical scheme for realizing the above purpose of the invention is as follows:
a melt processable polymeric material having the general structural formula:
wherein D is any one of thiophene-alkyl-thiophene, selenophene-alkyl-selenophene or bithiophene-alkyl-bithiophene;
a is a dipyridyl pyrrolopyrroledione unit;
n represents the number of repeating units of the polymer.
Wherein D is selected from any one of the following units:
a is as follows:
wherein n is1Represents the number of carbon atoms in the alkyl chain connecting the two aromatic groups in the D unit, n1An integer selected from 2 to 15;
r is a substituted or unsubstituted linear or branched alkyl group having 30 or less carbon atoms.
Further, n1An integer selected from 3 to 6; r is a branched alkyl group of 8 to 20 carbon atoms in number.
The preparation method of the melt-processable polymer material comprises the following steps:
(1) under the protection of inert gas, one of thiophene, selenophene or bithiophene reacts with dibromoalkane in a first organic solvent under the action of n-butyl lithium;
(2) under the protection of inert gas, reacting the product obtained in the step (1) with trimethyl tin chloride in a first organic solvent under the action of n-butyl lithium;
(3) and (3) under the protection of inert gas, reacting the product obtained in the step (2) with a halogen substituted dipyridyl pyrrolo-pyrrole-dione unit in a second organic solvent under the catalysis of a palladium complex.
In the step (1), the dibromo alkane is selected from one of dibromoethane, dibromopropane, dibromobutane, dibromopentane, dibromohexane, dibromoheptane, dibromooctane, dibromononane and dibromodecane; the molar ratio of one of thiophene, selenophene or bithiophene to dibromoalkane is (2-3) to 1. The reaction temperature in the step (1) is-5 ℃.
In the step (2), the molar ratio of the product obtained in the step (1) to trimethyl tin chloride is 1 (2-3); the reaction temperature of the step (2) is-90 to-70 ℃.
In the step (3), the palladium complex is selected from tetratriphenylphosphine palladium or a combination of tris (dibenzylideneacetone) dipalladium and tri-o-tolylphosphine; the addition amount of the palladium complex is 0.01-1% of the molar weight of the product obtained in the step (2); the reaction temperature of the step (3) is 75-120 ℃.
Wherein the first organic solvent is selected from one or more of tetrahydrofuran and dimethyltetrahydrofuran; the second organic solvent is selected from one or more of toluene, xylene or chlorobenzene.
The invention discloses application of a melt-processable polymer material in preparation of an organic spin valve device, wherein the polymer material is formed into a film by a melt processing method.
The invention has the beneficial effects that:
the invention provides a novel melt-processable polymer material, wherein the polymer material PDBPyTPT has a lower melting point, an organic spin valve device can be constructed by adopting a melt processing method, the device shows a spin valve effect as high as 13 percent, and the potential application prospect is shown in the field of organic spin electronics;
the method for preparing the organic spin valve device by adopting the melt processing method has the advantages of strong operability and easy repetition.
Drawings
FIG. 1 is a DSC curve of polymer PDBPyTPT.
FIG. 2 is a graph of the Magnetoresistance (MR) at room temperature for an organic spin valve device based on the polymer PDBPyTPT prepared by melt processing.
Detailed Description
The present invention will now be illustrated by the following preferred examples, which should not be construed as limiting the scope of the invention.
Unless otherwise indicated, all means or materials used in the examples are technical means or materials known in the art.
Example 1
A melt processable polymeric material having the formula:
this example also provides a method for preparing the polymer:
(1) under the conditions of nitrogen protection and low temperature (0 ℃), slowly dropwise adding n-butyllithium (1.2mol) into tetrahydrofuran dissolved with thiophene (1mol), and then adding 1, 3-dibromopropane (0.4mol) to obtain a precursor of a compound TPT;
(2) under the conditions of nitrogen protection and low temperature (-78 ℃), slowly dropwise adding n-butyllithium (2.4mol) into tetrahydrofuran in which a compound TPT precursor (1mol) is dissolved, and then adding trimethyl tin chloride (3mol) to obtain a compound TPT;
(3) under the protection of nitrogen and at the temperature of 110 ℃, a compound DBPyBr-20(1mmol) and a compound TPT (1mol) are subjected to a polymerization reaction in toluene for 12 hours under the action of a tetratriphenylphosphine palladium catalyst (0.01mmol), so as to obtain a polymer material PDBPyTPT.
The DSC curve of the polymer PDBPyTPT is shown in figure 1, indicating that the polymer material PDBPyTPT has a lower melting point.
EXAMPLE 2 organic spin valve device
In this example, a PDBPyTPT-based organic spin valve device was prepared and characterized using a melt processing method as follows:
the organic spin valve device based on the melt processing PDBPyTPT has the structure of Co/AlOx/PDBPyTPT/Ni80Fe20. First, in the cleaned SiO2The substrate is coated by electron beam evaporation20nm of ferromagnetic metal Co was evaporated as bottom electrode. Then, the electron beam evaporation method is continuously adopted to2nm of metallic Al is evaporated. Then, pdbpyttp was film-formed by spin coating and heated to above the melting point for 60 min. Finally, a top electrode 15nm Ni was evaporated by electron beam80Fe20. The electron beam evaporation process is carried out in a high vacuum chamber, and the organic layer film forming and melting process are carried out in an anhydrous and oxygen-free glove box.
FIG. 2 is the magnetoresistive curve (MR) at room temperature of an organic spin valve device based on the polymer PDBPyTPT prepared by a melt processing method, and the result shows that the organic spin valve device constructed by the melt processing method can show the spin valve effect of up to 13%.
Example 3
A melt processable polymeric material having the formula:
prepared by using selenophene as a starting material by the same method as in example 1.
Example 4
A melt processable polymeric material having the formula:
was prepared in the same manner as in example 1, using bithiophene as a starting material.
Finally, it should be noted that: the above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.
Claims (10)
2. A melt processable polymeric material according to claim 1 wherein D is selected from any one of the following units:
a is as follows:
wherein n is1Represents the number of carbon atoms in the alkyl chain connecting the two aromatic groups in the D unit, n1An integer selected from 2 to 15;
r is a substituted or unsubstituted linear or branched alkyl group having 30 or less carbon atoms.
3. A melt processable polymeric material according to claim 1 or 2 wherein n is n1An integer selected from 3 to 6; r is a branched alkyl group of 8 to 20 carbon atoms in number.
4. A method of producing a melt processable polymeric material according to any one of claims 1 to 3, comprising the steps of:
(1) under the protection of inert gas, one of thiophene, selenophene or bithiophene reacts with dibromoalkane in a first organic solvent under the action of n-butyl lithium;
(2) under the protection of inert gas, reacting the product obtained in the step (1) with trimethyl tin chloride in a first organic solvent under the action of n-butyl lithium;
(3) and (3) under the protection of inert gas, reacting the product obtained in the step (2) with a halogen substituted dipyridyl pyrrolo-pyrrole-dione unit in a second organic solvent under the catalysis of a palladium complex.
5. A method of producing a melt-processable polymer material according to claim 4, wherein in the step (1), the dibromoalkane is selected from one of dibromoethane, dibromopropane, dibromobutane, dibromopentane, dibromohexane, dibromoheptane, dibromooctane, dibromononane and dibromodecane; the molar ratio of one of thiophene, selenophene or bithiophene to dibromoalkane is (2-3) to 1.
6. A method of producing a melt processable polymeric material according to claim 5, wherein the reaction temperature in step (1) is from-5 ℃ to 5 ℃.
7. A method for preparing a melt-processable polymer material according to claim 4, wherein in the step (2), the molar ratio of the product obtained in the step (1) to the trimethyl tin chloride is 1 (2-3); the reaction temperature of the step (2) is-90 to-70 ℃.
8. A method of preparing a melt processable polymeric material according to claim 4, wherein in step (3), the palladium complex compound is selected from tetrakistriphenylphosphine palladium or a combination of tris (dibenzylideneacetone) dipalladium and tri-o-tolylphosphine; the addition amount of the palladium complex is 0.01-1% of the molar weight of the product obtained in the step (2); the reaction temperature in the step (3) is 75-120 ℃.
9. A method of preparing a melt processable polymeric material according to any one of claims 4 to 8, wherein the first organic solvent is selected from one or more of tetrahydrofuran, dimethyltetrahydrofuran; the second organic solvent is selected from one or more of toluene, xylene or chlorobenzene.
10. Use of a melt processable polymeric material according to any one of claims 1 to 3 in the manufacture of an organic spin valve device wherein the polymeric material is formed into a film by a melt processing method.
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US20160351814A1 (en) * | 2015-05-26 | 2016-12-01 | Purdue Research Foundation | Methods and compositions for enhancing processability and charge transport of polymer semiconductors |
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