CN113861388B - 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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- CN113861388B CN113861388B CN202110948260.1A CN202110948260A CN113861388B CN 113861388 B CN113861388 B CN 113861388B CN 202110948260 A CN202110948260 A CN 202110948260A CN 113861388 B CN113861388 B CN 113861388B
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- 239000002861 polymer material Substances 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 23
- 238000010128 melt processing Methods 0.000 claims abstract description 14
- 229920000642 polymer Polymers 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 12
- 239000000155 melt Substances 0.000 claims description 12
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 10
- 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 7
- 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
- 239000011261 inert gas Substances 0.000 claims description 6
- 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
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [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 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
- 230000008018 melting Effects 0.000 abstract description 5
- 238000002844 melting Methods 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 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
- 238000005566 electron beam evaporation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000005291 magnetic effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000004528 spin coating 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
- 229910004298 SiO 2 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
- 230000005611 electricity Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process 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
- 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
- 239000013557 residual solvent Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
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Abstract
The invention provides a melt-processable polymer material, 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, a preparation method and application thereof.
Background
Since the birth of the last 80 th century spintronics, people gradually recognize that a new generation of microelectronic devices which are more convenient to operate, more powerful, faster in processing speed and lower in energy consumption can be obtained by utilizing the spin properties of electrons, thereby realizing the leap development of the information age. Traditional spintronics materials tend to have strong spin-orbit coupling effect, and the spin relaxation time of electrons is short (nanosecond order), which severely limits the application of the spintronics materials in spintronics devices. The organic semiconductor material is mainly composed of light elements (H, C, N, O and the like) with low atomic numbers, the spin-orbit coupling effect is weak, the spin relaxation time of electrons is long (in the order of seconds), and great potential is reserved in the aspects of realizing efficient spin transport and room temperature spin control. At present, development of efficient spin transport materials has become a key point of sustainable development of organic spin electronics, and is also a necessary premise for further realizing electron spin control and constructing spin information operation processing type electronic devices.
In the aspect of preparing an organic spin electronic device, a thermal evaporation film forming method which is commonly adopted at present is utilized, and although a purer active layer film can be prepared and an external spin scattering center is not easy to introduce, the method is not suitable for an organic semiconductor material processed by a mainstream solution method at present. While organic films prepared by spin-coating solutions typically have residual solvents and vacancies caused by solvent evaporation, these defects tend to form spin scattering centers that impair the spin transport ability of the material.
In view of this, the present invention is specifically proposed.
Disclosure of Invention
In view of the shortcomings 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 spintronics for the first time by a melt processing technology, can reduce defects caused by film formation by a solution method in the melt processing film formation process, and weakens spin scattering. Moreover, the polymer molecule movement is aggravated 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 transportation.
It is a further 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 purposes of the invention is as follows:
a melt processable polymeric material having the structural formula:
wherein, D is any one of thiophene-alkyl-thiophene, selenophene-alkyl-selenophene or bithiophene-alkyl-bithiophene;
a is a bipyridylpyrrolopyrrole dione unit;
n represents the number of repeating units of the polymer.
Wherein D is selected from any one of the following units:
a is:
wherein n is 1 Represents the number of carbon atoms in the alkyl chain linking the two aromatic groups in the D unit, n 1 An integer selected from 2 to 15;
r is a substituted or unsubstituted straight or branched alkyl group having 30 or less carbon atoms.
Further, n 1 An integer selected from 3 to 6; r is a branched alkyl group having 8 to 20 carbon atoms.
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 benzothiophene reacts with dibromoalkane in a first organic solvent under the action of n-butyllithium;
(2) Under the protection of inert gas, the product obtained in the step (1) reacts with trimethyltin chloride in a first organic solvent under the action of n-butyllithium;
(3) And (3) reacting the product obtained in the step (2) with a halogen substituted bipyridyl pyrrolopyrrole dione unit in a second organic solvent under the catalysis of a palladium complex under the protection of inert gas.
Wherein in the step (1), the dibromoalkane is selected from one of dibromoethane, dibromopropane, dibromobutane, dibromopentane, dibromohexane, dibromoheptane, dibromooctane, dibromononane and dibromodecane; the mol ratio of one of thiophene, selenophene or benzothiophene to dibromoalkane is (2-3): 1. The reaction temperature of the step (1) is-5 ℃.
In the step (2), the molar ratio of the product obtained in the step (1) to trimethyltin chloride is 1 (2-3); the reaction temperature in the step (2) is-90 to-70 ℃.
In step (3), the palladium complex is selected from the group consisting of tetrakis triphenylphosphine 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 amount 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 dimethyl tetrahydrofuran; the second organic solvent is selected from one or more of toluene, xylene or chlorobenzene.
The melt-processable polymer material is applied to the preparation of an organic spin valve device, and is formed into a film by a melt processing method.
The invention has the beneficial effects that:
the invention provides a novel melt-processible polymer material, which has a low melting point PDBPyTPT, and can be used for constructing an organic spin valve device by adopting a melt processing method, wherein the device shows a spin valve effect of up to 13%, and has potential application prospects in the field of organic spin electronics;
the invention adopts the melt processing method to prepare the organic spin valve device, and has the advantages of strong operability and easy repetition.
Drawings
FIG. 1 is a DSC curve of the polymer PDBPyTPT.
Fig. 2 is a magnetic resistance curve (MR) at room temperature of a polymer PDBPyTPT-based organic spin valve device prepared using a melt processing method.
Detailed Description
The following preferred examples illustrate the invention but are not intended to limit the scope thereof.
The means or materials used in the examples are all technical means or materials known in the art unless specifically stated otherwise.
Example 1
A melt processable polymeric material having the structural formula:
the present example also provides a method of preparing the polymer:
(1) N-butyllithium (1.2 mol) is slowly dripped into tetrahydrofuran dissolved with thiophene (1 mol) under the protection of nitrogen and at a low temperature (0 ℃), and then 1, 3-dibromopropane (0.4 mol) is added to obtain a precursor of a compound TPT;
(2) N-butyllithium (2.4 mol) is slowly dripped into tetrahydrofuran dissolved with a compound TPT precursor (1 mol) under the protection of nitrogen and at a low temperature (-78 ℃), and then trimethyltin chloride (3 mol) is added to obtain the compound TPT;
(3) Under the protection of nitrogen and at the temperature of 110 ℃, the compound DBPyBr-20 (1 mmol) and the compound TPT (1 mol) are polymerized in toluene for 12 hours under the action of a tetraphenylphosphine palladium catalyst (0.01 mmol) to obtain the polymer material PDBPyTPT.
The DSC curve of the polymer PDBPyTPT is shown in FIG. 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 structure based on the melt processing PDBPyTPT is Co/AlOx/PDBPyTPT/Ni 80 Fe 20 . First, in the cleaned SiO 2 Electricity utilization on a substrateBeamlet evaporationA 20nm ferromagnetic metal Co was evaporated as bottom electrode. Subsequently, the electron beam evaporation method is continued for +.>Metal Al of 2nm is evaporated at a rate of 2 nm. Then, PDBPyTPT was formed into a film by spin coating and heated above the melting point for 60min. Finally, evaporating 15nm Ni on the top electrode by using electron beam 80 Fe 20 . The electron beam evaporation process is carried out in a high vacuum chamber, and the organic layer film forming and melt processing processes are carried out in a dry and oxygen-free glove box.
Fig. 2 is a magnetic resistance curve (MR) at room temperature of an organic spin valve device based on polymer PDBPyTPT prepared using a melt processing method, and shows that the organic spin valve device constructed using the melt processing method can exhibit a spin valve effect as high as 13%.
Example 3
A melt processable polymeric material having the structural formula:
the selenophene was used as a starting material and produced in the same manner as in example 1.
Example 4
A melt processable polymeric material having the structural formula:
the same procedure as in example 1 was followed except that benzothiophene was used as the starting material.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention, and are not limiting; although the 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 scheme described in the foregoing embodiments can be modified or some technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit and scope of the technical solutions of the embodiments of the present invention.
Claims (9)
1. The application of a melt-processable polymer material in the preparation of an organic spin valve device is characterized in that the polymer material is formed into a film by adopting a melt processing method, and the polymer material has the following structural general formula:
wherein D is any one of thiophene-alkyl-thiophene, selenophene-alkyl-selenophene or benzothiophene-alkyl-benzothiophene;
a is a bipyridylpyrrolopyrrole dione unit;
n represents the number of repeating units of the polymer.
2. Use of a melt processable polymer material according to claim 1 in the preparation of an organic spin valve device, wherein D is selected from any one of the following units:
a is:
wherein n is 1 Represents the number of carbon atoms in the alkyl chain linking the two aromatic groups in the D unit, n 1 An integer selected from 2 to 15;
r is a substituted or unsubstituted straight or branched alkyl group having 30 or less carbon atoms.
3. Use of a melt processable polymer material according to claim 2 in the preparation of an organic spin valve device, characterized in that n 1 An integer selected from 3 to 6; r is a branched alkyl group having 8 to 20 carbon atoms.
4. Use of the melt-processable polymeric material of claim 1 in the preparation of an organic spin valve device, wherein the method of preparing the melt-processable polymeric material comprises the steps of:
(1) Under the protection of inert gas, one of thiophene, selenophene or benzothiophene reacts with dibromoalkane in a first organic solvent under the action of n-butyllithium;
(2) Under the protection of inert gas, the product obtained in the step (1) reacts with trimethyltin chloride in a first organic solvent under the action of n-butyllithium;
(3) And (3) reacting the product obtained in the step (2) with a halogen substituted bipyridyl pyrrolopyrrole dione unit in a second organic solvent under the catalysis of a palladium complex under the protection of inert gas.
5. The use of a melt processable polymer material according to claim 4 in the preparation of an organic spin valve device, wherein in step (1) the dibromoalkane is selected from one of dibromoethane, dibromopropane, dibromobutane, dibromopentane, dibromohexane, dibromoheptane, dibromooctane, dibromononane, dibromodecane; the molar ratio of one of thiophene, selenophene or benzothiophene to dibromoalkane is (2-3): 1.
6. Use of a melt processable polymer material according to claim 5 in the preparation of an organic spin valve device, wherein the reaction temperature of step (1) is between-5 and 5 ℃.
7. The use of a melt processable polymer material according to claim 4 in the preparation of an organic spin valve device, wherein in step (2), the molar ratio of the product obtained in step (1) to trimethyltin chloride is 1 (2-3); the reaction temperature in the step (2) is-90 to-70 ℃.
8. The use of a melt processable polymer material according to claim 4 in the preparation of an organic spin valve device, wherein in step (3) the palladium complex is selected from the group consisting of tetrakis triphenylphosphine 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 amount of the product obtained in the step (2); the reaction temperature of the step (3) is 75-120 ℃.
9. Use of a melt processable polymer material according to any one of claims 4-8 in the preparation of an organic spin valve device, 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.
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