CN1310182A - Organic electronic material and its preparation - Google Patents
Organic electronic material and its preparation Download PDFInfo
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- CN1310182A CN1310182A CN 01105359 CN01105359A CN1310182A CN 1310182 A CN1310182 A CN 1310182A CN 01105359 CN01105359 CN 01105359 CN 01105359 A CN01105359 A CN 01105359A CN 1310182 A CN1310182 A CN 1310182A
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- mole
- organic electronic
- electronic material
- suspension liquid
- benzene
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Abstract
The organic molecular material is named as 3,9-di(dicyanomethylene)-2,4,8,10-tetratheospiro[5,5] undecane, has molecular expression of C13H18N4S4, and is yellowish solid with smelting point over 300 deg.c. It can form homogeneous amorphous film with excellent heat stability and may be used as molecular electronic material in, say, microelectronic device and molecular electronic device.
Description
The present invention relates to a kind of organic molecule material and preparation method thereof.
The performance of organic molecule material depends primarily on the structure of molecule itself and the character of functional group.Light, electricity, magnetic signal can be controlled and modify to the special organic molecule material of many structures, wherein some can replace inorganic semiconductor and metallic substance to be used to make multiple electron device, such as: electric memory, field-effect transistor, organic conducting wire, display device and electrical condenser or the like, application prospect is boundless.The advantage of organic electronic material is little, the easy acquisition of effect volume, cheap, but the film forming properties and the thermostability of most materials are relatively poor, and this has just limited the practical application of these materials.Therefore, design and synthesize the high-performance organic electronic material and just become important step in the investigation of materials.
The object of the present invention is to provide a kind of organic electronic material and preparation method thereof with high thermal stability.
The organic electronic material that the present invention proposes, its compound name is called: 3, two (the dicyano methylene radical)-2 of 9-, 4,8,10-four thia spiral shells [5,5] undecane, be designated as SCN, English name is: 3, and 9-di (dicyanomethylene)-2,4,8,10-tetrathiaspiro[5.5] undecane, molecular formula is C
13H
8N
4S
4The structural formula of this compound is:
The C that the present invention proposes
13H
8N
4S
4Be a kind of new compound, be light yellow solid, fusing point is greater than 300 ℃.This compound structure is more special, is spirane structure, so be not easy to tie prosperous.The enough vacuum thermal evaporation film forming of this compound energy, it is light yellow that film is, and the film of formation has good thermostability, and promptly (on 150 ℃) can long-time (greater than 3 hours) keep stable under the high temperature in atmospheric environment.Owing to be not easy crystallization, therefore the film that makes can not produce inhomogeneously because of crystallization, keeps uniform metamict easily.The inhomogeneity characteristics of the high-melting-point of this compound and film, particularly important when making molecular device and electron device makes it have wide practical value.For example, can be used for making microelectronic device and molecular electronic device etc.The synthetic cost of this compound S CN and commonly used molecular material (such as, TCNQ) suitable, but its performance more is better than TCNQ equimolecular material.
The synthetic method of The compounds of this invention is as follows:
Reaction process is carried out in nitrogen atmosphere, with sodium hydride (NaH)-benzene suspension liquid is a unit mole, (DMF is N with the propane dinitrile-DMF of 0.4-0.6 mole, the code name of dinethylformamide) drips of solution adds in above-mentioned sodium hydride-benzene suspension liquid, produce with hydrogen, at room temperature stir, the time was generally 10-50 minute; Be added dropwise to the dithiocarbonic anhydride-benzole soln of 0.5-0.75 mole then, continue to stir, obtain yellow suspension liquid; The tetraiodo that adds the 0.1-0.25 mole then, heated 5-24 hour in 50-100 ℃ for neopentane (that is: tetraiodo methylmethane); Remove benzene, remaining liquid is poured in the water, have yellow mercury oxide to separate out, filtration, drying are used DMF and acetonitrile recrystallization again, promptly get required compound SCN, are light yellow solid, and fusing point is greater than 300 ℃.
Ultimate analysis: C 44.87, H 2.40, and N 15.90%.
C
13Nucleus magnetic resonance ppm:38.3,40.5,73.9,112.5,188.7.
Embodiment:
Reaction process is carried out in nitrogen atmosphere.In reaction flask, drop into 0.8 gram sodium hydride (60%, 0.02 mole), add 20 milliliters of benzene, make suspension liquid under stirring.0.66 gram (0.01 mole) propane dinitrile is dissolved in N, in the dinethylformamide (DMF), and this solution (about 20 milliliters) is added drop-wise in the reaction flask, produce with hydrogen.Stir under the room temperature after 30 minutes, drip the benzole soln (about 10 milliliters) that contains 0.011 mole of carbon disulfide, continue stirring and obtained yellow suspension liquid in 30 minutes.Then, add 0.0048 mole of tetraiodo, heating more than 10 hours about 70 ℃ for neopentane (that is: tetraiodo methylmethane).Boil off benzene, debris is poured in 100 ml waters, have yellow mercury oxide to separate out, filtration drying is used DMF and acetonitrile recrystallization again, obtains SCN, is light yellow solid, and fusing point is greater than 300 ℃.With SCN vacuum thermal evaporation thin films, this film is light yellow, has good thermostability, can keep stable for a long time under 150 ℃ of high temperature, and the homogeneity of film is very good.This film can be used to prepare molecular switch, electrical storage etc.
Claims (2)
1, a kind of organic electronic material, its molecular formula are C
13H
18N
4S
4, its chemical structural formula is:
2, a kind of organic electronic material C
13H
18N
4S
4The preparation method, it is characterized in that reaction process carries out in nitrogen atmosphere, with sodium hydride-benzene suspension liquid is a unit mole, propane dinitrile-DMF the drips of solution of 0.4-0.6 mole is added in above-mentioned sodium hydride-benzene suspension liquid, produce with hydrogen, at room temperature stir, the time was generally 10-50 minute; Be added dropwise to the dithiocarbonic anhydride-benzole soln of 0.5-0.75 mole then, continue to stir, obtain yellow suspension liquid; The tetraiodo that adds the 0.1-0.25 mole then, heated 5-24 hour in 50-100 ℃ for neopentane; Remove benzene, in the entry of remaining liquid example, have yellow mercury oxide to fold, filtration, drying are used DMF and acetonitrile recrystallization again, promptly get required compound SCN.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011053593A CN1139594C (en) | 2001-02-20 | 2001-02-20 | Organic electronic material and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011053593A CN1139594C (en) | 2001-02-20 | 2001-02-20 | Organic electronic material and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1310182A true CN1310182A (en) | 2001-08-29 |
| CN1139594C CN1139594C (en) | 2004-02-25 |
Family
ID=4654440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB011053593A Expired - Fee Related CN1139594C (en) | 2001-02-20 | 2001-02-20 | Organic electronic material and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1139594C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106366135A (en) * | 2016-08-05 | 2017-02-01 | 宁波金特信钢铁科技有限公司 | Preparation method for spiroheterocyclic molecule electronic material |
-
2001
- 2001-02-20 CN CNB011053593A patent/CN1139594C/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106366135A (en) * | 2016-08-05 | 2017-02-01 | 宁波金特信钢铁科技有限公司 | Preparation method for spiroheterocyclic molecule electronic material |
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| Publication number | Publication date |
|---|---|
| CN1139594C (en) | 2004-02-25 |
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