DE3122992A1 - Process for preparing polysilane - Google Patents
Process for preparing polysilaneInfo
- Publication number
- DE3122992A1 DE3122992A1 DE19813122992 DE3122992A DE3122992A1 DE 3122992 A1 DE3122992 A1 DE 3122992A1 DE 19813122992 DE19813122992 DE 19813122992 DE 3122992 A DE3122992 A DE 3122992A DE 3122992 A1 DE3122992 A1 DE 3122992A1
- Authority
- DE
- Germany
- Prior art keywords
- liquid
- tetrahydrofuran
- polysilane
- lithium
- powder
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000548 poly(silane) polymer Polymers 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 12
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 8
- 239000000725 suspension Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 229910021417 amorphous silicon Inorganic materials 0.000 abstract description 4
- 229910003822 SiHCl3 Inorganic materials 0.000 abstract description 2
- 239000002243 precursor Substances 0.000 abstract description 2
- 229910003818 SiH2Cl2 Inorganic materials 0.000 abstract 1
- 239000000843 powder Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- 239000005052 trichlorosilane Substances 0.000 description 2
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910003826 SiH3Cl Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- SLLGVCUQYRMELA-UHFFFAOYSA-N chlorosilicon Chemical compound Cl[Si] SLLGVCUQYRMELA-UHFFFAOYSA-N 0.000 description 1
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/04—Hydrides of silicon
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Silicon Polymers (AREA)
- Silicon Compounds (AREA)
Abstract
Description
Beschreibung Die Erfindung betrifft ein Verfahren zur Herstellung eines unsubstituierten Polysilans mit der ungefähren Zusammensetzung #SiHn#x, wobei x groß ist -(wie zumindest 10) udd n 1 bis 2 beträgt Unsubstituierte Polysilane sind poteatielle Vorstufen für hydrierte amorphe Siliciumfilme. Diese Filme besitzen Eigenschaften wie Photoleitfähigkeit und können angewandt werden bei der Xerographie, für Bildverstärker und photoelektrische Vorrichtungen einschließlich Solarsellen, die Filme von solchem amorphem Silicium auf Substraten umfassen können. Derartige Solarzellen versprechen den wichtigen Vorteil von mäßigen Kosten für große Flächen bei einer guten Wirksamkeit. Description The invention relates to a method of manufacture an unsubstituted polysilane with the approximate composition # SiHn # x, where x is large - (like at least 10) and n is 1 to 2 unsubstituted polysilanes are potential precursors for hydrogenated amorphous silicon films. Own these films Properties such as photoconductivity and can be used in xerography, for image intensifiers and photoelectric devices including solar panels, which may include films of such amorphous silicon on substrates. Such Solar cells promise the important advantage of moderate costs for large areas with good effectiveness.
Es sind verschiedene Synthesen für Polysilane bekannt.Various syntheses for polysilanes are known.
Einige gehen aus von Verbindungen wie (Si3r2)1 oder Si5H10, die nicht im Handel erhältlich sind, wodurch die Zahl der durchzuführenden Stufen vergrößert wird. Ein anderes Verfahren geht aus von SiIIBr3, das so, wie es im allgemeinen hergestellt wird explosiv sein soll. Eine typische bekannte Synthese, die von Stock und Zaidler in berichte 56B(1923)986 angegeben ist, verläuft folgendermaßen: SiHCl3 + Na # (SiH)x.Some assume that compounds like (Si3r2) 1 or Si5H10 are not are commercially available, thereby increasing the number of steps to be performed will. Another method is based on SiIIBr3, the way it is in general manufactured is supposed to be explosive. A typical well-known synthesis, that of Stock and Zaidler in reports 56B (1923) 986, proceeds as follows: SiHCl3 + Na # (SiH) x.
Da das Natrium jedoch in Form eines Amalgams vorliegt, ist die Abtrennung des Produktes schwierig.However, since the sodium is in the form of an amalgam, the separation difficult of the product.
Ein anderes typisches bekanntes Verfahren, das von Stock und Somieski in Berichte, 56(1923)247 angegeben ist, verläuft folgendermaßen: SiH3Cl + Na -d(SiH2)g Hierbei ist jedoch die Ausbeute gering (theoretisches Maximum 2/3x) und das Hauptprodukt ist Monosilan, das bei Berührung mit Luft explodieren kann.Another typical known procedure, that of Stock and Somieski in reports, 56 (1923) 247, proceeds as follows: SiH3Cl + Na-d (SiH2) g Here, however, the yield is low (theoretical maximum 2 / 3x) and the main product is monosilane, which can explode on contact with air.
Ein anderes Verfahren, das Jedoch leicht zu einer Vielzahl von substituierten Ringverbindungen führt, ist angegeben von Matsumura, Brough und West in JCS Ohemical Communications 1978 S.1092 und verläuft folgendermaßen: Si(CH3)2Cl2 + Li(Tetrahydrofuran) #(CH3)2Si+x + 54 1/2% Ringverbindungen.Another method, however, easily substituted for a variety of Ring links are reported by Matsumura, Brough, and West in JCS Ohemical Communications 1978 p.1092 and proceeds as follows: Si (CH3) 2Cl2 + Li (tetrahydrofuran) # (CH3) 2Si + x + 54 1/2% ring compounds.
Das erfindungsgemäße Verfahren zur Herstellung eines unsubstituierten Polysilans (der ungefähren Zusammensetzung #SiHn#x, wobei x groß und n 1 bis 2 ist), umfaßt die Umsetzung von SiHmX4-m, wobei 1 ein Fluor-, Chlor-, Brom- oder Jodatom und m = 1, 2 oder 3 ist, mit Lithium in einer Suspension in einer Flüssigkeit die gegenüber den Reagentien und dem Produkt inert ist und in der das Polysilan unlöslich ist. X ist vorzugsweise ein Chloratom; x ist vorzugsweise mindestens 10; m ist vorzugsweise 1 oder 2 und insbesondere 2.The inventive method for producing an unsubstituted Polysilane (of approximate composition # SiHn # x, where x is large and n is 1 to 2), comprises the reaction of SiHmX4-m, where 1 is a fluorine, chlorine, bromine or iodine atom and m = 1, 2 or 3, with lithium in suspension in a liquid the is inert to the reagents and product and in which the polysilane is insoluble is. X is preferably a chlorine atom; x is preferably at least 10; m is preferably 1 or 2 and especially 2.
Das Molverhältnis von Litbium:Si E I4-m sollte größer sein als (4 - m):1 und vorzugsweise 2,5(4 - m):1 (d.h. 5:1 für Dihalogensilan) betragen. Das Gewichtsverhältnis von Lithium zu der Flüssigkeit kann z.B. 1:90 betragen.The molar ratio of Litbium: Si E I4-m should be greater than (4 - m): 1 and preferably 2.5 (4 - m): 1 (i.e. 5: 1 for dihalosilane). That The weight ratio of lithium to the liquid can be, for example, 1:90.
Die Flüssigkeit ist vorzugsweise eine solche, in der das ebenfalls anstehende LiX löslich ist und sie ist vorzugsweise in einer ausreichenden Menge vorhanden, um das gesamte entstehende LiX zu lösen. Eine geeignete Flüssigkeit ist Tetrahydrofuran.The liquid is preferably one in which that too pending LiX is soluble and it is preferably in a sufficient amount present to dissolve all of the resulting LiX. A suitable liquid is Tetrahydrofuran.
Die Erfindung wird anhand der folgenden Beißpiele näher erläutert, 3eispiel 1 093 g (0,04 Mol) Lithium wurden in 30 cm³ (27 g) sorgfältig getrocknetem und entgastem Tetrahydrofuran suspendiert. Diese Suspension wurde in Abwesenheit von Feuchtigkeit und Luft mit gasförmigem Dichlorsilan SiH2C12 (0,20 g; 0,002 Mol;) Anfangseindruck bei Raumtemperatur 532 mbar (400 torr) umgesetzt.The invention is explained in more detail with reference to the following bit games, Example 1 093 g (0.04 mol) of lithium was carefully dried in 30 cm³ (27 g) and degassed tetrahydrofuran suspended. This suspension was in the absence of moisture and air with gaseous dichlorosilane SiH2C12 (0.20 g; 0.002 mol;) Initial impression implemented at room temperature 532 mbar (400 torr).
Im Laufe der Zeit fiel ein orangefarbenes luftempfindliches Pulver aus (in diesem Falle nach 18 Stunden) und wurde von der Suspension innerhalb von nicht mehr als 24 Stunden entfernt, um eine weitere Umsetzung des Pulvers möglichst gering zu halten. Das Pulver sank zu Boden während das Lithium eher an der Oberfläche blieb. Das erleichterte die Trennung. Das Tetrahydrofuran zeigte, wenn es anschließend der Luft ausgesetzt warde, keine Reaktionsfähigkeit und das zeigt, daß Silanverbindungen (die in Tetrahydrofuran löslich wären) nicht in nennenswertem Ausmaß gebildet worden waren. Das bei der Reaktion entstandene Lithium-chlorid, das sich in Tetrahydrofuran löst, konnte aus diesem durch Zusatz von Hexan ausgefällt werden0 Das orangefarbene Pulver zeigte im IR-Spektrum Banden, die analog waren, denjenigen von dünnen Filmen von hydriertem amorphem Silicium, das hergestellt worden war durch Glimm-Entladungen.Over time, an orange air-sensitive powder fell off (in this case after 18 hours) and was removed from the suspension within no more than 24 hours away to allow further conversion of the powder if possible to keep it low. The powder sank to the bottom while the lithium tends to be on the surface stayed. That made the separation easier. The tetrahydrofuran showed when it was subsequently exposed to air, no reactivity and this shows that silane compounds (which would be soluble in tetrahydrofuran) were not formed to any appreciable extent was. The lithium chloride formed during the reaction, which is in tetrahydrofuran dissolves, could be precipitated from this by adding hexane0 The orange-colored Powder showed bands in the IR spectrum which were analogous to those of thin films of hydrogenated amorphous silicon produced by glow discharge.
Das Pulver wird daher als unsubstituiertes Polysilan mit der zusammensetzung #SiHn#x angesehen, wobei n ungefähr 2 ist und x (anders nachgewiesen) n$PoMP sein schien.The powder is therefore used as an unsubstituted polysilane with the composition Considered # SiHn # x, where n is approximately 2 and x (proven differently) to be n $ PoMP seemed.
beispiel 2 0,3 g (0,04 Mol) Lithium wurden in 30 om3 (27 g) sorgfältig getrocknetem und entgastem Tetrahydrofuran gelöste Diese Lösung wurde in Abwesenheit von Feuchtigkeit und Luft mit trookenem Trichlorsilan SiHOl3 (0,27 g; 0,002 Mol) bei Raumtemperatur umgesetzt. Das Trichlorsilan schien mit dem Tetrahydrofuran misohbar zu sein.Example 2 0.3 g (0.04 mole) of lithium in 30 om3 (27 g) were carefully This solution was dissolved in the absence of dried and degassed tetrahydrofuran of moisture and air with trooken trichlorosilane SiHOl3 (0.27 g; 0.002 mol) reacted at room temperature. The trichlorosilane appeared to be miscible with the tetrahydrofuran to be.
Im Laufe der Zeit schied sich ein braunes luftempfindliches, festes Pulver ab;(im vorliegenden Falle nach 18 Stunden) das in nicht mehr als 24 Stunden von der Suspension entfernt wurde um eine weitere Reaktion des Pulvers möglichst gering zu halten, Das Pulver sank in der Flüssigkeit zu Boden, während das Lithium eher an der Oberfläche schwamm, Das erleichterte dle Trennung0 Das Tetrahydrofuran zeigte keine Reaktionsfähigkeit, wenn es anschließend der Luft ausgesetzt wurde. Das zeigt, daß Ringverbindungen (die in Tetrahydrofuran löslich wären) nicht in nennenswertem Maße entstanden waren.In the course of time a brown, air-sensitive, firm color separated Powder off; (in the present case after 18 hours) that in no more than 24 hours was removed from the suspension to allow further reaction of the powder if possible To keep it low, the powder sank to the bottom in the liquid, while the lithium rather floated on the surface, that facilitated the separation0 the tetrahydrofuran showed no reactivity when subsequently exposed to air. This shows that ring compounds (which would be soluble in tetrahydrofuran) are not in to a significant extent.
Das braune Pulver wurde aufgrund des IR-Spektrums als unsubsti tuiertes Polysilan der Zusammensetzung (SiH+Xe wobei n ungefähr 1 ist angesehen. Aufgrund anderer Untersuchungen schien x 20 oder größer zu sein.The brown powder was identified as unsubstituted based on the IR spectrum Polysilane of the composition (SiH + Xe where n is considered approximately 1. Due other exams appeared to be x 20 or greater.
Claims (8)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8019050 | 1980-06-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3122992A1 true DE3122992A1 (en) | 1982-02-04 |
| DE3122992C2 DE3122992C2 (en) | 1990-07-19 |
Family
ID=10513960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813122992 Granted DE3122992A1 (en) | 1980-06-11 | 1981-06-10 | Process for preparing polysilane |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5727915A (en) |
| DE (1) | DE3122992A1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10059625A1 (en) * | 2000-09-18 | 2002-05-16 | Peter Plichta | Production of long-chain silanes for use as fuels comprises performing a modified Muller-Rochow synthesis with monochlorosilanes, partially methylated monochlorosilanes or monofluorosilane |
| WO2008031427A2 (en) | 2006-09-14 | 2008-03-20 | Rev Renewable Energy Ventures Inc. | Solid polysilane mixtures |
| US7485691B1 (en) | 2004-10-08 | 2009-02-03 | Kovio, Inc | Polysilane compositions, methods for their synthesis and films formed therefrom |
| US7943721B2 (en) | 2005-10-05 | 2011-05-17 | Kovio, Inc. | Linear and cross-linked high molecular weight polysilanes, polygermanes, and copolymers thereof, compositions containing the same, and methods of making and using such compounds and compositions |
| US8092867B2 (en) | 2006-10-06 | 2012-01-10 | Kovio, Inc. | Silicon polymers, methods of polymerizing silicon compounds, and methods of forming thin films from such silicon polymers |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6027705A (en) * | 1998-01-08 | 2000-02-22 | Showa Denko K.K. | Method for producing a higher silane |
| JP2003313299A (en) | 2002-04-22 | 2003-11-06 | Seiko Epson Corp | Higher order silane composition and method for forming silicon film using the composition |
| DE102010063823A1 (en) * | 2010-12-22 | 2012-06-28 | Evonik Degussa Gmbh | Process for the preparation of hydridosilanes |
| CN105658330B (en) | 2013-10-21 | 2017-07-11 | 三井化学株式会社 | The manufacture catalyst and the manufacture method of high order silanes of high order silanes |
-
1981
- 1981-06-10 JP JP9070781A patent/JPS5727915A/en active Granted
- 1981-06-10 DE DE19813122992 patent/DE3122992A1/en active Granted
Non-Patent Citations (1)
| Title |
|---|
| Chem. Berichte, Bd. 56, 1923, S. 247-252 * |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10059625A1 (en) * | 2000-09-18 | 2002-05-16 | Peter Plichta | Production of long-chain silanes for use as fuels comprises performing a modified Muller-Rochow synthesis with monochlorosilanes, partially methylated monochlorosilanes or monofluorosilane |
| US8057865B1 (en) | 2004-10-08 | 2011-11-15 | Kovio, Inc. | Polysilane compositions, methods for their synthesis and films formed therefrom |
| US8242227B2 (en) | 2004-10-08 | 2012-08-14 | Kovio, Inc. | Doped polysilanes, compositions containing the same, methods for making the same, and films formed therefrom |
| US7485691B1 (en) | 2004-10-08 | 2009-02-03 | Kovio, Inc | Polysilane compositions, methods for their synthesis and films formed therefrom |
| US7491782B1 (en) | 2004-10-08 | 2009-02-17 | Kovio, Inc. | Polysilane compositions, methods for their synthesis and films formed therefrom |
| US7723457B1 (en) | 2004-10-08 | 2010-05-25 | Kovio, Inc. | Polysilane compositions, methods for their synthesis and films formed therefrom |
| US8455604B1 (en) | 2004-10-08 | 2013-06-04 | Kovio, Inc. | Polysilane compositions, methods for their synthesis and films formed therefrom |
| US8236916B1 (en) | 2004-10-08 | 2012-08-07 | Kovio, Inc. | Polysilane compositions, methods for their synthesis and films formed therefrom |
| US7951892B1 (en) | 2004-10-08 | 2011-05-31 | Kovio, Inc. | Doped polysilanes, compositions containing the same, methods for making the same, and films formed therefrom |
| US8378050B2 (en) | 2005-10-05 | 2013-02-19 | Kovio, Inc. | Linear and cross-linked high molecular weight polysilanes, polygermanes, and copolymers thereof, compositions containing the same, and methods of making and using such compounds and compositions |
| US7943721B2 (en) | 2005-10-05 | 2011-05-17 | Kovio, Inc. | Linear and cross-linked high molecular weight polysilanes, polygermanes, and copolymers thereof, compositions containing the same, and methods of making and using such compounds and compositions |
| WO2008031427A3 (en) * | 2006-09-14 | 2008-12-11 | Rev Renewable Energy Ventures | Solid polysilane mixtures |
| WO2008031427A2 (en) | 2006-09-14 | 2008-03-20 | Rev Renewable Energy Ventures Inc. | Solid polysilane mixtures |
| US8092867B2 (en) | 2006-10-06 | 2012-01-10 | Kovio, Inc. | Silicon polymers, methods of polymerizing silicon compounds, and methods of forming thin films from such silicon polymers |
| US8461284B2 (en) | 2006-10-06 | 2013-06-11 | Kovio, Inc. | Silicon polymers, methods of polymerizing silicon compounds, and methods of forming thin films from such silicon polymers |
| US8846507B2 (en) | 2006-10-06 | 2014-09-30 | Thin Film Electronics Asa | Silicon polymers, methods of polymerizing silicon compounds, and methods of forming thin films from such silicon polymers |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5727915A (en) | 1982-02-15 |
| DE3122992C2 (en) | 1990-07-19 |
| JPS641404B2 (en) | 1989-01-11 |
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| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |