IP Library Granted Patent US 9,464,099
Granted Patent B2
US 9,464,099 · App. 14/435,528 · Granted Oct 11, 2016

Method for producing hydrosilanes containing carbon

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Quick Facts
Patent No.
US 9,464,099
App. No.
14/435,528
Granted
Oct 11, 2016
Kind
B2
Abstract

The present invention provides processes for preparing carbon-containing hydridosilanes, in which an optionally boron- or phosphorus-doped hydridosilane is reacted without catalyst and reducing agent with at least one carbon source selected from linear, branched or cyclic carbosilanes, halogenated hydrocarbons, carbenes, alkyl azides, diazomethane, dimethyl sulphate or alcohols, the carbon-containing hydridosilane oligomers obtainable by the process and the use thereof.

Claims (38)

1. A process for preparing carbon-containing hydridosilanes, in which

an optionally boron- or phosphorus-doped hydridosilane is reacted

without catalyst and reducing agent

with at least one carbon source selected from

linear or branched carbosilanes of the generic formula Si b H 2b+2−y R y where b≧2, 1≦y≦2b+2 and R=C 1 -C 10 -alkyl, C 6 -C 10 -aryl, C 7 -C 14 -aralkyl

cyclic carbosilanes of the generic formula Si c H 2c−y R y where c≧3, 1≦y≦2c and R=C 2 -C 10 -alkyl, C 6 -C 10 -aryl, C 7 -C 14 -aralkyl,

halogenated hydrocarbons of the generic formula C n H 2n+2−y X y where 1≦n≦5, 1≦y ≦12 and X=F, Cl, Br, I,

carbenes of the generic formula CRR′ with R, R′ =

—H, —F, —Br, —I, —C 1 -C 10 -(cyclo)alkyl, —C 2 -C 10 -(cyclo)alkenyl, —C 6 -C 10 -aryl,

—C 1 -C 10 -(cyclo)heteroalkyl, —C 2 -C 10 -(cyclo)heteroalkenyl, —C 5 -C 10 -heteroaryl,

—C 7 -C 14 -aralkyl,

—OR″ where R″ =—C 1 -C 10 -(cyclo)alkenyl, —C 2 -C 10 -(cyclo)alkenyl, —C 6 -C 10 -aryl,

—NR′″ 2 where R′″=—C 1 -C 10 -(cyclo)alkyl, —C 2 -C 10 -(cyclo)alkenyl, —C 6 -C 10 -aryl,

—Si n R IV 2n+1 where R IV =—H, —C 1 -C 10 -(cyclo)alkyl, —C 2 -C 10 -(cyclo)alkenyl, —C 6 -C 10 -aryl,

—(CO)—R v where R v =—H, —C 1 -C 10 -(cyclo)alkyl, —C 2 -C 10 -(cyclo)alkenyl, —C 6 -C 10 -aryl,

—(CO)—OR vi where R vi =—H, —C 1 -C 10 -(cyclo)alkyl, —C 2 -C 10 -(cyclo)alkenyl, —C 6 -C 10 -aryl,

—CN, —NC,

SR vii where R vii =—H, —C 1 -C 10 -(cyclo)alkyl, —C 2 -C 10 -(cyclo)alkenyl, —C 6 -C 10 -aryl,

—S(O) 2 R viii where R viii =—H, —C 1 -C 10 -(cyclo)alkyl, —C 2 -C 10 -(cyclo)alkenyl, —C 6 -C 10 -aryl,

—P(R ix ) 2 where R ix =—H, —C 1 -C 10 -(cyclo)alkyl, —C 2 -C 10 -(cyclo)alkenyl, —C 6 -C 10 -aryl,

or where R and R′ together represent a bidentate bridging radical selected from =C 3 -C 20 -(cyclo)alkyl, =C 3 -C 20 -(cyclo)alkenyl, =C 3 -C 20 -(cyclo)heteroalkyl, =C 3 -C 20 -(cyclo)heteroalkenyl or =C 6 -C 14 -(hetero)aralkyl,

—CO, CN − ,

alkyl azides of the generic formula N 3 R x where R x =—C 1 -C 10 -(cyclo)alkyl, —C 2 -C 10 -(cyclo)alkenyl, —C 6 -C 10 -aryl, —C 1 -C 10 -(cyclo)heteroalkyl, —C 2 -C 10 -(cyclo)heteroalkenyl, C 5 -C 10 -heteroaryl, —C 7 -C 14 -aralkyl,

diazomethane H 2 CN 2 ,

dimethyl sulphate C 2 H 6 O 4 S, or

alcohols of the generic formula HOR xi , where R xi =—C 1 -C 10 -(cyclo)alkyl, —C 2 -C 10 (cyclo)alkenyl, —C 6 -C 10 -aryl, —C 1 -C 10 -(cyclo)heteroalkyl, —C 2 -C 10 (cyclo)heteroalkenyl, —C 5 -C 10 -heteroaryl, or —C 7 -C 14 -aralkyl.

2. The process according to claim 1 , wherein the hydridosilane used as the reactant has the generic formula Si n {BH} x {PH} y H 2n+2 where n=3−10, x=0 or 1 and y =0 or 1, with the proviso that at least one of the parameters x and y=0.

3. The process according to claim 2 , wherein the hydridosilane used as the reactant has the generic formula Si n H 2+l where n=3−10.

4. The process according to claim 3 , wherein the reaction with the at least one carbon source is effected in the presence of at least one further hydridosilane compound having a weight-average molecular weight of at least 500 g/mol.

5. The process according to claim 3 , wherein the reaction of the hydridosilane with the carbon source is effected in the presence of at least one dopant selected from the group consisting of AlMe 3 , AlCl 3 , BCl 3 , BF 3 , B 2 H 6 , BH 3 :THF, BEt 3 ,BMe 3 , PH 3 and P 4 .

6. The process according to claim 1 , wherein the carbon source has a weight-average molecular weight of 300 to 4000 g/mol.

7. The process according to claim 1 , wherein the reaction is effected thermally and/or with electromagnetic irradiation.

8. A carbon-containing hydridosilane oligomer preparable by a process according to claim 1 .

9. A method for producing an electronic or optoelectronic component layer(s) comprising forming said layer(s) from a composition comprising a hydridosilane oligomer produced according to the process of claim 1 .

10. A photovoltaic, transitor or other electronic or optoeltronic component layer(s) produced by the method according to claim 9 .

11. A method for producing a silicon-containing layer(s) comprising forming layer(s) from a composition comprising a carbon-containing hydridosilane oligomer preparable according to claim 1 .

12. Silicon-containing layer(s) produced by the method according to claim 11 .

13. Elemental silicon-containing layer(s) produced by the according to claim 11 .

Assignments (3)
CHANGE OF NAME Recorded Jan 31, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051765/0166 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 1, 2015
From: EVONIK INDUSTRIES AG
To: EVONIK DEGUSSA GMBH
Reel/Frame 037174/0982 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 14, 2015
From: TRAUT, STEPHAN; WIEBER, STEPHAN; PATZ, MATTHIAS; COELLE, MICHAEL; STUEGER, HARALD; WALKNER, CHRISTOPH
To: EVONIK INDUSTRIES AG
Reel/Frame 035403/0466 →