IP Library › Granted Patent US 11,407,922
Granted Patent B2
US 11,407,922 · App. 16/087,464 · Granted Aug 9, 2022

Si-containing film forming compositions and methods of making and using the same

Inventors: Manish Khandelwal (Somerset, NJ); Sean Kerrigan (Princeton, NJ); Jean-Marc Girard (Versailles, FR); Antonio Sanchez (Tsukuba, JP); Peng Zhang (Montvale, NJ); Yang Wang (Garnet Valley, PA)
Assignees: L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude; American Air Liquide, Inc.
C09D183/16C07F7/10C08G77/60C08G77/62C08G77/70
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Quick Facts
Patent No.
US 11,407,922
App. No.
16/087,464
Granted
Aug 9, 2022
Kind
B2
Abstract

Si-containing film forming compositions are disclosed comprising a precursor having the formula [—NR—R 4 R 5 Si—(CH 2 ) t —SiR 2 R 3 —] n wherein n=2 to 400; R, R 2 , R 3 , R 4 , and R 5 are independently H, a hydrocarbon group, or an alkylamino group, and provided that at least one of R 2 , R 3 , R 4 , and R 5 is H; and R is independently H, a hydrocarbon group, or a silyl group. Exemplary pre-cursors include, but are not limited to, [—NH—SiH 2 —CH 2 —SiH 2 —] n , and [—N(SiH 2 —CH 2 —SiH 3 )—SiH 2 —CH 2 —SiH 2 —] n .

Claims (270)

1. A Si-containing film forming composition comprising a linear or branched oligomer or polymer containing a unit having the formula:

[—NR—R 4 R 5 Si—(CH 2 ) t —SiR 2 R 3 —] n   (II)

wherein t=1 to 4; n=2 to 400;

R 2 , R 3 , R 4 , and R 5 are independently H, a C 1 to C 6 hydrocarbon, or an alkylamino group having the formula NR″ 2 and each R″ is independently H, a C 1 -C 6 hydrocarbon, a C 6 -C 12 aryl, or NR″ 2 forms a cyclic amine group,

and provided that at least one of R 2 , R 3 , R 4 , and R 5 is H; and

R is H; a C 1 -C 6 hydrocarbon; a silyl group having the formula Si x R′ 2x+1 , with x=1 to 4 and each R′ is independently H, a C 1 -C 6 hydrocarbon group, or an alkylamino group having the formula NR″ 2 and each R″ is independently H, a C 1 -C 6 group, a C 6 -C 12 aryl, or NR″ 2 forms a cyclic amine group; or a R 1′ R 2′ Si(CH 2 ) b Si R 3′ R 4′ R 5′ group, with b=1 to 2 and R 1′ , R 2′ , R 3′ , R 4′ , and R 5′ are independently a H, a C 1 -C 6 hydrocarbon, a C 6 -C 12 aryl, or an alkylamino group having the formula NR″ 2 and each R″ is independently H, a C 1 -C 6 group, a C 6 -C 12 aryl, or NR″ 2 forms a cyclic amine group; and provided that at least one of R 1′ , R 2′ , R 3′ , R 4′ , and R 5′ is H; and

further wherein the oligomer or polymer has a molecular weight of 500 to 1,000,000 daltons.

2. The Si-containing film forming composition of claim 1 , wherein the linear or branched oligomer or polymer contains a unit having the formula [—NH—SiH 2 —(CH 2 ) t —SiH 2 —] n , with t=1-2.

3. The Si-containing film forming composition of claim 1 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of:

[—N(SiH 3 )—SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si 2 H 5 )—SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si 3 H 7 )—SiH 2 —(CH 2 ) t —SiH 2 —] n ,and

[—N(Si 4 H 9 )—SiH 2 —(CH 2 ) t —SiH 2 —] n , with t=1-2.

4. The Si-containing film forming composition of claim 1 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of

[—N(Si(Me) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(Et) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(iPr) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(nPr) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(Bu) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(iBu) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(tBu) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(amyl) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(hexyl) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(Me) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(Et) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(iPr) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(nPr) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(Bu) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(iBu) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(tBu) 2 )-SiH 2 —(CH 2 )t—SiH 2 —] n ,

[—N(SiH(amyl) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(hexyl) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (Me))-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (Et))-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (iPr))-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (nPr))-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (nBu))-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (iBu))-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (tBu))-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (amyl))-SiH 2 —(CH 2 ) t —SiH 2 —] n , and

[—N(SiH 2 (hexyl))-SiH 2 —(CH 2 ) t —SiH 2 —] n , with t=1-2.

5. The Si-containing film forming composition of claim 1 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of

[—N(SiH 2 —CH 2 —SiH 3 )—SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiMe 2 —CH 2 —CH 2 —SiMe 3 )—SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiEt 2 —CH 2 —SiEt 3 )—SiH 2 —(CH 2 ) t —SiH 2 —] n , and

[—N(SiEt 2 —CH 2 —CH 2 —SiEt 3 )—SiH 2 —(CH 2 ) t —SiH 2 —] n , with t=1-2.

6. The Si-containing film forming composition of claim 1 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of

[—N(Me)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Et)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(iPr)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(nPr)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Bu)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(iBu)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(tBu)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(amyl)-SiH 2 —(CH 2 ) t —SiH 2 —] n , and

[—N(hexyl)-SiH 2 —(CH 2 ) t —SiH 2 —] n , with t=1-2.

7. The Si-containing film forming composition of claim 1 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of

[—N(SiH 2 NMe 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 NEt 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 NiPr 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 NnPr 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 NMeEt)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(NMe 2 ) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n , and

[—N(SiH(NEt 2 ) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n , with t=1-2.

8. The Si-containing film forming composition of claim 1 , wherein the oligomer or polymer has a molecular weight of 1,000 to 100,000 daltons.

9. The Si-containing film forming composition of claim 1 , wherein the oligomer or polymer has a molecular weight of 3,000 to 50,000 daltons.

10. The Si-containing film forming composition of claim 1 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of

[—NH—SiH 2 —(CH 2 ) t —SiH(CH═CH 2 )—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(CH 2 —CH═CH 2 )—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NH 2 )—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NMe 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NMeEt)-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NEt 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NnPr 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NiPr 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NnBu 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NiBu 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NtBu 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NAmyl 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(Ncyclopentyl 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(Nhexyl 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(Ncyclohexyl 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NMeH)—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NEtH)—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NnPrH)—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NiPrH)—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NnBuH)—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NiBuH)—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NtBuH)—] n , and

[—NH—SiH 2 —(CH 2 ) t —SiH(NAmylH)—] n .

11. The Si-containing film forming composition of claim 1 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of

[—NH—SiH 2 —(CH 2 ) t —Si(CH═CH 2 ) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(CH 2 —CH═CH 2 ) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NH 2 ) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NMe 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NMeEt) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NEt 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NnPr 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NiPr 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NnBu 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NiBu 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NtBu 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NAmyl 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(Ncyclopentyl 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(Si(Nhexyl 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(Ncyclohexyl 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NMeH) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NEtH) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NnPrH) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NiPrH) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NnBuH) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NiBuH) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NtBuH) 2 —] n , and

[—NH—SiH 2 —(CH 2 ) t —Si(NAmylH) 2 —] n .

12. The Si-containing film forming composition of claim 1 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of

[—NH—SiH(CH═CH 2 )—(CH 2 ) t —SiH(CH═CH 2 )—] n ,

[—NH—SiH(CH 2 —CH═CH 2 )—(CH 2 ) t —SiH(CH 2 —CH═CH 2 )—] n ,

[—NH—SiH(NH 2 )—(CH 2 ) t —SiH(NH 2 )—] n ,

[—NH—SiH(NMe 2 )-(CH 2 ) t —SiH(NMe 2 )-] n ,

[—NH—SiH(NMeEt)-(CH 2 ) t —SiH(NMeEt)-] n ,

[—NH—SiH(NEt 2 )-(CH 2 ) t —SiH(NEt 2 )-] n ,

[—NH—SiH(NnPr 2 )-(CH 2 ) t —SiH(NnPr 2 )-] n ,

[—NH—SiH(NiPr 2 )-(CH 2 ) t —SiH(NiPr 2 )-] n ,

[—NH—SiH(NnBu 2 )-(CH 2 ) t —SiH(NnBu 2 )-] n ,

[—NH—SiH(NiBu 2 )-(CH 2 ) t —SiH(NiBu 2 )-] n ,

[—NH—SiH(NtBu 2 )-(CH 2 ) t —SiH(NtBu 2 )-] n ,

[—NH—SiH(NAmyl 2 )-(CH 2 ) t —SiH(NAmyl 2 )-] n ,

[—NH—SiH(Ncyclopentyl 2 )-(CH 2 ) t —SiH(Ncyclopentyl 2 )-] n ,

[—NH—SiH(Nhexyl 2 )-(CH 2 ) t —SiH(Nhexyl 2 )-] n ,

[—NH—SiH(Ncyclohexyl 2 )-(CH 2 ) t —SiH(Ncyclohexyl 2 )-] n ,

[—NH—SiH(NMeH)—(CH 2 ) t —SiH(NMeH)—] n ,

[—NH—SiH(NEtH)—(CH 2 ) t —SiH(NEtH)—] n ,

[—NH—SiH(NnPrH)—(CH 2 ) t —SiH(NnPrH)—] n ,

[—NH—SiH(NiPrH)—(CH 2 ) t —SiH(NiPrH)—] n ,

[—NH—SiH(NnBuH)—(CH 2 ) t —SiH(NnBuH)—] n ,

[—NH—SiH(NiBuH)—(CH 2 ) t —SiH(NiBuH)—] n ,

[—NH—SiH(NtBuH)—(CH 2 ) t —SiH(NtBuH)—] n , and

[—NH—SiH(NAmylH)—(CH 2 ) t —SiH(NAmylH)—] n .

13. A method of forming a Si-containing film on a substrate, the method comprising forming a solution comprising the Si-containing film forming composition of claim 1 ; and contacting the solution with the substrate via a spin coating, spray coating, dip coating, or slit coating technique to form the Si-containing film.

14. The method of claim 13 , wherein the linear or branched oligomer or polymer contains a unit having the formula [—NH—SiH 2 —(CH 2 ) t —SiH 2 —] n , with t=1-2.

15. The method of claim 13 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of:

[—N(SiH 3 )—SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si 2 H 5 )—SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si 3 H 7 )—SiH 2 —(CH 2 ) t —SiH 2 —] n , and

[—N(Si 4 H 9 )—SiH 2 —(CH 2 ) t —SiH 2 —] n , with t=1-2.

16. The method of claim 13 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of

[—N(Si(Me) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(Et) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(iPr) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(nPr) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(nBu) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(iBu) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(tBu) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(amyl) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Si(hexyl) 3 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(Me) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(Et) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(iPr) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(nPr) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(nBu) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(iBu) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(tBu) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(amyl) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(hexyl) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (Me))-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (Et))-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (iPr))-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (nPr))-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (nBu))-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (iBu))-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (tBu))-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 (amyl))-SiH 2 —(CH 2 ) t —SiH 2 —] n , and

[—N(SiH 2 (hexyl))-SiH 2 —(CH 2 ) t —SiH 2 —] n , with t=1-2.

17. The method of claim 13 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of

[—N(SiH 2 —CH 2 —SiH 3 )—SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiMe 2 —CH 2 —CH 2 —SiMe 3 )—SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiEt 2 —CH 2 —SiEt 3 )—SiH 2 —(CH 2 ) t —SiH 2 —] n , and

[—N(SiEt 2 —CH 2 —CH 2 —SiEt 3 )—SiH 2 —(CH 2 ) t —SiH 2 —] n , with t=1-2.

18. The method of claim 13 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of

[—N(Me)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(Et)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(iPr)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(nPr)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(nBu)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(iBu)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(tBu)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(amyl)-SiH 2 —(CH 2 ) t —SiH 2 —] n , and

[—N(hexyl)-SiH 2 —(CH 2 ) t —SiH 2 —] n , with t=1-2.

19. The method of claim 13 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of

[—N(SiH 2 NMe 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 NEt 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 NiPr 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 NnPr 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH 2 NMeEt)-SiH 2 —(CH 2 ) t —SiH 2 —] n ,

[—N(SiH(NMe 2 ) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n ,and

[—N(SiH(NEt 2 ) 2 )-SiH 2 —(CH 2 ) t —SiH 2 —] n , with t=1-2.

20. The method of forming a Si-containing film on a substrate of claim 13 , wherein the oligomer or polymer has a molecular weight of 1,000 to 100,000 daltons.

21. The method of forming a Si-containing film on a substrate of claim 13 , wherein the oligomer or polymer has a molecular weight of 3,000 to 50,000 daltons.

22. The method of claim 13 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of

[—NH—SiH 2 —(CH 2 ) t —SiH(CH═CH 2 )—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(CH 2 —CH═CH 2 )—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NH 2 )—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NMe 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NMeEt)-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NEt 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NnPr 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NiPr 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NnBu 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NiBu 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NtBu 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NAmyl 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(N-cyclopentyl 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(Nhexyl 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(N-cyclohexyl 2 )-] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NMeH)—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NEtH)—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NnPrH)—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NiPrH)—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NnBuH)—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NiBuH)—] n ,

[—NH—SiH 2 —(CH 2 ) t —SiH(NtBuH)—] n , and

[—NH—SiH 2 —(CH 2 ) t —SiH(NAmylH)—] n .

23. The method of claim 13 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of

[—NH—SiH 2 —(CH 2 ) t —Si(CH═CH 2 ) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(CH 2 —CH═CH 2 ) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NH 2 ) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NMe 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NMeEt) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NEt 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NnPr 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NiPr 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NnBu 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NiBu 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NtBu 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NAmyl 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(Ncyclopentyl 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(Nhexyl 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(Ncyclohexyl 2 ) 2 -] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NMeH) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NEtH) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NnPrH) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NiPrH) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NnBuH) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NiBuH) 2 —] n ,

[—NH—SiH 2 —(CH 2 ) t —Si(NtBuH) 2 —] n , and

[—NH—SiH 2 —(CH 2 ) t —Si(NAmyl 2 ) 2 -] n .

24. The method of claim 13 , wherein the linear or branched oligomer or polymer contains a unit having a formula selected from the group consisting of

[—NH—SiH(CH═CH 2 )—(CH 2 ) t —SiH(CH═CH 2 )—] n ,

[—NH—SiH(CH 2 —CH═CH 2 )—(CH 2 ) t —SiH(CH 2 —CH═CH 2 )—] n ,

[—NH—SiH(NH 2 )—(CH 2 ) t —SiH(NH 2 )—] n ,

[—NH—SiH(NMe 2 )-(CH 2 ) t —SiH(NMe 2 )-] n ,

[—NH—SiH(NMeEt)-(CH 2 ) t —SiH(NMeEt)-] n ,

[—NH—SiH(NEt 2 )-(CH 2 ) t —SiH(NEt 2 )-] n ,

[—NH—SiH(NnPr 2 )-(CH 2 ) t —SiH(NnPr 2 )-] n ,

[—NH—SiH(NiPr 2 )-(CH 2 ) t —SiH(NiPr 2 )-] n ,

[—NH—SiH(NnBu 2 )-(CH 2 ) t —SiH(NnBu 2 )-] n ,

[—NH—SiH(NiBu 2 )-(CH 2 ) t —SiH(NiBu 2 )-] n ,

[—NH—SiH(NtBu 2 )-(CH 2 ) t —SiH(NtBu 2 )-] n ,

[—NH—SiH(NAmyl 2 )-(CH 2 ) t —SiH(NAmyl 2 )-] n ,

[—NH—SiH(Ncyclopentyl 2 )-(CH 2 ) t —SiH(Ncyclopentyl 2 )-] n ,

[—NH—SiH(Nhexyl 2 )-(CH 2 ) t —SiH(Nhexyl 2 )-] n ,

[—NH—SiH(Ncyclohexyl 2 )-(CH 2 ) t —SiH(Ncyclohexyl 2 )-] n ,

[—NH—SiH(NMeH)—(CH 2 ) t —SiH(NMeH)—] n ,

[—NH—SiH(NEtH)—(CH 2 ) t —SiH(NEtH)—] n ,

[—NH—SiH(NnPrH)—(CH 2 ) t —SiH(NnPrH)—] n ,

[—NH—SiH(NiPrH)—(CH 2 ) t —SiH(NiPrH)—] n ,

[—NH—SiH(NnBuH)—(CH 2 ) t —SiH(NnBuH)—] n ,

[—NH—SiH(NiBuH)—(CH 2 ) t —SiH(NiBuH)—] n ,

[—NH—SiH(NtBuH)—(CH 2 ) t —SiH(NtBuH)—] n , and

[—NH—SiH(NAmylH)—(CH 2 ) t —SiH(NAmylH)—] n .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 10, 2019
From: GIRARD, JEAN-MARC; SANCHEZ, ANTONIO; ZHANG, PENG
To: L'AIR LIQUIDE, SOCIETE ANONYME POUR L'ETUDE ET L'EXPLOITATION DES PROCEDES GEORGES CLAUDE
Reel/Frame 047948/0913 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 10, 2019
From: KHANDELWAL, MANISH; KERRIGAN, SEAN
To: AIR LIQUIDE ADVANCED MATERIALS, INC.
Reel/Frame 048043/0063 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 31, 2018
From: WANG, YANG
To: AMERICAN AIR LIQUIDE, INC.
Reel/Frame 047876/0396 →
Continuity (2)
Provisional Application 62312352 · Mar 23, 2016
Related Publication 20190040279A1 · Feb 7, 2019