# US 11,999,827 B2 · Polycarbosilazane, and composition comprising the same, and method for producing silicon-containing film using the same

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,999,827 B2
- Document ID: US11999827B2
- Status: Granted
- Kind: B2
- Application number: 17/922,800
- Filed: 2021-05-04
- Published: 2023-06-08
- Granted: 2024-06-04
- Earliest claimed: 2020-05-07
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH
- Inventors: Toshiya Okamura; Tetsuo Okayasu; Thorsten Vom Stein
- Web page: https://patentgrep.com/patent/US11999827B2

## CPC

- C08G 77/60: in which all the silicon atoms are connected by linkages other than oxygen atoms
- C08G 77/62: Nitrogen atoms
- C09D 183/16: in which all the silicon atoms are connected by linkages other than oxygen atoms
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## Abstract

[Problem] To provide a polycarbosilazane making it possible to form a silicon-containing film which is bearable to acid etching, and a composition comprising the polycarbosilazane. [Means for Solution] The present invention provides a polycarbosilazane comprising a repeating unit of —[R1R2Si—(CH2)n]— and —(R3R4Si—NR5)—, wherein R1, R2, R3 and R4 are each independently a single bond, hydrogen or C1-4 alkyl; R5 is independently a single bond or hydrogen; and n is 1-2, and a composition comprising the polycarbosilazane. The present invention also provides a method for forming a silicon-containing film, comprising coating the composition above a substrate and heating.

## Claims

### Claim 1

A polycarbosilazane comprising a repeating unit represented by the following formula (1) and a repeating unit represented by the following formula (2):
wherein,
R1, R2, R3 and R4 are each independently a single bond, hydrogen or C1-4 alkyl;
R5 is independently a single bond or hydrogen;
and n is 1-2;
wherein a ratio of an integrated intensity between 1.7 and 2.2 ppm with respect to sum of an integrated intensity between 1.7 and 2.2 ppm and an integrated intensity between 1.0 and 1.6 ppm in 1H-NMR spectrum is 0.05 to 0.5;
wherein the polycarbosilazane is free of Si-Si bonds and
wherein the mass average molecular weight is 1,500 to 25,000 measured by gel permeation chromatography in terms of polystyrene.

### Claim 2 (depends on 1)

The polycarbosilazane according to claim 1, wherein the polycarbosilazane is a polyperhydrocarbosilazane.

### Claim 3 (depends on 1)

A composition comprising the polycarbosilazane according to claim 1 and a solvent.

### Claim 4 (depends on 3)

The composition according to claim 3, wherein the solvent is at least one selected from a group consisting of an aromatic compound, a saturated hydrocarbon compound, an unsaturated hydrocarbon compound, an ether compound, an ester compound, and a ketone compound.

### Claim 5 (depends on 3)

The composition according to claim 3, wherein the composition comprises 1 to 50 mass % of the polycarbosilazane based on the total mass of the composition.

### Claim 6 (depends on 3)

A method for producing a silicon-containing film comprises forming a coating above a substrate with the composition according to claim 3 and curing the coating.

### Claim 7 (depends on 6)

The method for producing a silicon-containing film according to claim 6, wherein the curing is performed under a water vapor atmosphere.

### Claim 8 (depends on 6)

The method for producing a silicon-containing film according to claim 6, wherein the curing is performed under a non-oxidizing atmosphere.

### Claim 9 (depends on 6)

A silicon-containing film obtainable by the method according to claim 6.

### Claim 10 (depends on 6)

A method for producing an electronic device, wherein the device comprising a silicon-containing film produced by the method according to claim 6.

### Claim 11

A polycarbosilazane comprising a repeating unit represented by the following formula (1) and a repeating unit represented by the following formula (2):
wherein,
R1, R2, R3 and R4 are each independently a single bond, hydrogen or C1-4 alkyl;
R5 is independently a single bond or hydrogen;
and n is 1-2;
wherein a ratio of an integrated intensity between 1.7 and 2.2 ppm with respect to sum of an integrated intensity between 1.7 and 2.2 ppm and an integrated intensity between 1.0 and 1.6 ppm in 1H-NMR spectrum is 0.05 to 0.5;
wherein the polycarbosilazane is polyperhydrocarbosilazane.

### Claim 12 (depends on 11)

A composition comprising the polycarbosilazane according to claim 11 and a solvent.

### Claim 13 (depends on 12)

The composition according to claim 12, wherein the solvent is at least one selected from a group consisting of an aromatic compound, a saturated hydrocarbon compound, an unsaturated hydrocarbon compound, an ether compound, an ester compound, and a ketone compound.

### Claim 14 (depends on 12)

The composition according to claim 12, wherein the composition comprises 1 to 50 mass % of the polycarbosilazane based on the total mass of the composition.