Cyclodisilazane derivative, method for preparing the same and silicon-containing thin film using the same

Patent metadata

Field	Value
Publication number	US-9809608-B2
Application number	US-201515110707-A
Country	US
Kind code	B2
Filing date	Jan 8, 2015
Priority date	Jan 8, 2014
Publication date	Nov 7, 2017
Grant date	Nov 7, 2017

Abstract

Provided are a novel cyclodisilazane derivative, a method for preparing the same, and a silicon-containing thin film using the same, wherein the cyclodisilazane derivative having thermal stability, high volatility, and high reactivity and being present in a liquid state at room temperature and under a pressure where handling is easy, may form a high purity silicon-containing thin film having excellent physical and electrical properties by various deposition methods.

First claim

The invention claimed is:

1. A cyclodisilazane derivative represented by the following Chemical Formula 1:

in Chemical Formula 1,
R 1 to R 3 are each independently hydrogen, halogen, (C1-C5)alkyl or (C2-C5)alkenyl, and
R 4 is C3 alkyl or (C2-C5)alkenyl.

2. The cyclodisilazane derivative of claim 1 , wherein it is selected from the following compounds:

3. A method for preparing a cyclodisilazane derivative represented by the following Chemical Formula 1, comprising:
preparing a diaminosilane derivative represented by the following Chemical Formula 4 by reacting a silane derivative represented by the following Chemical Formula 2 with an amine derivative represented by the following Chemical Formula 3; and
preparing the cyclodisilazane derivative represented by the following Chemical Formula 1 by an intramolecular cyclization reaction of the diaminosilane derivative represented by the following Chemical Formula 4 with a silane derivative represented by the following Chemical Formula 5 in the presence of (C1-C7)alkyllithium:

in Chemical Formulas 1 to 5,
R 1 to R 3 are each independently hydrogen, halogen, (C1-C5)alkyl or (C2-C5)alkenyl, and
R 4 is C3 alkyl or (C2-C5)alkenyl, and X is halogen.

4. The method of claim 3 , wherein the preparing of the diaminosilane derivative represented by Chemical Formula 4 is performed in the presence of a base represented by the following Chemical Formula 10 or (C1-C7)alkyllithium:
N(R 6 )(R 7 )(R 8 )  [Chemical Formula 10]

in Chemical Formula 10, R 6 to R 8 are each independently (C1-C7)alkyl.

5. A method for preparing a cyclodisilazane derivative represented by the following Chemical Formula 1-2, the method comprising:
preparing the cyclodisilazane derivative represented by the following Chemical Formula 1-2 by reacting a halocyclodisilazane derivative represented by the following Chemical Formula 1-1 with a metal hydride or an alkali metal derivative represented by the following Chemical Formula 8:

in Chemical Formulas 1-1, 1-2, and 8,
M is an alkali metal;
R 10 is each independently hydrogen or (C1-C5)alkyl;
at least one of R 1 to R 3 is halogen, and the remainder is hydrogen, halogen, (C1-C5)alkyl or (C2-C5)alkenyl;
R 4 is C3 alkyl or (C2-C5)alkenyl; and
at least one of R 1a to R 3a is hydrogen, and the remainder is hydrogen, (C1-C5)alkyl or (C2-C5)alkenyl, wherein when R 1 is halogen, R 1a is hydrogen, and when R 2 is halogen, R 2a a is hydrogen, and when R 3 is halogen, R 3a a is hydrogen.

6. A method for preparing a cyclodisilazane derivative represented by the following Chemical Formula 9, the method comprising:
preparing an aminosilane derivative represented by the following Chemical Formula 6 by reacting a silane derivative represented by the following Chemical Formula 2 with an amine derivative represented by the following Chemical Formula 3;
preparing a halocyclodisilazane derivative represented by the following Chemical Formula 7 by an intramolecular cyclization reaction of the aminosilane derivative represented by the following Chemical Formula 6 in the presence of (C1-C7)alkyllithium; and
preparing the cyclodisilazane derivative represented by the following Chemical Formula 9 by reacting the halocyclodisilazane derivative represented by the following Chemical Formula 7 with a metal hydride or an alkali metal derivative represented by the following Chemical Formula 8:

in Chemical Formulas 2, 3 and 6 to 9,
R 1 is halogen;
R 2 is hydrogen, halogen, (C1-C5)alkyl or (C2-C5)alkenyl;
R 4 is C3 alkyl or (C2-C5)alkenyl;
X is halogen;
M is an alkali metal;
R 10 is hydrogen or (C1-C5)alkyl;
R 1a is hydrogen;
wherein when R 2 is hydrogen or halogen, R 2a a is hydrogen, and
when R 2 is (C1-C5)alkyl or (C2-C5)alkenyl, R 2a is (C1-C5)alkyl or (C2-C5)alkenyl.

7. The method of claim 6 , wherein the preparing of the aminosilane derivative represented by Chemical Formula 6 is performed in the presence of a base represented by the following Chemical Formula 10 or (C1-C7)alkyllithium:
N(R 6 )(R 7 )(R 8 )  [Chemical Formula 10]

in Chemical Formula 10, R 6 to R 8 are each independently (C1-C7)alkyl.

8. The method of claim 6 , wherein the metal hydride is one or a mixture of two or more, selected from the group consisting of LiH, NaH, KH and LiAlH 4 .

9. A composition for depositing a silicon-containing thin film, comprising the cyclodisilazane derivative of claim 1 .

10. A method for manufacturing a silicon-containing thin film by using the cyclodisilazane derivative of claim 1 .

11. A silicon-containing thin film manufactured by including the cyclodisilazane derivative of claim 1 .

12. The method of claim 5 , wherein the metal hydride is one or a mixture of two or more, selected from the group consisting of LiH, NaH, KH and LiAlH4.

Assignees

• Dnf Co Ltd

Inventors

• Jang Se Jin
• Yang Byeong-Il
• Kim Sung Gi
• Kim Jong Hyun
• Kim Do Yeon
• Lee Sang-Do
• Seok Jang Hyeon
• Lee Sang Ick
• Kim Myong Woon

Classifications

• H10P14/69433

  the material being a silicon nitride not containing oxygen, e.g. SixNy or SixByNz · CPC title

• H10P14/69215

  the material being a silicon oxide, e.g. SiO2 · CPC title

• H10P14/6689

  the compound being a silazane · CPC title

• H10P14/6339

  deposition by cyclic CVD, e.g. ALD, ALE or pulsed CVD · CPC title

• H10P14/6336

  in the presence of a plasma [PECVD] · CPC title