AMINO-SILANE COMPOUND AND COMPOSITION FOR THE SILICON-CONTAINING THIN FILM COMPRISING THE SAME

Abstract

The present invention relates to an aminosilane compound and a composition for a silicon-containing thin film comprising the same, and more particularly, to an aminosilane compound and a composition for a silicon-containing thin film comprising the same having suitable properties that can be used as a precursor for forming a silicon-containing thin film and capable of replacing chlorosilanes.

Claims

1. A aminosilane compound represented by Formula 1: ##STR00009## wherein: R.sub.1 is selected from the group consisting of hydrogen, a C.sub.1-C.sub.20 alkyl group, a C.sub.2-C.sub.20 alkenyl group and a C.sub.2-C.sub.20 alkynyl group, R.sub.2 and R.sub.3 are each independently a primary or secondary amine group having a symmetrical or asymmetric structure, and the alkyl group, the alkenyl group, the alkynyl group and the amine group may be each further substituted with one or more substituents selected from the group consisting of halogen, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.2-C.sub.20 alkenyl group, a C.sub.2-C.sub.20 alkynyl group, a C.sub.6-C.sub.20 aryl group, a fluorenyl group, and a C.sub.2-C.sub.20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P.

2. The compound of claim 1, wherein R.sub.1 is an C.sub.1-C.sub.20 alkyl group, and R.sub.2 and R.sub.3 are a primary or secondary amine group substituted with an alkyl group.

3. The compound of claim 1, wherein R.sub.1 is hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, t-butyl, sec-butyl, n-pentyl, iso-pentyl, neo-pentyl, or sec-pentyl.

4. The compound of claim 1, wherein R.sub.2 and R.sub.3 are each independently methyl amine, dimethyl amine, ethyl amine, diethyl amine, ethyl methyl amine, propyl amine, dipropyl amine, iso-propyl amine, diiso-propyl amine, n-butyl amine, dibutyl amine, t-butyl amine, di-tert-butyl amine, n-pentyl amine, dipentyl amine, iso-pentyl amine, diisopentyl amine, neo-pentyl amine or sec-pentyl amine.

5. The compound of claim 1, wherein the aminosilane compound represented by Formula 1 is bis(ethylmethylamine)iso-propyl amino silazane (IPEM), bis(dimethylamine)t-butyl amino silazane (TBDM) or bis(ethylmethylamine)t-butyl amino silazane (TBEM).

6. A composition for depositing a silicon-containing thin film, wherein the silicon-containing thin film comprises the aminosilane compound of claim 1.

Description

DETAILED DESCRIPTION

[0015] The novel aminosilane compound according to an embodiment of the present invention may be represented by the following Formula 1.

##STR00002##

[0016] In Formula 1, each of symbols may be defined as follows.

[0017] R.sub.1 may be selected from the group consisting of hydrogen, a C.sub.1-C.sub.20 alkyl group, a C.sub.2-C.sub.20 alkenyl group and a C.sub.2-C.sub.20 alkynyl group.

[0018] Preferably, R.sub.1 may be a linear or branched saturated or unsaturated alkyl group, wherein an unsaturated alkyl group means an alkyl group containing at least one double bond or triple bond.

[0019] Where R.sub.1 is an alkyl group, the alkyl group is, for example, a C.sub.1-C.sub.10, a C.sub.1-C.sub.9, a C.sub.1-C.sub.8, a C.sub.1-C.sub.7, a C.sub.1-C.sub.6, a C.sub.1-C.sub.5, a C.sub.1-C.sub.4, a C.sub.1-C.sub.3, a C.sub.2-C.sub.4, a C.sub.3-C.sub.4, a C.sub.1, a C.sub.2, a C.sub.3, a C.sub.4, a C.sub.5, a C.sub.6, a C.sub.7, a C.sub.8, a C.sub.9, a C.sub.10 alkyl group, specifically, methyl, ethyl, n-propyl, iso-propyl, n-butyl, t-butyl, sec-butyl, n-pentyl, iso-pentyl, neo-pentyl or sec-pentyl.

[0020] R.sub.2 and R.sub.3 may be each independently an amine group. Preferably, R.sub.2 and R.sub.3 may be each independently an amine group substituted with an alkyl group or aryl group, more preferably, may be each independently an amine group substituted with an alkyl group, and may be a primary or secondary amine group having a symmetrical or asymmetric structure.

[0021] Specifically, R.sub.2 and R.sub.3 may be each independently methyl amine, dimethyl amine, ethyl amine, diethyl amine, ethyl methyl amine, propyl amine, dipropyl amine, iso-propyl amine, diiso-propyl amine, n-butyl amine, dibutyl amine, t-butyl amine, di-tert-butyl amine, n-pentyl amine, dipentyl amine, iso-pentyl amine, diisopentyl amine, neo-pentyl amine, sec-pentyl amine and the like.

[0022] The alkyl group, the alkenyl group, the alkynyl group and the amine group may be each further substituted with one or more substituents selected from the group consisting of halogen, a cyano group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.2-C.sub.20 alkenyl group, a C.sub.2-C.sub.20 alkynyl group, a C.sub.6-C.sub.20 aryl group, a fluorenyl group, and a C.sub.2-C.sub.20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P.

[0023] The compound represented by Formula 1 may be bis(ethylmethylamine)iso-propyl amino silazane(IPEM), bis(dimethylamine)t-butyl amino silazane(TBDM), or bis(ethylmethylamine)t-butyl amino silazane(TBEM).

[0024] The aminosilane compound according to one embodiment of the present invention represented by Formula 1 can be prepared using a non-polar solvent such as hexane, pentane, heptane, benzene and toluene, or a polar solvent diethyl ether, petroleum ether, tetrahydrofuran and 1,2-dimethoxy as a reaction solvent.

[0025] In another aspect of the present invention, the present invention provides a composition for depositing a silicon-containing thin film, wherein the silicon-containing thin film comprises the aminosilane compound represented by Formula 1.

[0026] Hereinafter, embodiments of the present invention will be described in more detail with reference to examples. These examples are for specifically explaining the present invention, and the scope of the present invention is not limited by the examples.

EXAMPLE

Example 1: Synthesis of bis(ethylmethylamine)iso-propyl amino silazane (IPEM)

[0027] Aminosilane compound according to Example 1 of the present invention can be prepared according to the following Reaction Schemes 1 and 2.

##STR00003##

##STR00004##

[0028] 7,500 g of tetrahydrofuran (THF) was putted in a 20 L reactor and it cooled to −20° C. Thereafter, 500 g (2.0 eq) of dichlorosilane was added and 500 g (2 eq) of trimethylamine was added. Then, 146.3 g (1.0 eq) of isopropyl amine was added at the same temperature, the mixture was warmed to room temperature. After the reaction was performed for 16 hours, the reaction product was filtered and the filtrate was cooled to −20° C. Thereafter, 585.08 g (4.0 eq) of ethyl methyl amine was added to the filtrate, and the reaction was performed at room temperature for 16 hours. When the reaction was completed, the reaction product was filtered and the filtrate was concentrated under reduced pressure. When the solvent was removed, fractional distillation purification was performed to obtain 440.78 g of the compound.

[0029] Obtaining 440.78 g of colorless liquid, yield: 76.37%, purity: GC-FID 98.78%, MS m/z C.sub.10H.sub.29N.sub.3Si.sub.2 (M+) 233.51, found 231.9

[0030] .sup.1H NMR (400 MHz, C.sub.6D.sub.6) δ 1.00 (t, 6H), δ 1.20(d, 6H), δ 2.48(s, 6H), δ 2.81-2.83 (q, 4H), δ 3.33-3.37(m, 1H) δ 4.82(s, 4H),

[0031] .sup.13C NMR (400 MHz, C.sub.6D.sub.6) δ 15.02, 26.05, 34.95, 45.65, 48.17

Example 2: Synthesis of bis(dimethylamine)t-butyl amino silazane (TBDM)

[0032] Aminosilane compound according to Example 2 of the present invention can be prepared according to the following Reaction Schemes 3 and 4.

##STR00005##

##STR00006##

[0033] 7,500 g of tetrahydrofuran (THF) was putted in a 20 L reactor and it cooled to −20° C. Thereafter, 500 g (2.0 eq) of dichlorosilane was added and 500 g (2 eq) of trimethylamine was added. Then, 181 g (1.0 eq) of t-butyl amine was added at the same temperature, and the mixture was warmed to room temperature. After the reaction was performed for 16 hours, the reaction product was filtered. The filtrate was cooled to −20° C. Thereafter, 446.21 g (4.0 eq) of dimethyl amine was added to the filtrate, and the reaction was performed at room temperature for 16 hours. When the reaction was completed, the reaction product was filtered and the filtrate was concentrated under reduced pressure. When the solvent was removed, fractional distillation purification was performed to obtain 380.79 g of the compound.

[0034] Obtaining 380.79 g of colorless liquid, yield: 70.1%, purity: GC-FID 98.3%, MS m/z C.sub.10H.sub.29N.sub.3Si.sub.2 (M+) 219.1, found 217.9

[0035] .sup.1H NMR (400 MHz, C.sub.6D.sub.6) δ 1.30 (s, 9H), δ 2.46(s, 12H), δ 4.93(s, 4H)

[0036] .sup.13C NMR (400 MHz, C.sub.6D.sub.6) δ 14.13, 33.72, 33.98, 44.56, 52.15

Example 3: Synthesis of bis(ethylmethylamine)t-butyl amino silazane (TBEM)

[0037] Aminosilane compound according to Example 3 of the present invention can be prepared according to the following Reaction Schemes 5 and 6.

##STR00007##

##STR00008##

[0038] 7,500 g of tetrahydrofuran (THF) was putted in a 20 L reactor and it cooled to −20° C. Thereafter, 500 g (2.0 eq) of dichlorosilane was added and 500 g (2 eq) of triethylamine was added. Then, 181 g (1.0 eq) of t-butyl amine was added at the same temperature, and the mixture was warmed to room temperature. After the reaction was performed for 16 hours, the reaction product was filtered. The filtrate was cooled to −20° C. Thereafter, 585.08 g (4.0 eq) of ethyl amine was added to the filtrate, and the reaction was performed at room temperature for 16 hours. When the reaction was completed, the reaction product was filtered and the filtrate was concentrated under reduced pressure. When the solvent was removed, fractional distillation purification was performed to obtain 435.65 g of the compound.

[0039] Obtaining 435.65 g of colorless liquid, yield: 71.21%, purity: GC-FID 98.3%, MS m/z C.sub.10H.sub.29N.sub.3Si.sub.2 (M+) 247.1, found 245.9

[0040] .sup.1H NMR (400 MHz, C.sub.6D.sub.6) δ 0.99-1.02 (t, 6H), δ 1.34(s, 9H), δ 2.47(s, 6H), δ 2.80-2.85 (q, 4H), δ 4.97(s, 4H)

[0041] .sup.13C NMR (400 MHz, C.sub.6D.sub.6) δ 14.13, 32.72, 33.98, 44.56, 55.16

[0042] Although exemplary embodiments of the present invention have been described for illustrative purposes, those skilled in the art will appreciate that various modifications can be made without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in the present invention are intended to illustrate the present invention, and the scope of the present invention is not limited by the embodiments. The scope of the present invention shall be construed on the basis of the accompanying claims, and it shall be construed that all of the technical ideas included within the scope equivalent to the claims belong to the present invention.