US-12624059-B2 - Organometallic compound, precursor composition comprising same, and method for manufacturing thin film using same

US12624059B2US 12624059 B2US12624059 B2US 12624059B2US-12624059-B2

Abstract

The present invention relates to a vapor deposition compound capable of being deposited as a thin film through vapor deposition and, in particular, to: an organometal-containing compound which can be applied to an atomic layer deposition (ALD) method or a chemical vapor deposition (CVD) method and has excellent reactivity, volatility, and thermal stability; a precursor composition comprising the organometallic compound; a method for manufacturing a thin film using the precursor composition; and an organometal-containing thin film manufactured using the precursor composition.

Inventors

Hyo-Suk Kim
Min-Sung Park
Min-Hyuk NIM
Jang-Hyeon Seok
Jung-Woo Park

Assignees

HANSOL CHEMICAL CO., LTD.

Dates

Publication Date: 20260512
Application Date: 20200803
Priority Date: 20200729

Claims (8)

1 . An organometallic compound represented by the following Chemical Formula 1: in Chemical Formula 1, M is Mn, Cu, Co, or Ni; a is 2; b is 1 or 2 (provided that when Mis Co, b is not 2); R 1 and R 2 are each independently hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms; R 3 is —OR 4 or —NR 5 R 6 ; R 4 is hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms; and R 5 and R 6 are each independently hydrogen, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkylsilyl group having 1 to 6 carbon atoms.
2 . The organometallic compound of claim 1 , wherein R 1 , R 2 , and R 4 are each independently any one selected from the group consisting of hydrogen, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, and a tert-butyl group.
3 . The organometallic compound of claim 1 , wherein R 5 and R 6 are each independently any one selected from the group consisting of hydrogen, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a methylsilyl group, a dimethylsilyl group, a trimethylsilyl group, and a triethylsilyl group.
4 . A precursor composition for vapor deposition comprising the organometallic compound according to claim 1 .
5 . A method for manufacturing a thin film, the method comprising a step of introducing the precursor composition for vapor deposition according to claim 4 into a chamber.
6 . The method of claim 5 , wherein the method for manufacturing a thin film includes an atomic layer deposition (ALD) method or a chemical vapor deposition method (CVD) method.
7 . The method of claim 5 , further comprising a step of injecting one or more selected from hydrogen (H 2 ), a compound containing oxygen (O) atoms, a compound containing nitrogen (N) atoms, or a compound containing silicon (Si) atoms as a reaction gas.
8 . The method of claim 7 , wherein the reaction gas is any one or more selected from water (H 2 O), oxygen (O 2 ), hydrogen (H 2 ), ozone (O 3 ), ammonia (NH 3 ), hydrazine (N 2 H 4 ), or silane.

Description

TECHNICAL FIELD The present invention relates to a vapor deposition compound capable of depositing a thin film through vapor deposition and, specifically, to a novel organometallic compound that can be applied to atomic layer deposition or chemical vapor deposition and has excellent reactivity, volatility, and thermal stability, a precursor composition comprising the organometallic compound, a method for manufacturing a thin film using the precursor composition, and an organometal-containing thin film manufactured using the precursor composition. BACKGROUND ART An organometallic precursor thin film can form a metal thin film, an oxide thin film, and a nitride thin film which have various compositions, and is variously applied in the semiconductor field. As methods for forming thin films, there are deposition methods such as CVD and ALD, and according to the high integration and ultra-miniaturization of semiconductor materials, the need for ALD method, which has advantages such as uniform thin film manufacturing, thin film thickness controllability, and high step coverage, is being emphasized. At this time, the precursor for use in the ALD method also plays a very important role, and requires high volatility and thermal stability. Among organometallic metal thin films, in particular, manganese metal thin films are applied to organic semiconductor electrodes and ferromagnetic electrode materials. Manganese oxide thin films can be used in electrode materials, electrochemical capacitors, soft magnetic materials, perovskite materials, lithium-based batteries of solid electrolytes, and catalysts. In addition, the manganese nitride thin film is a next-generation material that can be used as a copper diffusion barrier and a copper adhesion layer in the back-end-of-line copper connector of semiconductor material wiring, and various applications such as catalysts, batteries, memory devices, displays, and sensors are expected. Among the representative organometallic precursors currently known, manganese (Mn) precursors include carbonyl compound Mn2(CO)10, cyclopentadiene compound Mn(Cp)2, beta-diketonate compound Mn(tmhd)3, amidinate compound Mn(tBu-Me-amd)2, and the like. These are mostly solid compounds with relatively high melting points and low stability. In addition, when the thin film is deposited, impurity contamination may occur in the thin film. In addition, the compound Mn(MeCp)(CO)3 composed of a combination of two ligands is a liquid compound, but there is a disadvantage in that it has a high boiling point and low stability of the compound. In addition, the compound Mn(hfa)2(tmeda), which fills the coordination number by introducing an electron-donating ligand, has a much lower melting point than the beta-diketonate compound, but there is a disadvantage in that it is a solid compound and has a high deposition temperature. As such, it is necessary to develop a new organometallic precursor to improve the disadvantages of the precursors that have been used in the past. DISCLOSURE Technical Problem The present invention is to solve the problems of the existing organometallic precursors mentioned as described above, and an object of the present invention is to provide an organometallic precursor compound for thin film deposition having excellent reactivity, thermal stability, and volatility. Another object of the present invention is to provide a method for manufacturing a thin film using the organometallic precursor compound, and an organometal-containing thin film. However, the problem to be solved by the present application is not limited to the above-mentioned problems, and other problems not mentioned will be clearly understood by those skilled in the art from the description below. Technical Solution The present invention is to develop a novel organometallic compound having a low melting point and excellent volatility in a low temperature range and a precursor composition comprising the same by introducing an imidazole ligand into an alkoxide ligand having excellent reactivity and volatility, and it is intended to provide a novel organometallic precursor consisting of a combination of an alkoxide and an imidazole ligand. Furthermore, it is intended to provide a novel organometallic precursor in which the substituent of the alkoxide ligand is modified. One aspect of the present application provides an organometallic compound represented by Chemical Formula 1 below. in Chemical Formula 1, M is Mn, Cu, Co, Fe, or Ni;a is 2; b is 1 or 2 (provided that when M is Co, b is not 2);R1 and R2 are each independently hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms; R3 is —OR4 or —NR5R6;R4 is hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms; andR5 and R6 are each independently hydrogen, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkylsilyl group having 1 to 6 carbon atoms. Another aspect of the present application provides a precu