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Volatile copper(II) complexes for deposition of copper films by atomic layer deposition

Inactive Publication Date: 2005-01-06
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patent describes a process for forming copper deposits on a substrate by contacting it with a copper complex and a reducing agent. The invention also provides a 1,3-diimine copper complex and an article comprising it deposited on a substrate. Additionally, the patent describes a process for synthesizing diimines by contacting an alkylimino-monoketone with an alkylating agent, a primary alkyl amine, and a strong base. The invention also provides novel amino-imines. The technical effects of this patent include improved methods for forming copper deposits and the synthesis of diimines.

Problems solved by technology

However this approach has drawbacks in the preparation of interconnect layers, since halides adversely affect the properties of the interconnect layer.

Method used

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  • Volatile copper(II) complexes for deposition of copper films by atomic layer deposition
  • Volatile copper(II) complexes for deposition of copper films by atomic layer deposition
  • Volatile copper(II) complexes for deposition of copper films by atomic layer deposition

Examples

Experimental program
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Effect test

example 1

Preparation and Reduction of Bis(N-ethyl-4-ethylimino-2-pentene-2-aminato)copper(II)

The 1,3-diimine ligand, CH3CH2N═C(CH3)—CH2—C(CH3)═N—CH2CH3.HBF4, was prepared according to a literature procedure (McGeachin). The Cu(II)complex was prepared by reaction of the free base with copper(II) methoxide in methanol. Copper methoxide (0.268 g) was weighed into a 50-mL Erlenmeyer flask. A magnetic stir bar and 5 mL methanol were added. The free ligand was prepared from the tetrafluoroborate salt (1.00 g) by reaction with sodium methoxide; the methoxide solution was prepared by adding NaH (0.105 g) slowly to 5 mL methanol. This methanol solution was added all at once to the rapidly stirred copper methoxide solution along with an additional 5 mL methanol. A purple solution formed immediately. The mixture was stirred for 1 hour at room temperature. Solvent was removed under vacuum. The resulting solid was mixed with hexane; the resulting mixture was filtered through a sintered glass frit with ...

example 2

Preparation of MeC(NHMe)=CHC(═O)Me

Aqueous methylamine (100 g, 40% in water) was added, drop-wise, to 100 g 2,4-pentanedione. The addition was mildly exothermic; the addition rate was adjusted to keep the temperature between about 35 and 40° C. After the addition was complete, the resulting yellow liquid was stirred 1 hr at room temperature, then subjected to vacuum distillation. The still pot was heated under partial vacuum, such that the first distillation cut (presumably water) came over at 30-35° C. After this fraction was removed, the distillation was discontinued. The contents of the pot solidified upon cooling. By NMR analysis, the title compound was obtained (>95% purity) and in good yield (>90%).

example 3

Preparation of [MeC(NHMe)=CHC(OMe)Me][MeOSO3]

In the drybox, 4-(methylamino)-3-pentene-2-one (1.00 g) from Example 2 was dissolved in CH2Cl2 (2 mL) and was mixed with dimethylsulfate (1.00 g). The mixture initially formed a yellow solution, cool to the touch, but over the course of an hour, made a thick slurry with some warming. The slurry was filtered and the solids rinsed with CH2Cl2, with an isolated yield of 0.90 g (47%, based on dimethylsulfate). The NMR of the solid product was consistent with title compound.

In the drybox, 4-(methylamino)-3-pentene-2-one (1.08 g) was mixed with CH2Cl2 (0.5 mL) and the slurry combined with dimethylsulfate (1.00 g). The resulting solution was initially cool to the touch but over the course of an hour it solidified, becoming warm to the touch. This mixture was allowed to stand overnight on the stir plate at ambient temperature, then used for the subsequent reaction below. The in situ yield is nearly quantitative based on NMR analysis.

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Abstract

The present invention relates to novel 1,3-diimine copper complexes and the use of 1,3-diimine copper complexes for the deposition of copper on substrates or in or on porous solids in an Atomic Layer Deposition process. This invention also provides a process for making amino-imines and novel amino-imines.

Description

FIELD OF THE INVENTION The present invention relates to novel 1,3-diimine copper complexes and the use of 1,3-diimine copper complexes for the deposition of copper on substrates or in or on porous solids in an Atomic Layer Deposition process. This invention also provides a process for making amino-imines and novel amino-imines. TECHNICAL BACKGROUND The ALD (Atomic Layer Deposition) process is useful for the creation of thin films, as described by M. Ritala and M. Leskela in “Atomic Layer Deposition” in Handbook of Thin Film Materials, H. S. Nalwa, Editor, Academic Press, San Diego, 2001, Volume 1, Chapter 2. Such films, especially metal and metal oxide films, are critical components in the manufacture of electronic circuits and devices. In an ALD process for depositing copper films, a copper precursor and reducing agent are alternatively introduced into a reaction chamber. After the copper precursor is introduced into the reaction chamber and allowed to adsorb onto a substrate, t...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C249/02C07C251/12C07C251/16C07D213/74C07F1/08C23C16/18H01L21/285H10K99/00
CPCC07C251/12C07C251/16C07D213/74H01L21/3141C23C16/45525C23C16/45553H01L21/288C23C16/18Y10T428/31504H01L21/0228
Inventor BRADLEY, ALEXANDER ZAKTHORN, DAVID LINCOLNTHOMPSON, JEFFREY SCOTT
Owner EI DU PONT DE NEMOURS & CO
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