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JP-2026514534-A - A coating composition for preventing the collapse of semiconductor patterns, and a pattern coated using the same.

JP2026514534AJP 2026514534 AJP2026514534 AJP 2026514534AJP-2026514534-A

Abstract

The object of the present invention is to provide a coating composition that can prevent the collapse of a semiconductor device pattern by causing the contact angle between the pattern and water to approach 90°, and to provide a pattern coated with such a coating composition. The invention comprises a pattern collapse prevention coating material containing an amide compound represented by chemical formula (1) or a phosphorus compound represented by chemical formula (2), and an organic solvent. [Selection Diagram] Figure 1

Inventors

  • イ スジン
  • キム ギホン
  • ノ ウンス
  • イム ヒョンチャン
  • イ スンヒョン
  • イ スンフン

Assignees

  • ワイシーケム カンパニー リミテッド

Dates

Publication Date
20260511
Application Date
20240618
Priority Date
20230717

Claims (7)

  1. A pattern collapse prevention coating composition comprising a pattern collapse prevention coating material containing an amide compound represented by chemical formula (1) or a phosphorus compound represented by chemical formula (2), and an organic solvent. Chemical formula (1) [In the formula, R1, R2, and R3 are hydrogen, or an alkyl group having 1 to 8 carbon atoms, or a fluoroalkyl group having 1 to 8 carbon atoms, or a carbonyl group having 2 to 6 carbon atoms,] At least one of R1, R2, and R3 is either hydrogen or an alkyl group having 1 to 8 carbon atoms. At least one of R1, R2, and R3 is a fluoroalkyl group having 1 to 8 carbon atoms or a carbonyl group having 2 to 6 carbon atoms. Chemical formula (2) [In the formula, R1, R2, and R3 are hydrogen, or an alkyl group having 1 to 16 carbon atoms, or a fluoroalkyl group having 1 to 10 carbon atoms, or a perfluoroalkyl group having 3 to 10 carbon atoms,] At least one of R1, R2, and R3 is hydrogen. At least one of R1, R2, and R3 is an alkyl group having 1 to 16 carbon atoms, a fluoroalkyl group having 1 to 10 carbon atoms, or a perfluoroalkyl group having 3 to 10 carbon atoms.
  2. The pattern collapse prevention coating composition according to claim 1, characterized by comprising 5 to 30% by weight of a pattern collapse prevention coating substance containing an amide compound represented by chemical formula (1) or a phosphorus compound represented by chemical formula (2), and 70 to 95% by weight of an organic solvent.
  3. The amide compounds represented by the chemical formula (1) above include acetamide, n-propylamide, n-butanamide, N,N-dimethylbutanamide, N,N-dimethylacetamide, and 2,2,2-trifluoroacetamide. amide), 2,2,2-trifluoro-N,N-bis(trifluoromethyl)acetamide, pentafluoropropanamide, 2,2,3,3,4,4,4-heptafluorobutanamide 2,2,3,3,4,4,5,5,5-nonafluoropentanamide, diacetamide, N-propionylpropanamide, N-butyrylbutanamide, 2,2,2-trifluoro-N-(trifluoroacetyl)acetamide The pattern collapse prevention coating composition according to claim 2, characterized by being a compound selected from the group consisting of toamide (2,2,2-Trifluoro-N-(trifluoroacetyl)acetamide) and 2,2,2-trifluoro-N-(2-hydroxyethyl)acetamide (2,2,2-Trifluoro-N-(2-hydroxyethyl)acetamide), or a mixture of two or more of these.
  4. The phosphorus compounds represented by the chemical formula (2) above include monomethyl phosphate, monoethyl phosphate, propyl dihydrogen phosphate, butyl dihydrogen phosphate, monohexyl phosphate, monooctyl phosphate, decyl phosphate, dimethyl phosphate, and diethyl phosphate. Phosphate, dibutyl phosphate, dihexyl phosphate, 3,3,3-trifluoropropyl dihydrogen phosphate, 3,3,4,4,5,5,6,6,6-nonafluorohexyl dihydrogen phosphate, perfluorooctyl phosphate, perfluorodecyl phosphate (Bis(3,3,3-trifluoropropyl)hydrogen phosphate), (Bis(3,3,4,4,5,5,6,6,6-nonafluorohexyl)hydrogen phosphate) phosphate, bis(perfluorooctyl)phosphate, bis(perfluorodecyl)phosphate, mono-n-dodecyl phosphate, tributyl phosphate, 11-phosphonoundecanoic acid, hexadecylphosphonic acid, octylphosphonic acid The pattern collapse prevention coating composition according to claim 2, characterized by being a compound selected from the group consisting of (acid), tetradecylphosphonic acid, phosphate monoester having 8 to 18 carbon atoms, and phosphate diester, or a mixture of two or more of these.
  5. The pattern collapse prevention coating composition according to claim 2, characterized in that the organic solvent is a compound selected from the group consisting of a glycol compound having 4 to 20 carbon atoms, a glycol ether compound having 4 to 20 carbon atoms, an alkylene glycol alkyl ether compound having 4 to 20 carbon atoms, a silylamine compound having 3 to 12 carbon atoms, an alcohol having 1 to 10 carbon atoms, and a hydrocarbon having 6 to 10 carbon atoms, or a mixture of two or more of these.
  6. A pattern coated with the pattern collapse prevention coating composition described in any one of claims 1 to 5.
  7. A pattern coated with the pattern collapse prevention coating composition according to claim 6, characterized in that the pattern material contains at least one of polysilicon, silicon oxide, silicon nitride, titanium nitride, and tungsten.

Description

This invention relates to a pattern collapse prevention coating composition that can be used in memory semiconductor manufacturing for patterns having a high aspect ratio (aspect ratio of 15 or more). The miniaturization and high integration of devices necessitate the realization of fine patterns in semiconductor processes. To form such fine patterns, research and development are underway on methods such as the development of exposure equipment or the introduction of additional processes to miniaturize patterns. There is an urgent need for the development of process equipment and process technologies that can increase the integration density of semiconductor devices and realize the formation of structures with even finer dimensions in the nanometer range. To increase the integration density of semiconductor devices and enable the formation of structures with finer dimensions in the nanometer range, patterns with a high aspect ratio (the ratio of the vertical length to the horizontal length of the pattern) are used, which has resulted in the collapse of the patterns during the cleaning process. When the aspect ratio of the fine patterns formed on the device substrate was low, there were no problems with the wet cleaning method using distilled water. However, when the aspect ratio increased and the final cleaning was performed using only distilled water, the fine patterns collapsed. The force that induces the collapse of fine patterns formed on a substrate increases in proportion to the surface tension and the cosine θ (cosθ) value of the contact angle of the material used in the pattern formation process and cleaning relative to the fine patterns. Therefore, an alternative is sought by applying the principle that the smaller the surface tension, the smaller the force, and the following method is actually being applied. To solve the problem of fine pattern collapse, semiconductor manufacturers have adopted methods to reduce the surface tension on the pattern using alcohols such as isopropanol or surfactants. In recent years, as semiconductor manufacturing processes have become even more miniaturized, the horizontal dimension of patterns has become smaller and the vertical dimension has become larger compared to existing processes, resulting in a rapid increase in the aspect ratio of the patterns. Since the methods described above are insufficient to solve this problem, a method to resolve it is needed. As briefly mentioned above, factors that influence the force causing the fine pattern to collapse include the surface tension Γ of the cleaning solution, the aspect ratio due to the pattern height H, the spacing D between patterns, the pattern width W, and the contact angle between the pattern and the cleaning solution. In the manufacturing process of fine patterns, the final stage of the wet process involves spin-drying the wafer. According to the theory above, a crucial element was to use a cleaning agent with low surface tension to reduce the force of the cleaning solution being discharged during spin-drying. However, the fine patterns currently under development have extremely high aspect ratios, making it impossible to achieve a significant reduction in surface tension. Except for liquid helium, it is impossible to lower the surface tension to near 0 J/ m². Among commercially available substances, including surfactants, the lowest surface tension value is around 15 J/ m² . Numerous experiments have confirmed that using a cleaning solution with a surface tension value higher than this as the final cleaning solution cannot prevent the collapse of the fine patterns. In other words, there is a problem in that the effect of controlling surface tension to prevent the collapse of the fine pattern can no longer be expected. Korean Registered Patent Publication No. 10-1118437Korean Registered Patent Publication No. 10-1535200Korean Registered Patent Publication No. 10-1483484Korean Registered Patent Publication No. 10-1525152 This figure shows the measurement results for whether or not the pattern collapsed according to Example 1.This figure shows the measurement results for whether or not the pattern collapsed according to Comparative Example 1. The following describes in more detail the coating composition for preventing pattern collapse according to the present invention. The present invention provides a coating composition for preventing pattern collapse, comprising at least one selected from an amide compound represented by the following chemical formula (1) and a phosphorus compound represented by the following chemical formula (2), characterized in that when mixed with an organic solvent, a self-assembled monolayer is formed at the interface of the pattern, resulting in a water contact angle with the pattern of 80° to 100°. Chemical formula (1) [In the formula, R1, R2, and R3 are hydrogen, or an alkyl group having 1 to 8 carbon atoms, or a fluoroalkyl group having 1 to 8 carbon atoms, or a carbonyl group ha