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CN-121995695-A - Semiconductor photoresist composition and method for forming pattern using the same

CN121995695ACN 121995695 ACN121995695 ACN 121995695ACN-121995695-A

Abstract

The invention provides a semiconductor photoresist composition and a method for forming a pattern by using the same. The semiconductor photoresist composition includes an organometallic compound, a carboxylic acid compound represented by chemical formula 1, and a solvent. Chemical formula 1

Inventors

  • WU QINGYA
  • XIN CHENGXU
  • JIN MINHUI
  • YIN ZHIXIAN
  • Jiang Enmei
  • JIN ZHIMIN

Assignees

  • 三星SDI株式会社

Dates

Publication Date
20260508
Application Date
20251031
Priority Date
20241101

Claims (13)

  1. 1. A semiconductor photoresist composition comprising: an organometallic compound; a carboxylic acid compound represented by the formula 1, and The solvent is used for the preparation of the aqueous solution, Chemical formula 1 Wherein, in the chemical formula 1, L is a single bond, a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C2 to C10 alkenylene group, or a substituted or unsubstituted C2 to C10 alkynylene group, an Z 1 to Z 3 are each independently hydrogen, hydroxy, halogen, cyano-containing, ammonium, amide, nitro, carboxyl, ester, sulfone, sulfonate, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, or a combination thereof, Wherein at least one selected from L and Z 1 to Z 3 comprises a nitro group.
  2. 2. The semiconductor photoresist composition of claim 1, wherein L is a single bond or a substituted or unsubstituted C1 to C10 alkylene.
  3. 3. The semiconductor photoresist composition of claim 1, wherein Z 1 to Z 3 are each independently hydrogen, cyano, ammonium, amide, nitro, carboxyl, ester, or combinations thereof, wherein at least one selected from Z 1 to Z 3 is nitro.
  4. 4. The semiconductor photoresist composition of claim 1, wherein the carboxylic acid compound represented by chemical formula 1 is present in an amount of 0.01 to 5wt% based on 100 wt% of the semiconductor photoresist composition.
  5. 5. The semiconductor photoresist composition of claim 1, wherein the carboxylic acid compound represented by chemical formula 1 is selected from the group consisting of the compounds listed in group 1: Group 1 。
  6. 6. The semiconductor photoresist composition of claim 1, wherein the semiconductor photoresist composition further comprises one or more additives selected from the group consisting of surfactants, cross-linking agents, leveling agents, organic acids, quenchers, and combinations thereof.
  7. 7. The semiconductor photoresist composition of claim 1, wherein the organometallic compound comprises an organotin compound comprising at least one of an organoxy group or an organocarbonyloxy group.
  8. 8. The semiconductor photoresist composition of claim 1, wherein the organometallic compound is represented by chemical formula 2: Chemical formula 2 And (2) and Wherein, in the chemical formula 2, R 1 is selected from the group consisting of substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C7 to C30 aralkyl, R 2 to R 4 are each independently of the other substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C7 to C30 aralkyl 、-OR b 、-O(CO)R c 、-NR d R e 、-NR f (COR g )、-NR h C(NR i )R j 、-SR k or-S (CO) R l , Wherein R b is a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof, Wherein R c is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, Wherein R d and R e are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, Wherein R f and R g are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, Wherein R h 、R i , and R j are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, Wherein R k is a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof, Wherein R l is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, and At least one of R 2 to R 4 is selected from -OR b 、-O(CO)R c 、-NR d R e 、-NR f (COR g ) 、-NR h C(NR i )R j 、-SR k and-S (CO) R l , Wherein R b is a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof, Wherein R c is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, Wherein R d and R e are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, Wherein R f and R g are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, Wherein R h 、R i , and R j are each independently hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, Wherein R k is a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof, Wherein R l is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof.
  9. 9. The semiconductor photoresist composition according to claim 8, wherein at least one of R 2 to R 4 is selected from the group consisting of-OR b and-O (CO) R c , Wherein R b is a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C6 to C30 aryl, or a combination thereof, Wherein R c is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof.
  10. 10. The semiconductor photoresist composition according to claim 9, where R 1 is selected from the group consisting of substituted or unsubstituted C1 to C8 alkyl, substituted or unsubstituted C3 to C8 cycloalkyl, substituted or unsubstituted C2 to C8 alkenyl, substituted or unsubstituted C2 to C8 alkynyl, substituted or unsubstituted C6 to C20 aryl, and substituted or unsubstituted C7 to C20 aralkyl, R b is substituted or unsubstituted C1 to C8 alkyl, substituted or unsubstituted C3 to C8 cycloalkyl, substituted or unsubstituted C2 to C8 alkenyl, substituted or unsubstituted C2 to C8 alkynyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof, and R c is hydrogen, substituted or unsubstituted C1 to C8 alkyl, substituted or unsubstituted C3 to C8 cycloalkyl, substituted or unsubstituted C2 to C8 alkenyl, substituted or unsubstituted C2 to C8 alkynyl, substituted or unsubstituted C6 to C20 aryl, or a combination thereof.
  11. 11. The semiconductor photoresist composition of claim 1, wherein the organometallic compound is represented by chemical formula 3 or chemical formula 4: chemical formula 3 R 5 z SnO (2-(z/2)-(x/2)) (OH) x , In the chemical formula 3, the chemical formula is shown in the drawing, R 5 is a C1 to C31 hydrocarbon radical, 0 < z≤2 and 0 < (z+x). Ltoreq.4, and Chemical formula 4 R 6 a Sn b X c Y d , In the chemical formula 4, the chemical formula is shown in the drawing, R 6 is a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, a substituted or unsubstituted C2 to C20 aliphatically unsaturated organic group comprising one or more double or reference bonds, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C4 to C30 heteroaryl, a carbonyl, an oxirane, an oxetanyl, or a combination thereof, X is sulfur, selenium or tellurium, Y is-OR m OR-OC (=O) R n , Wherein R m is substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, and R n is hydrogen, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C2 to C20 alkenyl, substituted or unsubstituted C2 to C20 alkynyl, substituted or unsubstituted C6 to C30 aryl, or a combination thereof, and A. b, c, and d are each independently integers from 1 to 20.
  12. 12. A method of forming a pattern, comprising: Forming an etching target layer on a substrate; coating the semiconductor photoresist composition of claim 1 on the etching target layer to form a photoresist film; Patterning the photoresist film to form a photoresist pattern, and The etching target layer is etched using the photoresist pattern as an etching mask.
  13. 13. A system for forming a pattern, comprising: means for forming an etch target layer on a substrate; means for coating the semiconductor photoresist composition of claim 1 on the etching target layer to form a photoresist film; an apparatus for patterning the photoresist film to form a photoresist pattern, and Means for etching the etching target layer using the photoresist pattern as an etching mask.

Description

Semiconductor photoresist composition and method for forming pattern using the same Patent application related literature The present application claims priority and rights of korean patent application No. 10-2024-0153667 filed on the korean intellectual property office on month 11 of 2024, the entire contents of which are incorporated herein by reference. Technical Field One or more embodiments of the present disclosure relate to a semiconductor photoresist composition and a method of forming a pattern using the same. Background Extreme ultraviolet (extreme ultraviolet; EUV) lithography has become an important technique for manufacturing next-generation semiconductor devices such as advanced semiconductor chips (e.g., next-generation semiconductor chips). EUV lithography, using EUV radiation having a wavelength of 13.5 nm as an exposure light source, is capable of forming extremely fine patterns, for example, patterns having a critical dimension of 20 nm or less. Achieving high resolution patterning using EUV lithography requires the development of compatible photoresists capable of achieving resolutions below 16 nm. However, chemically amplified (CHEMICALLY AMPLIFIED; CA) photoresists currently face limitations in resolution, photospeed, and line edge roughness (line edge roughness; LER), which prevent their performance in advanced photolithography processes. In CA photoresists, acid catalyzed reactions can lead to image blurring, especially at small feature sizes, which limitation is also observed in electron beam lithography. Although CA photoresists are designed for high sensitivity, their typical elemental composition results in low gettering at 13.5 nm, thereby reducing sensitivity at EUV exposure. Furthermore, CA photoresists typically exhibit increased LER as the photospeed decreases, in part because of the random nature of the acid diffusion and reaction. These limitations create a need or desire for novel high performance photoresist materials suitable for EUV lithography. In response, research has turned to inorganic photoresist compositions, which are mainly used for negative tone patterning. These compositions are chemically modified by non-chemical amplification mechanisms to provide resistance to developer solutions. Inorganic photoresists typically contain elements with higher EUV absorption than hydrocarbons, provide improved sensitivity, reduced random effects, and lower LER. Inorganic photoresists, optionally mixed with elements such as niobium, titanium and/or tantalum, based on tungsten peroxy polyacids (peroxopolyacid), have been explored as radiation-sensitive materials for patterning. These materials have demonstrated efficacy in patterning large pitch features using bilayer configurations and various radiation sources, including deep UV, X-rays, and electron beams. For example, cationic metal oxide hafnium sulfate (HfSOx) materials, when combined with a peroxy complexing agent, have been able to image 15 nm half-pitch features via EUV projection exposure. While this system provides high performance and acceptable photospeed, it suffers from practical drawbacks of (i) the coating process involves corrosive sulfuric acid/hydrogen peroxide mixtures, resulting in poor shelf life stability, (ii) structural modification for performance enhancement is difficult, and (iii) development requires high concentrations of tetramethylammonium hydroxide (tetramethylammonium hydroxide; TMAH) solution (e.g., 25 wt%). To address these problems and challenges, recent efforts have focused on tin-containing molecules with strong EUV absorption. Among these molecules, organotin polymers have shown promise. Upon EUV exposure, the alkyl ligands dissociate and form oxygen bonds with adjacent chains, enabling negative tone patterning that is resistant to organic developer. Although these organotin polymers exhibit improved sensitivity, resolution, and LER, further enhancement is still needed or desired to meet commercial performance requirements. Disclosure of Invention One or more aspects of the embodiments of the present disclosure are directed to a semiconductor photoresist composition having excellent or suitable resolution characteristics and pattern adhesion by reducing the influence of variables during pattern formation, thereby improving CD (critical dimension) stability. One or more aspects of the embodiments of the present disclosure are directed to methods of forming patterns using semiconductor photoresist compositions. Additional aspects will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the embodiments presented herein. According to one or more embodiments of the present disclosure, a semiconductor photoresist composition includes an organometallic compound, a carboxylic acid compound represented by chemical formula 1, and a solvent: [ chemical formula 1] In chemical formula 1, L may be a single bond, a