# US 11,307,497 B2 · Compound, composition for forming organic film, substrate for manufacturing semiconductor apparatus, method for forming organic film, and patterning process > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,307,497 B2 - Document ID: US11307497B2 - Status: Granted - Kind: B2 - Application number: 16/293,150 - Filed: 2019-03-05 - Published: 2019-10-03 - Granted: 2022-04-19 - Earliest claimed: 2018-03-28 - Assignees: Shin-Etsu Chemical Co., Ltd. - Applicants: Shin-Etsu Chemical Co., Ltd. - Inventors: Seiichiro Tachibana; Takeru Watanabe; Keisuke Niida; Hiroko Nagai; Takashi Sawamura; Tsutomu Ogihara - Web page: https://patentgrep.com/patent/US11307497B2 ## CPC - G03F 7/025: Non-macromolecular photopolymerisable compounds having carbon-to-carbon triple bonds, e.g. acetylenic compounds (G03F7/075 takes precedence) - B33Y 70/00: Materials specially adapted for additive manufacturing - C07C 15/56: polycyclic condensed - C07D 335/12: Thioxanthenes - C08F 38/00: Homopolymers and copolymers of compounds having one or more carbon-to-carbon triple bonds - C09D 11/101: Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing - G03F 7/0037: {Production of three-dimensional images} - G03F 7/027: Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) - G03F 7/091: {characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement} - G03F 7/094: {Multilayer resist systems, e.g. planarising layers} - G03F 7/11: having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)} - H10P 50/287: {by chemical means} - H10P 76/20: of masks comprising organic materials - C07C 41/01: Preparation of ethers - C07C 215/46: having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton - G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G) - B33Y: ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10 ## Abstract A compound including two or more partial structures shown by the following general formula (1-1) in the molecule, wherein each Ar independently represents an aromatic ring optionally having a substituent or an aromatic ring that contains at least one nitrogen atom optionally having a substituent, and two Ars are optionally bonded with each other to form a ring structure; the broken line represents a bond with an organic group; B represents an anionic leaving group that is capable of forming a reactive cation due to effect of either or both of heat and acid. This provides a compound that is capable of curing under the film forming conditions in air or an inert gas without forming byproducts, and forming an organic under layer film that has good dry etching durability during substrate processing not only excellent characteristics of gap filling and planarizing a pattern formed on a substrate. ## Claims ### Claim 1 A composition for forming an organic film, comprising: (A) a compound shown by the following general formula (1-2), and (B) an organic solvent, wherein AR1 and AR2 each represent a benzene ring, a naphthalene ring, or a pyridine ring optionally having an alkoxy group, an alkenyloxy group, or an aryloxy group having 1 to 30 carbon atoms; “m” is 1; AR1 and AR2 form a bridged structure in which the aromatic rings of AR1 and AR2 are bonded with each other through X; X represents a single bond or any of groups shown by the following formulae (3); Y represents an n-valent organic group having 1 to 30 carbon atoms in which n=2 to 4 or an organic group-containing polymer having n-pieces of repeating units in which 2≤n≤1000; and R represents a hydrogen atom or a monovalent organic group having 1 to 30 carbon atoms. ### Claim 2 (depends on 1) The composition for forming an organic film according to claim 1, further comprising one or more components selected from the group consisting of (C) an acid generator, (D) a surfactant, (E) a compound having a partial structure of an aromatic ring other than the compound of the component (A), and (F) a plasticizer. ### Claim 3 (depends on 2) The composition for forming an organic film according to claim 2, wherein the component (E) has a weight average molecular weight of 500 to 100,000. ### Claim 4 (depends on 1) A substrate for manufacturing a semiconductor apparatus, comprising a basis substrate and an organic film formed on the basis substrate, the organic film being a cured material of the composition for forming an organic film according to claim 1. ### Claim 5 (depends on 1) A method for forming an organic film applied in a semiconductor apparatus manufacturing process, the method comprising: applying the composition for forming an organic film according to claim 1 on a body to be processed by spin coating; and heating the body to be processed, on which the composition for forming an organic film has been applied, at a temperature of 50° C. or more and 600° C. or less for 5 to 7200 seconds in an inert gas atmosphere to form a cured film. ### Claim 6 (depends on 1) A method for forming an organic film applied in a semiconductor apparatus manufacturing process, the method comprising: applying the composition for forming an organic film according to claim 1 on a body to be processed by spin coating; heating the body to be processed, on which the composition for forming an organic film has been applied, at a temperature of 50° C. or more and 300° C. or less for 5 to 600 seconds in air to form a coating film, and heating the body to be processed, on which the coating film has been formed, subsequently at a temperature of 200° C. or more and 600° C. or less for 10 to 7200 seconds in an inert gas atmosphere to form a cured film. ### Claim 7 (depends on 5) The method for forming an organic film according to claim 5, wherein the inert gas has an oxygen content of 1% or less. ### Claim 8 (depends on 5) The method for forming an organic film according to claim 5, wherein the body to be processed has steps or a structure with a height of 30 nm or more. ### Claim 9 (depends on 1) A patterning process comprising: forming an organic film on a body to be processed from the composition for forming an organic film according to claim 1; forming a silicon-containing resist middle layer film on the organic film from a resist middle layer film material containing silicon; forming a resist upper layer film on the silicon-containing resist middle layer film from a resist upper layer film material composed of a photoresist composition; forming a circuit pattern in the resist upper layer film; transferring the pattern to the silicon-containing resist middle layer film by etching using the resist upper layer film having the formed circuit pattern as a mask; transferring the pattern to the organic film by etching using the silicon-containing resist middle layer film having the transferred pattern as a mask; and transferring the pattern to the body to be processed by etching using the organic film having the transferred pattern as a mask. ### Claim 10 (depends on 1) A patterning process comprising: forming an organic film on a body to be processed from the composition for forming an organic film according to claim 1; forming a silicon-containing resist middle layer film on the organic film from a resist middle layer film material containing silicon; forming an organic antireflective film on the silicon-containing resist middle layer film; forming a resist upper layer film on the organic antireflective film from a resist upper layer film material composed of a photoresist composition to form a four-layered film structure; forming a circuit pattern in the resist upper layer film; transferring the pattern to the organic antireflective film and the silicon-containing resist middle layer film by etching using the resist upper layer film having the formed circuit pattern as a mask; transferring the pattern to the organic film by etching using the silicon-containing resist middle layer film having the transferred pattern as a mask; and transferring the pattern to the body to be processed by etching using the organic film having the transferred pattern as a mask. ### Claim 11 (depends on 1) A patterning process comprising: forming an organic film on a body to be processed from the composition for forming an organic film according to claim 1; forming an inorganic hard mask selected from a silicon oxide film, a silicon nitride film, a silicon oxynitride film, a titanium oxide film, and a titanium nitride film on the organic film; forming a resist upper layer film on the inorganic hard mask from a resist upper layer film material composed of a photoresist composition; forming a circuit pattern in the resist upper layer film; transferring the pattern to the inorganic hard mask by etching using the resist upper layer film having the formed circuit pattern as a mask; transferring the pattern to the organic film by etching using the inorganic hard mask having the transferred pattern as a mask; and transferring the pattern to the body to be processed by etching using the organic film having the transferred pattern as a mask. ### Claim 12 (depends on 1) A patterning process comprising: forming an organic film on a body to be processed from the composition for forming an organic film according to claim 1; forming an inorganic hard mask selected from a silicon oxide film, a silicon nitride film, a silicon oxynitride film, a titanium oxide film, and a titanium nitride film on the organic film; forming an organic antireflective film on the inorganic hard mask; forming a resist upper layer film on the organic antireflective film from a resist upper layer film material composed of a photoresist composition to form a four-layered film structure; forming a circuit pattern in the resist upper layer film; transferring the pattern to the organic antireflective film and the inorganic hard mask by etching using the resist upper layer film having the formed circuit pattern as a mask; transferring the pattern to the organic film by etching using the inorganic hard mask having the transferred pattern as a mask; and transferring the pattern to the body to be processed by etching using the organic film having the transferred pattern as a mask. ### Claim 13 (depends on 11) The patterning process according to claim 11, wherein the inorganic hard mask is formed by a CVD method or an ALD method. ### Claim 14 (depends on 9) The patterning process according to claim 9, wherein the circuit pattern is formed by a photolithography with a wavelength ranging from 10 nm to 300 nm, a direct drawing by electron beam, a nanoimprinting, or a combination thereof. ### Claim 15 (depends on 9) The patterning process according to claim 9, wherein the circuit pattern is developed by alkaline development or development with an organic solvent. ### Claim 16 (depends on 9) The patterning process according to claim 9, wherein the body to be processed is a semiconductor apparatus substrate or the semiconductor apparatus substrate coated with any of a metal film, a metal carbide film, a metal oxide film, a metal nitride film, a metal oxycarbide film, and a metal oxynitride film. ### Claim 17 (depends on 16) The patterning process according to claim 16, wherein the body to be processed contains silicon, titanium, tungsten, hafnium, zirconium, chromium, germanium, copper, silver, gold, aluminum, indium, gallium, arsenic, palladium, iron, tantalum, iridium, cobalt, manganese, molybdenum, or an alloy thereof.