# US 2025/0147423 A1 · Photolithographic rinse compositions and methods of forming patterns using the compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2025/0147423 A1 - Document ID: US20250147423A1 - Status: Published application - Kind: A1 - Application number: 18/737,042 - Filed: 2024-06-07 - Published: 2025-05-08 - Earliest claimed: 2023-10-30 - Assignees: Samsung Electronics Co., Ltd. - Applicants: Samsung Electronics Co., Ltd. - Inventors: JINJOO KIM; DAIKI MINAMI; WON-JOON SON; HYUNJI SONG; SONGSE YI - Web page: https://patentgrep.com/patent/US20250147423A1 ## CPC - G03F 7/38: Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)} - 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) ## Abstract Disclosed are photolithographic rinse compositions and methods of forming patterns using the same, the photolithographic rinse compositions including a gemini-type surfactant having a main chain including at least two hydrophobic groups and at least one hydrophilic group and at least two side chains branching from the main chain and including a hydrophilic group-including functional group, and a solvent. ## Claims ### Claim 1 A photolithographic rinse composition, comprising a gemini-type surfactant having a main chain including at least two hydrophobic groups, at least one hydrophilic group, at least two side chains branching from the main chain, and a hydrophilic group-including functional group; and a solvent. ### Claim 2 (depends on 1) The photolithographic rinse composition of claim 1, wherein the surfactant includes a compound represented by Chemical Formula 1: wherein, in Chemical Formula 1, Y1 and Y4 are each independently a substituted or unsubstituted C2 to C12 alkyl group that does not include fluorine; a substituted or unsubstituted C2 to C12 alkenyl group that does not include fluorine; a substituted or unsubstituted C2 to C12 alkynyl group that does not include fluorine, or any combination thereof, Y2 is a substituted or unsubstituted C1 to C10 alkylene group that does not include fluorine; a substituted or unsubstituted C2 to C10 alkenylene group that does not include fluorine; a substituted or unsubstituted C2 to C10 alkynylene group that does not include fluorine, or any combination thereof, X1 is a hydrophilic group, R1 and R2 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C5 alkyl group that does not include fluorine, a substituted or unsubstituted C2 to C5 alkenyl group that does not include fluorine, a substituted or unsubstituted C2 to C5 alkynyl group that does not include fluorine, or any combination thereof; R3 to R6 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted C2 to C5 alkenyl group, a substituted or unsubstituted C2 to C5 alkynyl group, a hydrophilic group, or any combination thereof, wherein at least two of R3 to R6 are hydrophilic groups; L1 to L4 are each independently a single bond, a substituted or unsubstituted C1 to C10 alkylene group that does not include fluorine, a substituted or unsubstituted C2 to C10 alkenylene group that does not include fluorine, a substituted or unsubstituted C2 to C10 alkynylene group that does not include fluorine, or any combination thereof; L5 to L8 are each independently a single bond, a substituted or unsubstituted C1 to C10 alkylene group that does not include fluorine, a substituted or unsubstituted C2 to C10 alkenylene group that does not include fluorine, a substituted or unsubstituted C2 to C10 alkynylene group that does not include fluorine, a substituted or unsubstituted C6 to C12 arylene group that does not include fluorine, or any combination thereof; and n1 is an integer from 0 to 5. ### Claim 3 (depends on 2) The photolithographic rinse composition of claim 2, wherein X1 is a nonionic hydrophilic group; and at least one of R3 to R6 is a nonionic hydrophilic group, and at least one of the other R3 to R6 is a nonionic hydrophilic group, an anionic hydrophilic group, a cationic hydrophilic group, or any combination thereof. ### Claim 4 (depends on 2) The photolithographic rinse composition of claim 2, wherein X1 is a nonionic hydrophilic group selected from an amide group (—NHC(═O)—), a thioamide group (—NHC(═S)—), an ester group (—OC(═O)—), and a sulfone group (—S(═O)2). ### Claim 5 (depends on 2) The photolithographic rinse composition of claim 2, wherein wherein when one or more of Y1 to Y4, R1 to R6, and L1 to L8 are substituted, each substitution is independently selected from a C1 to C5 alkyl group, a C2 to C5 alkenyl group, a C2 to C5 alkynyl group, or any combination thereof. ### Claim 6 (depends on 2) The photolithographic rinse composition of claim 2, wherein at least one of R3 to R6 includes an anionic hydrophilic group selected from a sulfonic acid salt (—SO3—), sulfonic acid (—SO3H), a carboxylic acid salt (—CO2—), carboxylic acid (—CO2H), dicarboxylic acid salt (—OC(O)(CH2)n2C(O)O−), dicarboxylic acid (—OC(O)(CH2)n2C(O)OH), phosphate (—HPO3−), and phosphoric acid (—H2PO4), wherein n2 is an integer from 1 to 5, and at least one of the other R3 to R6 includes a nonionic hydrophilic group selected from a hydroxy group, an amide group (—NHC(═O)—), a thioamide group (—NHC(═S)—), an ester group (—OC(═O)—), and a sulfone group (—S(═O)2), or an anionic hydrophilic group selected from a sulfonic acid salt (—SO3—), sulfonic acid (—SO3H), a carboxylic acid salt (—CO2−), carboxylic acid (—CO2H), dicarboxylic acid salt (—OC(O)(CH2)n2C(O)O−), dicarboxylic acid (—OC(O)(CH2)n2C(O)OH), phosphate (—HPO3−), and phosphoric acid (—H2PO4), wherein n2 is an integer from 1 to 5. ### Claim 7 (depends on 2) The photolithographic rinse composition of claim 2, wherein at least one of L3 and L4 further includes one or more hydrophilic groups. ### Claim 8 (depends on 7) The photolithographic rinse composition of claim 7, wherein the hydrophilic group is a nonionic hydrophilic group. ### Claim 9 (depends on 2) The photolithographic rinse composition of claim 2, wherein n1 is one of the integers from 0 to 2. ### Claim 10 (depends on 2) The photolithographic rinse composition of claim 2, wherein L5 to L8 are each independently a single bond; a substituted or unsubstituted C1 to C2 alkylene group that does not include fluorine; or a substituted or unsubstituted C6 to C10 arylene group that does not include fluorine. ### Claim 11 (depends on 1) The photolithographic rinse composition of claim 1, wherein the surfactant is included at a concentration of about 10 to about 10,000 ppm based on a total amount of the rinse composition. ### Claim 12 (depends on 1) The photolithographic rinse composition of claim 1, wherein at least one additional additive selected from an acid additive and a hydrophilic organic solvent is further included. ### Claim 13 (depends on 12) The photolithographic rinse composition of claim 12, wherein the acid additive is included at a concentration of about 1 to about 10,000 ppm based on a total amount of the rinse composition. ### Claim 14 (depends on 12) The photolithographic rinse composition of claim 12, wherein the hydrophilic organic solvent is included in an amount of about 0 to about 20 wt % based on a total 100 wt % of the solvent. ### Claim 15 (depends on 12) The photolithographic rinse composition of claim 12, wherein the additional additive is a unimolecular compound with a number average molecular weight of less than or equal to about 1,000. ### Claim 16 (depends on 1) The photolithographic rinse composition of claim 1, wherein the surfactant is selected from compounds listed in Group 1: ### Claim 17 (depends on 1) A method of forming patterns, comprising forming a photoresist film on a substrate; exposing a photoresist film; patterning the exposed photoresist film to form a photoresist pattern; and washing the photoresist pattern using the rinse composition of claim 1. ### Claim 18 (depends on 17) The method of claim 17, wherein in the washing of the photoresist pattern, the surfactant is distributed at the interface of the photoresist pattern-solvent and solvent-air, and a surface distribution ratio (m1/m2) calculated as the number of surfactant molecules (m1) distributed at the interface of the photoresist pattern-solvent relative to the number of molecules (m2) of the surfactant distributed at the solvent-air interface is greater than about 1.3. ### Claim 19 (depends on 17) The method of claim 17, wherein in the forming of the photoresist pattern, light having a wavelength range of about 5 nm to about 150 nm is used. ### Claim 20 (depends on 17) The method of claim 17, wherein the photoresist pattern has a pattern spacing of about 15 nm to about 40 nm.