# US 2019/0317403 A1 · Organic layer composition, organic layer, and method of forming patterns > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2019/0317403 A1 - Document ID: US20190317403A1 - Status: Published application - Kind: A1 - Application number: 16/340,728 - Filed: 2017-06-14 - Published: 2019-10-17 - Earliest claimed: 2016-11-10 - Assignees: Samsung SDI Co., Ltd. - Applicants: Samsung SDI Co., Ltd. - Inventors: Shinhyo BAE; Taeho KIM; Yushin PARK; Youjung PARK; Hyunji SONG; Hyunsoo LEE; Hyejin JANG - Web page: https://patentgrep.com/patent/US20190317403A1 ## CPC - G03F 7/0046: {with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence)} - G03F 7/0048: {characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents} - G03F 7/094: {Multilayer resist systems, e.g. planarising layers} - G03F 7/162: {Coating on a rotating support, e.g. using a whirler or a spinner} - G03F 7/20: Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00) - H10P 50/00: Etching of wafers, substrates or parts of devices - H10P 76/00: Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography - H10P 95/00: Generic processes or apparatus for manufacture or treatments not covered by the other groups of this subclass - C07C 13/567: with a fluorene or hydrogenated fluorene ring system - C07C 13/62: with more than three condensed rings - C07C 15/24: containing two rings - C07C 15/27: containing three rings - C07C 15/38: containing four rings - C07C 2602/10: the other ring being six-membered, e.g. tetraline - C07C 2603/02: Ortho- or ortho- and peri-condensed systems - G03F 7/0752: {in non photosensitive layers or as additives, e.g. for dry lithography} - 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) - H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10 - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract An organic layer composition includes an aromatic ring compound, an additive including perfluoroalkyl in the structure, and a solvent, wherein a fluoro (F) group included in the additive is included in an amount of greater than 0 wt % and less than or equal to 30 wt % based on a total weight, 100 wt % of the additive, and a surface tension decrease rate of the additive measured according to Condition 1 is 0.1% to 30%. The definition of Condition 1 is the same as described in the specification. ## Claims ### Claim 1 An organic layer composition, comprising an aromatic ring compound, an additive including perfluoroalkyl in the structure, and a solvent, wherein a fluoro (F) group included in the additive is included in an amount of greater than 0 wt % and less than or equal to 30 wt % based on a total weight, 100 wt % of the additive, and a surface tension decrease rate of the additive measured according to Condition 1 is 0.1% to 30%: [Condition 1] S1: a solution including the additive mixed with cyclohexanone is prepared wherein, an amount of the additive is 2 wt % based on 100 wt % of the solution, S2: a surface tension of the solution is measured at 25° C., and S3: a surface tension decrease rate of the additive is calculated according to Equation 1, Surface tension decrease rate (%) of an additive=((1−(surface tension of an additive measured at 25° C.))/(surface tension of cyclohexanone measured at 25° C.))×100. Equation 1 ### Claim 2 (depends on 1) The organic layer composition of claim 1, wherein the surface tension decrease rate of the additive is 1% to 25%. ### Claim 3 (depends on 1) The organic layer composition of claim 1, wherein the fluoro (F) group included in the additive is included in an amount of 0.001 wt % to 20 wt % based on a total weight, 100 wt % of the additive. ### Claim 4 (depends on 1) The organic layer composition of claim 1, wherein a carbon number of the perfluoroalkyl is 4 to 24. ### Claim 5 (depends on 1) The organic layer composition of claim 1, wherein the additive is perfluoroalkyl alcohol, perfluoroalkyl carboxylic acid, perfluoroalkyl sulfonic acid, perfluoro acrylate, perfluoro ether, or a combination thereof. ### Claim 6 (depends on 1) The organic layer composition of claim 1, wherein the additive is included in an amount of 0.001 wt % to 25 wt % based on a total amount of the organic layer composition. ### Claim 7 (depends on 1) The organic layer composition of claim 1, wherein the organic layer composition has an edge flexure decrease rate measured according to Condition 2 of 10% to 100%: [Condition 2] S1: an organic layer composition is spin-on coated at a speed of 1,500 rpm on a patterned 12″ silicon wafer, heat treatment is performed at 400° C. for 120 seconds to form a thin layer and a thickness of the thin layer is measured by a thin layer thickness measuring equipment, an edge part of the thin layer is defined to be a part by 600 μm from an edge of a coated thin layer toward a center, wherein, a coating thickness of the center of the thin layer and a coating thickness of a maximum hump at the edge part of the thin layer are measured and their difference is referred to as an edge flexure thickness, S2: a composition excluding the additive from the organic layer composition of S1 is prepared and the same process as S1 is repeated to measure an edge flexure thickness, S3: an edge flexure decrease rate is calculated according to Equation 2, Edge flexure decrease rate (%)=(1−(edge flexure thickness of thin layer manufactured from organic layer composition)/(edge flexure thickness of thin layer manufactured from composition excluding additive))×100. Equation 2 ### Claim 8 (depends on 1) The organic layer composition of claim 1, wherein the aromatic ring compound includes two or more substituted or unsubstituted benzene rings in the structure. ### Claim 9 (depends on 8) The organic layer composition of claim 8, wherein the aromatic ring compound includes one of moieties of Group 1 in the structure: wherein, in Group 1, M is a substituted or unsubstituted C1 to C5 alkylene group, —O—, —S—, —SO2—, or carbonyl. ### Claim 10 (depends on 1) The organic layer composition of claim 1, wherein the aromatic ring compound is a polymer having a weight average molecular weight of 500 to 200,000. ### Claim 11 (depends on 1) The organic layer composition of claim 1, wherein the aromatic ring compound is a monomolecule having a molecular weight of 500 to 1,300. ### Claim 12 (depends on 1) The organic layer composition of claim 1, wherein the solvent is one or more selected from the group consisting of propylene glycol, propylene glycol diacetate, methoxy propanediol, diethylene glycol, diethylene glycol butylether, tri(ethylene glycol)monomethylether, propylene glycol monomethylether, propylene glycol monomethylether acetate, cyclohexanone, ethyllactate, gamma-butyrolactone, N,N-dimethyl formamide, N,N-dimethyl acetamide, methylpyrrolidone, acetylacetone, and ethyl 3-ethoxypropionate. ### Claim 13 (depends on 1) The organic layer composition of claim 1, wherein the aromatic ring compound is included in an amount of 0.1 wt % to 30 wt % based on a total amount of the organic layer composition. ### Claim 14 (depends on 1) An organic layer manufactured from the organic layer composition of claim 1 and having an edge flexure decrease rate of 10% to 100% measured according to Condition 2: [Condition 2] S1: an organic layer composition is spin-on coated at a speed of 1,500 rpm on a patterned 12″ silicon wafer, heat treatment is performed at 400° C. for 120 seconds to form a thin layer and a thickness of the thin layer is measured by a thin layer thickness measuring equipment, an edge part of the thin layer is defined to be a part by 600 μm from an edge of a coated thin layer toward a center, wherein, a coating thickness of the center of the thin layer and a coating thickness of a maximum hump at the edge part of the thin layer are measured and their difference is referred to as an edge flexure thickness, S2: a composition excluding the additive from the organic layer composition of S1 is prepared and the same process as S1 is repeated to measure an edge flexure thickness, S3: an edge flexure decrease rate is calculated according to Equation 2, Edge flexure decrease rate (%)=(1−(edge flexure thickness of thin layer manufactured from organic layer composition)/(edge flexure thickness of thin layer manufactured from composition excluding additive))×100. Equation 2 ### Claim 15 (depends on 1) A method of forming patterns, comprising forming a material layer on a substrate, applying the organic layer composition of claim 1 on the material layer, heat-treating the organic layer composition to form a hardmask layer, forming a silicon-containing thin layer on the hardmask layer, forming a photoresist layer on the silicon-containing thin layer, exposing and developing the photoresist layer to form a photoresist pattern, selectively removing the silicon-containing thin layer and the hardmask layer using the photoresist pattern to expose a part of the material layer, and etching an exposed part of the material layer. ### Claim 16 (depends on 15) The method of forming patterns of claim 15, wherein the applying of the organic layer composition is performed using a spin-on coating method. ### Claim 17 (depends on 15) The method of forming patterns of claim 15, wherein the method further includes forming a bottom antireflective coating (BARC) before forming the photoresist layer.