Photoresist composition and method of forming photoresist pattern

Abstract

A method of forming a photoresist pattern includes forming a photoresist layer including a photoresist composition over a substrate. The photoresist composition includes metal particles and a thermally stable ligand attached to the metal particles. The thermally stable ligand includes branched or unbranched, cyclic or non-cyclic, C1-C7 alkyl groups or C1-C7 fluoroalkyl groups. The C1-C7 alkyl or C1-C7 fluoroalkyl groups include one or more of —CF 3 , —SH, —OH, ═O, —S—, —P—, —PO 2 , —C(═O)SH, —C(═O)OH, —C(═O)O—, —O—, —N—, —C(═O)NH, —SO 2 OH, —SO 2 SH, —SOH, or —SO 2 —. The photoresist layer is selectively exposed to actinic radiation, and the photoresist layer is developed to form a pattern in the photoresist layer. In an embodiment, the method includes heating the photoresist layer before selectively exposing the photoresist layer to actinic radiation.

What is claimed is: 
     
         1 . A photoresist composition, comprising:
 metal particles; and   a first ligand attached to the metal particles,   wherein the first ligand includes saturated C1-C7 organic groups, wherein the saturated C1-C7 organic groups are branched, unbranched, cyclic, or non-cyclic, and include H or F, and one or more of —CF 3 , —SH, —OH, ═O, —S—, —P—, —PO 2 , —C(═O)SH, —C(═O)NH, —SO 2 OH, —SO 2 SH, —SOH, and —SO 2 —.   
     
     
         2 . The photoresist composition of  claim 1 , wherein the metal particles are nanoparticles. 
     
     
         3 . The photoresist composition of  claim 1 , wherein the metal particles include one or more of titanium, zinc, zirconium, nickel, cobalt, manganese, copper, iron, strontium, tungsten, vanadium, chromium, tin, hafnium, indium, cadmium, molybdenum, tantalum, niobium, aluminum, cesium, barium, lanthanum, cerium, silver, antimony, combinations thereof, or oxides thereof. 
     
     
         4 . The photoresist composition of  claim 1 , wherein the photoresist composition further comprises a second ligand attached to the metal particles, wherein the second ligand is a different material than the first ligand. 
     
     
         5 . The photoresist composition of  claim 4 , wherein the second ligand is a carboxylic acid or sulfonic acid ligand,
 wherein the carboxylic acid or sulfonic acid is branched, unbranched, aliphatic, aromatic, substituted, or unsubstituted, and   wherein, when the second ligand is substituted, it is substituted with a substituent selected from a C1-C9 alkyl group, a C2-C9 alkenyl group, a C6-C9 phenyl group, or combinations thereof.   
     
     
         6 . The photoresist composition of  claim 1 , further comprising a solvent. 
     
     
         7 . The photoresist composition of  claim 6 , wherein the solvent is one or more of propylene glycol methyl ether acetate (PGMEA), propylene glycol monomethyl ether (PGME), 1-ethoxy-2-propanol (PGEE), γ-butyrolactone (GBL), cyclohexanone (CHN), ethyl lactate (EL), methanol, ethanol, propanol, n-butanol, acetone, dimethylformamide (DMF), isopropanol (IPA), tetrahydrofuran (THF), methyl isobutyl carbinol (MIBC), n-butyl acetate (nBA), or 2-heptanone (MAK). 
     
     
         8 . The photoresist composition of  claim 7 , wherein a concentration of the metal particles ranges from 0.5 wt. % to 15 wt. % based on a weight of the solvent and the metal particles. 
     
     
         9 . A resist composition, comprising:
 metal cores;   a first ligand attached to the metal cores,   wherein the first ligand includes C1-C7 alkyl groups or C1-C7 fluoroalkyl groups,   wherein the C1-C7 alkyl groups or C1-C7 fluoroalkyl groups are branched, unbranched, cyclic, or non-cyclic, and   wherein the C1-C7 alkyl groups or C1-C7 fluoroalkyl groups include one or more of —CF 3 , —SH, —OH, ═O, —S—, —P—, —PO 2 , —C(═O)SH, —C(═O)NH, —SO 2 OH, —SO 2 SH, —SOH, or —SO 2 —; and   a second ligand attached to the metal cores,   wherein the second ligand is a different material than the first ligand.   
     
     
         10 . The resist composition of  claim 9 , wherein the metal cores are formed of a plurality of metal nanoparticles. 
     
     
         11 . The resist composition of  claim 9 , wherein the metal cores include one or more of titanium, zinc, zirconium, nickel, cobalt, manganese, copper, iron, strontium, tungsten, vanadium, chromium, tin, hafnium, cadmium, molybdenum, tantalum, niobium, aluminum, cesium, barium, lanthanum, cerium, indium, silver, antimony, oxides thereof, or alloys thereof. 
     
     
         12 . The resist composition of  claim 9 , further comprising a solvent; and
 a concentration of the metal cores ranges from 0.5 wt. % to 15 wt. % based on a weight of the solvent and the metal cores.   
     
     
         13 . The resist composition of  claim 12 , wherein the concentration of the metal cores ranges from 1 wt. % to 7 wt. % based on the weight of the solvent and the metal cores. 
     
     
         14 . The resist composition of  claim 12 , wherein the second ligand is a carboxylic acid or sulfonic acid ligand,
 wherein the carboxylic acid or sulfonic acid is branched, unbranched, aliphatic, aromatic, substituted, or unsubstituted, and   wherein, when the second ligand is substituted, it is substituted with a substituent selected from one or more of a C1-C9 alkyl group, a C2-C9 alkenyl group, or a C1-C9 phenyl group.   
     
     
         15 . The resist composition of  claim 9 , wherein a concentration of the first ligand ranges from 7 wt. % to 99 wt. % based on a total weight of the first ligand and the second ligand. 
     
     
         16 . A photoresist composition, comprising:
 metal nanoparticles;   a thermally stable ligand attached to the metal nanoparticles,   wherein the thermally stable ligand includes saturated C1-C7 organic groups,   wherein the saturated C1-C7 organic groups are branched, unbranched, cyclic, or non-cyclic, and   wherein the C1-C7 organic groups include H or F, and one or more of —CF 3 , —SH, —OH, ═O, —S—, —P—, —PO 2 , —C(═O)SH, —C(═O)NH, —SO 2 OH, —SO 2 SH, —SOH, and —SO 2 —;   a second ligand attached to the metal nanoparticles,   wherein the second ligand is a carboxylic acid or sulfonic acid ligand,   wherein the carboxylic acid or sulfonic acid is branched, unbranched, aliphatic, aromatic, substituted, or unsubstituted, and   wherein, when the second ligand is substituted, it is substituted with a substituent selected from one or more of a C1-C9 alkyl group, a C2-C9 alkenyl group, or a C6-C9 phenyl groups; and   a solvent.   
     
     
         17 . The photoresist composition of  claim 16 , wherein the metal nanoparticles include one or more of titanium, zinc, zirconium, nickel, cobalt, manganese, copper, iron, strontium, tungsten, vanadium, chromium, tin, hafnium, cadmium, molybdenum, tantalum, niobium, aluminum, cesium, barium, lanthanum, cerium, indium, silver, antimony, oxides thereof, or alloys thereof. 
     
     
         18 . The photoresist composition of  claim 16 , wherein a concentration of the thermally stable ligand ranges from 7 wt. % to 99 wt. % based on a total weight of the thermally stable ligand and the second ligand. 
     
     
         19 . The photoresist composition of  claim 18 , wherein the concentration of the thermally stable ligand ranges from 15 wt. % to 85 wt. % based on the total weight of the thermally stable ligand and the second ligand. 
     
     
         20 . The photoresist composition of  claim 16 , further comprising a photoactive compound.