Single-component molecular resists containing bound photoacid generator functionality

A series of single-component molecular resists was designed, synthesized, characterized, and patterned using 100-keV e-beam lithography. An onium salt photoacid generator-based single-component resist system (referred to here as TAS) that creates a free photoacid upon exposure is shown to produce a low line edge roughness (LER) of 3.9 nm (3) but was limited in resolution due to photoacid diffusion. A different single-component molecular resist (referred to here as NBB) with a covalently bound nonionic photoacid generator, i.e., one in which the photoacid anion is bound to the resist core, was also synthesized. NBB was found to exhibit an improved resolution of 40 nm due to reduced photoacid diffusion while maintaining a good LER and line width roughness (LWR) of 3.9 nm and 5.6 nm, respectively. Despite the small size of NBB, it was found to exhibit a glass transition temperature of 82 °C. It also showed good adhesion, formed high-quality films, and showed no dark erosion during development. These compounds demonstrate that it is possible to form single-component molecular resists using both ionic and nonionic photoacid generators and that such small molecule resists can provide all the basic requirements to serve as functional chemically amplified resists.

[1]  H. Fukuda,et al.  Negative-Tone Polyphenol Resist using Intramolecular-Esterification Reaction for sub-50 nm Lithography , 2006 .

[2]  Clifford L. Henderson,et al.  Influence of solubility switching mechanism on resist performance in molecular glass resists , 2007 .

[3]  Robert L. Bristol,et al.  The tri-lateral challenge of resolution, photospeed, and LER: scaling below 50nm? , 2007, SPIE Advanced Lithography.

[4]  Clifford L. Henderson,et al.  Molecular glass photoresists containing photoacid generator functionality: a route to a single-molecule photoresist , 2007, SPIE Advanced Lithography.

[6]  R. Campbell,et al.  Polymerization of 4-Hydroxybenzenesulfonyl Chloride , 1973 .

[7]  Nelson Felix,et al.  Molecular Glass Resists as High‐Resolution Patterning Materials , 2008 .

[8]  Nelson Felix,et al.  Study of the Structure−Properties Relationship of Phenolic Molecular Glass Resists for Next Generation Photolithography , 2008 .

[9]  Taku Hirayama,et al.  New Photoresist Based on Amorphous Low Molecular Weight Polyphenols , 2004 .

[10]  Clifford L. Henderson,et al.  Influence of molecular weight and film thickness on the glass transition temperature and coefficient of thermal expansion of supported ultrathin polymer films , 2004 .

[11]  Mingxing Wang,et al.  Effects of photoacid generator incorporation into the polymer main chain on 193 nm chemically amplified resist behavior and lithographic performance , 2007 .

[12]  B. Kasemo,et al.  Transmission electron microscopy 'windows' for nanofabricated structures , 2004 .

[13]  Marie Krysak,et al.  Molecular glass resists for next-generation lithography , 2009, Advanced Lithography.

[14]  Suman Datta,et al.  Impact of line-width roughness on Intel's 65-nm process devices , 2007, SPIE Advanced Lithography.

[15]  Clifford L. Henderson,et al.  Single molecule chemically amplified resists based on ionic and non-ionic PAGs , 2008, SPIE Advanced Lithography.

[16]  Clifford L. Henderson,et al.  Mesoscale simulation of molecular glass photoresists: effect of PAG loading and acid diffusion coefficient , 2008, SPIE Advanced Lithography.

[17]  Junyan Dai,et al.  Molecular Glass Resists for High-Resolution Patterning , 2006 .

[18]  Yayi Wei,et al.  Evaluation of EUV resist materials for use at the 32 nm half-pitch node , 2008, SPIE Advanced Lithography.

[19]  K. Gonsalves,et al.  New resists for nanometer scale patterning by extreme ultraviolet lithography , 2005 .

[20]  Seung Wook Chang,et al.  Molecular glass photoresists for advanced lithography , 2006 .

[22]  Mingxing Wang,et al.  Fluorine-contained photoacid generators (PAGs) and corresponding polymer resists , 2008 .

[23]  H. Fukuda,et al.  Depth profile and line-edge roughness of partially O-1-ethoxyethylated low molecular weight amorphous polyphenol and poly(p-hydroxystyrene) base resists for electron-beam lithography , 2006 .

[24]  Gregg M. Gallatin Resist blur and line edge roughness (Invited Paper) , 2004, SPIE Advanced Lithography.

[25]  Bruno M. La Fontaine,et al.  Characterization of line-edge roughness in photoresist using an image fading technique , 2004, SPIE Advanced Lithography.

[26]  Mingxing Wang,et al.  Novel anionic photoacid generator (PAGs) and photoresist for sub-50-nm patterning by EUVL and EBL , 2007, SPIE Advanced Lithography.