Synthesis and Property of Tellurium-Containing Molecular Resist Materials for Extreme Ultraviolet Lithography System

Abstract

We examined the synthesis and resist properties of tellurium-containing molecular resist materials. By the condensation reaction of anisol, phenol, and 2-phenylphenol with tellurium tetrachloride (TeCl 4), dichloro di(4-hydroxyphenyl) telluride (CHPT), dichloro di(4-hydroxy-3-phenylbenz) telluride (CHBT), di(4-hydroxyphenyl) telluride (HPT), and di(4-hydoxy-3-phenylbenz) telluride (HBT) were synthesized. These were reacted with 2methyl-2-adamantyl bromo acetate, yielding corresponding compounds CHPT-AD, CHBT-AD, HPT-AD, and HBT-AD, respectively. By the examination of resist properties (thickness loss property, resist sensitivity, and etching durability), CHBT-AD could be good candidate for higher resolution EUV resist material.

Non-chemically Amplified Negative Molecular Resist Materials using Polarity Change by EUV Exposure

“…However, a good sensitivity curve could not be obtained in the case of TDP-BEPMSion. Presumably because of that transparency of TDP-BEPMSion might be low due to tellurium, which has high EUV absorption efficiency 14,15 .…”

“…For example, Ueda et al synthesized calix [4]resorcinarene with pendant t-butyloxycarbonyl group as a molecular resist and it's a thin film could offer a resist pattern with 1.5 μm L/S using UV exposure tool [3]. Our research group has also reported the development of molecular resist materials based on ladder cyclic oligomer noria ("noria" = water wheel in Latin) [4 -12], tannic acid derivative [13], and telluriumcontaining materials [14,15]. These molecular resists have been considered to achieve higher sensitivity, but their roughness of resist pattern could not improve.…”

Reaction mechanisms of Sn-complex-side-chain polymer used for extreme ultraviolet lithography, studied by electron pulse radiolysis and γ-radiolysis

“…In a next-generation resist process, the incorporation of elements with a large EUV absorption cross section into the resist formula will be required to suppress shot noise effects. Metal elements such as Ti, 7,8) Zr, 7,[9][10][11][12][13][14] Sn, [15][16][17][18][19] Sb, 20) Hf, 8,9,11) Bi, 21) and Te 22) have been examined as high-EUV absorption units.…”

Design of High-sensitive Resist Materials Based on Polyacetals

“…At present time, a chemically amplified resist (CAR) system is utilized to increase sensitivity [8][9][10][11]. We have also reported the synthesis of the higher sensitive EUV resist materials based on ladder cyclic oligomer noria derivatives ("noria" = water wheel in Latin) [12][13][14][15][16][17][18][19][20], tannic acid derivatives [21], tellurium-containing compounds [22][23], cage oligomer consistent of calixarene in the main chain [24], botryosin-type polymer [25], and iodinecontaining hyper branched polymer [26]. Consequently, resist sensitivities were consistent with the structures of resist materials and these results prompt us the systematical examination of the relationship between the sensitivity and the structure of the resist materials.…”