Depth Profile and Line-Edge Roughness of Low-Molecular-Weight Amorphous Electron Beam Resists

Hirayama, Taku; Shiono, Daiju; Matsumaru, Shogo; Ogata, Toshiyuki; Hada, Hideo; Onodera, Junichi; Arai, Tadashi; Sakamizu, Toshio; Yamaguchi, Atsuko; Shiraishi, Hiroshi; Fukuda, Hiroshi; Ueda, Mitsuru

doi:10.1143/jjap.44.5484

Cited by 41 publications

(28 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…48,56,57 Recently, molecular glass resists have attracted attention as candidates for high-resolution patterning. [58][59][60][61][62][63][64][65][66][67] Fréchet et al 68 reported EB resist materials based on dendritic polymer resins, resulting in 50-100 nm line and space patterns. Ochiai et al 69 reported negative-type high-resolution resists based on p-chloromethylmethoxycalix [4]arene.…”

Section: Synthesis Of Noria and Its Applications To Eb And Euv Resistmentioning

confidence: 99%

Development of Novel Photo-Functional Materials Based on Cyclic Oligomers

Kudo

Nishikubo

2009

Polym. J.

View full text Add to dashboard Cite

Novel photo-functional materials, such as refractive-index-changing materials, argon fluoride (ArF) resist materials, and electron beam (EB) resist materials, were designed based on the structures of calixarenes, cyclodextrin, and noria. The synthesis and refractive-index properties of calixarene derivatives containing photo-reactive groups, including azobenzene, norbornadiene, anthracene, cinnamate, and chalcone, were examined, and refractive-index changes (Án D 's) of between 0.007 and 0.061 were observed. The synthesis and patterning properties of a single-layer ArF photoresist system of -CD derivative containing t-butyl ester and fluorine were examined, and a well-resolved 100 nm line and space pattern was obtained on a silicon wafer. A new ladder-like macrocycle, noria (water wheel in Latin), was also synthesized and its application as an EB resist material was examined. The noria derivatives noria-COO t Bu containing t-butyl ester groups, noria-BOC containing t-butyloxycarbonyl group, and noria-acetal containing acetal groups had good physical properties and photo-reactivity. EBresist based on noria-COO t Bu and noria-BOC provided clear line and space patterns at a resolution of 70 and 50 nm, respectively.The development of novel photo-functional materials has contributed substantially to progress in the electronic and optoelectronic industries. Photo-reactive groups, such as radical-or cation-polymerizable groups, photo-isomerizable groups, and photo-removable groups, are useful for obtaining ultraviolet (UV)-cured resins, refractive-index-changing materials, and photo-resist materials, respectively. The physical properties of photo-functional materials, such as film-forming characteristics, thermal stability, mechanical properties, and photo-reactivity, depend primarily on the polymer or oligomer structure. Generally, the photochemical reactivity increases with decreasing glass transition temperature (T g ), due to increase of the molecular motion of polymer chains and functional groups.The photo-chemical reactivity of oligomers is usually greater than that of polymers, due to the lower T g of oligomers compared with polymers. However, the mechanical properties, thermal stability and film-forming properties of oligomer derivatives are inferior to those of polymer derivatives. However, if a linear oligomer is changed to a cyclic oligomer by coupling reaction of the two ends, the physical properties of the resulting cyclic oligomer are expected to be superior to those of the linear oligomer. Therefore, we considered that photofunctional cyclic oligomers might combine the advantages of photo-functional polymers and photo-functional oligomers. That is, photo-functional cyclic oligomers might have both high photo-chemical reactivity and good physical properties.Calixarenes are typical cyclic oligomers containing many hydroxyl groups, and are prepared easily by the reaction of phenols with aldehydes (Scheme 1). 1Although it is well known that calixarenes are attractive materials for use as host molecules in th...

show abstract

Section: Synthesis Of Noria and Its Applications To Eb And Euv Resistmentioning

confidence: 99%

Development of Novel Photo-Functional Materials Based on Cyclic Oligomers

Kudo

Nishikubo

2009

Polym. J.

View full text Add to dashboard Cite

show abstract

“…However, there is a serious problem among the resolution of pattern, sensitivity of the photo-chemical reaction, and roughness of the pattern, i.e., these relationships are well known as "trade-off". To overcome this "trade-off", many molecular glasses such as calixarenes, 1-10 dendritic oligomers, [11][12][13][14][15][16][17][18] low-molecular-weight oligomers, 19,20 and fullerenes 21 have been reported and their resolutions showed about 50 nm regions. Recently, we could design a ladder type cyclic oligomer "noria" (noria = water wheel in Latin), 22 and examined the synthesis, physical properties, and patterning properties of noria derivatives with pendant t-butyl ester groups, 23,24 t-butyloxycarbonyl groups, 25 adamantyl ester groups, 26,27 cyclohexyl acetal moiety, 28 and oxetanyl groups 29 using electron beam (EB) or EUV exposure systems.…”

Section: Introductionmentioning

confidence: 99%

Extreme Ultraviolet (EUV)-Resist Material Based on Noria (Water Wheel-like Macrocycle ) Derivatives with Pendant Alkoxyl and Adamantyl Ester Groups

Kudo

Nina

Sato

et al. 2012

J. Photopol. Sci. Technol.

View full text Add to dashboard Cite

“…Work by the Hirayama group at TOK investigated low-molecular-weight polyphenol, 4,4'-methylenebis[2-[di(2-methyl-4-hydroxy-5-cyclohexylphenyl)]methyl]phenol (3MC-MBSA). 2 They demonstrated that the film distribution in the depth direction for resist components. They discussed in detail what influence the resist components of 3MC-MBSA and two different photo-acid generator (PAG) types have on the pattern LER and the film distribution in achieving good resist performance.…”

Section: Introductionmentioning

confidence: 99%

Molecular resists for EUV and EB lithography

Takemoto

Ando

Edamatsu

et al. 2008

Advances in Resist Materials and Processing Technology XXV

View full text Add to dashboard Cite

Extreme ultraviolet lithography at a wavelength of 13.5 nm has been prepared for next generation lithography for several years. Of primary concern in EUV lithography is line edge roughness as well as high sensitivity. In recent years, various types of resist, such as protected PHS resin resist and molecular resist, have been investigated. In order to reduce LER, we have studied novel molecular resists which are promising alternative to polymeric photoresists for use as imaging materials with improved resolution and line edge roughness. The work reported in this paper has focused on the development of a new class of chemically amplified molecular resists that are composed of a single molecule which contains all of the different functionalities desired in a chemically amplified resists. For the purpose of improvement of the resist performance, we have designed the resist material of a protected polyphenol derivative (protected Compound A). PAG moiety is bonded to Compound A to achieve uniform PAG density and to control the acid diffusion length in a resist film. We analyzed uniformity of PAG density in a resist film by using gradient shaving preparation and TOF-SIMS analysis. From the TOF-SIMS spectra, the ions intensities of the PAG moiety are almost constant from the surface to the bottom of the film. Therefore, we can conclude that PAG is distributed homogeneously. Under e-beam exposure, a 100nm thick film of the PAG bonded molecular resist resolved lines down to 100nm. We also discussed the new design for molecular resists, their synthesis and lithographic performance.

show abstract

Depth Profile and Line-Edge Roughness of Low-Molecular-Weight Amorphous Electron Beam Resists

Abstract: Guided by the paper [10] by Polyakov and Rychkov, we compute the second variational derivative of a wavy plane Wilson surface observable, to find that a necessary condition for a proposed surface equation to be satisfied in the large-N limit is that we are in the critical dimension D = 6.

Cited by 41 publications

References 11 publications

Development of Novel Photo-Functional Materials Based on Cyclic Oligomers

Development of Novel Photo-Functional Materials Based on Cyclic Oligomers

Extreme Ultraviolet (EUV)-Resist Material Based on Noria (Water Wheel-like Macrocycle ) Derivatives with Pendant Alkoxyl and Adamantyl Ester Groups

Molecular resists for EUV and EB lithography

Contact Info

Product

Resources

About