A Negative-Working Alkaline Developable Photoresist Based on Calix[4]resorcinarene, a Cross-linker, and a Photoacid Generator

Nakayama, Tomonari; Haga, Kohji; Haba, Osamu; Ueda, Mitsuru

doi:10.1246/cl.1997.265

Cited by 46 publications

(35 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…8,9,22 Benzyl carbocations, which were formed from the crosslinker by acid catalysis, reacted with Noria-OEt to form the crosslinking products. At the same time, benzyl ethers also formed because of the self-condensation reaction of the crosslinker by heating and reaction with Noria-OEt.…”

Section: Resultsmentioning

confidence: 99%

“…[5][6][7] Ueda et al also reported a multicomponent, alkaline developable, negative-type photoresist composed of calixresorcin [4]arene, with 4,4¢-methylenebis[2,6-bis(hydroxymethyl)phenol] as a crosslinker and diphenyliodonium 9,10-dimethoxyanthracene-2-sulfonate as a photoacid generator (PAG), and they achieved a 150-nm resolution pattern. 8,9 Thereafter, many negative-or positive-type molecular resist materials have been reported using various molecular glasses. [10][11][12][13][14] More than 10 years ago, C-4-hydoroxyphenylcalix [4]resorcinarene derivatives containing tert-butyl groups (CRA ph -COO t Bu) were investigated as positive-type alkaline developable molecular resists.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Multicomponent negative-type photoresist based on Noria analog with 12 ethoxy groups

Niina

Kudo

Maruyama³

et al. 2011

Polym J

View full text Add to dashboard Cite

The characteristics of Noria analogs with 12 ethoxy groups and 12 hydroxy groups (Noria-OEt), which were synthesized by the condensation reaction of 3-ethoxyphenol with 1,5-pentanedial, were examined in detail. The solubility of the synthesized Noria-OEt in common organic solvents was better than that of Noria. In addition, Noria-OEt was soluble in 2.38 wt% tetrametyl ammonium hydroxide (TMAH) aqueous as a developer. The thermal stability and mechanical properties were similar to those of Noria because of the ladder structure and amorphous characteristics, which means that the film-forming properties were confirmed. These characteristics are advantageous for use as a molecular glass photoresist. The patterning properties of the negative-type, alkaline developable, multicomponent photoresist based on Noria-OEt, with polyfunctional benzyl alcohols as a crosslinker and a photoacid generator, were evaluated with an extreme ultraviolet lithography system. This negative-type photoresist with 2,4-dihydroxymethyl-6-methylphenol as a crosslinker gave a resolution pattern of 35 nm half-pitch with 10.0 mJ cm À2 .

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Multicomponent negative-type photoresist based on Noria analog with 12 ethoxy groups

Niina

Kudo

Maruyama³

et al. 2011

Polym J

View full text Add to dashboard Cite

show abstract

“…amplification ArF photo-resist materials have been reported using various polymers containing fluorine and alicyclic groups, such as adamantane and norbornane. 51,52 It was suggested that molecular size is an important consideration to achieve higher resolution, from the viewpoints of both photoreactivity and low line-edge roughness. 43 We designed new CD derivatives containing fluorine and tbutyl ester moieties as candidate high-performance ArF photoresist materials, 53 because we expected that CD derivatives would show good transmittance of vacuum ultraviolet (VUV) laser light.…”

Section: Arf Resist Materials Based On Cyclodex-trinmentioning

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

“…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

A Negative-Working Alkaline Developable Photoresist Based on Calix[4]resorcinarene, a Cross-linker, and a Photoacid Generator

Cited by 46 publications

References 4 publications

Multicomponent negative-type photoresist based on Noria analog with 12 ethoxy groups

Multicomponent negative-type photoresist based on Noria analog with 12 ethoxy groups

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

Contact Info

Product

Resources

About