Dissolution phenomena of phenolic molecular glass photoresist films in supercritical CO2

Felix, Nelson; Silva, Anuja De; Luk, Camille Man Yin; Ober, Christopher K.

doi:10.1039/b709649f

Cited by 21 publications

(20 citation statements)

References 27 publications

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“…[ 90 ] In general the molecular glass resist has a well-defi ned small-molecule core that bears protected base-soluble groups (such as hydroxyls and carboxyls) as shown in Figure 21b . With this approach the core chemistry can vary from calix [4]resorcinarenes (ringlike), [91][92][93] branched phenolic groups, [ 94,95 ] and hexaphenolic groups (disklike). [ 96,97 ] Early approaches with molecular resists led to low glass-transition temperatures, however, such problems were resolved by increased hydrogen bonding functionality and the design of the core structure.…”

Section: Advances By Materials Structurementioning

confidence: 99%

Photoresist Latent and Developer Images as Probed by Neutron Reflectivity Methods

Prabhu¹,

Kang²,

VanderHart³

et al. 2010

Advanced Materials

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Photoresist materials enable the fabrication of advanced integrated circuits with ever-decreasing feature sizes. As next-generation light sources are developed, using extreme ultraviolet light of wavelength 13.5 nm, these highly tuned formulations must meet strict image-fidelity criteria to maintain the expected performance gains from decreases in feature size. However, polymer photoresists appear to be reaching resolution limits and advancements in measurements of the in situ formed solid/solid and solid/liquid interface is necessary. This Review focuses on the chemical and physical structure of chemically amplified photoresists at the lithographic feature edge at length scales between 1 nm and 100 nm. Neutron reflectivity measurements provide insight into the nanometer-scale composition profiling of the chemical latent image at an ideal lithographic line-edge that separates optical resolution effects from materials processing effects. Four generations of advanced photoresist formulations were examined over the course of seven years to quantify photoresist/photoacid and photoresist/developer interactions on the fidelity of lithographic features. The outcome of these measurements complement traditional resist design criteria by providing the effects of the impacts of the photoresist and processing on the feature fidelity. These physical relations are also described in the context of novel resist architectures under consideration for next-generation photolithography with extreme-ultraviolet radiation.

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Section: Advances By Materials Structurementioning

confidence: 99%

Photoresist Latent and Developer Images as Probed by Neutron Reflectivity Methods

Prabhu¹,

Kang²,

VanderHart³

et al. 2010

Advanced Materials

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“…As has been shown in a previous study, [34] the relative dissolution rates of these protected phenolic MG resists are mostly determined by their T g . Analysis of the thermal data in Table 1 with respect to the measured dissolution rates in Figure 2 shows that molecules with higher T g require a higher pressure for dissolution in scCO 2 .…”

mentioning

confidence: 85%

Calix[4]resorcinarene Derivatives as High‐Resolution Resist Materials for Supercritical CO₂ Processing

2008

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Advances in the microelectronics industry are continuously driven by employing new technologies. A recent development has been to use small-molecule photoresists (or resists) instead of conventional polymeric resists as the patterning material. [1][2][3][4][5] These small molecules known as molecular glass resists (MG resists) possess several intrinsic structural advantages as compared to their polymeric counterparts, such as small and uniform molecular size. Despite their small size, these molecules have the potential to function as high-performance patterning materials owing to their high glass-transition temperatures (T g ) and their ability to form stable thin films similar to polymeric resists. The small molecular cross-section of 1-2 nm afforded by these materials is expected to facilitate high-resolution patterning. Indeed, extensive theoretical studies have shown that a reduction in molecular size and dispersity will also improve other aspects of patterning performance. [6,7] The small size of MG resists has also enabled the use of dry processing techniques such as the supercritical CO 2 (scCO 2 ) development of photoresists. scCO 2 has shown promise as an environmentally friendly replacement for traditional development solvents.[8] The many advantageous properties of scCO 2 such as high diffusivity, absence of surface tension, and tunable solvent power indicate several potential benefits over traditional liquid solvents. However, previous CO 2 -soluble polymeric resists have required large amounts of undesirable fluorination to impart solubility. [9][10][11] Owing to their small size, MG resists may be soluble in scCO 2 without the need for fluorine. Indeed, it has recently been shown that non-fluorinated MG resists heavier than 1000 g mol À1 are significantly soluble in scCO 2 , [12] although the ultimate molecular-weight limit for such solubility has yet to be determined. In the first report of sub-50 nm pattern development using scCO 2 , hexa(hydroxyphenyl)benzene MG resists have been developed using scCO 2 under modest temperature and pressure conditions. However, hexa(hydroxyphenyl)benzene is such a specialized material that structural modification of this scaffold is extremely difficult, and therefore opportunities for further exploration of the solubility and other properties via structural variation are quite limited. Although phenolic MG materials have been shown to be scCO 2 soluble, recent investigations of selected phenolic MG resists have shown that because of the plasticizing nature of scCO 2 , [13] it is necessary that scCO 2 -soluble MG resists possess a high T g to enable high-resolution patterning. It is thus necessary to start with a high-T g system where the thermal and CO 2 solubility properties can be systematically optimized via modifying the same structural platform.In previous work, we have reported the very high-resolution capability of MG resists based on calix[4]resorcinarene (or resorcinarene) derivatives using extreme UV (EUV) lithography. [3] In order to extend the use of t...

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“…It was reported that the dissolution rate of these MG resists in scCO 2 is mainly determined by their molecular weight. [33] In addition, the molecular structure and T g of MGs also affects its dissolution behavior due to effects of plasticization in scCO 2 . Sub-100 nm feature sizes have been demonstrated through scCO 2 development of both branched and ring MG resist structures with T g s higher than 100 8C.…”

Section: Development In Supercritical Carbon Dioxidementioning

confidence: 99%

Molecular Glass Resists as High‐Resolution Patterning Materials

2008

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The success of the semiconductor industry is based on the ability to fabricate hundreds of millions of devices on a single chip. In order to fulfill the ever‐shrinking feature sizes, the industry requires new patternable materials in order to operate in the sub‐50 nm regime. Molecular glass (MG) resists are a new type of patterning material that has gained considerable attention over the past few years. This Research News article describes the chemical and structural aspects of MGs as well as important concepts of MG resist design. We also highlight some of the recent advances in high‐resolution patterning capabilities with next‐generation imaging tools.

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Dissolution phenomena of phenolic molecular glass photoresist films in supercritical CO2

Cited by 21 publications

References 27 publications

Photoresist Latent and Developer Images as Probed by Neutron Reflectivity Methods

Photoresist Latent and Developer Images as Probed by Neutron Reflectivity Methods

Calix[4]resorcinarene Derivatives as High‐Resolution Resist Materials for Supercritical CO₂ Processing

Molecular Glass Resists as High‐Resolution Patterning Materials

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Dissolution phenomena of phenolic molecular glass photoresist films in supercritical CO2

Cited by 21 publications

References 27 publications

Photoresist Latent and Developer Images as Probed by Neutron Reflectivity Methods

Photoresist Latent and Developer Images as Probed by Neutron Reflectivity Methods

Calix[4]resorcinarene Derivatives as High‐Resolution Resist Materials for Supercritical CO2 Processing

Molecular Glass Resists as High‐Resolution Patterning Materials

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Calix[4]resorcinarene Derivatives as High‐Resolution Resist Materials for Supercritical CO₂ Processing