Study of the Structure−Properties Relationship of Phenolic Molecular Glass Resists for Next Generation Photolithography

Silva, Anuja De; Lee, Jin‐Kyun; André, Xavier; Felix, Nelson; Cao, Heidi B.; Deng, Hai; Ober, Christopher K.

doi:10.1021/cm702613n

Cited by 49 publications

(44 citation statements)

References 54 publications

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“…These compounds were protected with tert-butyl carbonyl (t-BOC) to varying degrees (50%-100%) by a standard base catalyzed reaction in the presence of 4-dimethyl amino pyridine (DMAP). The detailed synthesis and characterization these phenolic MG resists has been recently reported [17] . Trends in Tg for phenolic MG compounds.…”

Section: Resultsmentioning

confidence: 99%

Molecular glass resists for next generation lithography

et al. 2008

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The idea of using small molecules instead of polymers for next generation lithography may enable improved resolution and line edge roughness (LER). Rather than using polymeric materials we are focusing on a new class of materials known as molecular glasses (MGs). These are low molecular weight organic materials that demonstrate high glass transition temperatures despite their modest size. Unlike polymeric resists, these molecules have the added advantages of distinct size and uniformity. We have synthesized a series of molecular resists containing rigid aromatic backbones and phenolic moieties suited for electron beam and Extreme Ultraviolet (EUV) lithography as both positive tone and negative tone photoresists. An increase in glass transition temperature is observed with increasing size and rigidity. Glass transition temperatures (Tgs) between 80-130°C have been observed for t-BOC protected positive tone resists with molecular weights within the range of 800-1200g/mol. MGs with branched, dense structures are explored to design high Tg resist systems with improved sensitivity and contrast. The effects of protection ratio, high and low activation protecting groups, post exposure bake conditions, etch resistance and outgassing have been tested using selected phenolic MG resists. These new resist architectures are synthesized and evaluated to attain sub 30nm feature sizes required of candidates for next generation lithography.

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Section: Resultsmentioning

confidence: 99%

Molecular glass resists for next generation lithography

et al. 2008

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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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“…Bulky, dense structures based on similar design concepts to the phenylbenzene derivatives have also been developed. [16,17] Owing to their unique architecture, phenolic MGs show a more pronounced increase in T g with increasing molecular weight. MGs that consists of six or more hydroxyl groups possess a T g comparable to poly(4-hydroxy styrene) despite being an order of magnitude smaller in size.…”

Section: K Ober Et Al / Molecular Glass Resistsmentioning

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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Study of the Structure−Properties Relationship of Phenolic Molecular Glass Resists for Next Generation Photolithography

Cited by 49 publications

References 54 publications

Molecular glass resists for next generation lithography

Molecular glass resists for next generation lithography

Photoresist Latent and Developer Images as Probed by Neutron Reflectivity Methods

Molecular Glass Resists as High‐Resolution Patterning Materials

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