Positive Photoreactive Polyimides. II. Preparation and Characterization of Polyimide Precursors Containing α-(2-Nitrophenyl)ethyl Ester Side Chains

Kubota, Shigeru; Moriwaki, T.; Ando, Torahiko; Fukami, Akira

doi:10.1080/00222338708078150

Cited by 28 publications

(4 citation statements)

References 7 publications

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“…Recently, in order to avoid this problem, positive-working photosensitive polyimides that can be developed with water-based solutions have been developed. Kubota et al reported a positive-working photosensitive polyimide precursor prepared from pyromellitic acid di(alpha-(2-nitrobenzyl)ethyl)ester which caused the cleavage of ester linkages [3]. Omote and Yamaoka investigated nifedipine (1,4-dihydro-2,6-dimethyl-4-(nitrophenyl)-3,5pyridinedicarboxylic acid dimethylester) as a dissolution inhibitor in poly(amic acid)s after a post-exposure brake (PEB) [4].…”

Section: Introductionmentioning

confidence: 99%

A Novel Photosensitive Polyimide: A Polyimide Containing the Hydroxytriphenylamine Structure with Diazonaphthoquinone

Akimoto

Jikei²,

Kakimoto

2000

High Performance Polymers

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A novel photosensitive polyimide based on a polyimide containing the hydroxytriphenylamine structure (HTA-PI) and 2, 3, 4-tris[1-oxo-2-diazonaphthoquinone-4-sulfonyloxy] benzophenone (D4SB) as a photoreactive compound has been developed. The HTAPI was prepared by the ring-opening polyaddition of 4, 4′-hexafluoroisopropylidenebis(phthalic anhydride) (6FDA) and 4,4′-diamino-4″-hydroxytriphenylamine (DHTA), followed by thermal cyclization in refluxing N-methyl-2-pyrrolidone (NMP). The resulting polyimide film showed excellent transparency to 436 nm light. Photosensitive polyimide containing 30 wt% of D4SB showed a sensitivity of 800 mJ cm−2 and a contrast of 0.8 when it was exposed to 436 nm light followed by development with 5% tetramethylammonium hydroxide (TMAH) aqueous solution at 45°C.

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Section: Introductionmentioning

confidence: 99%

A Novel Photosensitive Polyimide: A Polyimide Containing the Hydroxytriphenylamine Structure with Diazonaphthoquinone

Akimoto

Jikei²,

Kakimoto

2000

High Performance Polymers

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“…In comparison with conventional photoresists, the advantages of PSPIs are not only demonstrated by the outstanding properties of polyimides (PIs), but also by the significant simplification of the pattern formation process. , Although the first commercial PSPIs were of the negative tone type, , the positive tone PSPIs ( p -PSPIs) are more desired on an industrial level. A variety of p -PSPIs have been developed using different chemistries, − in which the most popular ones are those composed of a PI precursor, poly(amic acid) (PAA), and a diazonaphthoquinone photoactive compound (DNQ PAC). In an effort to design PAA–DNQ type p -PSPIs with high contrast imaging, many approaches have been investigated. − These approaches can be divided into two aspects: modification of the PAA structures − and designing new PACs. − No matter which aspect was considered, it is inevitable to understand the interactions between PAA and PACs, and their dissolution inhibitation mechanisms for the design of good p -PSPIs.…”

Section: Introductionmentioning

confidence: 99%

A Computational Probe into the Dissolution Inhibitation Effect of Diazonaphthoquinone Photoactive Compounds on Positive Tone Photosensitive Polyimides

Zheng

Sittert

2017

J. Phys. Chem. C

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Positive tone photosensitive polyimides (p-PSPIs) composed of poly(amic acid) (PAA) and a diazonaphthoquinone photoactive compound (DNQ PAC) have been greatly contributed to the progress of microelectronics. However, the relationships among PAC molecular structures, hydrogen-bonding interactions, and dissolution inhibitation for p-PSPIs have not been well understood. In this study, multiscale molecular modeling was utilized to evaluate such relationships. Density functional theory (DFT) calculations were used to predict the polarity of various DNQ PAC models and their corresponding indenylidene ketene (IK) compounds. Molecular dynamics (MD) simulations were performed to mimic the interactions between DNQ PAC and PAA polymer chains by calculating parameters such as the energy of mixing (ΔE mix) and Flory–Huggins parameter (χAB). The computational results showed that χAB values of PACs containing mono functional phenols significantly differed before and after UV exposure. Their corresponding suppositional p-PSPI films were found to form a “skin layer” by covering a high concentration of PAC on the surface of the film. Experimental dissolution behavior measurements of selected p-PSPI films strongly supported the computational observations. Succinctly, this work demonstrated the applicability of atomistic molecular simulations for the evaluation of dissolution inhibitation effect of DNQ PACs and to understand the possible dissolution inhibition mechanisms of p-PSPIs.

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“…Kubota et al reported a positive-working polyimide resist precursor prepared from pyromellitic acid di(alpha-(2nitrobenzyl)ethyl)ester. Cleavage of the ester linkages occurred by the action of UV light [3]. Omote and Yamaoka investigated nifedipine (1,4-dihydro-2,6-dimethyl-4-(nitrophenyl)-3,5-pyridinedicarboxylic acid dimethylester) as a dissolution inhibitor in poly(amic acid)s after a post-exposure bake (PEB) [4].…”

Section: Introductionmentioning

confidence: 99%

Polyimide Containing an Acetal Structure with a Photoacid Generator: A Novel Positive Polyimide Photoresist

Akimoto

Kato²,

Jikei³

et al. 2000

High Performance Polymers

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A main-chain degradable photosensitive polyimide containing an acetal structure which degrades by the action of acid coming from a photoacid generator has been developed. Polyimides 4 were prepared by the reaction of bis(4-aminophenoxy)methane 1 and various tetracarboxylic anhydrides 2, followed by thermal treatment. In the resulting polyimides 4, 4f filmderivedfrom 4,4′-hexafluoroisopropylidenebis(phthalicanhydride)(6FDA)and 1 showedgood solubility in organic solvents and transparency to UV light. The acid-catalysed degradation reaction was confirmed by the model imide compound in the presence of p-toluenesulfonic acid. The system of the polyimide 4f containing 30 wt% of diphenyliodonium 9,10-dimethoxyanthracene-2-sulfonate (DIAS), which is a photoacid generator (PAG) showed a sensitivity of 150 mJ cm−2 with 436 nm light, when it was post-exposure baked at 140°C for 30 min, followed by development with 5% tetramethylammonium hydroxide solution at 45°C.

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Positive Photoreactive Polyimides. II. Preparation and Characterization of Polyimide Precursors Containing α-(2-Nitrophenyl)ethyl Ester Side Chains

Cited by 28 publications

References 7 publications

A Novel Photosensitive Polyimide: A Polyimide Containing the Hydroxytriphenylamine Structure with Diazonaphthoquinone

A Novel Photosensitive Polyimide: A Polyimide Containing the Hydroxytriphenylamine Structure with Diazonaphthoquinone

A Computational Probe into the Dissolution Inhibitation Effect of Diazonaphthoquinone Photoactive Compounds on Positive Tone Photosensitive Polyimides

Polyimide Containing an Acetal Structure with a Photoacid Generator: A Novel Positive Polyimide Photoresist

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