Synthesis and polymerization of N-(tert-butyloxycarbonyl)maleimide and facile deprotection of polymer side-chain t-BOC groups

Ahn, Kwang‐Duk; Lee, Young-Hun; Koo, Deok-II

doi:10.1016/0032-3861(92)90702-x

Cited by 32 publications

(28 citation statements)

References 9 publications

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“…The polymer system P-6 (t-BOC) shows in some cases (especially P-6 a) a smaller weight loss than the theoretical amount possibly due to a premature deprotection during polymer analogous reaction or due to storage conditions. Similar results are described by Ahn et al 12) for the homopolymer poly(t-BOC-maleimide). The smaller weight loss correlates with the virtual molecular weights (Tab.…”

Section: P-4 (P-6a)supporting

confidence: 90%

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Photoprocessable copolyimides with carbazole groups

Scheurer

Zentel²

1999

Macromol. Chem. Phys.

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SUMMARY: This paper describes copolymers from maleimides and methylvinyl isocyanate, which combine the properties of photoresists with those of semiconducting polymers. The maleimide unit is functionalized with t-BOC groups. The isocyanate group can -in principle -be reacted with various hole or electron transporting units as shown -in a first example -for carbazoles. A photopatterning of these polymers is possible by adding a photoacid generator. The photochemically generated protons splitt off the t-BOC groups by chemical amplification. The difference in solubility thus achieved allows photopatterning.

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Section: P-4 (P-6a)supporting

confidence: 90%

“…The group of Ahn used different N-protected maleimide-styrene copolymers as a thermally stable resist system [11][12][13][14] . The incorporation of the stiff maleimide unit is a possibility to increase the glass transition temperature (T g ) of the polymer.…”

Section: Introductionmentioning

confidence: 99%

Photoprocessable copolyimides with carbazole groups

Scheurer

Zentel²

1999

Macromol. Chem. Phys.

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“…40 As expected, Mitsunobu condensation of the furan/maleimide adduct ON with the alcohols CBA n (n ϭ 2-8) gave CBON n (n ϭ 2-8) in virtually quantitative yields. 30 The adducts CBON n were thermolyzed in refluxing toluene (retro-Diels-Alder reaction) and the target functionalized maleimides M n (n ϭ 2-8) were obtained in high yields (80 -96%) and high purity as demonstrated by elemental analysis, infrared spectroscopy and 1 H-and 13 C-NMR ( Figs.…”

Section: Synthesis Of Monomers M N (N ‫؍‬ 2-8)supporting

confidence: 62%

Synthesis and characterization of polymaleimides containing 4-cyanobiphenyl-based side groups for nonlinear optical applications

Gaṅgādhara

Noël

Thomas

et al. 1998

J. Polym. Sci. A Polym. Chem.

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A new homologous series of SCLCPs containing the 4‐cyanobiphenyl mesogenic group attached to the polymaleimide backbone through paraffinic spacers of two to eight methylene units have been prepared. All the polymers exhibit liquid crystalline behavior; specifically SAd‐ (or SC‐) like and nematic phases are observed. The glass transition temperature decreases from 150 to 43°C on increasing spacer length. The isotropization temperatures exhibit an odd–even effect on varying the length and parity of the spacer, in which the odd members exhibit the higher values. This is attributed to the change in the average shape of the side chain as the parity of spacer is varied. The isotropization temperatures (>300–120°C) and the mesophase thermal stabilities (190–60°C) are high. Comparison is made with polymers containing the same mesogenic group attached to backbones of decreasing rigidity. © 1998 John Wiley & Sons, Inc. J. Polym. Sci. A Polym. Chem. 36: 2531–2546, 1998

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“…A t-BOC protected maleimide monomer, t-BOCMI was reported to be very effective for solubilizing a polymer having the unit in aqueous alkaline solutions through conversion to a MI moiety by thermal or acidolytic deprotection. [2] Two (N-substituted) maleimides and t-BOCSt monomers were fed in the molar ratio of 1:1:2 and all the radical polymerizations were carried out at 55 °C in dioxane under nitrogen atmosphere with an AIBN initiator. Two terpolymers, P(TsOMI/MI/t-BOCSt) I Photopolym.…”

Section: Resultsmentioning

confidence: 99%

“…Only a few polymaleimides have been investigated their applicability as thermally stable resist materials in DUV region based on the chemical amplification concept. Those polymaleimides are the styrenic copolymers of N-(t-butyloxycarbonyl)maleimide (t-BOCMI) [2][3][4][5], t-BOC protected N-(phydroxyphenyl)maleimide [b], and N-(t-butoxy)maleimide (t-BuOMI). [7] Recently we have reported the functional polymers of N-tosyloxymaleimide (TsOMI) which generate p-toluenesulfonic acid (TsOH) effectively by DUV irradiation.…”

Section: Introductionmentioning

confidence: 99%

Terpolymers of tosyloxymaleimide for application as a polymeric photoacid generator in single-component resists.

Chung

Koo

Ahn³

1994

J. Photopol. Sci. Technol.

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Terpolymers of sulfonyloxymaleimides have been prepared as a new class of polymeric photoacid generator and their photochemical and thermal properties were investigated. The styrenic copolymers of N-tosyloxymaleimide (TsOMI) produced p-toluenesulfonic acid (TsOH) in solid state by deep UV irradiation and the amount of generated acid was determined by using a colorimetric method. Two terpolymers of TsOMI and p-(t-butyloxycarbonyloxy)styrene showed the capability of a single-component, chemically amplified resist system in deep UV region. Positive-and negative-tone images were obtained with sensitivity of 50 mJ/cm2.

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Synthesis and polymerization of N-(tert-butyloxycarbonyl)maleimide and facile deprotection of polymer side-chain t-BOC groups

Cited by 32 publications

References 9 publications

Photoprocessable copolyimides with carbazole groups

Photoprocessable copolyimides with carbazole groups

Synthesis and characterization of polymaleimides containing 4-cyanobiphenyl-based side groups for nonlinear optical applications

Terpolymers of tosyloxymaleimide for application as a polymeric photoacid generator in single-component resists.

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