Photogenerated base in polymer curing and imaging: Design of reactive styrenic copolymers susceptible to a base-catalyzed ?-elimination

Urankar, Edward J.; Fréchet, Jean M. J.

doi:10.1002/(sici)1099-0518(19971130)35:16<3543::aid-pola21>3.0.co;2-e

Cited by 4 publications

(2 citation statements)

References 2 publications

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“…However, only a few articles have mentioned photosensitive materials based on base-catalyzed reactions because of relatively low quantum yields for photobase generation of a photobase generator (PBG), leading to low photosensitivity. [21][22][23][24][25][26][27][28][29][30][31] To improve the photosensitivity, we have proposed the novel concept of base proliferation of basesensitive compounds, referred to as base amplifiers, that generate base molecules in a nonlinear manner by the action of a catalytic amount of base. [32][33][34][35] In fact, we demonstrated that the addition of the base amplifiers to a negative working photoresist consisting of PBG and poly(glycidyl methacrylate) (PGMA) resulted in a marked improvement in the photosensitivity by a factor of 50.…”

Section: Introductionmentioning

confidence: 99%

Novel base-sensitive polymers generating amino groups from their side chains in a nonlinear manner and their application to photoimaging materials

Igarashi¹,

Arimitsu

Seki

et al. 2008

J. Mater. Chem.

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We describe highly sensitive photopolymers consisting of a photobase generator (PBG), a basesensitive polymer, and a base amplifier that decomposed autocatalytically to release an amine molecule which resulted in the enhancement of base-catalyzed reactions of the base-sensitive polymer. Low molecular weight base molecules produced from the base amplifiers were widely diffused in the polymer film, resulting in the reduction of resolution power in the manner of ''air infection'' of low molecular weight basic species, although the photosensitivity was enhanced. To improve the performance, we have designed a novel base-sensitive polymer (1) tethering baseamplifying units that autocatalytically transform into amino groups attached to the polymer backbone. A film of 1 sensitized with PBG was decomposed autocatalytically by UV irradiation and subsequent heat treatment. This means that the base proliferation reaction of 1 proceeded regardless of its polymer structure. In addition, a film of 1 sensitized with PBG provided a positive working photoresist developable with an acidic aqueous solution and showed much higher photosensitivity when compared with conventional chemically amplified photoresists comprising PBG and base-labile polymers. Moreover, the use of base-amplifying polymer 1 led to prevention of ''air infection'', and improvement in the resolution power of photopolymers relying on base proliferation reactions when compared with base-sensitive photopolymers coupled with low molecular weight base amplifiers.

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Section: Introductionmentioning

confidence: 99%

Novel base-sensitive polymers generating amino groups from their side chains in a nonlinear manner and their application to photoimaging materials

Igarashi¹,

Arimitsu

Seki

et al. 2008

J. Mater. Chem.

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“…Photosensitive polymers are indispensable for this process as photoresists to protect metal surfaces while being subjected to an etching process. [1][2][3][4][5] To accomplish high photosensitivity, various chemical amplification systems have been developed in which photogenerated acid 6,7 or base [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] catalyses a chemical reaction in a resist film. While photosensitive materials based on basecatalysed reactions have merit for preventing erosion of metallic substrates, photobase generators generally have low quantum yields, which leads to low photosensitivity.…”

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confidence: 99%

Base-amplifying silicone resins with photobase-generating side chains and their application to negative-working photoresists

Furutani

Kobayashi

Gunji

et al. 2015

J. Polym. Sci. Part A: Polym. Chem.

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To accomplish high photosensitivity of resist systems including photobase generators, we have proposed the concept of base‐proliferation reactions that generate base molecules in a nonlinear manner by the action of a catalytic amount of base; however, excessive diffusion of generated base molecules is still a problem. We have designed novel functional silicone resins bearing both base‐amplifying units and photobase‐generating units, and synthesized resins with various composition ratios. The synthesized resins are decomposed autocatalytically after UV irradiation and subsequent heating at 100 °C, which indicates progression of base‐proliferation reactions. High photosensitivity (8.1 mJ cm−2) was recorded, and it was found that the photosensitivity is about 490 times enhanced by replacing a base‐catalytic reaction system with the base‐proliferation reaction system. Furthermore, a 4 × 10 µm line‐and‐space pattern has been successfully fabricated using the silicone resin. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 1205–1212

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Biocatalytic Cascade for the Synthesis of Enantiopure β‐Azidoalcohols and β‐Hydroxynitriles

et al. 2009

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A three-step, two-enzyme, one-pot reaction sequence starting from prochiral α-chloroketones leading to enantiopure β-azidoalcohols and β-hydroxynitriles is described. Asymmetric bioreduction of α-chloroketones by hydrogen transfer catalysed by an alcohol dehydrogenase (ADH) established the stereogenic centre in the first step to furnish enantiopure chlorohydrin intermediates. Subsequent biocatalysed ring closure to the epoxide and nucleophilic ring opening with

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Photogenerated base in polymer curing and imaging: Design of reactive styrenic copolymers susceptible to a base-catalyzed ?-elimination

Cited by 4 publications

References 2 publications

Novel base-sensitive polymers generating amino groups from their side chains in a nonlinear manner and their application to photoimaging materials

Novel base-sensitive polymers generating amino groups from their side chains in a nonlinear manner and their application to photoimaging materials

Base-amplifying silicone resins with photobase-generating side chains and their application to negative-working photoresists

Biocatalytic Cascade for the Synthesis of Enantiopure β‐Azidoalcohols and β‐Hydroxynitriles

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