Relief and Functional Photoimaging with Chemically Amplified Resists Based on Di-tert-Butyl Butenedioate-co-Styrene

Zhang, Chunhao; Vekselman, Alexander M.; Darling, Graham D.

doi:10.1021/cm00053a006

Cited by 38 publications

(26 citation statements)

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“…[1][2][3][4][5] In particular, fluorescence imaging photolithography has attracted a great deal of attention because of its promise for applications in the area of photonic/electronic devices such as optical data storage and displays. For example, fluorescence imaging technology may be useful for the formation of full-color displays with well-defined blue, green, and red fluorescence patterns.…”

Section: Introductionmentioning

confidence: 99%

“…These include protonation induced by a photoacid generator, [6,9,12,15,16] as well as chemical amplification catalyzed by a photoacid generator. [3,[17][18][19][20][21][22] Most of these preparation methods are based on photogenerated acids, although other methods precluding the use of photoacid generators have also been reported such as the photobleaching of fluorescent polymers. [7,13,14,23,24] Photobase generators are a group of compounds that produce a base upon irradiation.…”

Section: Introductionmentioning

confidence: 99%

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Red–Yellow Fluorescence Patterning of a Polymer Film Containing Phthalimido Carbamate Groups

Chae

Kim

2007

Adv Funct Materials

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Bicolor fluorescent micro‐patterns in the polymer film are prepared through the use of a new group of photobase generator containing phthalimido carbamate groups. The photobase generation from phthalimide carbamates is studied by examining the changes in pH, fluorescence intensity, and photo‐crosslinking of poly(glycidyl methacrylate). The product analysis of a model compound indicates that amine groups are produced from the photolytic cleavage of the C–N bond of the phthalimide carbamate groups. A copolymer containing phthalimide carbamate groups is applied to a bicolor fluorescent imaging material. Red‐yellow fluorescent micropatterns are obtained by treating the copolymer film, which is irradiated with 254 nm UV light through a photomask, with fluorescamine and rhodamine, consecutively. Various colored fluorescent micropatterns – green, red, or red‐yellow, are obtained on a single polymer film by varying the excitation wavelength.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Red–Yellow Fluorescence Patterning of a Polymer Film Containing Phthalimido Carbamate Groups

Chae

Kim

2007

Adv Funct Materials

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“…In practical application, this method has been applied to the preparation of optical waveguides and interferometers using microfeatures from organic polymers. [18][19][20] Moreover, the mTM method may also be applicable to the fluorescence image patterning of polymeric materials, with the added benefit of the formation of 3-D structures such as multilayered multichannels. Non-conjugated polymers, which involve aliphatic polyesters, intrinsically exhibit neither visible absorption nor fluorescence because of the forbidden transition due to the carbonyl group.…”

Section: Communicationmentioning

confidence: 99%

Three‐Dimensional Fluorescence Image Patterning of Network Aliphatic Polyester via Microtransfer Molding and Thermal Treatment

Yoon

Jeong

Kwak

2007

Macromol. Rapid Commun.

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This paper describes that three‐dimensional (3‐D) fluorescence image patterning of a network aliphatic polyester was successfully conducted by microtransfer molding (µTM) of the prepolymer and subsequent thermal treatment. A highly sticky, aliphatic ester prepolymer, containing a malonate moiety in the main chain, was obtained by a two‐step reaction, quantitatively. The 3‐D micropattern of the prepolymer was fabricated by µTM using polydimethylsiloxane (PDMS) as elastomeric mold. The patterns showed a clear shape without any residual layer. When the molded prepolymer was thermally treated, the patterns exhibited very distinct fluorescence images in a full color range of sky‐blue, yellowish green and red regions when excited at wavelengths of 325, 488, and 580 nm, respectively.magnified image

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“…[1][2][3][4][5][6][7][8][9][10][11] The concept of the 'precursor approach' is to use different electronic properties between the protected and unprotected forms. For example, a dye molecule is nonfluorescent when the key functional group of the dye molecule is protected with a protecting group.…”

mentioning

confidence: 99%

Fabrication of Patterned Fluorescence Images in Electrospun Microfibers

Lee¹,

Kim

2008

Bulletin of the Korean Chemical Society

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Recently, generation of patterned fluorescence images based on the "precursor approach" has gained much attention. [1][2][3][4][5][6][7][8][9][10][11] The concept of the 'precursor approach' is to use different electronic properties between the protected and unprotected forms. For example, a dye molecule is nonfluorescent when the key functional group of the dye molecule is protected with a protecting group. If the protecting group is removed under photoinduced chemical transformation, the fluorescence can be regenerated, allowing patterned fluorescent images in the polymer film by selective removal of the protecting group in the exposed areas. The "precursor approach" allows rapid and costeffective generation of patterned images in one step, without the need for additional wet developing processes.We have previously reported that the fluorescent quinizarin molecule can be readily converted to a nonfluorescent protected molecule t-BocQ by introduction of acid-labile tert-butoxycarbonyl (t-Boc) groups to the quinizarin hydroxyl moieties 1 (Scheme 1). 8 When the t-Boc groups were selectively removed by photogenerated acids, yellow fluorescent patterns were appeared in the UV exposed areas. Thus, the nonfluorescent t-BocQ precursor molecule was transformed to unprotected quinizarin by the photoinduced chemical transformation.The vast majorities of the fluorescence patterns generated based on the "precursor approach" have been fabricated in polymer film. During the course toward the development of fiber-based chemosensor systems, 12 we have discovered a new strategy for the fabrication of patterned fluorescence images in microfibers. The key strategy and procedure employed for the fluorescence patterning is schematically presented in Figure 1. A viscous chloroform solution containing the precursor molecule t-BocQ (1.3 wt%), poly-(methyl methacrylate) (PMMA) (19.6 wt%), and a photoacid generator (PAG), triphenylsulfonium triflate (0.6 wt%) is placed in a syringe. A high voltage (18 kV) is then applied to the metal syringe needle causing ejection of a charged polymer jet from the polymer solution. 13 The microfibers are collected on the surface of a grounded aluminum plate (15 cm from the needle). A scanning electron microscope (SEM) image confirms the formation of microfibers ( Figure 1). Photomasked UV irradiation of the electrospun fiber should generate strong acids from the PAG in the exposed areas. The photochemically produced strong acids should promote catalytic deprotection of the t-Boc groups from the precursor molecules, allowing patterned fluorescence images in the polymer fibers.In order to investigate the feasibility of fluorescence patterning, the polymer fiber mats obtained as described above were irradiated with 254 nm UV light through a photomask for 2 min. The UV-treated fiber mats were then placed on a hot plate (100 o C) for 1 min for a post-exposure

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Relief and Functional Photoimaging with Chemically Amplified Resists Based on Di-tert-Butyl Butenedioate-co-Styrene

Cited by 38 publications

References 0 publications

Red–Yellow Fluorescence Patterning of a Polymer Film Containing Phthalimido Carbamate Groups

Red–Yellow Fluorescence Patterning of a Polymer Film Containing Phthalimido Carbamate Groups

Three‐Dimensional Fluorescence Image Patterning of Network Aliphatic Polyester via Microtransfer Molding and Thermal Treatment

Fabrication of Patterned Fluorescence Images in Electrospun Microfibers

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