&lt;title&gt;Novel base-generating photoinitiators for deep-UV lithography&lt;/title&gt;

Kutal, Charles; Weit, Scott K.; Allen, Robert D.; Macdonald, Scott; Willson, C. Grant

doi:10.1117/12.46384

Cited by 5 publications

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“…catalyzes the oxidative decolorization of the red dye alizarin S by hydrogen peroxide in aqueous solution (39), and photoreleased base initiates cross-linking in thin films of an epoxide-containing photoresist (40)(41)(42).…”

Section: +mentioning

confidence: 99%

Photosensitive Metal—Organic Systems

Kutal

1993

Photosensitive Metal—Organic Systems

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Section: +mentioning

confidence: 99%

Photosensitive Metal—Organic Systems

Kutal

1993

Photosensitive Metal—Organic Systems

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“…The generation of base in certain polymer films modifies the properties of the films, causing a difference in solubility between exposed and unexposed areas. Such films can be developed to yield either a positive or negative images. , A wide variety of base-generating precursors including cobalt−amine complexes, sulfonamides, and carbamate derivatives have previously been explored. − As a part of an effort to design new precursors for tertiary amines, we have recently developed a system (Chart ) that releases tertiary amines via a reductive photoinduced electron-transfer process. The system is designed so that the light absorption step by the acceptor chromophore is decoupled from the step that releases the amine.…”

Section: Introductionmentioning

confidence: 99%

Mechanistic Studies of Photobase Generation from Ammonium Tetraorganyl Borate Salts¹

1998

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The photochemistry and photophysics of N,N,N-tributyl-N-acetonaphthone ammonium borate (1) and N,N,N-tributyl-N-acetobenzo[b]furan ammonium borate (2) have been investigated by steady-state spectroscopy, laser flash photolysis, and product analysis. Reaction of excited precursors leads to formation of tertiary amines by carbon-nitrogen bond cleavage. Laser flash photolysis and product analysis confirm homolytic carbonnitrogen bond scission and the formation of respective acetyl radicals which, in acetonitrile, dimerize to form coupled products. In all cases, photodissociation occurs with such a short lifetime that it could not be measured by nanosecond flash photolysis. The quantum yield of disappearance was found to be higher for salts of the triphenylbutyl borate anion than for those of the tetraphenyl borate anion. A proposed mechanism involves electron transfer from borate to the excited acceptors as the primary photochemical step. The rate constants for excited-state quenching correlate with the free energy for electron transfer, as estimated from the excited-state energies and the reduction potentials of the acceptors.

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“…During the past few years we have demonstrated that a promising alternative strategy for initiating useful chemistry involves the photochemical production of base . Thus thin films of an epoxide-functionalized polymer containing a cobalt(III) am(m)ine complex such as [Co(NH 3 ) 6 ](BPh 4 ) 3 or [Co(en) 3 ](BPh 4 ) 3 (en is ethylenediamine, BPh 4 - is tetraphenylborate) undergo photoinitiated cross-linking upon deep-UV irradiation and subsequent heating .…”

Section: Introductionmentioning

confidence: 99%

Imaging of Aliphatic Polycarbonates with Photogenerated Base

Davies¹,

Daly²,

Wang³

et al. 1996

Chem. Mater.

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A series of aliphatic polycarbonates based on the condensation copolymerization of the bischloroformate of 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCBD) with itself and the diols of 3-cyclohexene-1,1-dimethanol, 1,4-cyclohexanediol (CHD), in various molar ratios, exo,exo-tricyclo[2.2.1.02,6]heptane-3,5-diol, and 4,8-bis(hydroxymethyl)tricyclo[5.2.102,6]decane (BTD) were synthesized. Incorporation of cyclic and tricyclic repeat units produced polycarbonates with high glass transition temperatures (T g's), high molecular weights, and low refractive indexes. The crystallinity of the TMCBD homopolymer was minimized in the CHD/TMCBD copolymers with little effect on T g but with decreased thermal stability. Thermal analysis yields decomposition temperatures ranging from 354 °C for the TMCBD homopolymer to 292−298 °C for the CHD/TMCBD copolymers; all polymers undergo complete thermal degradation. Refractive indexes range from 1.493 for the 1:1 copolymer of BTD and TMCBD to 1.481 for the CHD/TMCBD copolymers. Thin films composed of an aliphatic polycarbonate and a base-releasing cobalt(III) photoinitiator can be imaged with deep-UV light. The polycarbonates selected for study were the 9:1 copolymer of CHD and TMCBD and the 1:1 copolymer of BTD and TMCBD. The first step of image formation is the efficient photoredox decomposition of the photoinitiator with the release of multiequivalents of Lewis base. In the case of [Co(en)3](BPh4)3 (en is ethylenediamine, BPh4 - is tetraphenylborate), photogenerated ethylenediamine cross-links the polymer chains via formation of bis(dicarbamate) linkages. Development with solvent dissolves the unirradiated areas to yield negative-tone images. For [Co(NH3)6](BPh4)3, photoreleased ammonia causes chain scission in the exposed regions of the film, and wet or dry development results in positive-tone images.

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<title>Novel base-generating photoinitiators for deep-UV lithography</title>

Cited by 5 publications

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Photosensitive Metal—Organic Systems

Photosensitive Metal—Organic Systems

Mechanistic Studies of Photobase Generation from Ammonium Tetraorganyl Borate Salts¹

Imaging of Aliphatic Polycarbonates with Photogenerated Base

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<title>Novel base-generating photoinitiators for deep-UV lithography</title>

Cited by 5 publications

References 0 publications

Photosensitive Metal—Organic Systems

Photosensitive Metal—Organic Systems

Mechanistic Studies of Photobase Generation from Ammonium Tetraorganyl Borate Salts1

Imaging of Aliphatic Polycarbonates with Photogenerated Base

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Mechanistic Studies of Photobase Generation from Ammonium Tetraorganyl Borate Salts¹