Base-Catalyzed Photosensitive Polyimide

McKean, Dennis R.; Wallraff, G. M.; Volksen, W.; Hacker, Nigel P.; Sanchez, Martha I.; Labadie, John W.

doi:10.1021/bk-1994-0537.ch028

Cited by 11 publications

(13 citation statements)

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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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“…McKean et al [7][8][9] reported a PSPI based on the photobase catalyzed imidation of poly(amic alkyl ester). Similarly, Frechét et al 10 reported the photogenerated amine acts as a catalyst in the imidation of precursor polymers containing amic acid or amic ester groups.…”

Section: Introductionmentioning

confidence: 99%

Positive-type photosensitive polyimide based on a photobase generator containing oxime-urethane groups as a photosensitive compound

et al. 2006

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The chemical structure of a semi-aromatic polyimide-I, which was prepared by the chemical imidization of cyclopentanetetracarboxylic dianhydride and 2,2-bis(4-aminophenyl)hexafluoropropane, was characterized by 13 C-NMR spectroscopy. The chemically imidized polyimide-I was used for the preparation of a photosensitive polyimide (PSPI) through the addition of benzophenone and benzophenone oxime hexamethylene diurethane (BOHD), a photobase generator containing oxime-urethane groups. The polyimide-I film containing benzophenone and BOHD was not soluble in 2.38 wt% tetrabutylammonium hydroxide solution in H 2 O. However, it became soluble following irradiation with 310 nm UV light. A positive tone image with a resolution of 5 µm was obtained with this PSPI, having sensitivity (D c ) of 1.2 J/cm 2 and contrast (γ p ) of 1.08. Thus, a polyimide, which is not intrinsically photosensitive, can become photosensitive through the addition of a photobase generator containing oxime-urethane groups as a photosensitive compound.

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“…6 Incorporation of based 2 systems. Generally, these systems rely on these photoactive materials into resist systems the photogeneration of a strong acid 3 to catalytithat function via an amine-catalyzed decarboxylcally modify the polymer matrix and change the ation 8 or imidization 9 processes have resulted in solubility characteristics of the resist film. This the desired modulation of solubility and image concept was first demonstrated for resist systems 4 formation.…”

Section: Introductionmentioning

confidence: 99%

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

Urankar

Fréchet

1997

J. Polym. Sci. A Polym. Chem.

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Base-Catalyzed Photosensitive Polyimide

Cited by 11 publications

References 0 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

Positive-type photosensitive polyimide based on a photobase generator containing oxime-urethane groups as a photosensitive compound

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

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