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

Abstract

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.

Study on synthesis and photochemical behavior of carbamate photobase generators for fluorescence imaging

“…It's worth mentioning that the photodecomposition reactions of PPrC, SPrC, and TKPrC were completed after 400 s irradiation, which correspond to the exposure dose of 1.80 J cm −2 . This suggests that the three photobase generators have high photosensitivity …”

“…This suggests that the three photobase generators have high photosensitivity. [25][26][27][28][29][30] This result indicates that amino groups are produced upon irradiation, since fluorescamine itself is not fluorescent and only becomes fluorescent after reaction with the amino groups. Figure 4(B) shows the relative fluorescence intensities of fluorescamine treated photobase generator solutions in ethanol at 480 nm as a function of UV exposure time.…”

“…19,20 Photobase generators are a group of compounds that produce bases upon irradiation. 21,22 These compounds have been applied as photochemical crosslinking agents for epoxy resins, [23][24][25][26] and also as photoresists, [27][28][29][30] surface modifiers, 31 and imidation catalysts for poly(amic ester)s. 32 However, there are few reports on photobase generating systems for the formation of fluorescence imaging systems comparing with photoradical and photoacid generators. Eun and co-collaborators constructed a film selectively emitting red, green, and blue fluorescence.…”

Effects of the aliphatic/aromatic structure on the miscibility, thermal, optical, and rheological properties of some polyimide blends

“…It is found out that packing density and segmental mobility of the polymer chains are determined by blend composition and type of crosslinking agent. The concept of conventional molecular blends has been extended to PIs [8–13], keen interest being paid to the application of dielectric (insulating or packaging) layers for microelectronic devices such as very large‐scale integration and/or ultra large‐scale integration [14]. Because these applications required simultaneously high thermal stability/low relative permittivity and good adhesion, the nanomorphology control of PI molecular blends was of crucial importance to adjust these properties.…”

Surface properties and blood compatibility of some aliphatic/aromatic polyimide blends

“…Effective methods for increasing the free volume include modification of the rigid‐rod polymer through side group attachment, and introduction of nonlinear monomers into the polymer backbone [16]. The concept of conventional molecular blends of PIs [17–22] generated keen interest for the application of dielectric layers (insulating or packaging), for microelectronic devices, such as very large‐scale integration and/or ultra‐large‐scale integration [23]. Because these applications required simultaneously high thermal stability/low relative permittivity and good adhesion, the nanomorphological control of PI molecular blends was of crucial importance to adjust these properties.…”