Low Temperature Curable, Positive-Tone, Photo-Definable Poly(Benzoxazole)

Negative-Working Photosensitive Poly(phenylene ether) Based on Poly(2,6-dimethyl-1,4-phenylene ether), a Cross-Linker, and a Photoacid Generator

“…Finally, HOCD was quantitatively converted into HOAD by refluxing it in acetic acid in the presence of sodium acetate. The chemical structure of HOAD was confirmed by FT-IR, 1 H NMR and 13 C NMR spectroscopy, and elemental analysis. The FT-IR spectrum showed characteristic absorptions at 1736 and 1246 cm -1 which can be assigned to carbonyl and ether groups stretching, respectively.…”

“…1 H NMR (CDCl 3 , δ, ppm): 1.51-1.55 (m, 4H, -CH 2 -), 1.80-1.89 (m, 4H, -CH 2 -), 2.07 (s, 12H, -COCH 3 ), 2.09 (s, 6H, -COCH 3 ), 2.36 (s, 12H, -CH 3 ), 3.76-3.80 (t, 4H, -CH 2 O-), 5.22 (s, 12H, -CH 2 OCdO). 13 Acid-Catalyzed Model Cross-Linking Reaction. To PPE (45.0 mg, 0.375 mmol) and PBA (5.00 mg, 0.023 mmol) in deuterated chloroform (0.6 mL, CDCl 3 ) in a NMR glass tube was added CH 3 SO 3 H (0.0005 g, 0.005 mmol: 1.3 mol % to PPE).…”

“…The infrared spectroscopy (IR) was taken with a Horiba FT-210 spectrophotometer. The 1 H and 13 C NMR spectra were obtained on a Bruker DPX-300S spectrometer ( 1 H at 300 MHz and 13 C at 75 MHz). Deuterated chloroform (CDCl 3 ) was used as solvent with tetramethylsilane (TMS) as an internal standard.…”

“…To remedy the warpage problem of thin silicon wafers, low-temperature thermal treatment of photosensitive thermally stable polymers (PSTSPs) is desirable because of the reduction in thermal stress. We have reported a series of low-temperature cyclization methods of PSPIs and PSPBOs to produce more useful applications in the microelectronics industry. ,,− It is also important to develop PSTSP resists which do not require high-temperature curing treatment. Engineering plastics with high thermal stability and excellent mechanical properties such as PPE and poly(ether ether sulfone) (PEES) are excellent candidates for the matrices of PSTSP resists because there is no need for conversion from precursors of matrix polymers. − In a preceding paper, we reported a negative-type PSPPE based on a matrix polymer PPE, a cross-linker 4,4′-methylenebis[2,6-bis(methoxymethyl)phenol] (MBMP), and DIAS as a PAG. , PSPPE consisting of PPE (73 wt %), MBMP (20 wt %), and DIAS (7 wt %) in 1,1,2,2-tetrachloroethane exhibited a high sensitivity ( D 0.5 ) of 58 mJ/cm 2 and good contrast (γ 0.5 ) of 9.5 when it was exposed to the i -line.…”

“…We have reported a series of low-temperature cyclization methods of PSPIs and PSPBOs to produce more useful applications in the microelectronics industry. 7,8,[11][12][13][14][15] It is also important to develop PSTSP resists which do not require high-temperature curing treatment. Engineering plastics with high thermal stability and excellent mechanical properties such as PPE and poly(ether ether sulfone) (PEES) are excellent candidates for the matrices of PSTSP resists because there is no need for conversion from precursors of matrix polymers.…”