Photosensitive fluorinated polyimides with a low dielectric constant based on reaction development patterning

Tomoko Miyagawa, Takafumi Fukushima, Toshiyuki Oyama, Takao Iijima, Masao Tomoi

Research output: Contribution to journalArticlepeer-review

57 Citations (Scopus)

Abstract

The fluorinated polyimide PK6FDA/HFBAPP) was prepared by the reaction of 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA) with 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane (HFBAPP) in l-methyl-2-pyrrolidone/toluene A multiblock copolyimide with both fluorinated and rigid-rod segments, PI(6FDA/HFBAPP)(BPDA/2-DMB), was prepared by the addition of a second dianhydride, 3,3′,4,4′-biphenyltetracarboxylic dianhydride (BPDA), and a second diamine, 2,2′-dimethylbenzidine (2-DMB), to the polyimide main chain. The potential lithographic performance of photosensitive polyimides composed of nonphotosensitive fluorine-containing polyimides and photosensitive diazonaphthoquinone (DNQ) was studied on the basis of a new imaging principle recently proposed by our laboratory, that is, reaction development patterning. Neat PI(6FDA/HFBAPP) showed a low dielectric constant (ε) of 2.41 and a low dissipation factor (tan δ) of 0.0027 at 20 GHz, and a 10-μm resolution of the fluorinated polyimide/DNQ system was demonstrated with reactive development with a solution including ethanolamine after ultraviolet exposure. Although slight changes in the dielectric properties were observed in the presence of DNQ residues, these values (ε = 2.63 and tan δ = 0.0033 at 20 GHz) were low enough for use in microelectronic applications. However, PI(6FDA/HFBAPP)(BPDA/2-DMB), having a lower coefficient of thermal expansion (CTE; 33 ppm/°C) than PK6FDA/HFBAPP) (49 ppm/°C), exhibited good positive photosensitivity, whereas the relatively low-CTE multiblock copolyimide displayed a much higher e value (3.48 at 1 MHz) than the highly fluorinated polyimide (2.88 at 1 MHz). A film consisting of PK6FDA/HFBAPPXBPDA/2-DMB) and the remaining DNQ derivatives showed a CTE value comparable to that of the neat polyimide film.

Original languageEnglish
Pages (from-to)861-871
Number of pages11
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume41
Issue number6
DOIs
Publication statusPublished - 2003 Mar 15
Externally publishedYes

Keywords

  • Diazonaphthoquinone compound
  • Dielectric properties
  • Photoresists
  • Polycondensation
  • Polyimides
  • Reaction development patterning (RDP)

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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