Synthesis and characterization of novel negative-working aqueous base developable photosensitive polyimide precursors

Lien-Chung Hsu, Ming Hsin Fan

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Through molecular designing, three poly(amic esters) (PAEs) have been synthesized from pyromellitic dianhydride (PMDA), 2,2′-bis-(3-amino-4- hydroxyphenyl) hexafluoropropane (BisAPAF), 4,4′-diaminodiphenyl ether (4,4′-ODA) and 2-hydroxyethyl methacrylate (HEMA). Due to the introduction of photosensitive acrylate groups and aqueous base soluble phenolic hydroxyl groups in the backbone, these poly(amic esters) can be used as the precursors of negative-working, aqueous base developable photosensitive polyimides (PSPIs). These poly(amic esters) were prepared by direct polymerization by using phenyl phosphonic dichloride (PPD) as an activator. The inherent viscosities of these polymers were 0.20 (dL/g). Their structures were characterized by Fourier transform infrared spectroscopy (FTIR) and 1H NMR. In order to improve the photolithographic performance of these PSPIs, different photosensitizers, photoinitiators and a crosslinker have been added in the PSPI formulations. Among them, the Michler's ketone (MK)/tribromomethyl phenyl sulfone (TBPS) system gave the best results. Using a 2.38wt% aqueous TMAH solution as a developer, patterns with a resolution of 10 μm were obtained from these PSPI formulations. In addition, the effects of the molecular structure of the precursors and the concentration of developer on the photosensitivity of the PSPI formulations were also discussed.

Original languageEnglish
Pages (from-to)1101-1109
Number of pages9
Journalpolymer
Volume45
Issue number4
DOIs
Publication statusPublished - 2004 Jan 2

Fingerprint

Polyimides
Esters
di-(4-aminophenyl)ether
Sulfones
Photosensitivity
Photosensitizing Agents
Photosensitizers
Ketones
Hydroxyl Radical
Molecular structure
Fourier transform infrared spectroscopy
Ethers
Polymers
Polymerization
Nuclear magnetic resonance
Viscosity

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

Cite this

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title = "Synthesis and characterization of novel negative-working aqueous base developable photosensitive polyimide precursors",
abstract = "Through molecular designing, three poly(amic esters) (PAEs) have been synthesized from pyromellitic dianhydride (PMDA), 2,2′-bis-(3-amino-4- hydroxyphenyl) hexafluoropropane (BisAPAF), 4,4′-diaminodiphenyl ether (4,4′-ODA) and 2-hydroxyethyl methacrylate (HEMA). Due to the introduction of photosensitive acrylate groups and aqueous base soluble phenolic hydroxyl groups in the backbone, these poly(amic esters) can be used as the precursors of negative-working, aqueous base developable photosensitive polyimides (PSPIs). These poly(amic esters) were prepared by direct polymerization by using phenyl phosphonic dichloride (PPD) as an activator. The inherent viscosities of these polymers were 0.20 (dL/g). Their structures were characterized by Fourier transform infrared spectroscopy (FTIR) and 1H NMR. In order to improve the photolithographic performance of these PSPIs, different photosensitizers, photoinitiators and a crosslinker have been added in the PSPI formulations. Among them, the Michler's ketone (MK)/tribromomethyl phenyl sulfone (TBPS) system gave the best results. Using a 2.38wt{\%} aqueous TMAH solution as a developer, patterns with a resolution of 10 μm were obtained from these PSPI formulations. In addition, the effects of the molecular structure of the precursors and the concentration of developer on the photosensitivity of the PSPI formulations were also discussed.",
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Synthesis and characterization of novel negative-working aqueous base developable photosensitive polyimide precursors. / Hsu, Lien-Chung; Fan, Ming Hsin.

In: polymer, Vol. 45, No. 4, 02.01.2004, p. 1101-1109.

Research output: Contribution to journalArticle

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