Fluorous solvent-soluble imaging materials containing anthracene moieties

Hye Jin Park, Heeyoung Jung, Soo Hyun Kim, Myeongjin Park, Ji Hoon Kim, Jongchan Son, Byung Jun Jung, Do Hoon Hwang, Changhee Lee, Jin Kyun Lee, Jong Geun Yoon, Soo Young Yoon

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8 Scopus citations


J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 1252-1259 Fluorous solvent-soluble, photoreactive polymers were designed using the photodimerization of anthracene moieties. Four random copolymers with Mn=20,000-27,000 were synthesized, involving an anthracene-containing monomer and a fluorinated methacrylate with varying compositions. The polymers showed sufficient solubility in the fluorous solvents but were rendered insoluble by UV irradiation. One of the copolymers, FSIM-2, shows promise as a photoreactive imaging material for the photolithographic patterning of OLED pixels.

Highly fluorinated photoresist polymers that can undergo photodimerization reactions were designed using an anthracene-based monomer. Through the random radical copolymerizations of 6-(anthracen-9-yl)hexyl methacrylate (AHMA) and semiperfluorodecyl methacrylate (FDMA) with four different compositions, polymers with Mn=20,000-27,000 (Mw/Mn=2.0-2.9) were prepared in benzotrifluoride. The polymers, in particular fluorous solvent-soluble imaging material-2 (FSIM-2), showed sufficient solubility in fluorous solvents, including hydrofluoroethers, but were rendered insoluble by UV exposure (365 nm). This photochemical solubility change was evaluated quantitatively by a quartz crystal microbalance technique, along with tracing the chemical reaction by UV-vis spectroscopy. Finally, FSIM-2 and fluorous solvents were applied to the photolithographic patterning of organic light-emitting diode pixels. In the patterning protocol involving the lift-off of resist films in fluorous solvents, FSIM-2 was recognized as a promising photoreactive material when compared with a reference polymer P(FDMA-MAMA), which necessitates acidolysis reactions for lithographic imaging.

Original languageEnglish
Pages (from-to)1252-1259
Number of pages8
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Issue number10
StatePublished - 15 May 2015


  • anthracene
  • fluoropolymers
  • fluorous solvent
  • organic light-emitting diode
  • photodimerization
  • photolithography
  • photoreactive effects
  • photoresists
  • synthesis


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