The Novel Diamine, Dianhydride, and Polyimide Based on Anthracene Core
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The Novel Diamine, Dianhydride, and Polyimide Based on Anthracene Core
Eunhye Shin1,2, Jong Chan Won1, Byoung Gak Kim1, Jae-Won Ka1, Kwang-Suk Jang1, Yun Ho Kim1, Jae-Sup Shin2 , and Jinsoo Kim1 1 Advanced Functional Materials Research Group, Korea Research Institute of Chemical Technology, 141 Gajeong-ro, Yuseong-gu, Daejeon, 305-600, Republic of Korea. 2 Department of Chemistry, Chungbuk National University, 52 Naesudong-ro, Heungdeok-gu, Cheongju, Chungbuk, 361-763, Republic of Korea ABSTRACT The lower dielectric constant (k) insulator is required for faster, smaller, and higher performance integrated circuit of the microprocessor and other advanced semiconductor devices that are so important to modern electronics and information technologies. Aromatic polyimides are among the candidate materials of low k due to their high thermal stability, mechanical strength and chemical resistance. In this work, we show an 2,6-di-tert-butyl-9,10-diphenylanthracene core based novel polyimide which has been designed to have the lower polar imide concentration compared to that of conventional polyimides as well as the synthesis and characterization of its constitutional units, diamine and dianhydride. INTRODUCTION Polyimides have been widely employed in the microelectronics industry because of their outstanding mechanical properties, chemical resistance, thermal stabilities, high glass-transition temperature and low dielectric constant [1]. The development of thermally stable polyimides with lower dielectric constant is strongly demanding for the fabrication of faster, smaller, and higher performance microelectronic devices [2]. It is well-known that decreasing the dielectric constant of polyimides can be achieved by reducing the polar imide concentration (weight fraction of imide linkage by molecular weight in repeating unit) and increasing polymer free volume [2-4]. As an effort to prepare suitable aromatic monomers for using the preparation of polyimide with lower dielectric constant while maintaining thermal stability, our strategy was a utilizing an anthracene moiety bearing space-occupying groups such as bulky alkyl and phenyl as a core unit of polyimide back bone. In this work, new kinds of aromatic diamine and dianhydride based on 2,6-di-tert-butyl9,10-diphenylanthracene, explicitly 2,6-di(tert-butyl)-9,10-bis(4-aminophenyl)-anthracene (BAPA) and 2,6-di(tert-butyl)-9,10-bis[4-(isobenzofuran-1,3-dionyl)]-anthracene (BBFA) were synthesized successfully. A novel anthracene-containing polyimide, PI (BAPA-BBFA) was synthesized by polycondensing BAPA with BBFA. In the mean time, the composition and structure of new monomers and the corresponding intermediates, as well as the structures and
thermal property of the subsequent polyamic acid and polyimide were characterized by means of 1 H-NMR, 13C-NMR, MS, FTIR, EA, and TGA.
EXPERIMENTAL DETAILS Materials Solvents and reactants were of reagent-grade quality and used as received. 2,6-di-tertbutyl-9,10-dibromoanthracene was prepared by tert-butylation at 2- and 6- position of a
