Development of new maleimides applied to spin-on carbon hardmask with characteristics of high heat resistance and good planarization

We had developed various Polyphenols and Xanthene derivatives such as NF7177C and NF0197 which showed high heat resistance. In this paper, we reported on new mareimide derivatives named "NeoFARIT N0XX (NFN0XX)" series which showed the highest heat resistance of our SOC materials [1]. To increase heat resistance drastically, we focused on Polyimides's structure. Generally speaking, polyimide resin shows the highest heat resistance in typical polymer. Introducing maleimide structure also resulted in increasing heat resistance of SOC materials drastically. For example, NeoFARIT N0XX" series show very slight weight loss to 400°C. Although the weight loss of NF0197, which showed the highest heat resistance in our phenol materials, was 4.7% at 400°C in the air in TG-DTA analysis, those of NFN001 and NFN005 were less than 1% in the same condition. Moreover, the weight loss of NFN001, NFN005 and NFN006 at 450°C in the air was less than 5%. While these materials showed highlighted heat resistance, they showed poor solubility in PGME and PGMEA. Then, we tried to improve the solubility of NFN0XX and developed NFN009 and NFN010 whose solubility in PGMEA was 30%. NFN009 showed not only good solubility in PGMEA but also high heat resistance comparable to NFN001, NFN005 and NFN006. We also try to improve the heat resistance of NFN0XX and developed NFN011 and its cured film showed slight shrinkage at 450°C bake.