Synthesis and Resist Properties of Calixarene Polymers with Pendant Haloalkyl Groups

We examined the condensation polymerization of t-butylcalix[8]arene (BCA[8]), p-t-butylcalix[4]arene (BCA[4]), and C-(4-t-butylbenz)calix[4]resorcinarene (BCRA[4]) with 1,3-adamantane dibromoacetate (ADB), yielding soluble polymers poly(BCA[8]-co-ADB), poly(BCA[4]-co-ADB), and poly(BCRA[4]-co-ADB), respectively. These polymers had good solubility, good film forming ability, and good thermal stability. It was anticipated that these polymers were applicable to positive-type resist materials. However, by the examination on the resist sensitivity using EUV exposure system, these polymers were applicable to negative type resist materials using THF as a developer. Furthermore, a negative clear resist pattern with 100nm resolution could be obtained by EB exposure system. These results indicated that poly(BCA[8]-co-ADB) and poly(BCRA[4]-co-ADB) have high potential to offer higher resolution negative pattern using EUV lithography system. © 2016SPST.