A series all-aromatic poly(esterimide)s with different molar ratios of N-(3 0 -hydroxyphenyl)-trimellitimide (IM) and 4hydroxybenzoic acid (HBA) (IM/HBA 5 0.3/0.7 and 0.7/0.3) was prepared with the aim to design flexible high T g films. Melt-pressed films, either from high molecular weight polymer or cured phenylethynyl precursor oligomers, exhibit T g s in the range of 200 8C to 242 8C and are brittle. After a thermal stretching procedure, the films became remarkably flexible and very easy to handle. In addition, the thermally stretched 3-IM/7-HBA and 7-IM/3-HBA films show tensile strengths of 108 MPa and 169 MPa, respectively. Thermal treatment increased the T g of 3-IM/7-HBA from 205 8C to 248 8C, whereas the T g of 7-IM/3-HBA increased from 230 8C to 260 8C.Most ketone-, ether-, and amide-based monomers are symmetric two-ring moieties. Imide-based monomers, on the other hand, are nonlinear or kinked three-ring systems. [21][22][23][24][25][26][27] The aromatic content is increased but the asymmetry suppresses T m Additional Supporting Information may be found in the online version of this article.