A highly efficient and feasible "condensation followed by annulation" synthetic approach was developed to afford a subset of 9-ring-fused quinacridone derivatives on a 10 g scale. Despite the amenable intermolecular hydrogen-bonding ability of these rigid molecules, good solubility in common organic solvents and solution processability into uniformed thin films were achieved. Integrated advantages in the synthesis and properties make these compounds ideal building blocks for high-performance dyes and optoelectronic materials.