Broadband refractive optics realized from high index materials provide compelling design solutions for the next generation of observatories for the Cosmic Microwave Background (CMB), and for sub-millimeter astronomy. In this paper, work is presented which extends the state of the art in silicon lenses with metamaterial antireflection (AR) coatings towards larger bandwidth and higher frequency operation. Examples presented include octave bandwidth coatings with less than $0.5%$ reflection, a prototype 4:1 bandwidth coating, and a coating optimized for 1.4 THz. For these coatings the detailed design, fabrication and testing processes are described as well as the inherent performance trade offs.