For the future of optical interconnect, high optical coupling efficiency is required for high density multilayer optical printed wiring board (OPWB). Hence, we propose optical pin as optical coupling devices between surface devices and the multi-layer channel of OPWB using self-written waveguide (SWW) with mask-transfer method. SWW-pin is passively aligned and mask-transfer provides precise positioning between surface device and channel waveguide. This makes these technology is a promising technology for coupling device. A comparison of coupling efficiency of three cases methods is performed-using ray-tracing simulation. The calculation for optical coupling efficiency with vertical pin of -0.05 dB is achieved. The proposed of an easy and sufficient fabrication concept using MTSW method with the application of prism are expected. The vertical pin technologies are anticipated to be useful in the future of high optical coupling devices of the multi-layer and multi-channel waveguides and /or a multi-core optical fiber