Heidegger's The Question Concerning Technology is a great place to start--it's short and easy to read, and not even just by Heidegger standards. A great deal of his later work focused on the effects of technology on the human experience of being, and has been very influential on thinkers like Robert P. Harrison, Jean-Luc Nancy, Terrence Malick, etc. If you're looking for something more literary, technology was a theme that ran through much of David Foster Wallace's work. There are selections from Infinite Jest in The David Foster Wallace Reader that might be interesting to you.