ITextSharp is not a library linked in your project output; it's an assembly referenced by your project output. And while VB.Net builds one executable from your source code, the CLR still needs all the referenced assemblies in the same folder as your executable.
To make everything work, you can distribute ITextSharp assemblies along with your app. Alternatively, if you indeed need only one file, you can use ILMerge
on your project output and the assemblies you want included. However, you might need to determine all the correct assemblies you need merged. I wouldn't revommend using this tool, unless you understand how it works.
Note: If you want to use ILMerge with .Net v4.0, read this page.