Yes, there are restrictions in the file name on the device. As @rtiangha said, calibre should sanitize the name and path. Did you remove the file that wasn't being imported before sending it from calibre? If so, when the import failed for it, that stopped the import from processing later books.
For the record, the KoboTouch driver uses the regex "[\/\\\?%\*:;\|\"\'><\$!]" to match invalid characters in the path. Any matches are changed to an underscore. Calibre will do some other things, mainly about the path length, but I don't remember it makes other changes to characters like this.
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