"Clipboard" didnt seem to support files. With Tk::Clipboard I tested:

use Tk;
use Tk::clipboard;

use strict;
use warnings;
#use diagnostics;

#print Clipboard->paste;

my $mw = new MainWindow;

#my $clip = Tk::clipboard::clipboardGet( -type => 'FILE_NAME' );

$mw->clipboardClear;
$mw->clipboardAppend(-format=>"FILE_NAME", -type => 'FILE_NAME', "--",
+ "C:\\test\\gaga.txt");

#print $clip;

MainLoop;
[download]

No luck. Pasting in explorer having this runing didn't do anything with the file.