There have been a number of cases in which designs for individual letters have been held to be “artistic works” for the purposes of copyright. Although copyright in some popular typefaces has expired, many popular typeface designs are still in copyright.

If you are generating documents or designs using a computer, the real issue is whether you are licensed to use the software that includes and generates that font. Check the licence agreement which accompanies the software, or any statements from the relevant company (for example, on its website, or in the “readme” files that often accompany software). These are likely to state what you can do with the software and the font. If you are outsourcing the printing of documents, it may be that the printing company will need its own licensed copy of the relevant font software.