In Lucee V4.5.3.018 in Lucee/lib there was a file called "fonts.jar" and it was possible to modify it to include customer fonts for special fonts used in the generated PDF.
In Lucee V220.127.116.11 there is a totally other module structure. The jar-file
"lucee-18.104.22.168-20160815.221815-3.jar" contains no elements which show a possible extension for customer fonts.
A possible point of implentation is in "lucee/Tomcat/lucee-server/bundles/PDFBox-0-7-3.jar".
In the Lucee server/web administrator there is a menue item "bundles". The module "PDFBox" is listed with the related version but marked as "not loaded".
I have implemented a customer ttf-font into this jar, modified the properties-file and restarted the server service.
But I think it's logical for a "not loaded" bundle, that there was no effect.
IIS 10, Tomcat 8