The relationship between woodcut printing and books has an interesting history all of its own, predating the invention of movable type and the printing revolution. In fact, entire books were printed as woodcuts during a period of the 15th century in Europe. See the Wikipedia article on block books for an introduction to woodblock printing of full books.
Bookplates, or ex libris as they are often called – Latin for “from the books of,” have an equally interesting history. Marking ownership of books and other printed materials has a long history. The practice dates back reliably to inscriptions and “book curses” from the medieval period, but some fringe scholars argure for their presence dating back to even ancient Egypt.
By the late 15th century, we have the first recognizable example of the modern bookplate, courtesy of the Carthusian monk Hildebrand Brandenburg from Biberach in the Holy Roman Empire (today’s Germany).
Like most woodcuts of the period, it was printed in a single black color (as compared to the much rarer practice of seperate red and black printings combined into a composite image), and like many woodcuts, hand coloring was added. The design itself appears decided heraldic in nature, with an escutcheon charged with an ox on a blue field, the shield itself held by an angelic supporter. History doesn’t record if Brother Brandenburg was a member of the nobility and if these were his arms or if the design was only a creative exercise.
Surviving bookplates from the early years of the early modern period remain relatively rare until the 17th century when the woodcuts were largely superseded by engravings. However, the master Dürer is reported to have created at least six in the opening years of the 16th century.