1992.
Tryouts 1 - Fill patterns.
64K Portrait and landscape formats, printed using the Star LC-10 set for high quality.
Both these files, though not pixel dense (very large black areas), would have taken about 40 minutes to print at high quality. The draft versions about 10 - 15 minutes.
The first image uses eight different patterns, the second image uses two.
These were made to see how fill patterns could be used with larger designs and what the printed output would look like. In the first image the letter H is left blank/white and in the second the centre circle area is black - these were included for comparison.
Back in 1992, depending on the quality of the printer, what you could see on the screen was sometimes quite different from the final hardcopy.
There are other comparative files like these but unfortunately I can no longer print them off