"The first seal shall be broken when a righteous man sheds blood in Hell."
When John dies, he goes to hell where he is tortured everyday by Alastair so that he tortures other souls to get himself off the rack. Later Alastair, reveals to Dean that his father never broke, i.e. never accepted his deal.
However, Dean succumbed and gave in to Alastair in just 3 months(30 yrs in human years) and tortured souls for the next 10(human) years. In S04E11 Family Remains, Dean even confesses to Sam that he enjoyed torturing souls, as he finally had the chance to dish out the same pain that he'd endured for the past thirty years.
TLDR: John and Dean are both righteous men but the first seal was not broken by John as he never gave in to Alastair's torture.
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