Could someone explain to me the Skyrim's icon/logo?
I understand Morrowind's, it's about Azura.
Oblivion's is about Oblivion gates, it's a daedric symbol, same symbol used for conjuration magic.
So what about Skyrm's icon. First of all what does the Dargon at the imperial flag stand for and why do Imperials have an "obssesion" with dragons(Dragon armour in oblivion for example) and what does this dragon have to do with Skyrim's dragons and Alduin?
The Dragon and Diamond represents the Dragonborn Emperor. While the current Medes dynasty are not Dragonborn, the Alessians, Remans and Septims were.
The breaking diamond represents the Empire (and thus the old world order) breaking apart and probably the fact that we are the last Dragonborn.
As for why they care about Dragons... it is due to Alessia, the first Dragonborn Empress who also made Dragon god Akatosh the leading deity of Imperial religion. The Empire of Tamriel serves the Dragonborn and the Dragonborn protect the Empire and with it, Tamriel. And since this is a game about a Dragonborn, it makes sense for a Dragonborn symbol to be there.