Preheat the oven to 400˚F. Line a baking sheet with foil. Add the tomatoes, 1/4 cup of the olive oil, garlic cloves, red pepper flakes, oregano, thyme, basil, kosher salt, and ground black pepper to the pan. Toss until the ingredients are evenly coated then position the tomatoes so that the cut side is facing up. Roast them in the oven for 40-45 mins until caramelized and lightly browned. Set aside.