Object occlusion boundary detection is a fundamental and crucial research problem in computer vision. Solving this problem is challenging as we encounter extreme boundary/non-boundary class imbalance during the training of an object occlusion boundary detector. In this paper, we propose to address this class imbalance by up-weighting the loss contribution of false negative and false positive examples with our novel Attention Loss function. We also propose a unified end-to-end multi-task deep object occlusion boundary detection network (DOOBNet) by sharing convolutional features to simultaneously predict object boundary and occlusion orientation. DOOBNet adopts an encoder-decoder structure with skip connection in order to automatically learn multi-scale and multi-level features. We significantly surpass the state-of-the-art on the PIOD dataset (ODS F-score of .702) and the BSDS ownership dataset (ODS F-score of .555), as well as improving the detecting speed to as 0.037 s per image on the PIOD dataset.