Early risk diagnosis and driving anomaly detection from vehicle stream are of great benefits in a range of advanced solutions towards Smart Road and crash prevention, although there are intrinsic challenges, especially lack of ground truth, definition of multiple risk exposures. This study proposes a domain-specific automatic clustering (termed Autocluster) to self-learn the optimal models for unsupervised risk assessment, which integrates key steps of risk clustering into an auto-optimisable pipeline, including feature and algorithm selection, hyperparameter auto-tuning. Firstly, based on surrogate conflict measures, indicator-guided feature extraction is conducted to construct temporal-spatial and kinematical risk features. Then we develop an elimination-based model reliance importance (EMRI) method to unsupervised-select the useful features. Secondly, we propose balanced Silhouette Index (bSI) to evaluate the internal quality of imbalanced clustering. A loss function is designed that considers the clustering performance in terms of internal quality, inter-cluster variation, and model stability. Thirdly, based on Bayesian optimisation, the algorithm selection and hyperparameter auto-tuning are self-learned to generate the best clustering partitions. Various algorithms are comprehensively investigated. Herein, NGSIM vehicle trajectory data is used for test-bedding. Findings show that Autocluster is reliable and promising to diagnose multiple distinct risk exposures inherent to generalised driving behaviour. Besides, we also delve into risk clustering, such as, algorithms heterogeneity, Silhouette analysis, hierarchical clustering flows, etc. Meanwhile, the Autocluster is also a method for unsupervised multi-risk data labelling and indicator threshold calibration. Furthermore, Autocluster is useful to tackle the challenges in imbalanced clustering without ground truth or priori knowledge
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