The purpose of this study is to examine patterns of uses of grammar in context and utilize them to build instructional materials for on-site Korean language teaching. In order to build a list of Korean negative expressions, this study collects the negative expressions from Korean teaching materials and learners’ dictionaries and calculates their overlapping frequencies. Data used in this study covers thirty six Korean textbooks of six kinds published by university-affiliated Korean language educational institutions and Korean learners’ dictionaries of 3 kinds. This study collects a list of negative expressions by analyzing a corpus and investigates a variety of context information based on semi-spoken and spoken corpus. In order to analyse the context characteristics of negative expressions according to speaker’s utterance intention, this study searches the examples from corpus and puts a tag on every footnotes information associated with discourse genre characteristics of the target sentence, the dialogue user relations (speaker and listener information), each speaker’s utterance intention in Excel. The results from this study are summarized as follows. First, ‘안 –지 않다’ sentence structure shows distinctive features from speaker’s utterance intention according to sentence ending forms. However, there appear no distinctive characteristics according to speaker’s gender, status, and the relationship between speaker and listeners. It is mostly used in informal environments and mainly used actively in a conversation. Second, impolite forms of ‘-지 못해’ and polite forms of ‘-지 못해(요)’ show differences in terms of utterance intention used in the actual corpus and confirms gender differences in the intended utterance. Also women have preference for a long negation of ‘-지 못해(요)’ compared to men. In case of use other than denying, its usage is limited to the situation where the listener has equal to or lower status than the speaker.