If you do not know what OOAD or UML is, or have just basic understanding, then the best book is Applying UML and Patterns : An Introduction to Object-Oriented Analysis and Design and Iterative Development by Craig Larman.
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This book is exceptionally well written and covers not just basics of OOAD and UML in a clear and accessible way, but also related topics of basics of requirements engineering, software project management and software architecture. I strongly recommend this book over any general software engineering book. The book is very up-to-date and covers latest trends – many of which I do not necessarily agree with –but it’s an invaluable resource for getting up-to-speed in this area.
If you are already familiar with basics of OOAD and UML, you will want to read the book Designing Concurrent, Distributed, and Real-Time Applications with UML by Hassan Gomaa.
With less clear writing and harder to digest organization, this book is nevertheless the best work so far from the perspective of realistic examples, exposing real difficulties in achieving good analysis and design artifacts, and integrating other important system engineering topics, in particular handling real-time and distribution issues, within an OOAD method and specification. This book is by far the closest in the advice to what I have experienced on non trivial projects. So, if you are involved in analysis and design of a non trivial system, and want to rely upon object-oriented technology, read this book.
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JavaWorld
December 1999