The easiest way is to use custom validator on some transition that will not allow to pass if there are some conditions regarding worklog entries met. I.e. you will not be able to resolve the issue until you fix the worklog entries. Not completely what you nead - but the easiest workaround that will help to achieve the goal.
As for the custom validator - the easiest way is to write script validator with https://jamieechlin.atlassian.net/wiki/display/GRV/Validators or write your own plugin with that validator https://developer.atlassian.com/display/JIRADEV/Creating+Workflow+Extensions
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