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In addition to looking at the documentation linked by kennethk (and also at perlretut; see in particular the section titled 'Looking ahead and looking behind'), perhaps some insight as to the effect of the  \b (and \B) zero-width word (and non-word) boundary assertions can be gained by split-ting one of the OPed example strings on each assertion:

>perl -wMstrict -le "my $line2 = 'I:\$AVG\hello.log'; printf qq{'$_' } for split /\b/, $line2; print qq{\n}; printf qq{'$_' } for split /\B/, $line2; " 'I' ':\$' 'AVG' '\' 'hello' '.' 'log' 'I:' '\' '$A' 'V' 'G\h' 'e' 'l' 'l' 'o.l' 'o' 'g'

In reply to Re^3: regex not matching special char by AnomalousMonk
in thread regex not matching special char by mnooning

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