To reproduce: use the following code snippet:

DataTable dt = new DataTable();
dt.Columns.Add("Id", typeof(int));
dt.Columns.Add("Name", typeof(string));
dt.Columns.Add("IsActive", typeof(bool));

for (int i = 0; i < 20; i++)
{
    if (i % 5 == 0)
    {
        dt.Rows.Add(i, "Item" + i, true);
    }
    {
        dt.Rows.Add(i, "Item" + i, DBNull.Value);
    }
}

this.radGridView1.DataSource = dt;
this.radGridView1.AutoSizeColumnsMode = GridViewAutoSizeColumnsMode.Fill;
this.radGridView1.EnableFiltering = true;


Try to filter by "Name" column via entering "4". As a result an InvalidCastException occurs.

Workaround: initialize default value for the cells belonging to GridViewCheckBoxColumn with false if  it is DBNull:

foreach (GridViewRowInfo r in this.radGridView1.Rows)
            {
                if (r.Cells["IsActive"].Value == DBNull.Value)
                {
                    r.Cells["IsActive"].Value = false;
                }
            }