Are the duplicate imports photos you have taken with the iPhone camera or downloads from WhatsApp or similar?
Could you tell us a bit more about the Settings on your iPhone? Depending on the Settings on the iPhone the Mac may not be able to recognise images as already imported. Images will appear over and over again as new images, if you are converting the images to another format when importing, or if you are using iCloud Photos or My Photo Stream on the iPhone and the iPhone is downloading new copies of the photos from iCloud. Both could be creating new files, that cannot be recognised as duplicates, because the duplicate detection is checking for identical files. Please check these Settings:
- Is the iPhone Camera set to take the photos in the space saving High Efficiency format "HEIF"? Settings > Camera > Formats? If yes, you should not convert the photos to JPEG, when downloading from the iPhone. https://support.apple.com/en-us/HT207022#working
- Is Settings > Photos > Transfer to Mac or PC set to "Automatic"? If yes, this will disable the duplicate detection. Set it to "Keep Originals", so the photos will not be converted to JPEGs but transferred as HEIC files, or the HEIC files on the iPhone will always appear as new files.
- Is My Photo Stream enabled? Settings > Photos > Upload to my Photo Stream? If you want to be able to import manually from the iPhone, disable it. The downloads from my Photo Stream will be downsized and appear as new photos on the Mac. Using My Photo Stream in combination with a manual download will make things difficult, if you are using Live Photos and Videos on your iPhone. It does not support the new formats on the iPhone 11 Pro Max well.
- Is iCloud Photos enabled on your iPhone with "Optimise iPhone Storage"? Settings > Photos > iCloud Photos. And Settings > Photos > Optimise iPhone Storage? If yes, you have to select the new photos, when downloading manually from the iPhone. The "Optimise" option is occasionally removing high resolution images from the iPhone. Many of your originals will only be in iCloud and not on the iPhone at all. You can only download photos, that are currently not "optimised" and will get random result, including many duplicates.
With an iPhone11 Pro Max and a Mac with Catalina you will have the least trouble with transferring your photos, if you pick one horse and ride it, but do not mix the methods of transferring
- Either use only iCloud Photos on both devices - this is the most convenient method
- Or use only the manual transfer without any iCloud services for photos.