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US 10,591,818 B2Granted
Nadic anhydride polymers and photosensitive compositions derived therefrom
AssigneePromerus, LLC
InventorsBrian Knapp, Cheryl Burns
Life of this patent
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Abstract
Various vinyl addition polymers of nadic anhydride are disclosed. Examples of such polymers include copolymers and terpolymers of nadic anhydride with a wide variety of norbornene-type monomers. The nadic anhydride polymers are found to be useful in forming a wide variety of photosensitive compositions, both positive and negative, which are capable of forming high resolution imagable films exhibiting excellent dielectric properties (low-k) and thermal properties, and thus are useful in the fabrication of a variety of microelectronic and optoelectronic devices, among others.
Claims20
A copolymer consisting of a first repeat unit which is derived from a monomer selected from the group consisting of:
- 3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione (nadic anhydride);
- and
- 5-methyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione;
- and a second repeat unit which is derived from a monomer selected from the group consisting of:
- 2-(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)ethyl acetate (NBCH2GlyOAc);
- 2-(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)ethanol (NBCH2GlyOH);
- trioxanonanenorbornene (NBTON);
- tetraoxadodecanenorbomnene (NBTODD);
- 5-(3-methoxybutoxy)methyl-2-norbornene (NB-3-MBM);
- 5-(3-methoxypropoxy)methyl-2-norbornene (NB-3-MPM);
- 5-(2-(2-ethoxyethoxy)ethyl)bicyclo[2.2.1]hept-2-ene;
- 5-(2-(2-(2-propoxyethoxy)ethoxy)ethoxy)bicyclo[2.2.1]hept-2-ene;
- 2-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (HFANB);
- 4-(bicyclo[2.2.1]hept-5-en-2-yl)-1,1,1-trifluoro-2-(trifluoromethyl)butan-2-ol (HFACH2NB);
- 5-(bicyclo[2.2.1]hept-5-en-2-yl)-1,1,1-trifluoro-2-(trifluoromethyl)pentan-2-ol (HFACH2CH2NB);
- 2-((bicyclo[2.2.1]hept-5-en-2-ylmethoxy)methyl)-1,1,1,3,3,3-hexafluoropropan-2-ol;
- and
- 2-((2-(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)ethoxy)methyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (GlyHFIPNB).
15 more elements
A terpolymer consisting of a first repeat unit which is derived from a monomer selected from the group consisting of:
- 3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione (nadic anhydride);
- and
- 5-methyl-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione;
- and a second re eat unit which is derived from a monomer selected from the group consisting of:
- 2-(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)ethyl acetate (NBCH2GlyOAc);
- 2-(bicyclo[2.2.1]hept-5-en-2-ylmethoxy)ethanol (NBCH2GlyOH);
- trioxanonanenorbornene (NBTON);
- tetraoxadodecanenorbornene (NBTODD);
- 5-(3-methoxybutoxy)methyl-2-norbornene (NB-3-MBM);
- 5-(3-methoxypropoxy)methyl-2-norbornene (NB3-MPM);
- 5-(2-(2-(2-propoxyethoxy)ethoxy)ethoxy)bicyclo[2.2.1]hept-2-ene;
- 2-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (HFANB);
- 4-(bicyclo[2.2.1]hept-5-en-2-yl)-1,1,1-trifluoro-2-(trifluoromethyl)butan-2-ol (HFACH2NB);
- 5-bicyclo[2.2.1]hept-5-en-2-yl)-1,1,1-trifluoro-2-(trifluoromethyl)pentan-2-ol (HFACH2CH2NB);
- 2-((bicyclo[2.2.1]hept-5-en-2-ylmethoxy)methyl)-1,1,1,3,3,3-hexafluoropropan-2-ol;
- and
- 2-((2-bicyclo[2.2.1]hept-5-en-2-ylmethoxy)ethoxy)methyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (GlyHFIPNB);
- and
- a third repeat unit which is derived from a monomer selected from the group consisting of:
- bicyclo[2.2.1]hept-2-ene (NB);
- 5-methylbicyclo[2.2.1]hept-2-ene (MeNB);
- 5-ethylbicyclo[2.2.1]hept-2-ene (EtNB);
- 5-hexylbicyclo[2.2.1]hept-2-ene (HexNB);
- 5-octylbicyclo[2.2.1]hept-2-ene (OctNB);
- 5-decylbicyclo[2.2.1]hept-2-ene (DecNB);
- 5-(hex-5-en-1-yl)bicyclo[2.2.1]hept-2-ene (HexenylNB);
- bicyclo[2.2.1]hept-5-en-2-ylmethanamine;
- tert-butyl (bicyclo[2.2.1]hept-5-en-2-ylmethyl)carbamate;
- tert-butyl 4-((bicyclo[2.2.1]hept-5-en-2-ylmethyl)amino)-4-oxobutanoate;
- (E)-4-((bicyclo[2.2.1]hept-5-en-2-ylmethyl)amino)-2,3-di methyl-4-oxobut-2-enoic acid;
- N-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)-2,3,4,5,7-pentahydroxyheptanamide;
- N-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)-1,1,1-trifluoromethanesulfonamide;
- 1-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)-3,4-dimethyl-1H-pyrrole-2,5-dione (MeDMMINB);
- 1-(3-(bicyclo[2.2.1]hept-5-en-2-yl)propyl)-3,4-dimethyl-1H-pyrrole-2,5-dione (PrDMMINB);
- 1-(4-(bicyclo[2.2.1]hept-5-en-2-yl)butyl)-3,4-dimethyl-1H-pyrrole-2,5-dione (BuDMMINB);
- 1-(6-(bicyclo[2.2.1]hept-5-en-2-yl)hexyl)-3,4-dimethyl-1H-pyrrole-2,5-dione (HexDMMINB);
- bicyclo[2.2.1]hept-5-en-2-ylmethyl acetate (NBMeOAc);
- 2-((bicyclo[2.2.1]hept-5-en-2-ylmethoxy)methyl)oxirane (MGENB);
- 2-(bicyclo[2.2.1]hept-5-en-2-yl)oxirane;
- 2-(6-(bicyclo[2.2.1]hept-5-en-2-yl)hexyl)oxirane;
- and
- 5-phenethylbicyclo[2.2.1]hept-2-ene (PENB);
- bicyclo[2.2.1]hept-5-ene-2-carboxylic acid;
- N-(2,2,2-trifluoroacetyl)bicyclo[2.2.1]hept-5-ene-2-carboxamide;
- 2-(bicyclo[2.2.1]hept-5-en-2-yl)acetic acid (NBCH2CO2H);
- 3-(bicyclo[2.2.1]hept-5-en-2-yl)propanoic acid (NBCH2CH2CO2H);
- ethyl 3-(bicyclo[2.2.1]hept-5-en-2-yl)propanoate;
- tert-butyl 3-(bicyclo[2.2.1]hept-5-en-2-yl)propanoate;
- 4-(bicyclo[2.2.1]hept-5-en-2-yl)butanoic acid (NBCH2CH2CH2CO2H);
- 2-(bicyclo[2.2.1]hept-5-en-2-yl)-N-(2-hydroxyphenyl)acetamide;
- 3-(bicyclo[2.2.1]hept-5-en-2-yl)-N-(2-hydroxy henyl)propanamide;
- 4-(bicyclo[2.2.1]hept-5-en-2-yl)phenol;
- 4-(bicyclo[2.2.1]hept-5-en-2-ylmethyl)-2-methoxyphenol.
50 more elements
Dependencies are inferred from the claim text.