Silicon-based antireflective coating compositions

An antireflective coating composition comprising:

• a) a polymer comprising a siloxane polymer having at least one Si—OH group and at least one Si—OR group, where R is condensation stabilizing group optionally having a reactive functional group, wherein the siloxane polymer, when placed into propylene glycol monomethyl ether solvent at 20 weight % solid, has a weight average molecular weight increase of less than or equal to 50% after aging for one week at 40° C. as measured by GPC;
• and
• b) a solvent,
• wherein the polymer has at least one Si—OH group and at least one Si—OR group, where R is a condensation stabilizing group optionally having a reactive functional group, wherein the condensation stabilizing group R was introduced by replacing some, but not all Si—OH by reacting the polymer with a compound selected from the group consisting of trimethoxysilane, triethoxysilane, methyl dimethoxysilane, ethyl diethoxysilane, methyl dimethoxychlorosilane, methyl methoxydichlorosilane, diphenyl dichlorosilane, dimethyl t-butylchlorosilane, dimethyl methoxychlorosilane, methyl dimethoxychlorosilane, ethylmethoxydichlorosilane, diethyl methoxychlorosilane, tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-i-propoxysilane, tetra-n-butoxysilane, methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, i-propyltrimethoxysilane, propyltriethoxysilane, n-butyltrimethoxysilane, n-butyltriethoxysilane, n-pentyltrimethoxysilane, n-hexyltrimethoxysilane, n-heptyltrimethoxysilane, n-octyltrimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, cyclohexyltrimethoxysilane, cyclohexyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, 3-chloropropyltrimethoxysilane, 3-chloropropyltriethoxysilane, 3,3,3-trifluoropropyltrimethoxysilane, 3,3,3-trifluoropropyltriethoxysilane, 2-hydroxyethyltrimethoxysilane, 2-hydroxyethyltriethoxysilane, 2-hydroxypropyltrimethoxysilane, 2-hydroxypropyltriethoxysilane, 3-hydroxypropyltrimethoxysilane, 3-hydroxypropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 3-isocyanatepropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyl-triethoxysilane, (3-glycidoxypropyl)tripropoxysilane, 3-glycidoxypropyltri(2-methoxyethoxy)silane, 2,3-epoxypropyltriethoxysilane, 3,4-epoxybutyltriethoxysilane, 4,5-epoxypentyltriethoxysilane, 5,6-epoxyhexyltriethoxysilane, 5,6-epoxyhexyltrimethoxysilane, 4-(trimethoxysilyl)butane-1,2-epoxide, 3-(triethoxysilyl)propylsuccinic anhydride, 3-(trimethoxysilyl)propylsuccinic anhydride, 3-(methyldimethoxysilyl)propylsuccinic anhydride, 3-(methyldiethoxysilyl)propylsuccinic anhydride, 3-ureidopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, dimethyldimethoxysilane, dimethyldiethoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, di-n-propyldimethoxysilane, di-n-propyldiethoxysilane, di-i-propyldimethoxysilane, di-i-propyldiethoxysilane, di-n-butyldimethoxysilane, di-n-butyldiethoxysilane, di-n-pentyldimethoxysilane, di-n-pentyldiethoxysilane, di-n-hexyldimethoxysilane, di-n-hexyldiethoxysilane, di-n-heptyldimethoxysilane, di-n-heptyldiethoxysilane, di-n-octyldimethoxysilane, di-n-octyldiethoxysilane, di-n-cyclohexyldimethoxysilane, di-n-cyclohexyldiethoxysilane, diphenyldimethoxy-silane, diphenyldiethoxysilane, methyltriacetyloxysilane, dimethyldiacetyloxy-silane, N-(3-triethoxysilylpropyl)-4-hydroxybutyramide, 3-(triethoxysilylpropyl)-p-nitrobenzamide, triethoxysilylpropylethylcarbamate, vinyltris(methylethylketoximino)silane, vinylmethyl-bis(methylethylketoximino)silane, tetrakis(methylethylketoximino)silane, phenyltris(methylethylketoximino)silane, diphenylbis(methylethylketoximino)-silane, dimethylbis(methylethylketoximino)silane, methyltris(methylethylketoximino)silane, 2-hydroxy-4-(3-triethoxysilylpropoxy)-diphenylketone, and 2-hydroxy-4-(3-methyldiethoxysilylpropoxy)diphenylketone, bis(triethoxysilyl)ethane, 2,2-bis(allyloxymethyl)-1-trimethylsiloxybutane, 2,2-bis(3-triethoxysilylpropoxymethyl)-1-trimethylsiloxybutane, 3,3-bis(trichlorosilylpropoxymethyl)-5-oxa-tridecane, and 1,3-bis(3-trichlorosilylpropoxy)-2-decyloxypropane, and mixtures thereof.

An antireflective coating composition comprising:

• a) a polymer comprising a siloxane polymer having at least one Si—OH group and at least one Si—OR group, where R is condensation stabilizing group optionally having a reactive functional group, wherein the siloxane polymer, when placed into propylene glycol monomethyl ether solvent at 20 weight % solid, has a weight average molecular weight increase of less than or equal to 50% after aging for one week at 40° C. as measured by GPC;
• and
• b) a solvent,
• wherein the siloxane polymer comprises
• units of M-type, D-type T-type and Q-type, such that at least one unit of T-type, trifunctional silane, and one unit Q-type, tetrafunctional silane are present, where Ra, Rb, and Rc are selected from hydrocarbon, epoxy-functional, and anhydride-functional groups, and R10 is selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, alkaryl, aralkyl, (alkyl)acrylate, (alkyl)acryloxyalkyl, (alkyl)acryloxyalkenyl, an epoxy-functional group, and an anhydride-functional group;
• wherein p has a value of 0.5 when the associated oxygen atom is bonded to another silicon atom, and a value of 1 when the associated oxygen atom is bonded to other than a silicon atom, with the proviso that at least one p in each T and Q unit has a value of 0.5;
• and further where each R10 is independently selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, aryl, alkaryl, aralkyl, (alkyl)acrylate, (alkyl)acryloxyalkyl, (alkyl)acryloxyalkenyl, an epoxy-functional group and an anhydride-functional group;
• and further where the sum of the number of T and Q units in the siloxane polymer being greater than or equal to 50% of the sum of M, D, T and Q-type units.