Polyarylene materials
View Patent ↗Certain polyarylene oligomers having improved solubility are useful in forming dielectric material layers in electronics applications.
1. An oligomer comprising as polymerized units a first monomer comprising two cyclopentadienone moieties, a second monomer having the formula (1), and a third monomer having the formula (2)
wherein a is the number of R groups and is an integer from 0 to 4; b is 1 or 2; each R is independently chosen from C 1-4 alkyl, halo C 1-4 alkyl, C 1-4 alkoxy, C 1-4 aralkyl, and optionally substituted C 6-10 aryl; each R 1 is independently H or optionally substituted C 6-10 aryl; R 2 is H, optionally substituted C 1-10 alkyl, optionally substituted C 7-12 aralkyl, optionally substituted C 6-10 aryl, or R 3 ; and R 3 is a polar moiety selected from the group consisting of carboxyl, C 2-12 aliphatic carboxylate, hydroxy C 1-10 alkyl, C 7-20 aryl carboxylic acid, C 8-20 aryl carboxylic acid anhydride, C 7-20 aryl carboxylates, C 7-20 aryl amide, and C 8-20 aryl imide.
2. The oligomer of claim 1 wherein the third monomer is selected from the group consisting of propiolic acid, acetylene dicarboxylic acid, phenyl propiolic acid, ethynyl benzoic acid, ethynyl phthalic acid, propargyl alcohol, 2-methyl-3-butyn-2-ol, xylityl propiolate, ethynyl phthalic anhydride, ethynyl phthalimide, ethynyl benzamide, 2-butyn-1,4-diol diacetate; 3-butyn-2-one; 1-ethynyl-1-cyclohexanol; 1-ethynylcyclohexylamine; 1-ethnylcyclopentanol; ethynylaniline; N-(ethynylphenyl)acetamide; 2-carbamoyl-5-ethynylbenzoic acid; ethynyl-nitrobenzene; propioamaide; N-hydroxyl -propiolamide; 2-aminobut-3-ynoic acid, and mixtures thereof.
3. The oligomer of claim 1 wherein the first monomer and the second monomer are present in a mole ratio of from 1:1.001 to 1:1.95.
4. The oligomer of claim 1 wherein the first monomer has the formula
wherein each R 4 is independently chosen from H, or optionally substituted phenyl; and Ar 1 is an aromatic moiety.
5. The oligomer of claim 1 wherein b=1.
6. The oligomer of claim 5 further comprising another second monomer wherein b=2.
7. A composition comprising the oligomer of claim 1 and an organic solvent.
8. The composition of claim 7 wherein the organic solvent is chosen from propylene glycol methyl ether, propylene glycol methyl ether acetate, methyl 3-methoxypropionate, ethyl lactate, anisole, N-methyl pyrrolidone, gamma-butyrolactone, ethoxybenzene, benzyl propionate, and mixtures thereof.
9. A method of forming a dielectric material layer comprising: disposing a layer of the composition of claim 7 on a substrate surface; removing the organic solvent; and curing the oligomer to form a dielectric material layer.
10. An oligomer comprising as polymerized units a first monomer comprising two cyclopentadienone moieties, a second monomer having the formula (1), and a third monomer having the formula (2)
wherein a is the number of R groups and is an integer from 0 to 4; b is 1 or 2; each R is independently chosen from C 1-4 alkyl, halo C 1-4 alkyl, C 1-4 alkoxy, C 1-4 aralkyl, and optionally substituted C 6-10 aryl; each R 1 is independently H or optionally substituted C 6-10 aryl; R 2 is H, optionally substituted C 1-10 alkyl, optionally substituted C 7-12 aralkyl, optionally substituted C 6-10 aryl, or R 3 ; and R 3 is a a hydrocarbyl moiety having from 1 to 20 carbon atoms and one or more functional groups chosen from —C(O)—, —NO 2 , and —NR 9 R 10 , where R 9 and R 10 are independently chosen from H, C 1-10 alkyl, C 7-16 aralkyl, and C 6-10 aryl.