Multifunctional unsymmetrically substituted monomers and polyarylene compositions therefrom
A monomer suitable for use in forming low dielectric constant films in semiconductor devices comprising i) two dienophile groups (A-functional groups) attached to a single aromatic ring and ii) a second ring structure comprising two conjugated carbon-to-carbon double bonds and a leaving group L (B-functional group), characterized in that said single aromatic ring is directly covalently attached to one of the double bonded carbons of the B functional group or to a fused aromatic ring containing two such double bonded carbons of the B-functional group, and one A-functional group of one monomer is capable of reaction under cycloaddition reaction conditions with the B-functional group of a second monomer to thereby form a polymer.
1. A monomer corresponding to the formula:
wherein L is —O—, —S—, —N═N—, —(CO)—, —(SO 2 )—, or —O(CO)—;
Z is independently in each occurrence hydrogen, halogen, an unsubstituted or inertly substituted aromatic group, an unsubstituted or inertly substituted alkyl group, or two adjacent Z groups together with the carbons to which they are attached form a fused aromatic ring, and in one occurrence, Z is
wherein,
R 1 is independently each occurrence selected from the group consisting of hydrogen, halo, C 1-4 alkyl, C 6-60 aryl, and C 7-60 inertly substituted aryl groups; and
R 2 is independently each occurrence selected from the group consisting of hydrogen, C 1-4 alkyl, C 6-60 aryl, and C 7-60 inertly substituted aryl groups.
2. A monomer according to claim 1 which is a 2- or 3-di(arylethynyl)aryl-substituted cyclopentadienone compound.
3. A monomer according to claim 2 represented by the formula:
wherein R3 is C 6-20 aryl or inertly substituted aryl.
4. A monomer according to claim 3 where in R3 is phenyl, biphenyl, p-phenoxyphenyl or naphthyl.
5. A monomer comprising a single aromatic ring that has two acetylenic groups attached to it, and said single aromatic ring being directly, covalently attached to a 2,4-cyclopentadienone or benz-2,4-cyclopentadienone ring structure, characterized in that the cyclopentadienone of one monomer is capable of reacting under cycloaddition reaction conditions with an acetylene group of a second monomer, thereby resulting in formation of an aromatic ring.
6. A spin-coatable, curable composition comprising a monomer according to claim 1 , an optional solvent, and an optional pore forming material.
7. A spin-coatable, curable composition comprising a monomer according to claim 5 , an optional solvent, and an optional pore forming material.
8. A method of forming an insulating film on an electrical device comprising coating the device with a composition according to claim 6 , removing the optional solvent, curing the monomer, and optionally removing the optional pore forming material.
9. A method of forming an insulating film on an electrical device comprising coating the device with a composition according to claim 7 , removing the optional solvent, curing the monomer, and optionally removing the optional pore forming material.
10. An electrical device comprising an insulating film prepared according to claim 8 .
11. An electrical device comprising an insulating film prepared according to claim 9 .