Arylcyclobutenes
View Patent ↗Arylclobutene-containing multi-functional monomers are useful in the preparation of arylcyclobutene-based polymer coatings. Compositions comprising one or more arylclobutene-containing multi-functional monomers and one or more oligomers comprising as polymerized units one or more arylcyclobutene monomer provide arylcyclobutene-based polymer coatings having reduced stress. Such compositions are useful in the manufacture of electronic devices.
1. A compound of the formula (1)
wherein each A is independently chosen from —CR 3 R 4 —O—, —C(═O)O—, and —C(═O)NH—; each B is independently chosen from —CR 3 R 4 — and —C(═O)—; each R is independently chosen from halo, cyano, hydroxy, carboxy, C 1-6 alkoxy, C 1-6 alkyl, C 1-6 haloalkyl, C 2-6 alkenyl, carboxy C 1-6 alkyl, —(C═O)—C 1-6 alkyl, —G—(C═O)—C 1-6 alkyl, —(C═O)—G—C 1-6 alkyl, —O—C 4-20 aryl, —(C═O)—C 4-20 aryl, —G—(C═O)—C 4-20 aryl, and —(C═O)—G—C 4-20 aryl; each of R 1 , R 2 , R 3 and R 4 is independently chosen from H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, and C 4-15 aryl; Z is an organic radical having 2 to 50 carbon atoms; G is O or N(R′) 2 ; each R′ is independently chosen from H, C 1-6 alkyl, C 4-10 aryl, and C 7-15 aralkyl; x is the number of R groups and is an integer of from 0 to 2; m is an integer of from 1 to 6; n is an integer of from 0 to 5; and m+n=3 to 6.
2. The compound of claim 1 wherein m=1 to 4.
3. The compound of claim 1 wherein n=0 to 3.
4. The compound of claim 1 wherein A is —CR 3 R 4 —O— or —C(═O)O—.
5. The compound of claim 1 wherein Z has one or more ether linkages, one or more hydroxyl moieties, or a combination of one or more ether linkages and one or more hydroxyl moieties.
6. The compound of claim 1 wherein each R 1 and R 2 is independently chosen from H, C 1-10 alkyl, and C 2-10 alkenyl.
7. The compound of claim 1 wherein B is —CR 3 R 4 —.
8. A polymer comprising as polymerized units one or more compounds of claim 1 .
9. A composition comprising one or more oligomers comprising as polymerized units one or more arylcyclobutene monomers, and one or more compounds of claim 1 .
10. The composition of claim 9 further comprising one or more organic solvents.
11. The composition of claim 9 wherein the one or more arylcyclobutene oligomers has the formula
wherein B 1 is an n-valent linking group; Ar is a polyvalent aryl group and the carbon atoms of the cyclobutene ring are bonded to adjacent carbon atoms on the same aromatic ring of Ar; m is an integer of 1 or more; n is an integer of 1 or more; and each R 10 is a monovalent group.
12. The composition of claim 9 further comprising one or more photoactive compounds.
13. A method of forming a film on a substrate comprising: providing a substrate; coating a layer of a composition of claim 9 on a surface of the substrate; and curing the coating.