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US 9,923,158 B2Granted
Photocurable polymeric dielectrics and methods of preparation and use thereof
AssigneesBASF SE, Flexterra, Inc.
InventorsJordan Quinn, He Yan, Yan Zheng, Christopher Newman, Silke Annika Koehler, Antonio Facchetti, Thomas Breiner
Life of this patent
Estimating the term…
Abstract
Disclosed are polymer-based dielectric compositions (e.g., formulations) and materials (e.g. films) and associated devices. The polymers generally include photocrosslinkable pendant groups; for example, the polymers can include one or more coumarin-containing pendant groups.
Claims6
A vinyl polymer, having a formula:
- wherein:
- Q is -(L″)p-L′″;
- L″, at each occurrence, independently is selected from the group consisting of —Y″—, —(Y″)m—O—, —Y″—Si(R4)2—, —O—Si(R4)2—, and a covalent bond;
- L′″ is linked to the coumarin moiety in the formula and is selected from the group consisting of —C(O)—, —C(O)—O—, —O—C(O)—, —C(O)—Y″′—O—, —O—Y″′—C(O)—, —C(O)—Y′″—NR4—, —NR4—Y′″—C(O)—, —O—S(O)k—, —O—Y′″—S(O)k—, and a covalent bond:
- Y″, at each occurrence, is selected from the group consisting of a divalent C1-6 alkyl group, a divalent C2-6 alkenyl group, and a divalent C6-14 aryl group, wherein each of the C1-6 alkyl group, the C2-6 alkenyl group, and the C6-14 aryl group is optionally substituted with 1-5R5 groups;
- Y″′ is selected from the group consisting of a divalent C1-6 alkyl group, a divalent C2-6 alkenyl group, and a divalent C6-14 aryl group, wherein each of the C1-6 alkyl group, the C2-6 alkenyl group, and the C6-14 aryl group is optionally substituted with 1-5R5 groups;
- k is 0, 1, or 2;
- m is 1, 2, 3, 4, 5, or 6;
- p is an integer in a range from 1 to 10
- W″ is selected from the group consisting of a) H, b) a halogen, c) a C1-20 alkyl group, d) a C2-20 alkenyl group, e) a C1-20 haloalkyl group, f) a C3-14 cycloalkyl group, g) a C6-14 aryl group, h) a 3 -14 membered cycloalkyl group, and i) a 5-14 membered heteroaryl group, wherein each of the C1-20 alkyl group, the C2-20 alkenyl group, the C1-20 haloalkyl group, the C3-14 cycloalkyl group, the C6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1 to 5 substituents independently selected from the group consisting of a halogen, —CN, an oxo group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a —C(O)—C1-6 alkyl group, a —C(O)—C1-6 haloalkyl group, and a —C(O)—O—C1-6 alkyl group;
- x, x′, x″, and y independently are a real number, wherein 0<x<1.0 ≦x′<1.0≦x″<1.0<y<1 , and x+x′+x″+y=1
- n is an integer in a range from 10 to 1,000;
- R1 and R2 are independently selected from the group consisting of a) H, b) halogen, c) —CN, d) —NO2, e) —OR4, f) —N(R4)2, g) —CHO, h) —C(O)R4, i) —C(O)OR4, j) —C(O)N(R4)2, k) a C1-20 alkyl group, l) a C2-20 alkenyl group, m) a C2-20 alkynyl group, n) a C1-20 alkoxy group, o) a C1-20 alkylthio group, p) a C1-20 haloalkyl group, q) a —Y—C3-14 cycloalkyl group, r) a —Y—C6-14 aryl group, s) a —Y-3-14 membered cycloheteroalkyl group, and t) a —Y-5-14membered heteroaryl group, wherein each of the C1-20 alkyl group, the C2-20 alkenyl group, the C2-20 alkynyl group, the Y—C3-14 cycloalkyl group, the Y—C6-14 aryl group, the Y-3 -14 membered cycloheteroalkyl group, and the Y-5-14 membered heteroaryl group is optionally substituted with 1-5 R5 groups;
- R4, at each occurrence, independently is selected from the group consisting of a) H, b) a C1-20 alkyl group, c) a C2-20 alkenyl group, d) a C2-20 alkynyl group, e) a C1-20 alkoxy group, f) a C1-20 alkylthio group, g) a C1-20 haloalkyl group, h) a —Y—C3-14 cycloalkyl group, i) a —Y—C6-14 aryl group, j) a —Y-3-14 membered cycloheteroalkyl group, and k) a —Y-5-14 membered heteroaryl group, wherein each of the C1-20 alkyl group, the C2-20 alkenyl group, the C2-20 alkynyl group, the Y—C3-14 cycloalkyl group, the Y—C6-14 aryl group, the Y-3-14membered cycloheteroalkyl group, and the Y-5-14 membered heteroaryl group is optionally substituted with 1-5 R5 groups;
- R5, at each occurrence, is independently selected from the group consisting of a) halogen, b) —CN, c) —NO2, d) —OH, e) —O—C6-14 aryl, f) —NH2, g) —NH—C1-10 alkyl, h) alkyl)2, —NH—C6-14 aryl, j) —N(C1-10 alkyl)-C6-14 aryl, k) —N(C6-14 aryl)2, l) —CHO, m) —C(O)—C1-10 alkyl, n) —C(O)—C6-14 aryl, o) —C(O)OH, p) —C(O)—OC1-10 alkyl, q) —C(O)—OC6-14 aryl, r) —C(O)NH2, s) —C(O)NH—C1-10 alkyl, t) —C(O)N(C1-10 alkyl)2, u) —C(O)NH—C6-14 aryl, v) —C(O)N(C1-10 alkyl)-C6-14 aryl, w) —C(O)N(C6-14 aryl)2, x) a C1-10 alkyl group, y) a C2-10 alkenyl group, z) a C2-10 alkynyl group, aa) a C1-10 alkoxy group, ab) a C1-10 alkylthio group, ac) a C1-10 haloalkyl group, ad) a —Y—C3-14 cycloalkyl group, ae) a —Y—C6-14 aryl group, af) a —Y-3-14 membered cycloheteroalkyl group, and ag) a —Y-5-14 membered heteroaryl group, wherein each of the C1-10 alkyl group, the C2-10 alkenyl group, the C2-10 alkynyl group, the Y—C3-14 cycloalkyl group, the Y—C6-14 aryl group, the Y-3-14 membered cycloheteroalkyl group, and the Y-5-14 membered heteroaryl group is optionally substituted with 1-5 substituents independently selected from the group consisting of a halogen, CN, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a —O—C1-6 haloalkyl group, a —C(O)—C1-6 alkyl group, a —C(O)—C1-6 haloalkyl group, and a —C(O)—O—C1-6 alkyl group, and
- wherein Y, at each occurrence, is a divalent C1-6 alkyl group, a divalent C2-6 alkenyl group, a divalent C2-6 alkenyl group, or a covalent bond.
13 more elements
A vinyl polymer, selected from the group consisting of:
- wherein n is an integer in a range from 10 to 1,000.
Dependencies are inferred from the claim text.