Interlayer for electronic devices

Patent metadata

Field	Value
Publication number	US-9647213-B2
Application number	US-201514823037-A
Country	US
Kind code	B2
Filing date	Aug 11, 2015
Priority date	Sep 2, 2010
Publication date	May 9, 2017
Grant date	May 9, 2017

Abstract

Embodiments in accordance with the present invention provide for the use of polycycloolefins in electronic devices and more specifically to the use of such polycycloolefins as interlayers applied to fluoropolymer layers used in the fabrication of electronic devices, the electronic devices that encompass such polycycloolefin interlayers and processes for preparing such polycycloolefin interlayers and electronic devices.

First claim

We claim:

1. A polymer composition comprising
A) a polycycloolefinic polymer that contains one or more repeating units having a crosslinkable group,
B) an adhesion promoter compound comprising a surface-active functional group and a crosslinkable functional group that is capable of reacting with the said crosslinkable group of the repeating unit of the polycycloolefinic polymer
wherein the polycycloolefinic polymer comprises one or more repeat units of the formula (I) is formed from a norbornene-type monomer by addition polymerization,

wherein
Z is —CH 2 —, —CH 2 —CH 2 — or —O—,
m is an integer from 0 to 5,
R 1 , R 2 , R 3 and R 4 are the same or different and are hydrogen, C 1 -C 25 hydrocarbyls, C 1 -C 25 halohydrocarbyls or C 1 -C 25 perhalohydrocarbyl;
or where one or more of the carbons atoms in the hydrocarbyl, halohydrocarbyl or perhalohydrocarbyl is replaced by a heteroatom containing moiety selected independently from O, N, P, or Si,
with the proviso that at least one R 1 , R 2 , R 3 and R 4 has a pendent crosslinkable group.

2. The polymer composition of claim 1 , wherein the adhesion promoter is a compound of formula III
G-A′-P  III

wherein G is a surface-active group, A′ is a spacer group or a single bond, and P is a crosslinkable group.

3. The polymer composition of claim 2 , wherein the surface active group of the adhesion promoter is of formula —SiR 12 R 13 R 14 , or of formula —NH—SiR 12 R 13 R 14 , wherein R 12 , R 13 and R 14 are identical or different and are halogen, C 1 -C 12 -alkoxy, C 1 -C 12 -alkylamino, optionally substituted C 5 -C 20 -aryloxy or optionally substituted C 2 -C 20 -heteroaryloxy, and wherein one or two of R 12 , R 13 and R 14 may also denote C 1 -C 12 -alkyl, optionally substituted C 5 -C 20 -aryl and optionally substituted C 2 -C 20 -heteroaryl.

4. The polymer composition of claim 3 , wherein the crosslinkable group of the adhesion promoter is a maleimide, a 3-monoalkyl-maleimide, a 3,4-dialkylmaleimide, an epoxy, a vinyl, an acetyl, an indenyl, a cinnamate or a coumarin group, or the crosslinkable group comprises a substituted or unsubstituted maleimide portion, an epoxide portion, a vinyl portion, a cinnamate portion or a coumarin portion.

5. The polymer composition of claim 1 , wherein the surface active group of the adhesion promoter is of formula —SiR 12 R 13 R 14 , or of formula —NH—SiR 12 R 13 R 14 , wherein R 12 , R 13 and R 14 are identical or different and are halogen, C 1 -C 12 -alkoxy, C 1 -C 12 -alkylamino, optionally substituted C 5 -C 20 -aryloxy or optionally substituted C 2 -C 20 -heteroaryloxy, and wherein one or two of R 12 , R 13 and R 14 may also denote C 1 -C 12 -alkyl, optionally substituted C 5 -C 20 -aryl and optionally substituted C 2 -C 20 -heteroaryl.

6. The polymer composition of claim 1 , wherein the crosslinkable group of the adhesion promoter is a maleimide, a 3-monoalkyl-maleimide a 3,4-dialkylmaleimide, an epoxy, a vinyl, an acetyl, an indenyl, a cinnamate or a coumarin group, or the crosslinkable group comprises a substituted or unsubstituted maleimide portion, an epoxide portion, a vinyl portion, a cinnamate portion or a coumarin portion.

7. The polymer composition of claim 2 , wherein the adhesion promoter is a compound having the following structure

wherein
R 12 , R 13 and R 14 are selected from halogen, silazane, C 1 -C 12 -alkoxy, C 1 -C 12 -alkylamino, optionally substituted C 5 -C 20 -aryloxy and optionally substituted C 2 -C 20 -heteroaryloxy, and wherein one or two of R 12 , R 13 and R 14 may also denote C 1 -C 12 -alkyl, optionally substituted C 5 -C 20 -aryl and optionally substituted C 2 -C 20 -heteroaryl,
A′ is a spacer group or a single bond, and
R 10 and R 11 are each independently H or a C 1 -C 6 alkyl group.

8. The polymer composition of claim 7 , wherein A′ is a C 1 to C 30 alkylenes or branched C 3 to C 30 alkylenes or cyclic C 5 to C 30 alkylenes, each being unsubstituted or mono- or poly-substituted by F, Cl, Br, I or CN and optionally can have one or more non-adjacent CH 2 groups replaced, in each case independently from one another, by —O—, —S—, —NH—, —NR 18 —, —SiR 18 R 19 —, —C(O)—, —C(O)O—, —OC(O)—, —OC(O)—O—, —S—C(O)—, —C(O)—S—, —CH═CH— or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another, and R 18 and R 19 are independently of each other H, methyl, ethyl or a C 3 to C 12 linear or branched alkyl.

9. The polymer composition of claim 7 , wherein A′ is —CH 2 CH 2 —S—CH 2 CH 2 —, —CH 2 CH 2 —NH—CH 2 CH 2 — or —(SiR 18 R 19 —O) p —, with p being an integer from 2 to 12.

10. The polymer composition of claim 1 , where the polycycloolefinic polymer comprises a first type of repeating unit selected from fluorinated repeating units and a second type of repeating unit selected from crosslinkable repeating units.

11. The polymer composition of claim 10 , wherein said first type of repeating unit is formed from a monomer selected from NBCH 2 C 6 F 5 , NBC 6 F 5 , NBCH 2 C 6 F 2 , NBCH 2 C 6 H 4 CF 3 or NBalkylC 6 F 5 , and second type of repeating unit is formed from a monomer selected from the group consisting of

12. The polymer composition as claimed in claim 1 , wherein the polymer has one or more the repeating units of the formula (I) and one or more repeating units of the formula (II)

wherein
Z is —CH 2 —, —CH 2 —CH 2 — or —O—,
m is an integer from 0 to 5,
R 5 , R 6 , R 7 and R 8 are the same or different and are independently selected from hydrogen, C 1 -C 25 hydrocarbyls, C 1 -C 25 halohydrocarbyls or C 1 -C 25 perhalohydrocarbyl; or where one or more of the carbons atoms in the hydrocarbyl, halohydrocarbyl or perhalohydrocarbyl is replaced by a heteroatom containing moiety selected independently from O, N, P, or Si,
the repeating units of formula (I) being distinct from the repeating units of formula (II).

13. The polymer composition of claim 12 , wherein the repeating units of the formula (I) or (II) are formed from monomers selected from the group consisting of formula 1-54:

14. The polymer composition as claimed in claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are identical or different and are an hydrogen, C 1 -C 25 alkyl, a C 2 -C 24 alkenyl, a C 2 -C 24 alkynyl, a C 5 -C 25 cycloalkyl, a C 6 -C 24 aryl or a C 7 -C 24 aralkyl, or where at least one of the hydrogen atom in the alkyl, alkenyl, alkynyl, cycloalkyl, aryl or aralkyl is replaced by a halogen atom, or ether, epoxy, glycidyl ether, a

Assignees

• Merck Patent Gmbh
• Promerus Llc

Inventors

• Müller David Christoph
• Miskiewicz Pawel
• Cull Toby
• Wierzchowiec Piotr
• Bell Andrew
• Elce Edmund
• Rhodes Larry F
• Fujita Kazuyoshi
• Ng Hendra
• Kandanarachchi Pramod
• Smith Steven

Classifications

• C08L45/00 Primary

  Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers (of cyclic anhydrides or imides C08L35/00; of cyclic esters of polyfunctional acids C08L31/00) · CPC title

• C08F232/00 Primary

  Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system · CPC title

• H01L51/0043 Primary

  Electricity · mapped topic

• C08L2203/20

  use in electrical or conductive gadgets · CPC title

• H01L51/0529

  Electricity · mapped topic