Interlayer for electronic devices

Patent metadata

Field	Value
Publication number	US-9583713-B2
Application number	US-201113223784-A
Country	US
Kind code	B2
Filing date	Sep 1, 2011
Priority date	Sep 2, 2010
Publication date	Feb 28, 2017
Grant date	Feb 28, 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. An interlayer that is in direct contact with a dielectric layer in an organic electronic device, said interlayer consisting essentially of a polycycloolefinic polymer, or a polymer composition containing a polycycloolefinic polymer, said polycycloolefinic polymer comprising a first type of repeating unit in accordance with formula I:

wherein Z is selected from —CH 2 —, —CH 2 —CH 2 — or —O—, m is an integer from 0 to 5, each of R 1 , R 2 , R 3 and R 4 are independently selected from H, a C 1 to C 25 hydrocarbyl, a C 1 to C 25 halohydrocarbyl or a C 1 to C 25 perhalocarbyl group or one of R 1 , R 2 , R 3 and R 4 has a pendant crosslinkable group and the other R 1 , R 2 , R 3 and R 4 are defined above, and

the dielectric layer comprises a fluoropolymer.

2. The interlayer of claim 1 , wherein m is 0 or 1.

3. The interlayer of claim 1 , wherein one of R 1 , R 2 , R 3 and R 4 has a pendant crosslinkable group.

4. The interlayer of claim 3 , wherein the pendant crosslinkable group is a latent crosslinkable group.

5. The interlayer of claim 3 , wherein the pendant crosslinkable group is a maleimide, a 3-monoalkylmaleimide, a 3,4-dialkylmaleimide, an epoxy, a vinyl, an acetyl, an indenyl, a cinnamate or a coumarin group, or the pendant crosslinkable group comprises a substituted or unsubstituted maleimide portion, an epoxide portion, a vinyl portion, a cinnamate portion or a coumarin portion.

6. The interlayer of claim 3 , wherein the first type of repeating unit having a pendant crosslinkable group is derived from any one of the following monomers:

where n is an integer from 1 to 8, Q 1 and Q 2 are each independently of one another —H or —CH 3 , and R′ is —H or —OCH 3 .

7. The interlayer of claim 3 , wherein the polycycloolefinic polymer comprises a second type of repeating unit, such second type being distinct from the first type.

8. The interlayer of claim 1 , wherein the polycycloolefinic polymer further comprises one or more types of repeating units in accordance with formula II

wherein Z is selected from —CH 2 —, —CH 2 —CH 2 — or —O—, m is an integer from 0 to 5, each of R 5 , R 6 , R 7 and R 8 are independently selected from H, a C 1 to C 25 hydrocarbyl, a C 1 to C 25 halohydrocarbyl or a C 1 to C 25 perhalocarbyl group, and wherein the repeating units of formula II are distinct from the repeating units of formula I.

9. The interlayer of claim 1 , wherein the polycycloolefinic polymer comprises two, three or more than three different types of repeating units in accordance with formula I or II

wherein Z is selected from —CH 2 —, —CH 2 —CH 2 — or —O—, in is an integer from 0 to 5, each of R 1 , R 2 , R 3 and R 4 and R 5 , R 6 , R 7 and R 5 are independently selected from H, a C 1 to C 25 hydrocarbyl, a C 1 to C 25 halohydrocarbyl or a C 1 to C 25 perhalocarbyl group, and wherein the repeating units of formula I are distinct from the repeating units of formula II.

10. The interlayer of claim 1 , wherein the polymer composition comprises a blend of a first polycycloolefinic polymer and a second polycycloolefinic polymer.

11. The interlayer of claim 10 , wherein the polymer composition is a blend of a first polycycloolefinic polymer having one or more types of repeating units of formula I, and a second polycycloolefinic polymer having one or more types of repeating units of formula II

wherein Z is selected from —CH 2 —, —CH 2 —CH 2 — or —O—, m is an integer from 0 to 5, each of R 1 , R 2 , R 3 and R 4 and R 5 , R 6 , R 7 and R 8 are independently selected from H, a C 1 to C 25 hydrocarbyl, a C 1 to C 25 halohydrocarbyl or a C 1 to C 25 perhalocarbyl group, and wherein the repeating units of formula I are distinct from the repeating units of formula II.

12. The interlayer of claim 1 , wherein the polymer composition further comprises one or more of a solvent, a crosslinking agent, an optional reactive solvent, stabilizer, a UV sensitizer and a thermal sensitizer.

13. The interlayer of claim 1 , wherein the polymer or polymer composition contains one or more repeating units having a crosslinkable group, and the interlayer further comprises an adhesion promoter which is a 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 polymer or polymer composition.

14. The interlayer of claim 13 , 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.

15. The interlayer of claim 14 , 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 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.

16. The interlayer of claim 14 , wherein the crosslinkable group of the adhesion promoter is selected from 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.

17. The interlayer of claim 13 , wherein the adhesion promoter is a compound having the following structure

where SiR 12 R 13 R 14 is as defined in claim 15 , A′ is as defined in claim 16 , and R 10 and R 11 are each independently H or a C 1 -C 6 alkyl group.

18. The interlayer of claim 1 , wherein the polymer or polymer composition contains one or more repeating units having a crosslinkable group, and the interlayer further comprises a crosslinker which is a compound comprising two or more crosslinkable functional groups that are capable of reacting with the crosslinkable group of the said repeating unit of the polymer or polymer composition.

19. The interlayer of claim 18 , wherein the crosslinker is a compound of formula IV1 or IV2
P—X—P  IV1

H 4-m C(A″p-P) m   IV2

where X is A″-X′-A″, X′ is, O, S, NH, or a single bond, A″ is a single covalent bond or a connecting, spacer or bridging group, P is a crosslinkable group, and m is 2, 3 or 4.

20. The interlayer of claim 19 , wherein the crosslinkable group of the crosslinker is selected from 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

Assignees

• Mueller David Christoph
• Miskiewicz Pawel
• Cull Toby
• Wierzchowiec Piotr
• Bell Andrew
• Elce Edmund
• Rhodes Larry F
• Fujita Kazuyoshi
• Ng Hendra
• Kandanarachchi Pramod
• Smith Steven
• Merck Patent Gmbh
• Promerus Llc

Inventors

• Mueller 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

• Y10T428/31938

  Polymer of monoethylenically unsaturated hydrocarbon · CPC title

• H01L51/0545

  Electricity · mapped topic

• H01L51/0035

  Electricity · mapped topic