PHOTOCURABLE POLYMERIC DIELECTRICS AND METHODS OF PREPARATION AND USE THEREOF

• US 20110215334A1
• Filed: 11/20/2009
• Published: 09/08/2011
• Est. Priority Date: 11/24/2008
• Status: Active Grant

• Current Assignee: Flexterra, Inc.
• Original Assignee: BASF SE, Polyera Corporation
• Inventors: Zheng, Yan, Yan, He, Facchetti, Antonio, Breiner, Thomas, Quinn, Jordan, Koehler, Silke Annika, Newman, Christopher
• Granted Patent: US 8,937,301 B2
• Time in Patent Office: Days
• US Class Current: 257/66
• CPC Class Codes: B05D 3/06 by exposure to radiation B05D3/02 takes precedence ; plasma treatment B05D3/141
• CPC Class Codes: C08F 118/12 with unsaturated alcohols containing three or more carbon atoms
• CPC Class Codes: C08F 12/22 Oxygen
• CPC Class Codes: C08F 12/24 Phenols or alcohols
• CPC Class Codes: C08F 212/22 Oxygen
• CPC Class Codes: C08F 212/32 containing two or more rings
• CPC Class Codes: C08F 216/10 Carbocyclic compounds
• CPC Class Codes: C08F 220/14 Methyl esters , e.g. methyl (meth)acrylate
• CPC Class Codes: C08G 61/02 Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
• CPC Class Codes: C09D 125/18 Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
• CPC Class Codes: H01B 3/442 from aromatic vinyl compounds
• CPC Class Codes: H01B 3/447 from acrylic compounds
• CPC Class Codes: H10K 10/471 the gate dielectric comprising only organic materials
• CPC Class Codes: H10K 85/141 comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
• CPC Class Codes: H10K 85/151 Copolymers
• CPC Class Codes: H10K 85/6574 comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: Y10T 428/31938 Polymer of monoethylenically unsaturated hydrocarbon

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.

Claims

1-21. -21. (canceled)

22. A thin film transistor device, comprising:

a dielectric layer;

a semiconductor layer;

a gate electrode;

a source electrode; and

a drain electrode;

wherein the dielectric layer is disposed between the semiconductor layer and the gate electrode;

wherein the source electrode and the drain electrode are in contact with the semiconductor layer,

wherein the dielectric layer comprises a polymeric film, the polymeric film comprising a polymer comprising a repeating unit having a pendant group comprising an optionally substituted coumarin-6-yl moiety.

23. The device of claim 22, wherein the optionally substituted coumarin-6-yl moiety has a formula:

24. The device of claim 23, wherein R¹ and R² independently are selected from the group consisting of H, F, —

CN, and CF₃.

25. The device of claim 23, wherein R³, at each occurrence, is independently selected from the group consisting of a halogen, OH, —

CN, a C_1-6 alkyl group, a C_1-6 haloalkyl group, and a C_1-6 alkoxyl group.

26. The device of claim 22, wherein the polymer is selected from the group consisting of a vinyl polymer, a siloxane polymer, polymaleimide, polyethylene amine, and at least one copolymer thereof, and comprises a repeating unit having a pendant group comprising an optionally substituted coumarin-6-yl moiety.

27. The device of claim 22, wherein the polymer is a vinyl polymer selected from the group consisting of polystyrene, polyvinyl phenol, polyvinyl alcohol, polyvinyl acetate, polymethyl methacrylate, and at least one copolymer thereof, and comprises a repeating unit having a pendant group comprising an optionally substituted coumarin-6-yl moiety.

28. The device of claim 22, wherein the polymer comprises at least one repeating unit of a formula selected from the group consisting of:

29. The device of claim 22, wherein the polymer comprises at least one repeating unit of a formula selected from the group consisting of:

30. The device of claim 22, wherein the polymer has at least one selected from the group consisting of:

a dielectric constant between about 1.1 and about 5.0;

a glass transition temperature (T_g) between about 100°

C. and about 200°

C.;

a solubility of greater than about 0.1 mg/mL in a solvent selected from the group consisting of anisole, xylene, cyclopentanone, cyclohexane and cyclohexanone;

a maximum absorbance wavelength in the range of about 250 nm and about 500 nm; and

a molecular weight between about 10,000 Da and about 100,000 Da.

31. The device of claim 22, configured as a top-gate device structure and comprising an interlayer between the dielectric layer and the semiconductor layer.

32. A vinyl polymer, polymerized from one or more vinyl monomers, wherein at least one of the vinyl monomers is vinyl phenol or a derivative of the vinyl phenol, and the vinyl polymer comprises a repeating unit having a pendant group comprising an optionally substituted coumarin moiety.

33. The vinyl polymer of claim 32, wherein the optionally substituted coumarin moiety has a formula:

34. The vinyl polymer of claim 33, wherein at least one of the vinyl monomers has a formula:

35. The vinyl polymer of claim 32, wherein at least one of the vinyl monomers is an acrylate.

36. The vinyl polymer of claim 32, wherein the optionally substituted coumarin moiety is introduced after the one or more vinyl monomers are polymerized.

37. The vinyl polymer of claim 32, having a formula:

38. The vinyl polymer of claim 32, selected from the group consisting of:

39. The vinyl polymer of claim 32, selected from the group consisting of:

a dielectric constant between 1.1 and 5.0;

a glass transition temperature (T_g) between about 100°

C. and about 200°

C.;

a solubility of greater than about 0.1 mg/mL in a solvent selected from the group consisting of anisole, xylene, cyclopentanone, cyclohexane, and cyclohexanone;

a maximum absorbance wavelength in a range of about 250 nm and about 450 nm; and

a molecular weight between about 10,000 Da and about 100,000 Da.

40. A method of preparing a dielectric material, the method comprising:

preparing a solution comprising the vinyl polymer of claim 32;

depositing the solution onto a substrate to provide a coating; and

exposing the coating to radiation to induce crosslinking and create a crosslinked dielectric material.

41. A dielectric material, prepared by the method of claim 40, having a leakage current density of less than or about 1×

10<sup>−

8</sup> A/cm² at 2 MV/cm.