Electronic devices comprising structured organic films

• US 9,097,995 B2
• Filed: 03/03/2010
• Issued: 08/04/2015
• Est. Priority Date: 03/04/2009
• Status: Expired due to Fees

• Current Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Original Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Inventors: Heuft, Matthew A., Cote, Adrien
• Primary Examiner(s): YAMNITZKY, MARIE ROSE
• Application Number:
  US12/716,571
• Publication Number:
  US 20100224867A1
• Time in Patent Office: 1,980 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: B82Y 10/00 Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: C09B 23/12 the polymethine chain being branched "branched" means that the substituent on the polymethine chain forms a new conjugated system, e.g. most trinuclear cyanine dyes
• CPC Class Codes: C09B 23/148 Stilbene dyes containing the moiety -C6H5-CH=CH-C6H5 stilbene azo dyes C09B29/00
• CPC Class Codes: C09B 23/164 containing one nitrogen atom
• CPC Class Codes: C09B 26/02 Hydrazone dyes hydrazone-azo dyes C09B56/18
• CPC Class Codes: C09B 5/62 Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09B 57/008 Triarylamine dyes containing no other chromophores
• CPC Class Codes: C09B 69/109 containing other specific dyes
• CPC Class Codes: G03G 15/75 Details relating to xerographic drum, band or plate, e.g. replacing, testing electrographic recording members per se G03G5/00
• CPC Class Codes: G03G 2215/00957 Compositions
• CPC Class Codes: G03G 5/0592 Macromolecular compounds characterised by their structure or by their chemical properties, e.g. block polymers, reticulated polymers, molecular weight, acidity
• CPC Class Codes: G03G 5/0596 Macromolecular compounds characterised by their physical properties
• CPC Class Codes: G03G 5/0618 containing oxygen and nitrogen
• CPC Class Codes: G03G 5/14791 Macromolecular compounds characterised by their structure, e.g. block polymers, reticulated polymers, or by their chemical properties, e.g. by molecular weight or acidity
• CPC Class Codes: G03G 5/14795 Macromolecular compounds characterised by their physical properties
• CPC Class Codes: H10K 10/471 the gate dielectric comprising only organic materials
• CPC Class Codes: H10K 10/484 characterised by the channel regions
• CPC Class Codes: H10K 10/701 Organic molecular electronic devices
• CPC Class Codes: H10K 50/11 : characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/115 : comprising active inorganic nanostructures, e.g. luminescent quantum dots
• CPC Class Codes: H10K 50/12 : comprising dopants
• CPC Class Codes: H10K 50/805 : Electrodes
• CPC Class Codes: H10K 71/10 : Deposition of organic active material
• CPC Class Codes: H10K 71/12 : using liquid deposition, e.g. spin coating
• CPC Class Codes: H10K 71/15 : characterised by the solvent used
• CPC Class Codes: H10K 71/20 : Changing the shape of the active layer in the devices, e.g. patterning
• CPC Class Codes: H10K 71/30 : Doping active layers, e.g. electron transporting layers
• CPC Class Codes: H10K 71/40 : Thermal treatment, e.g. annealing in the presence of a solvent vapour
• CPC Class Codes: H10K 71/80 : using temporary substrates
• CPC Class Codes: H10K 85/10 : Organic polymers or oligomers
• CPC Class Codes: H10K 85/20 : Carbon compounds, e.g. carbon nanotubes or fullerenes
• CPC Class Codes: H10K 85/30 : Coordination compounds
• CPC Class Codes: H10K 85/60 : Organic compounds having low molecular weight H10K85/10 - H10K85/50 take precedence
• CPC Class Codes: H10K 85/761 : Biomolecules or bio-macromolecules, e.g. proteins, chlorophyl, lipids or enzymes
• CPC Class Codes: Y10T 428/26 : Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
• CPC Class Codes: Y10T 428/261 : In terms of molecular thickness or light wave length
• CPC Class Codes: Y10T 428/31504 : Composite [nonstructural laminate]

Abstract

An electronic device comprising a structured organic film with an added functionality comprising a plurality of segments and a plurality of linkers arranged as a covalent organic framework, wherein the structured organic film may be a multi-segment thick structured organic film.

Claims

1. An electronic device comprising:

a structured organic film (SOF) comprising a plurality of segments including at least a first segment type, a plurality of linkers including at least a first linker type arranged as a covalent organic framework (COF), wherein

the first linker type is selected from the group consisting of a single atom linker, a single covalent bond linker, an ester linker, a ketone linker, an ether linker, a carbonate linker, an amide linker, an amine linker, an imine linker, and a urethane linker,

each segment type of the plurality of segments is composed of carbon and at least one atom that is not carbon, wherein the at least one atom that is not carbon is an atom of an element selected from the group consisting of hydrogen, nitrogen, oxygen, phosphorous, selenium, fluorine, boron, and sulfur, and

the SOF is a substantially defect-free film having less than 10 pinholes, pores or gaps greater than about 250 nanometers in diameter per cm².

2. The electronic device of claim 1, wherein the electronic device is selected from the group consisting of radio frequency identification tags, photoreceptors, organic light emitting diodes, and thin film transistors.

6. The electronic device of claim 1, wherein the SOF is a composite SOF comprising secondary components and/or additives.

7. The electronic device of claim 1, wherein the SOF has an added functionality selected from the group consisting of a hydrophobic added functionality, a superhydrophobic added functionality, a hydrophilic added functionality, a lipophobic added functionality, a lipophilic added functionality, a photochromic added functionality and an electroactive added functionality.

8. The electronic device of claim 7, wherein the added functionality of the SOF arises from an inclined property of the segments of the SOF.

9. The electronic device of claim 7, wherein the added functionality of the SOF does not arise from an inclined property of the segments of the SOF.

10. The electronic device of claim 1, wherein the SOF has a thickness of from about 20 nm to about 5 mm.

11. The electronic device of claim 1, wherein the first linker type is the single atom linker, the single covalent bond linker, the ester linker, the ketone linker, the ether linker, or the carbonate linker.

13. The electronic device of claim 1, wherein the first linker type is the ester linker, the ketone linker, the ether linker, or the carbonate linker.

15. The electronic device of claim 1, wherein the first linker type is the ether linker.

17. The electronic device of claim 1, wherein the SOF further comprises a second linker type having a structure that is different from the first linker type.

19. The electronic device of claim 1, wherein the SOF possesses thermal stability at temperatures higher than 400°

C.

3. An electronic device comprising:

a structured organic film (SOF) comprising a plurality of segments including at least a first segment type, a plurality of linkers including at least a first linker type arranged as a covalent organic framework (COF), wherein

the electronic device is a electrophotographic imaging member, the electrophotographic imaging member comprising;

a supporting substrate, an electrically conductive ground plane, a charge blocking layer, a charge generating layer, a charge transport layer, an overcoat layer, and a ground strip,

the first linker type is selected from the group consisting of a single atom linker, a single covalent bond linker, an ester linker, a ketone linker, an ether linker, a carbonate linker, an amide linker, an amine linker, an imine linker, and a urethane linker,

each segment type of the plurality of segments is composed of carbon and at least one atom that is not carbon, wherein the at least one atom that is not carbon is an atom of an element selected from the group consisting of hydrogen, nitrogen, oxygen, phosphorous, selenium, fluorine, boron, and sulfur, and

the SOF is a substantially defect-free film having less than 10 pinholes, pores or gaps greater than about 250 nanometers in diameter per cm², and a thickness of between 1 and 15 microns.

4. The electronic device of claim 3, wherein the charge transport layer or the overcoat layer comprises the SOF.

5. The electronic device of claim 4, wherein the SOF has an electroactive added functionality.

12. The electronic device of claim 3, wherein the first linker type is the single atom linker, the single covalent bond linker, the ester linker, the ketone linker, the ether linker, or the carbonate linker.

14. The electronic device of claim 3, wherein the first linker type is the ester linker, the ketone linker, the ether linker, or the carbonate linker.

16. The electronic device of claim 3, wherein the first linker type is the ether linker.

18. The electronic device of claim 3, wherein the SOF further comprises a second linker type having a structure that is different from the first linker type.

20. An electronic device comprising:

a structured organic film (SOF) comprising

a plurality of segments consisting of a segment composed of carbon and at least one atom that is not carbon, wherein the at least one atom that is not carbon is an atom of an element selected from the group consisting of hydrogen, nitrogen, oxygen, phosphorous, selenium, fluorine, boron, and sulfur, and

a plurality of linkers including at least a first linker type, where the plurality of segments and the plurality of linkers are arranged as a covalent organic framework (COF), wherein

the first linker type is selected from the group consisting of a single atom linker, a single covalent bond linker, an ester linker, a ketone linker, an ether linker, a carbonate linker, an amide linker, an amine linker, an imine linker, and a urethane linker, and

the SOF is a substantially defect-free film having less than 10 pinholes, pores or gaps greater than about 250 nanometers in diameter per cm².