Method of manufacturing organic oriented film and method of manufacturing electronic device

• US 5,546,889 A
• Filed: 09/30/1994
• Issued: 08/20/1996
• Est. Priority Date: 10/06/1993
• Status: Expired due to Term

• Current Assignee: Matsushita Electric Industrial Company Limited (Panasonic Holdings Corporation)
• Original Assignee: Matsushita Electric Industrial Company Limited (Panasonic Holdings Corporation)
• Inventors: Yang, Yang, Wakita, Katsuya, Hotta, Shu, Sonoda, Nobuo
• Primary Examiner(s): KUNEMUND, ROBERT M
• Application Number:
  US08/315,354
• Time in Patent Office: 690 Days
• Field of Search: 117/925, 117/927, 117/84
• US Class Current: 117/84
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C30B 11/00 Single-crystal growth by normal freezing or freezing under temperature gradient, e.g. Bridgman-Stockbarger method C30B13/00, C30B15/00, C30B17/00, C30B19/00 take precedence; under a protective fluid C30B27/00
• CPC Class Codes: C30B 23/02 Epitaxial-layer growth
• CPC Class Codes: C30B 25/02 Epitaxial-layer growth
• CPC Class Codes: C30B 29/54 Organic compounds
• CPC Class Codes: H01B 1/127 comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
• CPC Class Codes: H01B 1/128 comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes
• CPC Class Codes: H01L 21/0212 the material being fluoro carbon compounds, e.g.(CFx) n, (CHxFy) n or polytetrafluoroethylene
• CPC Class Codes: H01L 21/02271 deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition H01L21/02266 takes precedence
• CPC Class Codes: H01L 21/3127 Layers comprising fluoro (hydro)carbon compounds, e.g. polytetrafluoroethylene
• CPC Class Codes: H10K 10/462 Insulated gate field-effect transistors [IGFETs]
• CPC Class Codes: H10K 10/466 Lateral bottom-gate IGFETs comprising only a single gate
• CPC Class Codes: H10K 10/474 the gate dielectric comprising a multilayered structure
• 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 71/191 characterised by provisions for the orientation or alignment of the layer to be deposited
• CPC Class Codes: H10K 85/113 Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
• CPC Class Codes: H10K 85/114 Poly-phenylenevinylene; Derivatives thereof
• CPC Class Codes: Y10S 428/91 Product with molecular orientation
• CPC Class Codes: Y10T 428/3154 Of fluorinated addition polymer from unsaturated monomers

Abstract

A method of manufacturing an organic electronic device having a substrate and a pair of electrodes facing each other, including the steps of forming a polytetrafluoroethylene oriented film on a substrate, and contacting an oligothiophene compound with the polytetrafluoroethylene oriented film to form an organic oriented film on the polytetrafluoroethylene oriented film between the pair of electrodes wherein the long axis of oligothiophene molecules is oriented to the orientation of the polytetrafluoroethylene oriented film and crystallized.

Claims

1. A method of manufacturing a conducting organic oriented film comprising the steps of

forming a polytetrafluoroethylene oriented film on a substrate, and

contacting an oligothiophene compound represented by Formula (1) with the polytetrafluoroethylene oriented film:

##STR5## wherein n represents an integer of 3 to 6, and R represents a hydrogen atom or an alkyl group having 1 to 2 carbon atoms.

2. The method of manufacturing a conducting organic oriented film according to claim 1, wherein the step of contacting said oligothiophene compound with said polytetrafluoroethylene oriented film is carried out using a gaseous-phase method or a casting method.

3. The method of manufacturing a conducting organic oriented film according to claim 1, wherein said polytetrafluoroethylene oriented film is heated when said oligothiophene compound is contacted with said polytetrafluoroethylene oriented film.

4. The method of manufacturing a conducting organic oriented film according to claim 1, wherein said oligothiophene compound has a polymerization degree between four and six.

5. The method of manufacturing a conducting organic oriented film according to claim 1, wherein the α

position at the ends of the oligothiophene molecules is substituted by a group selected from the group consisting of alkyl groups, alkylthio groups and trimethylsilyl group.

6. The method of manufacturing a conducting organic oriented film according to claim 5, wherein said alkyl group or alkylthio group has one or two carbon atoms.

7. A method of manufacturing an organic electronic device having a substrate and a pair of electrodes facing each other, comprising the steps of

forming a polytetrafluoroethylene oriented film on a substrate, and

contacting an oligothiophene compound with said polytetrafluoroethylene oriented film to form an organic oriented film on said polytetrafluoroethylene oriented film between said pair of electrodes wherein the long axis of oligothiophene molecules is oriented to the orientation of said polytetrafluoroethylene oriented film and crystallized.

8. The method of manufacturing an organic electronic device according to claim 7, wherein at least two oligothiophene compounds are contacted with said polytetrafluoroethylene oriented film.

9. The method of manufacturing an organic electronic device according to claim 7, wherein said oligothiophene compound has a polymerization degree between four and six.

10. The method of manufacturing an organic electronic device according to claim 7, wherein the α

position at the ends of the oligothiophene molecules is substituted by a group selected from the group consisting of alkyl groups, alkylthio groups and trimethylsilyl group.

11. The method of manufacturing an organic electronic device according to claim 10, wherein said alkyl group or alkylthio group has one or two carbon atoms.

12. The method of manufacturing an organic electronic device according to claim 7, wherein the step of contacting said oligothiophene compound with said polytetrafluoroethylene oriented film is carried out using a gaseous-phase method or a casting method.

13. The method of manufacturing an organic electronic device according to claim 12, wherein said polytetrafluoroethylene oriented film is heated when said oligothiophene compound is contacted with said polytetrafluoroethylene oriented film by said gaseous-phase method.

14. A method of manufacturing an organic electronic device having a substrate and a pair of electrodes facing each other, comprising the steps of

forming a polytetrafluoroethylene oriented film on a substrate, and

contacting a polyphenylene vinylene represented by Formula (2) or its derivative with said polytetrafluoroethylene oriented film to form an organic oriented film on said polytetrafluoroethylene oriented film between said pair of electrodes:

##STR6## wherein n represents an integer.

15. The method of manufacturing an organic electronic device according to claim 14, wherein said polyphenylene vinylene derivative is poly(2-methoxy, 5-(2'"'"'-ethylhexyloxy)-1,4-phenylene vinylene) represented by Formula (3):

##STR7## wherein n represents an integer.

16. The method of manufacturing an organic electronic device according to claim 14, wherein the step of contacting said polyphenylene vinylene or its derivative with said polytetrafluoroethylene oriented film is carried out using a casting method.