Electronic device using organic thin film, and electronic apparatus containing the same

Patent metadata

Field	Value
Publication number	US-9825232-B2
Application number	US-201314767032-A
Country	US
Kind code	B2
Filing date	Aug 21, 2013
Priority date	Feb 12, 2013
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

The present invention provides a high-performance, highly homogeneous, highly stable electronic device by forming an extremely uniform interface between an insulator and an organic semiconductor, as well as an electronic apparatus using the same. The present invention relates to an electronic device which contains, as a component, an organic thin film in which a geometric two-dimensional arrangement is formed regularly by interdigitating skeletal structures of a positive three-pronged shape of triptycene and by adding a first molecule extending out of one plane of a two-dimensional molecular structure of the triptycene skeletal structure. The invention also relates to an electronic apparatus and the like which contains the electronic device in the interior of the electronic apparatus.

First claim

The invention claimed is:

1. An electronic device comprising, as a component:
an organic thin film comprising a Janus-type triptycene derivative represented by the following Formula [I];

(in Formula [I], three R 1 's are an identical group, R 1 represents a divalent saturated or unsaturated hydrocarbon group having from 2 to 60 carbon atoms, the hydrocarbon group may optionally have one or more substituents, and one or more carbon atoms in the hydrocarbon group may be optionally substituted with oxygen atom, sulfur atom, silicon atom, or —NR 5 — (here, R 5 represents a hydrogen atom, an alkyl group having from 1 to 10 carbon atoms, or an aryl group having from 6 to 30 carbon atoms),
three R 2 's are the same as or different from one another and each independently represent a group different from a group —X—R 1 —Z, and R 2 represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an amino group, a mono alkyl-substituted amino group, a dialkyl-substituted amino group, an alkyl group which has from 1 to 10 carbon atoms and may optionally have one or more substituents, an alkenyl group which has from 2 to 10 carbon atoms and may optionally have one or more substituents, an alkynyl group which has from 2 to 10 carbon atoms and may optionally have one or more substituents, an alkoxy group which has from 1 to 10 carbon atoms and may optionally have one or more substituents, an alkylthio group which has from 1 to 10 carbon atoms and may optionally have one or more substituents, a formyl group, an alkylcarbonyl group which has from 1 to 10 carbon atoms and may optionally have one or more substituents, an alkoxycarbonyl group which has from 1 to 10 carbon atoms and may optionally have one or more substituents, an alkylcarbonyloxy group which has from 1 to 10 carbon atoms and may optionally have one or more substituents, an aryl group which has from 6 to 30 carbon atoms and may optionally have one or more substituents, or a 5- to 8-membered heteroaryl group which has from 1 to 5 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and from 2 to 10 carbon atoms and may optionally have one or more substituents,
three X's are an identical group, and X represents a linker group consisting of a divalent atomic group composed of from 1 to 5 atoms selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, carbon atom, and silicon atom, and one or more hydrogen atoms if necessary, and
three Z's are an identical group, and Z represents a hydrogen atom, a group capable of being bonded to or adsorbed on a surface of a solid substrate, or an end group consisting of a monovalent atomic group composed of from 1 to 15 atoms selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, carbon atom, phosphorus atom, halogen atom, and silicon atom, and one or more hydrogen atoms if necessary).

2. The electronic device according to claim 1 , wherein the electronic device is a transistor, a capacitor, a diode, a thyristor, an electroluminescent device, a sensor, or a memory.

3. The electronic device according to claim 2 , wherein the electronic device is a capacitor.

4. The electronic device according to claim 3 , wherein the capacitor is a capacitor having a dielectric layer comprising a first dielectric composed of the organic thin film between electrodes.

5. The electronic device according to claim 4 , wherein the dielectric layer further comprises a second dielectric.

6. The electronic device according to claim 5 , wherein the second dielectric is an organic dielectric.

7. The electronic device according to claim 5 , wherein the organic thin film and the second dielectric are in a layered structure.

8. The electronic device according to claim 1 , wherein the electronic device is a thin film transistor.

9. The electronic device according to claim 8 , wherein the thin film transistor is an organic thin film transistor including a gate electrode, a source electrode, a drain electrode, and a gate insulating layer on a substrate.

10. The electronic device according to claim 9 , wherein the gate insulating layer comprises an insulating material and the organic thin film.

11. The electronic device according to claim 10 , wherein the gate insulating layer comprises a layered body of the insulating material and the organic thin film.

12. The electronic device according to claim 10 , wherein the insulating material of the gate insulating layer is an organic insulating material.

13. The electronic device according to claim 9 , wherein the thin film transistor further includes a channel layer composed of a semiconductor.

14. The electronic device according to claim 13 , wherein the channel layer is an organic semiconductor layer.

15. The electronic device according to claim 14 , wherein a boundary portion between the gate insulating layer and the organic semiconductor layer in the thin film transistor includes the organic thin film.

16. The electronic device according to claim 15 , wherein the gate insulating layer, the organic thin film and the organic semiconductor layer are in a layered structure.

17. The electronic device according to claim 15 , wherein the three groups —X—R 1 —Z are oriented on the gate insulating layer side and the three R 2 's are oriented on the organic semiconductor layer side.

18. The electronic device according to claim 13 , wherein the organic thin film and the semiconductor of the channel layer are layered.

19. The electronic device according to claim 13 , wherein the source electrode and/or the drain electrode of the thin film transistor is formed between the organic thin film and the channel layer.

20. The electronic device according to claim 19 , wherein the channel layer is an organic semiconductor layer.

21. A circuit board comprising:
the electronic device according to claim 1 in an electronic circuit.

22. An electronic apparatus comprising:
the electronic device according to claim 1 in the interior thereof.

23. The electronic apparatus according to claim 22 , being an electronic paper, an organic EL display, or a liquid crystal display.

24. An electronic device material comprising an organic thin film comprising a Janus-type triptycene derivative represented by the following Formula [I];

(in Formula [I], three R 1 's are an identical group, R 1 represents a divalent saturated or unsaturated hydrocarbon group having from 2 to 60 carbon atoms, the hydrocarbon group may optionally have one or more substituents, and one or more carbon atoms in the hydrocarbon group may be optionally substituted with oxygen atom, sulfur atom, silicon atom, or —NR 5 — (here, R 5 represents a hydrogen atom, an alkyl group having from 1 to 10 carbon atoms, or an aryl group having from 6 to 30 carbon atoms),
three R 2 's are the same as or different from one another and each independently represent a group different from a group —X—R 1 —Z, and R 2 represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, an amino group, a mono alkyl-substituted amino group, a dialkyl-substituted amino group, an alkyl group which has from 1 to 10 carbon atoms and may optionally have one or more

Assignees

• Japan Science & Tech Agency

Inventors

• Fukushima Takanori
• Shoji Yoshiaki
• Ishiwari Fumitaka
• Sekitani Tsuyoshi
• Someya Takao

Classifications

• C07C43/215

  having unsaturation outside the six-membered aromatic rings · CPC title

• C07C43/225

  containing halogen · CPC title

• C07C2603/86

  containing four rings · CPC title

• C07C2603/90

  containing more than four rings · CPC title

• C07C43/21

  containing rings other than six-membered aromatic rings · CPC title