Organic thin film, and organic semiconductor device and organic transistor using same

Patent metadata

Field	Value
Publication number	US-10158087-B2
Application number	US-201414773053-A
Country	US
Kind code	B2
Filing date	Mar 6, 2014
Priority date	Mar 7, 2013
Publication date	Dec 18, 2018
Grant date	Dec 18, 2018

Abstract

The present invention provides an organic thin film and an organic transistor having high performance stability and mobility. Specifically, there are provided an organic thin film including a compound containing a charge transporting molecular unit A having a structure of an aromatic fused ring system and a unit B serving as a side chain, the compound having a bilayer structure; an organic semiconductor device including the organic thin film; and an organic transistor including the organic thin film used as an organic semiconductor layer.

First claim

The invention claimed is:

1. An organic thin film comprising: a compound, which is a liquid crystal compound, containing a charge transporting molecular unit A having a structure of an aromatic fused ring system represented by the general formula (1) and a side chain, wherein the film has a bilayer structure formed of the liquid crystal compound, indicating a bimolecular layer-like structure, in which two charge transporting molecular units A face each other to form a pair, thereby forming a paired layer such that peaks corresponding to a length of two molecules forming the paired layer are observed in X-ray structure analysis,

wherein the side chain is an optionally substituted alkyl group having 2 to 20 carbon atoms, an optionally substituted alkenyl group having 2 to 20 carbon atoms, an alkyloxy group having 2 to 20 carbon atoms, an alkylthio group having 2 to 20 carbon atoms, or a group represented by the general formula (2):
(CH 2 ) n —X—(CH 2 ) m —CH 3   (2)

wherein X represents S, O, or NH, m represents an integer of 0 to 17, and n represents an integer of 2 or more,
wherein the compound further contains a cyclic structure unit C linked to the charge transporting molecular unit,
wherein the compound exhibits a liquid crystal phase selected from the group consisting of SmB, SmBcrystal, SmI, SmF, SmG, SmE, SmJ, SmK, and SmH, and
wherein the number (NC) of number of rings in the cyclic structure unit C and the number (NA) of fused rings in the charge transporting molecular unit A satisfy the relationship: NA≥NC.

2. The organic thin film according to claim 1 , wherein the cyclic structure unit C is a unsubstituted aromatic hydrocarbon group, an aromatic hydrocarbon group substituted with a halogen or a lower alkyl group having 1 to 4 carbon atoms, an unsubstituted heteroaromatic group, a heteroaromatic group substituted with a halogen or a lower alkyl group having 1 to 4 carbon atoms, or represented by (3) or (4):

(wherein Ar 1 represents an unsubstituted aromatic hydrocarbon group, an aromatic hydrocarbon group substituted with a halogen or a lower alkyl group having 1 to 4 carbon atoms, an unsubstituted heteroaromatic group, or a heteroaromatic group substituted with a halogen or a lower alkyl group having 1 to 4 carbon atoms, Ar 2 represents an optionally substituted aromatic hydrocarbon group, R′ represents an unsubstituted aromatic hydrocarbon group, an aromatic hydrocarbon group substituted with a halogen or a lower alkyl group having 1 to 4 carbon atoms, an unsubstituted heteroaromatic group, or a heteroaromatic group substituted with a halogen or a lower alkyl group having 1 to 4 carbon atoms).

3. A method for producing an organic thin film according to claim 1 , the method comprising a step of subjecting the organic thin film to annealing.

4. An organic semiconductor device comprising the organic thin film according to claim 1 .

5. An organic transistor comprising the organic thin film according to claim 1 , the organic thin film being used as an organic semiconductor layer.

6. An organic semiconductor device comprising an organic thin film produced by the method for producing an organic thin film according to claim 3 .

7. An organic transistor comprising an organic thin film produced by the method for producing an organic thin film according to claim 3 , the organic thin film being used as an organic semiconductor layer.

Assignees

• Dainippon Ink & Chemicals
• Tokyo Inst Tech
• Dic Corp Tokyo

Inventors

• Hanna Junichi
• Iino Hiroaki
• Watanabe Yasuyuki
• Koike Junichiro
• Maki Hiroshi
• Tachikawa Yutaka
• Miyawaki Atsuhisa
• Sakurai Yoshinobu

Classifications

• C09K19/3491

  having sulfur as hetero atom · CPC title

• H01L51/0074 Primary

  Electricity · mapped topic

• H01L51/0076

  Electricity · mapped topic

• H01L51/0026

  Electricity · mapped topic

• H01L51/0558

  Electricity · mapped topic