Tetrathiafulvalene derivative, and organic film and organic transistor using the same

A technology of tetrathiafulvalene and its derivatives, which can be used in the field of raw materials for charge transport materials and organic electronic devices, and can solve problems such as mobility reduction

Inactive Publication Date: 2012-02-29
RICOH KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The ionization potentials of DB-TTF and DN-TTF each containing nitrogen atoms are improved compared to DB-TTF and DN-TTF which do not contain nitrogen atoms, but the mobility is significantly reduced

Method used

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  • Tetrathiafulvalene derivative, and organic film and organic transistor using the same
  • Tetrathiafulvalene derivative, and organic film and organic transistor using the same
  • Tetrathiafulvalene derivative, and organic film and organic transistor using the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104]

[0105] The synthetic route of compound (3) is as follows.

[0106]

[0107] Synthesis process

[0108]

[0109] Methanol (100 mL) in which lithium chloride (1.00 g) had been dissolved was added dropwise to sodium borohydride (10.22 g), and then THF (50 mL) was added thereto. The resulting mixture was cooled to -10°C, and then 1,3-dithiol-2-thione-4,5-dimethyldicarboxylic acid dissolved in THF (100 mL) was added dropwise to the cooled mixture Esters: 1-1 (10.0 g). After the dropwise addition was complete, the resulting mixture was stirred in an ice bath for 3 hours. After the reaction was completed, the reaction solution was poured into ice water (1 L) and extracted with ethyl acetate, followed by washing with saturated saline solution. The organic layer was dried over magnesium sulfate. The magnesium sulfate was removed by filtration. Recrystallization was performed with ethyl acetate to obtain 4,5-bis(hydroxymethyl)-1,3-dithiol-2-thione: 1-2 in a yield o...

Embodiment 2

[0141] The bis(6,9-dihydro-6,9-ethylideneanthracene[2,3-d])tetrathiafulvalene synthesized in Example 1 was used by the following method: tetrathiafulvalene derivative Object (3) to produce organic membranes.

[0142] An N-type silicon substrate including a thermally oxidized film with a film thickness of 300 nm was dipped and washed in concentrated sulfuric acid for 24 hours, and then dipped in a toluene solution (1 mM) of a silane coupling agent (octyltrichlorosilane). Then, the substrate was subjected to ultrasonic treatment for 5 minutes to form a monomolecular film on the surface of the silicon oxide film.

[0143] On the substrate prepared by the above method, at a back pressure of up to 10 -4 Pa, deposition rate is 0.1 And under the condition that the semiconductor film thickness is 50nm, the bis(6,9-dihydro-6,9-bridge ethylidene anthracene [2,3-d])tetrathiafulvalene obtained in Example 1:( 3) Vapor deposition is performed to obtain a smooth and uniform organic film....

Embodiment 3

[0146]

[0147] The synthetic route of compound (1) is as follows.

[0148]

[0149] Synthesis process

[0150]

[0151] The three-necked flask was purged with nitrogen, and then charged with bis(6,9-dihydro-6,9-endoethylideneanthracene [2,3-d]) tetrathiafulvalene: Tetrathiafulvalene derivation Compound (3) (0.20 g). Subsequently, the flask was placed on a hot plate set at 280°C. The yellow powder of tetrathiafulvalene derivative (3) changes into bis(anthracene[2,3-d])tetrathiafulvalene within minutes: the red powder of tetrathiafulvalene derivative (1) ( Yield: 99%).

[0152] Elemental analysis

[0153] Measured value (mass%) Calculated value (mass%)

[0154] C 71.15 71.39

[0155] H 2.77 3.20

[0156] Bis(anthracene[2,3-d])tetrathiafulvalene was analyzed by infrared spectroscopy (KBr), and the results are shown in image 3 middle.

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Abstract

A tetrathiafulvalene derivative expressed by General Formula (I): General Formula (I) in General Formula (I), X represents an atom selected from a carbon atom, a sulfur atom, and a nitrogen atom, and Xs may be the same or different; provided that when X is the carbon atom or the nitrogen atom, R1 to R8 each represent one of a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, and a substituted or unsubstituted thioalkoxy group, and may be the same or different; and Y1 and Y2 each represent one of structures expressed by General Formulas (II) and (III), and may be the same or different: General Formula (II) General Formula (III).

Description

technical field [0001] The present invention relates to novel tetrathiafulvalene derivatives, and organic electronic devices using said novel tetrathiafulvalene derivatives, such as organic TFTs, electrochromic displays, EL displays, organic semiconductor materials and for charge Raw materials for conveying materials. Background technique [0002] Tetrathiafulvalene (TTF) and its derivatives are molecules with strong electron donating properties, and together with electron acceptor molecules such as tetracyanoquinodimethane (TCNQ), form charge transfer complexes. The resulting charge-transfer complex exhibits metallic conductivity. The charge transfer complexes are expected to be used in many applications such as organic superconductors, organic magnetic materials, organic electrochromic materials and organic electroluminescent materials. [0003] In recent years, thin film transistors using organic semiconductors have attracted attention. Conventional methods of fabricat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/06C07D495/04H01L29/786H01L51/05H01L51/30
CPCC07D339/06C07D495/04H10K85/6576H10K10/484H10K10/466C07D409/04H10K10/00
Inventor 篠田雅人山本谕匂坂俊也加藤拓司冈田崇后藤大辅松本真二毛利匡贵
Owner RICOH KK
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