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[1]benzothieno[3,2-b][1]benzothiophene compound and method for producing the same, and organic electronic device using the same

一种苯并噻吩、2-b的技术，应用在有机电子器件领域，能够解决难处理、四氯苯高沸点难除去、氧或水不稳定等问题，达到低漏电流、高载流子迁移率、高开/关比的效果

Inactive Publication Date: 2011-04-06
RICOH KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In those cases, the tetrachlorobenzene molecule was separated from the pentacene precursor, but tetrachlorobenzene has a high boiling point and is difficult to remove from the reaction system
In addition, its toxicity has also been concerned
[0011] Also, any of these examples has the problem that the converted semiconductor molecules are unstable to oxygen or water, thus being difficult to handle in the atmosphere
[0012] For those reasons, the above conventionally known compounds and their precursors clearly have process adaptability problems, and there is a need for novel precursors and methods of making the same

Method used

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  • [1]benzothieno[3,2-b][1]benzothiophene compound and method for producing the same, and organic electronic device using the same
  • [1]benzothieno[3,2-b][1]benzothiophene compound and method for producing the same, and organic electronic device using the same
  • [1]benzothieno[3,2-b][1]benzothiophene compound and method for producing the same, and organic electronic device using the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0206] Synthesis of Precursor 1

[0207] Precursor 1 was synthesized according to Scheme 7.

[0208]

[0209]

[0210] Charge derivative 7 (492.5 mg, 1 mmol), derivative 11 (1299 mg, 2.1 mmol) and dimethylformamide (hereinafter referred to as DMF) / toluene (10 mL, 1 / 1=volume / volume), bubbled with argon for 30 minutes, and then further loaded with Pd 2 (dba) 3 (2 mole%, 18.3mg), P(o-toly) 3 (tri-o-cresyl phosphate) (8 mol%, 24.4 mg), DMF / toluene (4 mL), bubbled with argon for 10 minutes, and heated at 80° C. (±5° C.) for 12 hours. The three-necked flask was cooled to room temperature, and charged with toluene (100 mL) and saturated salt solution (200 mL) to separate the organic phase. The aqueous phase was extracted 3 times from the remaining liquid with toluene (50 mL). The remaining organic phase was added to the separated organic phase, and washed with saturated potassium fluoride aqueous solution (200 mL), and further washed 3 times with saturated saline solution....

Embodiment 2

[0223] Synthesis of Precursor 2

[0224] Precursor 2 was synthesized according to Scheme 8.

[0225]

[0226]

[0227] Charge derivative 7 (1968mg, 4.0mmol), derivative 15 (4089mg, 9.2mmol), K 3 PO 4 ·nH 2 O (13.6 g) and DMF (80 mL), bubbled with argon for 30 minutes, and then further charged with Pd (PPh 3 ) 4 (368 mg, 0.4 mmol), bubbled with argon for 10 minutes, and heated at 85°C (±5°C) for 9 hours. The three-necked flask was cooled to room temperature, the contents were filtered through celite, and the celite was washed with toluene (100 mL). The filtrate was poured into saturated aqueous ammonium chloride (400 mL), and toluene (200 mL) was added thereto to separate the organic phase. The aqueous phase was extracted 3 times from the remaining liquid with toluene (50 mL). The remaining organic phase was added to the separated organic phase, and washed 3 times with saturated saline solution. The organic phase was dried over magnesium sulfate, and the filtrate w...

Embodiment 3

[0240] Synthesis of Precursor 3

[0241] Precursor 3 was synthesized according to Scheme 9.

[0242]

[0243]

[0244] Charge derivative 7 (492.5 mg, 1 mmol), derivative 20 (1460 mg, 2.1 mmol) and DMF / toluene (10 mL, 1 / 1 = volume / volume) in a three-necked flask, bubble with argon for 30 minutes, Then further loaded into Pd 2 (dba) 3 (2 mole%, 18.3mg), P(o-toly) 3 (8 mol%, 24.4 mg), DMF / toluene (6 mL, 1 / 1 = v / v), bubbled with argon for 10 minutes, and heated at 80°C (±5°C) for 9 hours. The three-necked flask was cooled to room temperature, and the precipitate was filtered and washed with methanol and hexane. The precipitate was dissolved in chloroform, and the filtrate passed through a pad of silica gel was dried to obtain orange crystals (amount: 840 mg, yield: 80.0%)

[0245] The obtained analysis results of Precursor 3 are as follows.

[0246] 1 H NMR (500MHz, CDCl 3 , TMS, δ): 8.17 (d, J=1.7Hz, 2H), 7.87 (d, J=8.0Hz, 2H), 7.70 (dd, J 1 = 1.7Hz,J 2 =8.0Hz, 2H)...

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Abstract

A [1]benzothieno[3,2-b][1]benzothiophene compound expressed by General Formula (I): General Formula (I) where X and Y are each independently a hydrogen atom; a halogen atom; or a functional group having a straight or branched aliphatic alkyl group optionally having a halogen atom, a functional group having an alicyclic alkyl group optionally having a halogen atom, a functional group having a straight or branched aliphatic alkenyl group optionally having a halogen atom, a functional group having an alicyclic alkenyl group optionally having a halogen atom, a functional group having a carboxyl group, or a functional group having a thiol group, as a partial structure; and X and Y are the same or each independently different, provided that at least one of X and Y has a straight or branched aliphatic alkenyl group, an alicyclic alkenyl group, a carboxyl group or a thiol group, as a partial structure.

Description

technical field [0001] The present invention relates to [1]benzothieno[3,2-b][1]benzothiophene compound precursors which can be easily produced from 3,2-b][1]Benzothiophene compound, method for producing the compound, and organic electronic device using the compound. The compound of the present invention is useful as a material for various organic electronic elements such as photoelectric conversion elements, thin film transistor elements, light emitting elements and the like. Background technique [0002] In recent years, organic thin film transistors using organic semiconductor materials have been actively researched and developed. The organic semiconductor material can be easily formed into a thin film by an easy method such as a wet method such as printing, spin coating and the like. Compared with thin film transistors using inorganic semiconductor materials, thin film transistors using organic semiconductor materials also have the advantage that the temperature of the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04H01L51/05H01L51/30H01L51/40
CPCH01L51/0558H01L51/0074C07D495/04Y02E10/549H10K85/6576H10K10/484H10K30/00
Inventor 后藤大辅鸟居昌史堀内保有贺保生野弘匂坂俊也山本谕折户武志毛利匡贵冈田崇加藤拓司松本真二
Owner RICOH KK
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