Indenoperylene compound, material for organic thin-film photovotaic cell containing indenoperylene derivative, and organic thin-film photovotaic cell using same

A technology for solar cells and organic thin films, applied in the preparation of perylene derivatives, organic compounds, organic chemistry, etc., can solve the problems of undisclosed perylene derivatives, etc., and achieve the effect of excellent photoelectric conversion characteristics

Inactive Publication Date: 2013-05-08
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, perylene derivatives having diarylamino and / or dialkylamino groups are not disclosed

Method used

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  • Indenoperylene compound, material for organic thin-film photovotaic cell containing indenoperylene derivative, and organic thin-film photovotaic cell using same
  • Indenoperylene compound, material for organic thin-film photovotaic cell containing indenoperylene derivative, and organic thin-film photovotaic cell using same
  • Indenoperylene compound, material for organic thin-film photovotaic cell containing indenoperylene derivative, and organic thin-film photovotaic cell using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0224] Embodiment 1 (synthesis of compound A)

[0225] The raw material A of compound A was synthesized in the following procedure.

[0226] [chem 22]

[0227]

[0228] Compound A was synthesized as follows.

[0229] [chem 23]

[0230]

[0231] Under nitrogen atmosphere, make raw material A (1.2g, 8.9mmol), diphenylamine (0.4g, 2.4mmol, 1.2eq.), tris (dibenzylideneacetone) dipalladium (0) (0.03g, 0.03 mmol, 3% Pd), sodium tert-butoxide (0.3g, 2.8mmol, 1.4eq.) was suspended in anhydrous toluene (50ml), and tri-tert-butylphosphine / toluene solution (2.8M, 0.017ml, 0.048mmol , 0.8eq. relative to Pd), reflux was carried out for 7 hours. The reaction mixture was filtered through a pad of silica gel, washing with toluene (100ml). The red oily solid obtained by distilling off the filtrate from the solvent was purified by column chromatography (silica gel / hexane+17% dichloromethane, followed by hexane+33% dichloromethane) to obtain a red solid (1.2 g, 86%).

[0232] Variou...

Embodiment 2

[0236] Embodiment 2 (manufacture of organic thin film solar cell)

[0237] A 25 mm x 75 mm x 0.7 mm thick glass substrate with an ITO transparent electrode was cleaned ultrasonically for 5 minutes in isopropyl alcohol, and then washed with UV ozone for 30 minutes. Load the cleaned glass substrate with transparent electrode wires on the substrate holder of the vacuum evaporation device, on the surface of the side where the transparent electrode wires as the lower electrodes are first formed, pass through the resistor in such a way as to cover the transparent electrodes heated and evaporated with Compound A (p-type material) was formed into a film with a film thickness of 30 nm.

[0238] Then, on the compound A film, evaporated by resistance heating and Make the film thickness 60nm C 60 (n-type material) film formation. Further, as a buffer layer, to A 10 nm bathocuproine (BCP) film was formed. Finally, as a counter electrode, metal Al was vapor-deposited with a film th...

Embodiment 3

[0264] [Synthesis of Compound B]

[0265] Compound B was synthesized according to the following synthetic route.

[0266] [chem 28]

[0267]

[0268] [chem 29]

[0269]

[0270] [Synthesis of raw material B]

[0271]Under a nitrogen atmosphere, 2,2,6,6-tetramethylpiperidine (6.6 g, 47 mmol, 1.5 eq.) was dissolved in anhydrous THF (60 ml) and cooled to -43°C in a dry ice / methanol bath. A n-butyllithium / hexane solution (1.6mol / l, 28ml, 47mmol, 1eq.toTMP) was added dropwise thereto, and stirred at -23°C for 20 minutes. The reaction mixture was cooled to -74°C, triisopropyl borate (15ml, 65mmol, 2eq.) was added, and after 5 minutes, 4-bromotriphenylamine / anhydrous THF solution (8g, 39mmol / 15ml). The reaction mixture was stirred at -74°C to room temperature for 10 hours and left overnight. Cool the reaction mixture in a water bath, slowly add 5% hydrochloric acid aqueous solution (100ml) to inactivate it, dilute it with ethyl acetate (150ml), take out the organic layer...

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Abstract

An indenoperylene derivative represented by a formula (A-1), wherein in the formula (A-1), at least one of R 1 to R 16 is an amino group represented by the formula (A-2). In the formula (A-2), R a and R b are a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms or a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms.

Description

technical field [0001] The present invention relates to a novel indenoperylene derivative, a material for an organic thin-film solar cell comprising the novel indenoperylene derivative, and an organic thin-film solar cell using the material. In addition, the present invention relates to a material for an organic thin film solar cell containing an indenoperylene derivative, and an organic thin film solar cell using the same. Background technique [0002] An organic thin-film solar cell is a device that exhibits electrical output with respect to light input, and is a device that exhibits a different response from an electroluminescence (EL) element that exhibits light output with respect to electrical input. Solar cells classified as one type of organic thin-film solar cells have recently attracted much attention as green energy, and their research and development has been flourishing against the backdrop of fossil fuel depletion problems and global warming problems. [0003]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61H01L51/42
CPCC07C2103/54C07C211/61H01L51/006H01L51/4253C07C217/92H01L51/424H01L51/0056Y02E10/549C09B57/008C09B3/14C07C2603/54Y02P70/50H10K85/624H10K85/633H10K30/30H01L31/04H10K30/00H10K30/20
Inventor 安川圭一岩本伸太郎池田秀嗣东海林弘
Owner IDEMITSU KOSAN CO LTD
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