Unlock instant, AI-driven research and patent intelligence for your innovation.

Phenanthroline compound, electron transport material obtained from said compound, and organic thin-film photovoltaic cell comprising said compound

A technology of solar cells and organic thin films, applied in the field of new phenanthroline compounds, can solve unspoken problems related to the utilization of organic thin film solar cells, and achieve the effect of high-efficiency photoelectric conversion characteristics

Inactive Publication Date: 2013-03-06
IDEMITSU KOSAN CO LTD
View PDF6 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Patent Document 3 discloses an electron-transporting laminate film using perylenetetracarboxylic acid imide represented by the following formula, but does not mention the use of organic thin-film solar cells

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Phenanthroline compound, electron transport material obtained from said compound, and organic thin-film photovoltaic cell comprising said compound
  • Phenanthroline compound, electron transport material obtained from said compound, and organic thin-film photovoltaic cell comprising said compound
  • Phenanthroline compound, electron transport material obtained from said compound, and organic thin-film photovoltaic cell comprising said compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0166] Embodiment 1: the synthesis of phenanthroline compound (2-A)

[0167] [chemical 14]

[0168]

[0169] (1) Synthesis of Intermediate A1

[0170] Under nitrogen atmosphere, in 4-bromo-phthalic anhydride (15g, 66.1mmol), methylamine (40%inH 2 O) (8.26mL, 99.1mmol), sodium acetate (8.67g, 106mmol) was added with acetic acid (100mL), heated and stirred for 6 hours to reflux. Water (200 mL) was added to the reaction mixture, and the precipitate was filtered to obtain a white solid (15.2 g, 96%).

[0171] The NMR determination of the solid is shown below ( 1 H-NMR) results.

[0172] 1 H-NMR (400MHz, CDCl 3 , TMS) δ: 3.18 (s, 3H), 7.71 (d, J8.0, 1H), 7.84 (d, J8.0, 1H), 7.98 (s, 1H).

[0173] (2) Synthesis of Intermediate A2

[0174] Under nitrogen atmosphere, add intermediate A1 (10g, 41.7mmol), bis(pinacolate) diboron (13g, 50.0mmol), 1,1'-bis(diphenylphosphino)ferrocene] dichloride Palladium(II) dichloromethane complex (0.65g, 0.80mmol), potassium acetate (30g, 3...

Embodiment 2

[0179] Embodiment 2: the synthesis of phenanthroline compound (2-B)

[0180] [chemical 15]

[0181]

[0182] Under nitrogen atmosphere, add intermediate A2 (0.33g, 1.15mmol), 3-bromophenanthroline (0.2g, 0.77mmol), cesium carbonate (0.63g, 2.0mmol) synthesized in Example 1 (2), four (Triphenylphosphine)palladium(0) (0.027 g, 0.023 mmol), 1,2-dimethoxyethane (10 mL), and stirred at 80° C. for 6 hours. Water (50 mL) was added to the reaction mixture, and the precipitate was filtered to obtain a yellow solid (compound (2-B); 0.23 g, 90%).

[0183] 1 H-NMR (400MHz, CDCl 3 , TMS) δ: 3.24(s, 3H), 7.69(d, J8.0, 1H), 7.90(s, 1H), 8.03(d, J8.0, 1H), 8.13(d, J8.0, 1H ), 8.26-8.31(m, 2H), 8.50(d, J8.0, 1H), 9.24(d, J8.0, 1H), 9.46(d, J8.0, 1H).

Embodiment 3

[0184] Embodiment 3: the synthesis of phenanthroline compound (2-D)

[0185] [chemical 16]

[0186]

[0187] Under nitrogen atmosphere, add intermediate A2 (1.0g, 3.6mmol), 4-bromophenyl-2-phenanthroline (1.0g, 2.99mmol) and cesium carbonate (1.75g, 5.4mmol), tetrakis(triphenylphosphine)palladium(0) (0.17g, 0.15mmol), 1,2-dimethoxyethane (30mL), and stirred at 80°C for 6 hours. Water (50 mL) was added to the reaction mixture, and the precipitate was filtered to obtain a yellow solid (compound (2-D); 1.00 g, 81%).

[0188] 1 H-NMR (400MHz, CDCl 3 , TMS) δ: 3.23(s, 3H), 7.66(d, J8.0, 2H), 7.81-7.87(m, 4H), 7.94(d, J8.0, 2H), 8.02(d, J8.0 , 1H), 8.18(d, J8.0, 2H), 8.28(d, J8.0, 1H), 8.36(d, J8.0, 1H), 8.50d, J8.0, 2H), 9.26(d , J8.0, 1H).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
areaaaaaaaaaaa
thicknessaaaaaaaaaa
Login to View More

Abstract

Provided is a compound represented by a formula (1). (L represents a single bond or a divalent radical, bonded at one location from among the 6-, 8-, and 9-positions, which are represented by * in 1,10-Phenanthroline. Rg represents a substituted or unsubstituted benzene ring or naphthalene ring, and X represents an oxygen atom or N-R4.)

Description

technical field [0001] The present invention relates to a novel phenanthroline compound, an electron transport material containing the compound, a material for an organic thin film solar cell, an organic thin film solar cell using the same, and a stacked organic thin film solar cell. Background technique [0002] Against the backdrop of the depletion of fossil fuels and global warming, solar cells have recently attracted attention as a green energy source, and their research and development has been actively conducted. Conventionally, silicon-based solar cells represented by single-crystal Si, polycrystalline Si, and amorphous Si have been put into practical use. However, the demand for next-generation solar cells has gradually increased due to high prices and shortage of raw material Si. [0003] Against such a background, organic solar cells are inexpensive and have no fear of shortage of raw materials, and thus attract attention as next-generation solar cells of silicon-b...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04H01L51/42H10K99/00
CPCH01L51/424B82Y10/00H01G9/2009H01G9/2072C07D471/04H01L51/0072H01L51/006H01L51/0046H01L2251/308H01L51/0056Y02E10/549H01L51/4273C09B57/00Y02E10/542H10K85/211H10K85/624H10K85/633H10K30/20H10K85/6572H10K2102/103H10K30/50H10K30/40H10K30/353
Inventor 安川圭一前田龙志东海林弘
Owner IDEMITSU KOSAN CO LTD