Spirofluorene bisbenzoacridine organic semiconductor material, preparation method and use method thereof

A technology of dibenzoacridine and organic semiconductors, applied in semiconductor/solid-state device manufacturing, semiconductor devices, chemical instruments and methods, etc., to achieve the effect of broad research space, application prospects and high selectivity products

Inactive Publication Date: 2011-11-02
NANJING UNIV OF POSTS & TELECOMM
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  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There have been many chemical reactions that use solar energy to promote electron transfer or rearrangement in molecules to generate new substances. However, there are no related reports on the catalytic synthesis of spirofluorene dibenzoacridine organic semiconductor materials using solar energy.

Method used

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  • Spirofluorene bisbenzoacridine organic semiconductor material, preparation method and use method thereof
  • Spirofluorene bisbenzoacridine organic semiconductor material, preparation method and use method thereof
  • Spirofluorene bisbenzoacridine organic semiconductor material, preparation method and use method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1、14

[0060] Embodiment 1, 14-hydrogen-spirofluorene dibenzoacridine (X 1 =X 2 =X 3 =X 4 =X 5 = Ar 1 = Ar 2 =H) synthesis:

[0061]

[0062] In a 200ml two-necked flask, add 9-fluorenone (5.0g, 1eq), 1-naphthylamine (3.97g, 1eq) and 1-naphthylamine hydrochloride (15g, 3eq), vacuumize and fill with nitrogen three times, in Under nitrogen protection, add 1,2-dichlorobenzene solvent (15ml) and heat to 180°C for 7 hours, then quickly add polyphosphoric acid (5ml), continue to react at 180°C for 20 hours, after cooling, pour into the reaction flask Add 6mol / L sodium hydroxide solution (50ml) for washing, and ultrasonically dissolve part of the solid for 20min, pour the liquid into a 1000ml separating funnel, then add dichloromethane (80ml) to the reaction flask for washing, ultrasonically for 20min, The dissolved liquid is also poured into a separatory funnel, and 300ml of common saline solution is added in the separatory funnel, extracted three times with dichloromethane (abou...

Embodiment 2

[0064] Example 2, 2'-bromo-14-hydrogen-spirofluorene dibenzoacridine (X 1 =X 2 =X 3 =X 4 =X 5 = H; Ar 1 = H, Ar 2 =Br or Ar 1 =Br, Ar 2 =H) synthesis:

[0065]

[0066] The synthetic route is basically the same as in Example 1. The starting materials and dosage of this synthesis are: fluorenone derivatives 2-bromo-9-fluorenone (5.0g, 1eq), 1-naphthylamine (2.77g, 1eq) and 1- Naphthylamine hydrochloride (10.41 g, 3 eq). 3.28 g of a light yellow solid with a purity >98% was obtained, with a yield of 33.2%. The NMR of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.18(d, J=8.4Hz, 2H), 7.83(d, J=7.6Hz, 1H), 7.77(d, J=8.0Hz, 2H), 7.74(s, 1H), 7.71(d, J=8.1Hz, 1H), 7.67(t, J=7.7Hz, 2H), 7.54(d, J=7.3Hz, 2H), 7.52-7.48(m, 1H), 7.43-7.38(m, 1H), 7.36 (s, 1H), 7.24 (t, J=6.8Hz, 2H), 7.14 (d, J=8.6Hz, 2H), 6.37 (d, J=8.6Hz, 2H). 13 C NMR(101MHz,CDCl3)δ159.59,157.43,138.42,138.04,133.31,132.49,131.01,129.83,128.94,128.87,127.92,126.69,126.32,126.12,126.00,122.39...

Embodiment 3、2

[0067] Example 3, 2', 7'-dibromo-14-hydrogen-spirofluorene dibenzoacridine (X 1 =X 2 =X 3 =X 4 =X 5 = H; Ar 1 = Ar 2 =Br) synthesis:

[0068]

[0069] The synthetic route is basically the same as that in Example 1. The starting materials and dosage of this synthesis are: derivatives of fluorenone 2,7-dibromo-9-fluorenone (5.0g, 1eq), 1-naphthylamine (2.12g, 1eq) and 1-naphthylamine hydrochloride (10.68 g, 4 eq). 2.37 g of a light yellow solid with a purity >98% was obtained, with a yield of 27%. The NMR of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.18(d, J=8.4Hz, 2H), 7.79(d, J=7.8Hz, 2H), 7.76(s, 1H), 7.69(dt, J=7.0, 3.6Hz, 4H), 7.55( t, J=7.5Hz, 2H), 7.51(dd, J=8.2, 1.8Hz, 2H), 7.35(d, J=1.7Hz, 2H), 7.16(d, J=8.6Hz, 2H), 6.35( d, J=8.6Hz, 2H). 13 C NMR (101MHz, CDCl3) δ159.20, 137.16, 133.35, 132.45, 131.25, 129.92, 128.97, 126.33, 126.16, 126.10, 122.50, 122.35, 121.34, 121.32, 119.09, 1176.39, 5

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Abstract

A spirofluorene bisbenzoacridine organic semiconductor material is a novel n-type spiroarene organic semiconductor material with a cross structure. The material relates to application fields of fine organic synthesis, organic dyes and photoelectric devices. The spirofluorene bisbenzoacridine organic semiconductor material is hopefully applied in aspects of organic electroluminescence, organic laser, photovoltaic cells, electricity storage devices and the like. The invention discloses a method for preparing the spirofluorene bisbenzoacridine organic semiconductor material and use thereof. Because of having a non-planar structure and electrophilic properties thereof, a preliminary effect that the spirofluorene bisbenzoacridine organic semiconductor material is used as a red electroluminescent material and an electronic receptor material of an organic solar cell is achieved, wherein the spirofluorene bisbenzoacridine organic semiconductor material disclosed by the invention has green synthesis advantages; the material can be modified by a plurality of groups more conveniently; device properties can be greatly improved; the spirofluorene bisbenzoacridine organic semiconductor material is hopefully used as an efficient photovoltaic material; and the spirofluorene bisbenzoacridine organic semiconductor material has good industrialization production and a business prospect.

Description

technical field [0001] The invention belongs to the technical fields of fine organic synthesis, organic dyes and organic photoelectric devices. It specifically relates to a method for preparing spirofluorene dibenzoacridine organic semiconductor materials, and relates to the application of these materials in the fields of fine organic synthesis, organic dyes, organic electroluminescence, organic lasers, photovoltaic cells, and electric storage devices. technical background [0002] Acridone and its derivatives are an important class of organic dyes or pigments. Individual acridone molecules or their simple modified compounds have been studied well and have been widely used; for molecules containing spirofluorene structures, due to their The factor of non-planar structure with perpendicular crossings has thus been widely introduced into optoelectronic materials to achieve spectral stability of materials by modulating supramolecular interactions of chromophores. In 1954, Bell...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/02C07D219/04C07D219/06C07D409/04C07D409/14C07D401/04C09K11/06H01L51/46H01L51/54
CPCY02E10/549Y02E10/50
Inventor 解令海黄维孙鹏举杨阳仪明东张广维
Owner NANJING UNIV OF POSTS & TELECOMM
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