Spiro [fluorene-9, 9-xanthene]-class hole transport material and application thereof

A hole-transporting material, xanthene technology, applied in photovoltaic power generation, electrical components, circuits, etc., can solve problems such as commercial application limitations, achieve efficient separation and transport of charges, facilitate large-scale commercial preparation, high hole Effects of Mobility and Conductivity

Inactive Publication Date: 2017-07-25
孙立成 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] In summary, although the existing spiro[fluorene-9,9-oxanthene]-type hole-transporting materials can effectively inhibit the intermolecular π-π stacking due to their vertical spiro ring structure, thus improving solubility, It has excellent performance in thermal stability and other aspects, but there are still various defects that limit its practical commercial application

Method used

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  • Spiro [fluorene-9, 9-xanthene]-class hole transport material and application thereof
  • Spiro [fluorene-9, 9-xanthene]-class hole transport material and application thereof
  • Spiro [fluorene-9, 9-xanthene]-class hole transport material and application thereof

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preparation example Construction

[0059] The preparation method of the spiro[fluorene-9,9-oxanthene] type hole transport material of the present invention adopts different synthesis schemes according to the number of different N-nuclear structural units to be prepared. According to the number of N-nuclear structural units and the number of spiro[fluorene-9,9-oxanthene] in the target product, those skilled in the art can designate an appropriate synthesis scheme according to the prior art. The applicant first provides a synthesis method of a class of more specific products, aiming to guide those skilled in the art to use similar methods to complete the synthesis of other compounds. Described synthetic method comprises the steps:

[0060] (1) Under nitrogen protection, at room temperature, add dry toluene, 3 molar parts of 2,7-dibromospiro[fluorene-9,9-oxanthene], 0.02 molar parts of palladium acetate, 0.04 Molar parts of 1,1′-bis(diphenylphosphino)ferrocene, 1 molar part of 4,4′-dimethoxydiphenylamine and 1.5 ...

Embodiment 1

[0067] N2-(2-(bis(4-methoxyphenyl)amine)spiro[fluorene-9,9′-oxanthene]-7-yl)-N2,N7,N7-tetrakis(4-methoxyphenyl) ) spiro[fluorene-9,9'-oxanthene]-2,7-diamine (X26) synthesis, according to the following route:

[0068]

[0069] (1) Synthesis of 7-bromo-N,N-bis(4-methoxybenzene)spiro[fluorene-9,9′-oxanthene]-2-amine (TBrSFX):

[0070]Under nitrogen protection, at room temperature, dry toluene (20ml), 2,7-dibromospiro[fluorene-9,9-oxanthene] (2.94g, 6.0mmol), palladium acetate (9.0mg , 0.04mmol), 1,1'-bis(diphenylphosphino)ferrocene (44.4mg, 0.08mmol), 4,4'-dimethoxydiphenylamine (0.46g, 2.0mmol) and tert-butanol Sodium (0.29g, 3.0mmol) was stirred overnight at 100°C. After cooling, the reaction was quenched with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and separated by silica gel column chromatography to obtain 1.00 g of a light yellow solid with a yield of 78%. It was identified as 7-bromo-N,N-bis(4-methoxybenzene)spiro[fluorene-9,9′-oxanth...

Embodiment 2

[0076] N2,N2″-([1,1′-biphenyl]-4,4′-diyl)bis(N2,N7,N7-tetrakis(4-methoxybenzene)spiro[fluorene-9,9′- The synthesis of xanthene]-2,7-diamine (X36) follows the following route:

[0077]

[0078] Specifically, the final product was prepared by using a one-pot Fabuchwald (Buchwald) reaction: under nitrogen protection, at room temperature, dry toluene (10 mL), tris(dibenzylideneacetone) dipalladium (3.1 mg , 0.03mmol), 1,1′-bis(diphenylphosphino)ferrocene (DPPF) (5.2mg, 0.05mmol) and 4,4′-dibromo-1,1′-biphenyl (156mg, 0.5 mmol), stirred for 10 minutes. Next, sodium tert-butoxide (120mg, 1.25mmol) and p-methoxyaniline (123mg, 1.00mmol) were added to the solution, and the temperature was raised to 90°C for 8 hours of reaction. Thereafter, trace the plate with TLC until the raw material spots disappear. Then, sodium tert-butoxide (120 mg, 1.25 mmol), TBrSFX (670.5 mg, 1.05 mmol) and toluene were added. The solution was warmed to 100°C and stirred overnight. After the reaction,...

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Abstract

A spiro [fluorene-9, 9-xanthene]-class hole transport material and application thereof are disclosed, the spiro [fluorene-9, 9-xanthene]-class hole transport material is an aromatic-amine compound using spiro [fluorene-9, 9-xanthene] as a core-shell structure, the aromatic-amine compound has one or more than 1 N nuclear structure unit, two adjacent N nuclear structure units are connected by a connecting group, the N nuclear structure unit meets the general formula F, and Rx, Ry and Rz are substitutes or connecting groups. Compared with similar products in the prior art, the spiro [fluorene-9, 9-xanthene]-class hole transport material is the aromatic-amine compound using the spiro [fluorene-9, 9-xanthene] as the core-shell structure, has higher glass transition temperature and thermal decomposition temperature, higher redox potential, and higher hole mobility and conductivity, and has great application value and broad application prospects in the field of perovskite solar cells and other organic electronic devices.

Description

technical field [0001] The invention relates to a class of spiro[fluorene-9,9-oxanthene] hole transport materials and a preparation method thereof, and relates to the use of such materials in perovskite solar cells, organic solar cells, organic electroluminescent devices, and Applications in field effect transistors, organic photodetectors, organic lasers, organic nonlinear optics, organic electrical storage, and chemical and biological sensing. The invention belongs to the technical field of organic semiconductor and photoelectric material. [0002] technical background [0003] Since 2009, Tsutomu Miyasaka, a professor at Toin Yokohama University in Japan, first reported a perovskite-based crystal structure (CH 3 NH 3 wxya 3 , X represents a halogen element) since the solar cell of the light-absorbing material (J.Am.Chem.Soc., 2009, 131(17), pp 6050–6051), perovskite solar cells (perovskite solar cells) have caused a whole world wide attention. In the past 7 years, the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/96C07D405/14C07D409/14H01L51/42H01L51/46H01L51/50H01L51/54H01L51/00
CPCC07D311/96C07D405/14C07D409/14H10K99/00H10K85/636H10K85/6576H10K85/6574H10K85/6572H10K30/00H10K50/00Y02E10/549
Inventor 孙立成徐勃
Owner 孙立成
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