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Spiro[fluorene-9,9-oxanthene] hole transport materials and their applications

A technology of hole transport material, xanthene, which is applied in the fields of organic semiconductors and optoelectronic materials, can solve problems such as commercial application limitations, and achieve the effects of efficient separation and transport of charges, high hole mobility and conductivity, and broad application prospects

Inactive Publication Date: 2020-06-19
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-oxanthene] hole transport materials and their applications
  • Spiro[fluorene-9,9-oxanthene] hole transport materials and their applications
  • Spiro[fluorene-9,9-oxanthene] hole transport materials and their applications

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preparation example Construction

[0059] The preparation method of the spiro[fluorene-9,9-xanthene] type hole transport material of the present invention adopts different synthesis schemes according to the number of different N-core structural units to be prepared. According to the number of N-core structural units and the number of spiro[fluorene-9,9-xanthene] in the target product, those skilled in the art can specify an appropriate synthesis scheme according to the prior art. The applicant first provides a synthetic method of a more specific product, aiming to guide those skilled in the art to use a similar method 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 mole parts of 2,7-dibromospiro[fluorene-9,9-xanthene], 0.02 mole parts of palladium acetate, 0.04 Molar parts of 1,1'-bis(diphenylphosphino)ferrocene, 1 molar part of 4,4'-dimethoxydiphenylamine and 1.5 molar parts of sodium ...

Embodiment 1

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

[0068]

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

[0070]Under nitrogen protection, at room temperature, dry toluene (20ml), 2,7-dibromospiro[fluorene-9,9-xanthene] (2.94g, 6.0mmol), palladium acetate (9.0mg) were added to a two-necked flask , 0.04mmol), 1,1'-bis(diphenylphosphino)ferrocene (44.4mg, 0.08mmol), 4,4'-dimethoxydiphenylamine (0.46g, 2.0mmol) and tert-butanol Sodium (0.29 g, 3.0 mmol) was stirred at 100 degrees Celsius overnight. 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 pale yellow solid with a yield of 78%. It was identified as 7-bro...

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, a one-pot Buchwald reaction was used to prepare the final product: under nitrogen protection, at room temperature, dry toluene (10 mL), tris(dibenzylideneacetone)dipalladium (3.1 mg) were added to a two-necked flask. , 0.03 mmol), 1,1'-bis(diphenylphosphino)ferrocene (DPPF) (5.2 mg, 0.05 mmol) and 4,4'-dibromo-1,1'-biphenyl (156 mg, 0.5 mmol) and stirred for 10 minutes. Next, sodium tert-butoxide (120 mg, 1.25 mmol) and p-methoxyaniline (123 mg, 1.00 mmol) were added to this solution, the temperature was raised to 90 degrees Celsius, and the reaction was carried out for 8 hours. Thereafter, follow with a TLC spot plate until the starting spot disappears. Then, sodium tert-butoxide (120 mg, 1.25 mmol), TBrSFX (670.5 mg, 1.05 mmol) and toluene were added. The solution ...

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Abstract

A spiro[fluorene-9,9-xanthene] hole-transporting material and its application, the material is an aromatic amine compound with a core-shell structure of spiro[fluorene-9,9-xanthene], The compound contains more than one N-nuclear structural unit, and two adjacent N-nuclear structural units are connected by a linking group, and the N-nuclear structural unit conforms to the general formula F: Rx, Ry and Rz is a substituent or a linking group. The material described in the present invention is an aromatic amine compound with a core-shell structure of polyspiro [fluorene-9,9-oxanthene]. Compared with existing similar products, it has a higher glass transition temperature and thermal decomposition temperature; has a higher redox potential; has higher hole mobility and conductivity; in perovskite solar cells and other organic electronics The field of devices has great application value and broad application prospects.

Description

technical field [0001] The invention relates to a class of spiro[fluorene-9,9-xanthene] hole transport materials and a preparation method thereof, and relates to the use of such materials in perovskite solar cells, organic solar cells, organic electroluminescence devices, Field effect transistors, organic photodetectors, organic lasers, organic nonlinear optics, organic electrical storage, and chemical and biological sensing. It belongs to the technical field of organic semiconductors and optoelectronic materials. [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 PbX 3 , X represents a halogen group element) as a light-absorbing material for solar cells (J.Am.Chem.Soc., 2009, 131(17), pp 6050–6051), perovskite solar cells (perovskite solar cells). worldwide attention. In the past seven years, the efficiency of perovskite solar cells has incr...

Claims

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Application Information

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Patent Type & Authority Patents(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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