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Bipolar bisthieno[3,2-b:2',3'-d] thiophene derivatives and applications thereof

A technology of no-trithiophene and derivatives, applied in the field of bipolar no-trithiophene derivatives, can solve the problems of low luminous efficiency, short service life and limited understanding of devices, and achieve high color purity and efficiency, high vitrification temperature, the effect of avoiding close accumulation

Active Publication Date: 2013-08-07
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, people's understanding of the electronic behavior of such chiral, cross-conjugated materials is still very limited.
[0004] At present, the biggest obstacle to the full practical application of OLED technology is the low luminous efficiency and short service life of the device.

Method used

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  • Bipolar bisthieno[3,2-b:2',3'-d] thiophene derivatives and applications thereof
  • Bipolar bisthieno[3,2-b:2',3'-d] thiophene derivatives and applications thereof
  • Bipolar bisthieno[3,2-b:2',3'-d] thiophene derivatives and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Example 1 2,6-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)dithieno[3,2-b:2',3'-d]thiophene-4,4 - Synthesis of Dioxide (Compound 1):

[0066] Add 3.84g 2,6-dibromodithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide (10.0mmol) and 6.15g3,6- Di-tert-butyl-9H-carbazole (22.0mmol), dissolve DMAC (N,N-dimethylacetamide) with 60mL, then add K 2 CO 3 (8.30g, 60.0mmol), stirred under nitrogen for 1 hour to remove the oxygen in the reaction flask. Then add 0.190 g (1.0 mmol) of cuprous iodide, and reflux under vigorous stirring. The reaction process is tracked and detected by TLC. After reacting for 24 hours, add 50 mL of deionized water to the reaction solution, filter to remove insoluble matter, separate the water phase from the organic phase, extract the water phase with ethyl acetate (30 mL each time, 3 times), mix the organic phase and reduce pressure Concentrate to about 5 mL by distillation, and separate by column chromatography, using ethyl acetate:n-hexane (1:10, v / v) as eluent....

Embodiment 2

[0067] Example 2 9,9'-(3,5-di-tert-butyl-4,4-dioxydithieno[3,2-b:2',3'-d]thiophene-2,6-diyl ) bis(3,6-dicyano-9H-carbazole) (compound 2)

[0068] With 2,6-dibromo-3,5-di-tert-butyldithieno[3,2-b:2',3'-d]thiophene-4,4-dioxide and 3,6-dicyano Base-9H-carbazole was used as the starting material to prepare according to the synthetic method of compound 1 in Example 1. Using DEI-MS to identify the compound, formula C 44 h 30 N 6 o 2 S 3 , detection value [M+1] + =771.63, the calculated value is 770.94.

Embodiment 3

[0069] Example 3 9,9'-(3,5-di-tert-butyl-4-oxydithieno[3,2-b:2',3'-d]thiophene-2,6-diyl)bis( 3,6-dicyano-9H-carbazole) (compound 3)

[0070] With 2,6-dibromo-3,5-di-tert-butyldithieno[3,2-b:2',3'-d]thiophene-4-oxide and 3,6-dicyano-9H -Carbazole is the starting material and is prepared according to the synthetic method of compound 1 in Example 1. Using DEI-MS to identify the compound, formula C 44 h 30 N 6 OS 3 , detection value [M+1] + =755.88, the calculated value is 754.94.

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Abstract

The present invention relates to bipolar bisthieno[3,2-b:2',3'-d] thiophene derivatives and applications thereof. According to the derivatives, bisthieno[3,2-b:2',3'-d] thiophene groups serve as a center; by oxidation of the sulfur atom at site 4 to form bisthieno[3,2-b:2',3'-d] thiophene-4-oxides and bisthieno[3,2-b:2',3'-d] thiophene-4,4-dioxides, the electron transport property of bisthieno[3,2-b:2',3'-d] thiophene is improved; and simultaneously, a carbazole derivative or an aromatic amine compound having a good hole transport property is respectively introduced into 2 and 6 sites of the oxidized bisthieno[3,2-b:2',3'-d] thiophene, combining the advantages of both. By regulating the molecular structures of different parts of the molecule, the bisthieno[3,2-b:2',3'-d] thiophene derivatives is allowed to have hole and electron transport properties to form a bipolar transport material. The bipolar bisthieno[3,2-b:2',3'-d] thiophene material has a twisted non-planar spatial structure, thus effectively preventing tight accumulation of molecules. Experimental results show that the material of the invention has a high thermal stability and a glass transition temperature, and the material is separately used as an electron transport material, a hole transport material and a luminescent material for organic electroluminescent devices, electroluminescence with very high color purity and efficiency can be obtained.

Description

technical field [0001] The invention relates to a bipolar trithiophene derivative and its application, belonging to the field of organic photoelectric materials. Background technique [0002] The origin of organic electroluminescent devices (OLEDs) can be traced back to the 1960s. Pope et al. applied DC voltage to anthracene single crystals to make them emit light. However, due to the high driving voltage (100V) and relatively high brightness and efficiency low, without much attention. With the continuous improvement of technology. In 1987, C.W.Tang et al. of Kodak Company used 8-hydroxyquinoline aluminum (AIq 3 ) is a light-emitting material, and a double-layer sandwich structure OLED device is made by vacuum evaporation method. The turn-on voltage is only a few volts, and the brightness can reach up to 1000cd / m 2 , marking OLED has taken an important step towards practical application and has become an important milestone in the field of organic electroluminescence. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/14C09K11/06H01L51/54
Inventor 林存生徐凯孙虎白震高宪鹏郭文波孟凡民
Owner VALIANT CO LTD
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