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Novel spirofluorene xanthene organic electroluminescent material and preparation method thereof

A technology of spirofluorene xanthene and luminescent materials, applied in the field of organic synthesis

Inactive Publication Date: 2014-03-26
方圆环球光电技术盐城有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the relevant patents are all photoelectric materials based on spirofluorene xanthene cores containing phenolic hydroxyl groups, and those containing secondary amino groups, pyrrolyl groups, indolyl groups, carbazolyl groups, benzimidazole groups or derivatives of the groups. The optoelectronic material with spirofluorene xanthene core has not been reported

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Compound 1-1 Synthesis

[0026]

[0027] In a 50mL three-necked flask, add the compound 2 (1.72 g, 4.1 mmol), compound 3 (0.90 g, 4.1 mmol) and sodium tert-butoxide (0.47 g, 4.9 mmol) in 15 mL of anhydrous toluene solution, stirred at room temperature for 30 min to prepare solution a. Add Pd(OAc) to 10 mL of dry anhydrous toluene 2 (23 mg, 0.1 mmol) and tri-tert-butylphosphine (83 mg, 0.41 mmol) to prepare solution b. Solution b was added to solution a and refluxed for 10 h. Cool to room temperature, extract with toluene, wash with water, and dry the organic layer with MgSO 4 Remove moisture, filter, and spin evaporate. 10 mL of a 1:10 mixed solvent of dichloromethane and petroleum ether was used as an eluent for column chromatography to obtain a white solid with a yield of 55%. It was irradiated with blue light at a wavelength of 254 nm and HPLC (100% methanol ), R t = 6.18 min; Ms Calcd: 549; Ms Found: 550 (M+1) + .

Embodiment 2

[0028] Example 2: Compounds 1-2 Synthesis

[0029]

[0030] In a 50mL three-necked flask, add the compound 2 (1.72 g, 4.1 mmol), compound 4 (0.75 g, 4.1 mmol) and sodium tert-butoxide (0.47 g, 4.9 mmol) in 15 mL of anhydrous toluene solution, stirred at room temperature for 30 min to prepare solution a. Add Pd(OAc) to 10 mL of dry anhydrous toluene 2 (23 mg, 0.1 mmol) and tri-tert-butylphosphine (83 mg, 0.41 mmol) to prepare solution b. Solution b was added to solution a and refluxed for 10 h. Cool to room temperature, extract with toluene, wash with water, and dry the organic layer with MgSO 4 Remove moisture, filter, and spin evaporate. 10 mL of a 1:10 mixed solvent of dichloromethane and petroleum ether was used as an eluent for column chromatography to obtain a white solid with a yield of 55%. It was irradiated with blue light at a wavelength of 254 nm and HPLC (100% methanol ), Rt =6.43 min; Ms Calcd: 513; Ms Found: 514 (M+1) + .

Embodiment 3

[0031] Example 3: Compounds 1-3 Synthesis

[0032]

[0033] In a 50mL three-necked flask, add the compound 2 (1.72 g, 4.1 mmol), compound 5 (1.15 g, 4.1 mmol) and sodium tert-butoxide (0.47 g, 4.9 mmol) in 15 mL of anhydrous toluene solution, stirred at room temperature for 30 min to prepare solution a. Add Pd(OAc) to 10 mL of dry anhydrous toluene 2 (23 mg, 0.1 mmol) and tri-tert-butylphosphine (83 mg, 0.41 mmol) to prepare solution b. Solution a was added to solution b and refluxed for 10 h. Cool to room temperature, extract with toluene, wash with water, and dry the organic layer with MgSO 4 Remove moisture, filter, and spin evaporate. 10 mL of a 1:10 mixed solvent of dichloromethane and petroleum ether was used as an eluent for column chromatography to obtain a white solid with a yield of 60%. The blue light was irradiated by an ultraviolet lamp with a wavelength of 254 nm, and HPLC (100% methanol ), R t =3.37 min; Ms Calcd: 611; Ms Found: 612(M+1) + .

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Abstract

The invention provides a novel spirofluorene xanthene organic electroluminescent material and a preparation method thereof. The material is synthesized by connecting a functional group to the 2 position of spirofluorene xanthenes as a center unit, and has a structure represented by a general formula in the specification; and in the general formula, R represents a secondary amino group, a pyrryl group, an indolyl group, a carbazyl group, a benzimidazolyl group, or derivative groups of the above groups. The compound has the advantages of simple synthetic method, easy processing, easy purification and low cost. The above organic electroluminescent compound emits blue light, can be used in luminescent materials, can be used as a hole transport material or an electron transfer material, and is hopeful to be widely used in organic light-emitting diode devices, organic electrical storage devices, organic solar batteries, organic laser diode devices and organic field effect transistors.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a novel 2-substituted spirofluorene-9,9'-oxanthene compound efficiently synthesized in one step, so that it can be applied in the field of organic electroluminescence. Background technique [0002] As an extremely important part of modern science and technology, the impact of flat panel display technology on human life and production has become more and more significant, and related research has attracted more and more attention. Monochrome cathode ray display (CRT), color liquid crystal display (LCD), plasma flat panel display (PDP), electroluminescence display (FED) and other mainstream display technologies have undergone tremendous changes, but there are irreparable shortcomings. It has been unable to meet people's demand for lighter, more portable, and more excellent performance flat panel displays in the information society. [0003] Organic electroluminescent devices (OLEDs)...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D311/96C07D405/04H01L51/54H01L51/30H01L51/46
CPCY02E10/549
Inventor 刘屹东高涛
Owner 方圆环球光电技术盐城有限公司
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