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Novel organic electroluminescent compound and preparation thereof

A compound and electroluminescence technology, applied in the field of 2,7-position homosubstituted spirofluorene-9,9'-xanthene compounds

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 based on secondary amino groups, pyrrolyl groups, indolyl groups, carbazolyl groups, benzimidazole groups or derivative groups 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 50 mL three-necked flask, add the compound 2 (2.0 g, 4.1 mmol), compound 3 (1.80 g, 8.2 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. Filtration, rotary evaporation, 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%, and a blue light was irradiated by an ultraviolet lamp with a wavelength of 254 nm. HPLC (100% methanol), R t =3.44 min; Ms Calcd: 766; Ms Found: 767(M+1) + .

Embodiment 2

[0028] Example 2: Compounds 1-2 Synthesis

[0029]

[0030] In a 50 mL three-necked flask, add the compound 2 (2.0 g, 4.1 mmol), add compound 4 (1.50 g, 8.2 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. To 10 mL of dry anhydrous toluene was added sodium tert-butoxide (0.47 g, 4.9 mmol), Pd(OAc) 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 10h. Cool to room temperature, extract with toluene, wash with water, and dry the organic layer with MgSO 4Remove moisture. Filtration, rotary evaporation, 10 mL of a 1:10 mixed solvent of dichloromethane and sherwood oil was used as an eluent for column chromatography to obtain a white solid with a yield of 64%, and a blue light was irradiated by an ultraviolet lamp with a wavelength of 254 nm. HPLC (80% methanol, 20% water), R t...

Embodiment 3

[0031] Embodiment 3: compound 1-3 Synthesis

[0032]

[0033] In a 50 mL three-necked flask, add the compound 2 (2.0 g, 4.1 mmol), compound 5 (2.31 g, 8.2 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. To 10 mL of dry anhydrous toluene was added sodium tert-butoxide (0.47 g, 4.9 mmol), Pd(OAc) 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. Filtration, rotary evaporation, 10 mL of a 1:10 mixed solvent of dichloromethane and sherwood oil was used as an eluent for column chromatography to obtain a white solid with a yield of 58%, and a wavelength of 254nm was irradiated by an ultraviolet lamp to emit blue light, HPLC (80% methanol, 20% water), R t...

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Abstract

The invention provides a novel organic electroluminescent compound and a preparation method thereof. The compound is synthesized by connecting heterogeneous functional groups to 2,7 positions of spirofluorene xanthene 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 is synthesized through a one-step method, the synthesis method is simple, the above prapred micro-molecular compound luminescence material has a good dissolvability, and the organic electroluminescent compound emits blue light, and can be used in luminescent materials, so the compound is hopeful to be used for making efficient organic light-emitting diode devices, and can be widely used in 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 2,7 homogeneously substituted spirofluorene-9,9'-oxanthene compound, which 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) are ultra-thin, fully cu...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D311/96C07D405/14H01L51/54H01L51/30H01L51/46
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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