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An organic electroluminescent compound

A technology of luminescence and compounds, applied in the field of organic electroluminescence compounds, can solve problems such as poor device efficiency and lifespan, unsatisfactory users, short blue light wavelength, etc., and achieve outstanding market potential, promote development, and high color purity Effect

Active Publication Date: 2020-02-21
EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the various compounds disclosed in the above prior art often have the following defects: the emitted blue light wavelength is too short, which is harmful to human eyes; or the efficiency and lifespan shown in the device are not good; and the color purity is relatively poor, Can not meet the user's requirements

Method used

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  • An organic electroluminescent compound
  • An organic electroluminescent compound
  • An organic electroluminescent compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 Preparation of Compound 11

[0043]

[0044] Step 1: Synthesis of Intermediate 1

[0045]

[0046] Dissolve raw material 1 (21.2 g, 100 mmol) and methyl 2,5-dibromoterephthalate (35.2 g, 100 mmol) in 500 ml of toluene solution, then add 100 ml of 2M aqueous sodium carbonate and 100 ml of ethanol was degassed with nitrogen for one hour, and the catalyst tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4, 3.5 g, 3 mmol), under stirring conditions, heated to 100 ° C, reacted for 24 hours, cooled to room temperature, added dichloromethane and deionized water, extracted the organic phase, dried with anhydrous magnesium sulfate, filtered, reduced Compressed, concentrated, separated and purified by silica gel column, the eluent is petroleum ether / ethyl acetate=4:1 (v:v), to obtain about 34.2 g (78 mmol) of pure intermediate 1, and the yield is about 78%. .

[0047] Mass spectrum MS of intermediate 1 [ESI + ] m / z = 438.16 (theoretical value is 438.01).

...

Embodiment 2

[0076] Example 2 Preparation of Compound 13

[0077]

[0078] 13

[0079] Steps 1 to 6: Synthesis of Intermediates 1-6

[0080] The synthesis method and specific steps of intermediate 1-6 are the same as those in Example 1.

[0081] Step 7: Synthesis of Intermediate 8

[0082]

[0083] 4-Methyl-1-aniline (5.4 g, 50 mmol), 4-bromodibenzofuran (12.4 g, 50 mmol), bis(dibenzylideneacetone)palladium (0.8 g, 1.5 mmol), tris A mixture of tert-butylphosphine (0.6 g, 3 mmol) and toluene (100 ml) was heated to 90°C under argon flow, followed by sodium tert-butoxide (0.3 g, 3 mmol) and heated under argon atmosphere to 110°C and stirred for 12 hours. The reaction mixture was cooled to room temperature, and water was added for liquid separation; the solvent of the obtained organic layer was concentrated, and the obtained solid was purified by silica gel column chromatography to obtain intermediate 8 (20.2 g, 39 mmol), 78% yield Rate.

[0084] Mass spectrum MS of intermediate 8 ...

Embodiment 3

[0089] Example 3 Photoluminescence Spectrum Detection

[0090] Dissolve compound 11 and compound 13 in toluene solvent, the concentration is about 10 -4 mol / L, on the E1PLMM010 photoluminescence spectrometer, with 300 nm as the excitation light, the main peaks of the photoluminescence (PL) spectra of the two are shown in Table 1.

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Abstract

The invention provides an organic electroluminescent compound. The structure of the organic electroluminescent compound is represented by the formula (I), wherein R1 to R9 individually represent H, ahalogen atom, a cyano group, a C1-C20 alkyl group, a C1-C20 halogenated alkyl group, a C3-C20 cycloalkyl group, a C3-C20 halogenated cycloalkyl group, a C1-C20 alkoxyl group, a C1-C20 silicyl group, an aryloxyl group with a cyclization carbon number of 6-30, an aryl group with a cyclization carbon number of 6-30, and a heterocyclic aryl group with a cyclization carbon number of 6-30; X1 is one ofO, S, S=O, and O=S=O; X2 and X 3 individually represent C or N; m and n individually represent 0 or 1; and p represents an integer of 0 to 4. The compound is used as a doping material of an OLED luminescent layer, and the obtained OLED device has the advantages of long service life, high thermal decomposition temperature, good thermal stability, and excellent luminescent efficiency and color purity.

Description

technical field [0001] The invention relates to an organic electroluminescent material, in particular to an organic electroluminescent compound. Background technique [0002] Organic Light-Emitting Diodes (Organic Light-Emitting Diodes, hereinafter referred to as "OLED") have the characteristics of self-luminescence, compared with liquid crystal display technology, it has high contrast, wide viewing angle, fast response, low power consumption, and good color reproducibility As well as the huge advantages of being able to realize flexible devices, it has been widely commercialized in the fields of display and lighting. [0003] With the development of organic electroluminescent materials, red light materials and green light materials have basically met the needs of display. However, blue light materials lag behind red and green light in terms of luminous efficiency and lifetime due to their wide bandgap characteristics and difficulty in charge injection. In addition, some B...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/77C07D307/91C09K11/06C07F7/10H01L51/54H01L51/50
Inventor 王历平
Owner EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD