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An organic electroluminescent compound

An electroluminescence and compound technology, applied in the field of organic electroluminescence compounds, can solve the problems of lack of color purity and service life, and achieve the effects of high hole mobility and glass transition temperature, low operating voltage and long service life

Active Publication Date: 2020-11-03
EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, similarly, when the above various compounds are used in blue OLEDs, the color purity and service life are still lacking, so there is room for improvement.

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

[0049] Example 1 Preparation of Compound 8

[0050] Step 1: Synthesis of Intermediate 1

[0051]

[0052] Dissolve o-dibromobenzene (23.6g, 100.0mmol) and 2-naphthaleneboronic acid (17.2g, 100.0mmol) in 200ml of toluene, then add 2M aqueous sodium carbonate solution (50.0ml), and tetrahydrofuran (50.0ml); After removing the air with nitrogen blowing, the catalyst tetrakis(triphenylphosphine)palladium (347mg, 3.0mmol) was added rapidly; and under the protection of nitrogen, heated to 90°C and stirred overnight; then, ethyl acetate and water were added , after stirring, standing, and layering, the organic phase was extracted, and dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure, and silica gel column chromatography was used, and the eluent was petroleum ether, and finally the pure intermediate 1 (21.1 g, 75.0mmol), the reaction yield of this step is 75%.

[0053] Mass Spectrometric Characterization of Intermediate 1: MS[ESI + ] m / z=2...

Embodiment 2

[0069] Example 2 Preparation of Compound 2

[0070] Step 1: Synthesize intermediate 1, which is the same as Step 1 in Example 1;

[0071] Step 2: Synthesize intermediate 2, which is the same as step 2 in Example 1;

[0072] Step 3: Synthesize intermediate 3, which is the same as step 3 in Example 1;

[0073] Step 4: Synthesis of Intermediate 8

[0074]

[0075] Aniline (4.7g, 50.0mmol), 4-bromodibenzofuran (12.4g, 50.0mmol), bis(dibenzylideneacetone) palladium (860mg, 1.5mmol), tri-tert-butylphosphine (600mg, 3mmol ) and toluene (100ml), heated to 90°C under argon flow, added sodium tert-butoxide (288mg, 3mmol), heated to 110°C under argon atmosphere, and stirred for 12 hours. Then, 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 (10.0 g, 40.5 mmol), 81% yield.

[007...

Embodiment 3

[0081] Example 3 Preparation of Compound 16

[0082] Step 1: Synthesis of Intermediate 4

[0083]

[0084] Dissolve o-dibromobenzene (23.6g, 100.0mmol) and 9-phenanthreneboronic acid (22.2g, 100.0mmol) in 200ml of toluene, then add 2M aqueous sodium carbonate solution (50.0ml), and tetrahydrofuran (50.0ml); After removing the air with nitrogen blowing, quickly add the catalyst tetrakis(triphenylphosphine) palladium (347mg, 3.0mmol); under the protection of nitrogen, heat to 90°C and react overnight, then add ethyl acetate and water, stir, Stand still, separate layers, extract the organic phase, and dry with anhydrous magnesium sulfate, remove solvent under reduced pressure, use silica gel column chromatography, eluent is sherwood oil, finally obtains pure intermediate 4 (24.0g, 72.3mmol ), the reaction yield of this step is 72%.

[0085] Mass Spectrometric Characterization of Intermediate 4: MS[ESI + ] m / z=333.52 (C 20 h 13 Br, the theoretical value is 332.02). Step 2...

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Abstract

The present invention provides an organic electroluminescent compound, which has a structure represented by the following formula (I) or (II): wherein, R 1 ~R 4 Selected from: H, halogen, cyano, C1-C20 chain alkyl, C1-C20 halogenated chain alkyl, C3-C20 cycloalkyl, C3-C20 halogenated cycloalkyl, C1-C20 Alkoxy, C1-C20 silyl group, aryloxy group with 6-30 ring carbons, aromatic hydrocarbon group with 6-30 ring carbons and heterocyclic aromatic hydrocarbon group with 6-30 ring carbons; Ar 1 and Ar 2 Each is independently selected from: an aromatic hydrocarbon group with 6 to 30 ring carbons and a heterocyclic aromatic hydrocarbon group with 6 to 30 ring carbons. The organic electroluminescent compound of the present invention has excellent electron blocking performance and higher glass transition temperature; the OLED device prepared by using the organic electroluminescent compound of the present invention shows lower operating voltage and higher current efficiency, and has a longer service life; therefore, it has a wide range of application values ​​and excellent market potential.

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] In OLED devices, the most critical performance indicators are the service life of OLED devices, current efficiency, operating voltage, and achievable color values. In order to improve the performance of these aspects of OLED devices, the existing OLED devices generally adopt a multilayer structure, including: hole injection layer (HIL), hole transport...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/91C09K11/06C07C211/54C07D333/76C07C211/61C07C211/58H01L51/54H01L51/50
CPCC09K11/06C07C211/54C07C211/58C07C211/61C07D307/91C07D333/76C09K2211/1011C09K2211/1088C09K2211/1092H10K85/623H10K85/622H10K85/626H10K85/633H10K85/6576H10K85/6574H10K50/18H10K50/15H10K50/11
Inventor 王历平
Owner EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD