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An organic electroluminescent compound

An electroluminescence and compound technology, applied in the field of materials, can solve the problems of poor service life, unbalanced hole and electron transport properties, and low efficiency, and achieve the effect of long service life and good fluorescence quantum efficiency.

Active Publication Date: 2019-12-27
EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such as the technical solution disclosed in Chinese patent CN103222082, the organic materials currently used for blue electroluminescence are mainly aromatic vinyl compounds, but this compound has poor heat resistance and is easily cracked in the sublimation process
As another example, Chinese patent CN1394195 discloses a derivative of anthracene, which can also be used as a blue light material, but its efficiency is low and cannot meet the requirements of today's display
As another example, the compound used for the blue light-emitting material in the technical solution disclosed in Chinese patent CN101018760 is still not good in terms of service life due to the unbalanced transport performance of holes and electrons.

Method used

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  • An organic electroluminescent compound
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  • An organic electroluminescent compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The synthesis of embodiment 1 compound (1)

[0043]

[0044] The first step, the synthesis of intermediate a1, its chemical reaction formula is as follows:

[0045]

[0046] Dissolve p-bromoiodobenzene (28.3g, 100mmol), thiophenol (11.0g, 100mmol) and anhydrous potassium carbonate (27.6g, 200mmol) in 200mL of dimethyl sulfoxide, and heat to 120 ℃, reacted for 12 hours, cooled to room temperature, poured the reaction solution into 1L of deionized water, added 500mL of dichloromethane for extraction, combined the organic phases, removed the solvent under reduced pressure, and separated and purified with silica gel chromatography to obtain pure Intermediate a1 (20.0 g, 75 mmol), yield 75%, mass spectrum MS [ESI+] m / z=264.21 (theoretical value 263.96).

[0047] The second step, the synthesis of intermediate a2, its chemical reaction formula is as follows:

[0048]

[0049] Add intermediate a1 (13.3g, 50mmol) to 150mL of acetic acid and heat to 100°C; then add 20m...

Embodiment 2

[0056] The synthesis of embodiment 2 compound (3)

[0057]

[0058] The first step is to synthesize intermediate a1, for specific steps refer to the first step of Example 1;

[0059] In the second step, intermediate a2 is synthesized. For specific steps, refer to the second step in Example 1;

[0060] In the third step, intermediate b3 is synthesized, and its chemical reaction formula is as follows:

[0061]

[0062] Intermediate a2 (10.7g, 30mmol), dibenzofuran-4-amino (6.4g, 35mmol), bis(dibenzylideneacetone)palladium (578mg, 0.9mmol), tri-tert-butylphosphine (182mg, The mixture of 0.9mmol) and toluene (200ml) was heated to 90°C under argon gas flow, after adding sodium tert-butoxide (115mg, 1.2mmol), heated to 110°C under argon atmosphere, and stirred for 18 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 g...

Embodiment 3

[0070] Embodiment 3 uses the OLED device manufacturing method of compound (1)

[0071] A transparent electrode made of indium tin oxide with a film thickness of 120 nm was provided on a glass substrate with a size of 25×75×1.1 mm. Then the glass substrate is subjected to oxygen plasma treatment, and after cleaning, the substrate is placed on a vacuum evaporation device.

[0072] First, HT-1 and Dopant-1 were co-evaporated at a weight ratio of 95:5 as a hole injection layer with a thickness of 150 nm. Then 20nm of HT-2 was evaporated on it as a hole transport layer. Next, EM-1 was used as a light-emitting material, and the above-mentioned compound (1) was used as a dopant material in a 95:5 weight ratio to form a light-emitting layer with a thickness of 30 nm.

[0073] Finally, 30 nm of ET-1 was evaporated as the electron transport layer, followed by 1.5 nm of cesium fluoride (CsF), followed by 120 nm of aluminum as the cathode.

[0074] The compounds HT-1, Dopant-1, HT-2, E...

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Abstract

The invention discloses an organic electroluminescence compound, the structural formula of which is shown in the following general formula (I): wherein, R 1 and R 2 Each independently selected from: a hydrogen atom, a C1-C20 alkyl group or a halogenated alkanyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or Unsubstituted C6~C30 heteroaryl; Ar 1 and Ar 2 Each independently selected from: substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C6~C30 heteroaryl; L 1 , L 2 and L 3 Each is independently selected from: a substituted or unsubstituted C6-C30 arylene group. The above-mentioned compounds can be used as OLED doping materials, and the OLED devices made with them exhibit good fluorescence quantum efficiency, carrier balance transport characteristics and thermal stability, and have a long service life, and have good prospects for application in the AMOLED industry.

Description

technical field [0001] The invention relates to a material, in particular to an organic electroluminescent compound and its application in OLED devices. Background technique [0002] As a brand-new display technology, organic light-emitting diode (OLED) has unparalleled advantages of existing display technologies in various performances, such as all-solid-state, self-luminous, high brightness, high resolution, wide viewing angle (170 degrees Above), fast response, thin thickness, small size, light weight, flexible substrate, low voltage DC drive (3-10V), low power consumption, wide operating temperature range, etc., making it a very wide range of application markets, such as Lighting systems, communication systems, vehicle displays, portable electronic devices, high-definition displays and even military fields. [0003] With the development of organic electroluminescent materials, red light materials and green light materials have basically met the needs of display. Due to...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C317/36C07D307/91C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07C317/36C07D307/91C09K2211/1088C09K2211/1011H10K85/633H10K85/6574H10K50/00
Inventor 王历平
Owner EVERDISPLAY OPTRONICS (SHANGHAI) CO LTD