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Organic electroluminescent material and application thereof

An electroluminescent material and luminescent technology, applied in luminescent materials, organic chemistry, circuits, etc., can solve the problems of poor voltage stability of red light OLED materials, reduce the interaction of red light materials, and poor voltage and current color stability, etc., to achieve Enhance charge transfer absorption and fluorescence emission intensity, reduce concentration quenching phenomenon, and good voltage stability

Inactive Publication Date: 2014-09-03
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, organic light-emitting materials for OLED displays still have many problems, such as: high cost, poor voltage stability, etc.
Especially for red light materials in OLED displays, the problem of poor voltage stability is particularly prominent
The currently developed OLED red light materials basically contain electron-withdrawing groups (acceptors) and electron-donating groups (donors). However, there are relatively strong electrostatic interactions and π-π interactions between these groups. , these effects lead to poor voltage stability of red OLED materials
In order to reduce the interaction between red light materials, doping is generally used to dilute the concentration of red light materials, but this method often complicates the fabrication process of devices
In addition, the doping method is prone to phase separation, which will reduce the stability of the device and bring problems such as poor thermal stability and poor color stability to voltage and current.

Method used

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  • Organic electroluminescent material and application thereof
  • Organic electroluminescent material and application thereof
  • Organic electroluminescent material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Organic electroluminescence material, structural formula is:

[0032] ...compound 4(I), wherein (2-Ethylhexyl).

[0033] The preparation method of compound 4 (I), comprises the following steps:

[0034]

[0035] Synthesis of compound 6 (2,1,3-benzothiadiazole):

[0036] Add compound 5 (o-phenylenediamine) (10.8g, 0.1mol) and thionyl chloride (53mL) into a three-neck round bottom flask, stir rapidly, and add pyridine (1mL) dropwise into the flask at 0°C , and then the mixture was refluxed for 24h; the excess thionyl chloride was removed by distillation under reduced pressure, and after the system was cooled to room temperature, it was poured into distilled water (250mL); it was purified by steam distillation to obtain a crude product, and then Extracted with methyl chloride (3*50 mL), dried over anhydrous magnesium sulfate, and concentrated the filtrate to obtain a white needle-like compound with a yield of about 82%. Mp=43.7-44.0°C; 1 H-NMR (400MHz, CDCl 3 )...

Embodiment 2

[0048] Organic electroluminescence material, structural formula is:

[0049] ...4(Ⅱ), of which (2-Ethylhexyl).

[0050] The preparation method of compound 4 (II), comprises the following steps:

[0051]

[0052] The synthesis of Compound 6 and Compound 3 refers to Example 1.

[0053] Synthesis of compound 8 (N-ethylhexylphenothiazine):

[0054] Weigh phenothiazine (10g, 31.10mmol) and NaH (1g, 41.70mmol) in a 100ml flask, then add DMF (40ml), stir at room temperature for 30min, add bromoisoctane (8.06g, 41.70mmol), and Stir overnight, add water to the system to stop the reaction, extract three times with trichloro, wash the organic layer with brine, and then wash with anhydrous MgSO 4 Dry overnight, remove the solvent by rotary evaporation, and pass through a column (silica gel, n-hexane:ethyl acetate=9:1, v / v) to obtain a yellow oily liquid. 1 H-NMR (400MHz, CDCl 3 )δ7.15(t, J=7.0Hz, 4H), 6.89(d, J=8.0Hz, 4H), 3.73(s, 2H), 1.93(m, 1H), 1.25-1.44(m, 8H), 0.83-0.93...

Embodiment 3

[0062] Organic electroluminescence material, structural formula is ...4(Ⅲ), of which (2-Ethylhexyl).

[0063] The preparation method of compound 4 (Ⅲ), comprises the following steps:

[0064]

[0065]

[0066] The synthesis of Compound 6 and Compound 3 refers to Example 1.

[0067] Synthesis of compound 9 (4-[(2-ethylhexyl)oxy]-1-iodobenzene):

[0068] Mix 4-iodophenol (4.0g, 18.18mmol), K 2 CO 3 (3.76g, 27.20mmol) and bromoethylhexyl (3.68g, 19.05mmol) in DMF (10mL), heated to 100°C under nitrogen protection, and stirred for 50h. After the reaction, the mixture was poured into 100 mL of distilled water and extracted with dichloromethane (3*50 mL). The organic layer was washed twice with distilled water, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and purified by column (silica gel, n-hexane) to obtain a colorless liquid compound (3.50 g, 58%). 1 H-NMR (400MHz, CDCl 3 )δ7.51(d, J=8.8Hz, 2H), 6.65(d, J=8.8Hz, 2H), 3.78...

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Abstract

The invention relates to an organic electroluminescent material and an application thereof and belongs to the technical field of photoelectric materials. The general formula of the organic electroluminescent material is shown in the specification, wherein R is C6-20 straight chain or branched chain alkyl or C6-20 straight chain or branched chain alkoxyl. The organic electroluminescent material is taken as a red light material for preparing non-doped OLED apparatuses. The prepared target product can be processed in a solution form and has good voltage stability. The CIE (Coherent Infrared Energy) 1931 coordinates are close to those of an OLED standard red light material and the organic electroluminescent material is expected to be used as the OLED standard red light material.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials, and in particular relates to an organic electroluminescent material which is stable to voltage and can be processed by solution, and also relates to its application. Background technique [0002] In the past 20 to 30 years, organic electroluminescent (OLED) materials have achieved rapid development. The three primary colors (red, green, and blue) for OLED displays have been available, and their luminescent materials can meet the requirements in terms of brightness and efficiency. . However, organic light-emitting materials for OLED displays still have many problems, such as high cost and poor voltage stability. Especially for red light materials in OLED displays, the problem of poor voltage stability is particularly prominent. The currently developed OLED red light materials basically contain electron-withdrawing groups (acceptors) and electron-donating groups (donors). However,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D417/14C07D285/14H01L51/54
Inventor 刘应良曹少魁毕晓漫徐慎刚
Owner ZHENGZHOU UNIV
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