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Electroluminescent organic material based on benzothiazolyl

An electroluminescent material, benzothiazolyl-based technology, applied in the direction of luminescent materials, zinc organic compounds, chemical instruments and methods, etc., can solve problems such as substituents affecting luminescence, and other properties without a systematic understanding, to achieve Improvement of electron transport performance, overcoming unbalanced carrier transport, and high thermal stability

Active Publication Date: 2009-07-15
TAIYUAN UNIV OF TECH
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  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0004] For metal organic light-emitting materials, the emission color and performance depend on the HOMO / LUMO energy level of the material and the lowest π→π* electronic transition of the ligand. People have been trying to adjust the HOMO of the material by introducing substituents on the ligand. / LUMO energy level, although some success has been achieved, there is no systematic understanding of how substituents affect luminescence and other properties of materials

Method used

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  • Electroluminescent organic material based on benzothiazolyl
  • Electroluminescent organic material based on benzothiazolyl
  • Electroluminescent organic material based on benzothiazolyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Add 3.23mL of o-aminothiophenol and 4.56g of 3-methylsalicylic acid into a 250mL three-necked flask with 30mL of toluene, heat to fully dissolve the 3-methylsalicylic acid, stop heating, and slowly add the catalyst phosphorus trichloride dropwise 0.75mL, after the dropwise addition, the system was heated to 80°C for 2.5h under reflux, filtered, and recrystallized with absolute ethanol to obtain colorless crystals of (3-methyl 2-hydroxyphenyl)benzothiazole with a yield of 65 %. The reaction equation is as follows:

[0046]

[0047] Weigh 4.8g (3-methyl 2-hydroxyphenyl) benzothiazole and add it into a 250mL three-necked flask filled with 20mL of anhydrous methanol, heat to dissolve (3-methyl 2-hydroxyphenyl) benzothiazole, slowly Add dropwise 20 mL of anhydrous methanol dissolved in 1.83 g of zinc acetate, react under reflux for 2.5 h, and heat filter to obtain 2-(3-methyl 2-hydroxyphenyl) benzothiazole zinc, abbreviated as Zn(3-MeBTZ) 2 , the reaction equation is as...

Embodiment 2

[0057] Add 3.23mL of o-aminothiophenol and 4.56g of 5-methylsalicylic acid into a 250mL three-necked flask with 30mL of toluene, heat to fully dissolve the 5-methylsalicylic acid, stop heating, and slowly add the catalyst phosphorus trichloride dropwise 0.7mL, after the dropwise addition, the system was heated to 85°C for reflux reaction for 2h, filtered, and recrystallized with absolute ethanol to obtain colorless crystals of (5-methyl 2-hydroxyphenyl)benzothiazole with a yield of 70% . The reaction equation is as follows:

[0058]

[0059] Weigh 3.6g (5-methyl 2-hydroxyphenyl) benzothiazole and add it into a 250mL three-necked flask filled with 20mL of anhydrous methanol, heat to dissolve (5-methyl 2-hydroxyphenyl) benzothiazole, slowly Add 20 mL of anhydrous methanol dissolved with 1.37 g of zinc acetate dropwise, react under reflux for 2 h, and heat filter to obtain 2-(5-methyl 2-hydroxyphenyl) benzothiazole zinc, abbreviated as Zn(5-MeBTZ) 2 , the reaction equation i...

Embodiment 3

[0068] Add 3.23mL of o-aminothiophenol and 6.18g of 4-trifluoromethylsalicylic acid into a 250mL three-necked flask, add 50mL of toluene, heat to fully dissolve 4-trifluoromethylsalicylic acid, stop heating, and slowly add catalyst three Phosphorus chloride 0.8mL, after the dropwise addition, the system was heated to 85°C to reflux for 2h, filtered, and recrystallized with absolute ethanol to obtain colorless crystals of (4-trifluoromethyl 2-hydroxyphenyl)benzothiazole , yield 80%. The reaction equation is as follows:

[0069]

[0070] Weigh 5.9g (4-trifluoromethyl 2-hydroxyphenyl)benzothiazole and add it into a 250mL three-necked flask filled with 30mL of anhydrous methanol, and heat to make (4-trifluoromethyl 2-hydroxyphenyl)benzothiazole Dissolve thiazole, slowly add 20 mL of anhydrous methanol solution with 1.83 g of zinc acetate dropwise, react under reflux for 2 h, and heat filter to obtain 2-(4-trifluoromethyl 2-hydroxyphenyl) benzothiazole zinc, abbreviated as Zn ...

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Abstract

The invention relates to an organic electroluminescent material Zn (n-RBTZ) 2 based on benzothiazolyl, which has the structure general formula shown in formula (I) and is prepared by leading ligand material which is the product obtained by the reaction between salicylic acid ramification and ortho-amino thiophenol to react with zinc acetate. The Zn (n-RBTZ) 2 prepared by the invention has higher thermal stability, and fluorescence quantum efficiency of the Zn (n-RBTZ) 2 is higher than that of Zn (BTZ) 2, so that the electron transport performance of the material is improved, the phenomenon of unbalanced carrier transport in a cavity layer and a luminous layer in an organic electroluminescent device is overcome, and the stability of the device is improved. The Zn (n-RBTZ) 2 is blue light emitting material with good performance, which has broad band luminescent spectrum and can be expected to be compounded with other colors such as red to realize white light emission. In the formula, R represents C1-C3 alkyl, C1-C3 alkoxy, or C1-C3 alkyl or halogen atom substituted by one or more halogen atom (s).

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and relates to an organic electroluminescent material, in particular to a benzothiazolyl-based organic electroluminescent material. Background technique [0002] In 1994, N. Nakamura et al first reported the blue light material 2-(2-hydroxyphenyl) benzoxazole zinc (Zn(BOX) 2 ) preparation and its luminescent properties, the material has a maximum brightness of 20cd / cm2 at a driving voltage of 29V 2 , the emission peak is 475nm. Subsequently, in 1996, under the inspiration of the experimental method of N.Nakamura et al., the Y.Hamada group prepared another near-white light-emitting material, 2-(2-hydroxyphenyl)benzothiazole zinc (Zn(BTZ) 2 ), the study found that Zn(BTZ) 2 The maximum luminous brightness can reach 10190cd / cm when the driving voltage is 8V 2 , significantly better than Zn(BOX) 2 ; Hua Yulin experimental group of Tianjin University of Technology on ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F3/06
Inventor 许并社许慧侠房晓红陈柳青王华郝玉英
Owner TAIYUAN UNIV OF TECH
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