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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AI-Extracted 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 H...
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Method used

Adopt Zn (3-MeBTZ) 2 to make double-layer organic electroluminescence device, device structure ITO/NPB/[Zn (3-MeBTZ) 2] 2/Al, test its electroluminescent spectrum as shown in Figure 4 It is shown that the emission ...
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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).

Application Domain

Luminescent compositionsZinc organic compounds

Technology Topic

Organic electroluminescenceZinc Acetate Dihydrate +10

Image

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

Examples

  • Experimental program(11)

Example Embodiment

[0044] Example 1
[0045] Add 3.23mL o-aminothiophenol and 4.56g 3-methylsalicylic acid to a 250mL three-necked flask with 30mL of toluene, heat to fully dissolve 3-methylsalicylic acid, stop heating, and slowly add the catalyst phosphorus trichloride dropwise 0.75mL, after the addition, the system was heated to 80°C and refluxed for 2.5h, 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 into a 250mL three-necked flask containing 20mL of anhydrous methanol, heat to dissolve (3-methyl2-hydroxyphenyl)benzothiazole, slowly Add dropwise 20 mL of anhydrous methanol with 1.83 g of zinc acetate, react under reflux for 2.5 hours, and then hot filter to obtain zinc 2-(3-methyl-2-hydroxyphenyl)benzothiazole, abbreviated as Zn(3-MeBTZ) 2 , The reaction equation is as follows:
[0048]
[0049] Zn(3-MeBTZ) obtained by the reaction 2 Put it on the aluminum foil paper, put it into a glass tube covered with aluminum foil paper on the inner surface, put the glass tube in a tube furnace, draw a vacuum for 30 minutes, heat up to 250°C, hold for 50 minutes, and then heat up to 390°C for 6 hours , Cool down to room temperature with the furnace under vacuum, collect Zn(3-MeBTZ) 2 Yellow bulk crystal, the size of the obtained single crystal is 0.20×0.13×0.07mm. Carry out chemical structure and material performance test, the infrared spectrum is as shown in figure 1 As shown, the single crystal structure is as figure 2 Shown.
[0050] Its single crystal structure is bimolecular structure, triclinic crystal system, P-1 space group, crystal data and collected information are as follows:
[0051]
[0052] The bond length and bond angle of the chemical bond formed by coordination with metallic zinc are shown in the following table:
[0053]
[0054] The photoluminescence spectrum of the obtained material is as image 3 Shown: the emission peak is at 510nm, located in the blue-green light region.
[0055] Using Zn (3-MeBTZ) 2 Fabrication of double-layer organic electroluminescent device, device structure ITO/NPB/[Zn(3-MeBTZ) 2 ] 2 /Al, test its electroluminescence spectrum such as Figure 4 As shown, the emission peak is at 518nm, the spectral bandwidth is 135nm, and the current-voltage-brightness curve of the device is as Figure 5 As shown, it has better rectification characteristics, and the starting voltage of the device is 12.7V.

Example Embodiment

[0056] Example 2
[0057] Add 3.23mL o-aminothiophenol and 4.56g 5-methylsalicylic acid to a 250mL three-necked flask with 30mL of toluene, heat to fully dissolve 5-methylsalicylic acid, stop heating, and slowly add the catalyst phosphorus trichloride dropwise 0.7mL, after the dropwise addition, heat the system to 85°C and reflux for 2h, filter, and recrystallize with absolute ethanol to obtain (5-methyl-2-hydroxyphenyl)benzothiazole colorless crystals with a yield of 70% . The reaction equation is as follows:
[0058]
[0059] Weigh 3.6g (5-methyl 2-hydroxyphenyl) benzothiazole into a 250 mL three-necked flask containing 20 mL of anhydrous methanol, heat to dissolve (5-methyl 2-hydroxyphenyl) benzothiazole, slowly Add dropwise 20mL of anhydrous methanol with 1.37g of zinc acetate, react under reflux for 2h, and then hot filter to obtain 2-(5-methyl-2-hydroxyphenyl)benzothiazole zinc, abbreviated as Zn(5-MeBTZ) 2 , The reaction equation is as follows:
[0060]
[0061] Zn(5-MeBTZ) obtained by the reaction 2 Put it on the aluminum foil paper, put it into a glass tube covered with aluminum foil paper on the inner surface, put the glass tube in a vacuum tube furnace, draw a vacuum for 35 minutes, heat it up to 280°C, keep it warm for 40 minutes, then heat it up to 410°C and keep it for 6 hours , Cool down to room temperature with the furnace under vacuum, collect Zn(5-MeBTZ) 2 Yellow bulk crystals, the chemical structure and material properties are tested, the single crystal structure is like Figure 6 As shown, for the sake of clarity, all hydrogen atoms are omitted in the drawing. The single crystal structure is a bi-molecular structure, and there is a weak π-π molecular interaction between the two molecules. The single crystal test information and unit cell parameters are shown in the following table:
[0062]
[0063] The bond length and bond angle of the chemical bond formed by coordination with metallic zinc are shown in the following table:
[0064]
[0065] The photospectrogram of 2-(5-methyl-2-hydroxyphenyl) benzothiazole zinc is as follows Figure 7 As shown, the emission peak is located at 496nm in the blue region.
[0066] Using Zn (5-MeBTZ) 2 Fabrication of double-layer organic electroluminescent device, device structure ITO/NPB/[Zn(5-McBTZ) 2 ] 2 /Al, test its electroluminescence spectrum such as Figure 8 As shown, the emission peaks are at 522 nm and 639 nm. The voltage and current curves of the device are as Picture 9 As shown, it has good rectification characteristics, and the device turn-on voltage is 10.7V.

Example Embodiment

[0067] Example 3
[0068] Add 3.23mL o-aminothiophenol and 6.18g 4-trifluoromethylsalicylic acid into a 250mL three-necked flask, add 50mL 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 and refluxed for 2h, filtered, and recrystallized with absolute ethanol to obtain (4-trifluoromethyl 2-hydroxyphenyl) benzothiazole colorless crystals , The yield is 80%. The reaction equation is as follows:
[0069]
[0070] Weigh 5.9 g (4-trifluoromethyl 2-hydroxyphenyl) benzothiazole into a 250 mL three-necked flask containing 30 mL of anhydrous methanol, and heat to make (4-trifluoromethyl 2-hydroxyphenyl) benzothiazole The thiazole is dissolved, and 20 mL of anhydrous methanol solution containing 1.83 g of zinc acetate is slowly added dropwise, and the reaction is carried out under reflux for 2 hours, and then hot filtered to obtain zinc 2-(4-trifluoromethyl 2-hydroxyphenyl) benzothiazole, abbreviated as Zn (4-tfBTZ) 2 , The reaction equation is as follows:
[0071]
[0072] Zn(4-tfBTZ) obtained by the reaction 2 Put it on the aluminum foil paper, put it into a glass tube covered with aluminum foil paper on the inner surface, put the glass tube in a vacuum tube furnace, draw a vacuum for 40 minutes, heat it up to 280°C, keep it warm for 40 minutes, then heat it up to 425°C and keep it for 6 hours , And cool to room temperature with the furnace under vacuum to obtain Zn(4-tfBTZ)2 Yellow massive single crystal.
[0073] To Zn(4-tfBTZ) 2 The performance of the test, the photospectrogram such as Picture 10 As shown, the emission peak is located at 478nm.

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