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1,3,5-triazine derivative and application thereof in white organic electroluminescent light emitting diode

A technology of triazine derivatives and compounds, applied in the field of 1,3,5-triazine derivatives and its application in white light organic electroluminescent diodes, which can solve problems other than light-emitting mechanism

Inactive Publication Date: 2013-12-11
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because fluorescent materials can only utilize singlet excitons that account for 25% of the total number of excitons in the light-emitting layer, the theoretical internal quantum efficiency of this mechanism can only reach 25%, which is obviously not an efficient light-emitting mechanism.

Method used

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  • 1,3,5-triazine derivative and application thereof in white organic electroluminescent light emitting diode
  • 1,3,5-triazine derivative and application thereof in white organic electroluminescent light emitting diode
  • 1,3,5-triazine derivative and application thereof in white organic electroluminescent light emitting diode

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] The synthetic route of compound I1 is as follows:

[0074]

[0075] Synthesis of compound I1: 0.240g 2-chloro-4,6-diphenyl-1,3,5-triazine, 0.287g4-(9H-9-carbazolyl)phenylboronic acid, 0.116g tetrakis(triphenyl) phosphine palladium), 6mL of sodium carbonate solution with a concentration of 2mol / L, 8mL of toluene and 4mL of ethanol (analytical grade) were heated and stirred at 90°C for 12h under nitrogen protection. After the reaction solution was extracted with chloroform, washed with water and dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was separated on a silica gel column. The eluent used was a mixture of dichloromethane and petroleum ether at a volume ratio of 1:4. After drying in a vacuum oven, 0.309 g of white solid I1 was obtained with a yield of 65%.

[0076] MS (m / e) of product I1: 475, corresponding to: C33H22N4=475; 1 H NMR (400MHz, CDCl 3 )δ9.03(d,J=8.5Hz,2H),8.82(dd,...

Embodiment 2

[0078] The synthetic route of compound I2 is as follows:

[0079]

[0080] Synthesis of compound I2: 0.900g 2-chloro-4,6-diphenoxy-1,3,5-triazine, 0.867g4-(9H-9-carbazolyl)phenylboronic acid, 0.346g tetrakis(tri Phenylphosphine palladium), 9 mL of sodium carbonate solution with a concentration of 2 mol / L, 12 mL of toluene (analytical pure) and 6 mL of ethanol (analytical pure) were heated and stirred at 45 °C for 10 h under nitrogen protection. After the reaction solution was extracted with chloroform, washed with water and dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was separated on a silica gel column, and the eluent used was a mixture of dichloromethane and petroleum ether at a volume ratio of 1:3. After drying in a vacuum oven, 1.214 g of white solid I2 was obtained, with a yield of 80%.

[0081] MS (m / e) of product I2: 506, corresponding to: C33H22N4O2=506; 1 H NMR (400MHz, CDCl ...

Embodiment 3

[0083] The synthetic route of compound I3 is as follows:

[0084]

[0085] Synthesis of compound I3: 0.240g 2-chloro-4,6-diphenyl-1,3,5-triazine, 0.280g 4-triphenylamine borate, 0.116g tetrakis(triphenylphosphine palladium), the concentration is 2mol / 6 mL of sodium carbonate solution in L, 8 mL of toluene (analytical pure) and 4 mL of ethanol (analytical pure) were heated and stirred at 90 ° C for 12 h under nitrogen protection. After the reaction solution was extracted with chloroform, washed with water and dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was separated on a silica gel column, and the eluent used was a mixture of dichloromethane and petroleum ether at a volume ratio of 1:4. After drying in a vacuum oven, 0.350 g of light yellow solid I3 was obtained, with a yield of 74%.

[0086] MS (m / e) of product I3: 476, corresponding to: C33H24N4=476; 1 H NMR (400MHz, CDCl 3 )δ8.75(d...

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Abstract

The invention discloses a 1,3,5-triazine derivative. The derivative is a compound with a structure of a formula I. The compound of the formula I can emit high-efficiency blue fluorescence and meanwhile has higher triplet state energy; so that the compound of the formula 1 can sensitize green and red phosphorescent doped materials while emitting the high-efficiency blue fluorescence, so that the technological conditions for preparing WOLEDs (White Organic Light Emitting Diode) are met. Meanwhile, the invention also discloses a preparation method of the compound of the formula 1 and application in preparation of the white light organic electroluminescent diode.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a 1,3,5-triazine derivative and its application in white light organic electroluminescent diodes. Background technique [0002] In recent years, the research on white light organic electroluminescent materials and devices has received great attention from international academic circles, governments and industries. Countries and regions such as the United States, Europe, Japan, etc. have launched major research programs (the Next Generation Lighting Initiative of the United States, the European Union OLLA, Japan 21Century Lighting Program) to strengthen research in this field, because white organic electroluminescent technology (WOLED) is expected to become one of the most important solid-state light source technologies in the new generation. The theory of WOLED predicts that the electro-optical conversion efficiency will be several times, even more than ten tim...

Claims

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Application Information

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IPC IPC(8): C07D403/10C07D251/24C07D251/20C07D403/14C09K11/06H01L51/54
Inventor 张晓宏刘小可郑才俊
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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