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Terpyridyl derivative and application thereof to white light organic electroluminescent diode

A technology of terpyridine and its derivatives, which is applied in the direction of luminescent materials, organic chemistry, circuits, etc., and can solve problems other than the luminescent mechanism

Inactive Publication Date: 2014-07-16
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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  • Terpyridyl derivative and application thereof to white light organic electroluminescent diode
  • Terpyridyl derivative and application thereof to white light organic electroluminescent diode
  • Terpyridyl derivative and application thereof to white light organic electroluminescent diode

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Synthesis of compound I1: the synthetic route is as follows:

[0084]

[0085] Synthesis of intermediate M1: Dissolve 3.7g of p-bromobenzaldehyde in 100ml of methanol solution, then add 0.8g of NaOH into methanol, and after it is completely dissolved, add 4.425ml of 40mmol 4-acetylpyridine dropwise to the methanol solution, at room temperature After 24 hours of reaction, the reaction solution was extracted with chloroform, washed with water and dried over anhydrous sodium sulfate, and 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 was dichloromethane:methanol=20:1v / v. After vacuum drying, 4.8g of white solid M1 of 62% was obtained.

[0086] Synthesis of compound I1: 0.7gM1, 0.57g4-(9H-9-carbazolyl)phenylboronic acid, 0.231g, tetrakistriphenylphosphine palladium (Pd(PPh 3 ) 4 ), 6mL of 2M sodium carbonate, 18mL of toluene and 9mL of absolute ethanol were heated and s...

Embodiment 2

[0090] The synthetic route of compound I2 is as follows:

[0091]

[0092] The synthesis of intermediate M1 is the same as in Example 1.

[0093] Synthesis of compound I2: 0.7g M1, 0.65g bis(4-tert-butylphenyl)amine, 0.021g bis(dibenzylideneacetone) palladium (Pd(dba)2) (Is the Chinese correct?) g2-di Cyclohexylphosphonium-2',4',6'-triisopropylbiphenyl (x-phos), 0.7g sodium tert-butoxide (tBuONa) and 30mL toluene 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, and the eluent was dichloromethane:methanol=20:1v / v. After vacuum drying, 0.846g of white solid I2 was obtained with a yield of 80%.

[0094] Product MS (m / e): 588, corresponding to: C41H40N4=588, proving that the compound is I2. 1H NMR (400MHz, CDCl3...

Embodiment 3

[0097] The synthetic route of compound I3 is as follows:

[0098]

[0099]The synthesis of intermediate M1 is the same as in Example 1.

[0100] The synthesis of compound I3: the M1 of 0.7g, 0.58g4-boric acid triphenylamine), 0.231g tetrakistriphenylphosphine palladium (Pd(PPh 3 ) 4 ) 2M sodium carbonate, 18mL toluene and 9mL absolute ethanol 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, and the eluent was dichloromethane:methanol=20:1v / v. After vacuum drying, 0.835g of white solid I3 was obtained with a yield of 84%.

[0101] Product MS (m / e): 552, corresponding to: C39H28N4=552, proving that the compound is I3. 1H NMR (400MHz, CDCl3) δ8.83 (s, 4H), 8.20 (d, J=5.2Hz, 4H) ,8.14(s,2H),7.80(dd,J=20.6,8.4H...

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Abstract

The invention discloses a terpyridyl derivative. The derivative has a structure shown as a formula I which is as shown in the specification. The terpyridyl derivative having a structure shown as the formula I is taken as an organic electroluminescent material which efficiently emits blue fluorescent light and is high in color purity, fluorescent quantum yield, electroluminescence efficiency, film-forming property and thermal stability, easy to modify, and various in structural forms. A light-emitting material made of the material can be taken as a main body material of sensitized phosphorescent molecules. A white light device made of the material is simpler in structure, simpler in manufacturing process, and lower in cost.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a terpyridine 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 times ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D213/38C07D409/14C07D405/14C09K11/06H01L51/54
CPCC09K11/06C07D213/38C07D401/14C07D405/14C07D409/14C09K2211/1029C09K2211/1088C09K2211/1092H10K85/624H10K85/615H10K85/653H10K85/655H10K85/631H10K85/654H10K85/6576H10K85/6572Y02B20/00
Inventor 张晓宏刘传林郑才俊欧雪梅李凡
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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