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Organic electroluminescent material and application thereof

An electroluminescent material and luminescent technology, applied in the field of materials, can solve problems such as poor film stability, and achieve the effects of excellent film stability, reduced turn-on voltage, and good film stability

Active Publication Date: 2016-02-24
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (CAS-RN: 123847-85-8, referred to as NPB) It is one of the most widely used triarylamine hole transport materials. NPB has the advantages of fast hole transport speed and low price. However, according to literature reports, the glass transition temperature Tg of NPB is only 98 °C. poor film stability

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

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preparation example Construction

[0029] The preparation method of the organic electroluminescent material in the present invention is as follows:

[0030] Taking the target C01 as an example, its synthesis route is shown in the following formula. The synthesis methods of other target compounds in the present invention are similar to the synthesis methods of C01. The specific synthesis methods are detailed in the following examples.

[0031]

[0032]

[0033] The present invention prepares the mentioned triarylamine small molecule organic electroluminescent material with spiro ring structure through the above method.

[0034] Preparation examples

[0035] The partial structure of the specific organic electroluminescent material synthesized in the present invention is as follows. For ease of reference below, the structural formulas of the above compounds are numerically subscripted and correspond to the compounds in the examples, for example, structural formula C01 corresponds to compound C01, structural formula C02 co...

Embodiment 1

[0042] Example 1 Preparation of compound 2 as an intermediate

[0043]

[0044] Preparation of compound 1: In a 2L three-necked flask equipped with a constant pressure dropping funnel, add magnesium metal (5.1g, 0.21mol), and dissolve 1-bromodibenzofuran (49.1g, 0.2mol) in 450g tetrahydrofuran, Place it in a constant pressure dropping funnel and use nitrogen protection. Heat the three-necked flask until the temperature in the bottle reaches 65°C. Add the 1-bromodibenzofuran solution in tetrahydrofuran through the constant pressure dropping funnel. Add 1-bromo at first One-fifth of the total amount of dibenzofuran in tetrahydrofuran solution, after the reaction is initiated, slowly drip the remaining part, and the dripping is completed for 1.5 hours, and react for 1 hour at the reflux temperature for use. Dissolve 2-bromofluorenone (51.8g, 0.2mol) in 220g tetrahydrofuran, then slowly pour it into the above three-necked flask, and react at reflux temperature for 3h. After the react...

Embodiment 2

[0047] Example 2 Preparation of Compound C01

[0048]

[0049] In a 100mL three-neck flask, add compound 2 (4.1g, 10mmol), N-phenyl-2-naphthylamine (2.63g, 12mmol), sodium tert-butoxide (1.92g, 20mmol), palladium acetate (0.01g, 0.04 mmol), tri-tert-butylphosphine (0.016g, 0.08mmol), mixed xylene (40mL), N 2 Protect, heat to reflux, keep the reaction for 8 hours, stop the reaction, cool to 25°C, add 30 mL of deionized water, stir for 5 minutes, separate the liquids, collect the organic phase, and remove the solvent to obtain the target C01 crude product, using silica gel column layer After purification, the eluent is cyclohexane:dichloromethane=2:1 (V / V) to obtain the crude product of the target product, which is recrystallized using absolute ethanol as the solvent to obtain the target product C01, 3.2 g of off-white solid. A chemical vapor deposition system was used for further sublimation purification at a sublimation temperature of 345° C. to obtain 2.8 g of compound C01 with ...

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Abstract

The invention relates to an organic electroluminescent material and an application thereof. The electroluminescent material has a molecular structure as shown in a formula (I), has relatively good thin film stability and suitable molecular energy level, can serve as a hole-transport material, and is applied to the field of organic electroluminescent.

Description

Technical field [0001] The invention relates to the field of materials, in particular to an organic electroluminescent material and its application. Background technique [0002] Organic electroluminescence diode (OLED) was produced in the 1980s. After more than two decades of development, the technology has gradually matured. At present, organic electroluminescence technology is mainly used in two fields, respectively For full-color display and white light lighting, products based on OLED display technology have gradually achieved industrialization. For example, the technology has been widely used in products such as smart phones and curved TVs. [0003] Small-molecule organic electroluminescent devices have a multilayer sandwich structure, and each layer is responsible for different functions. For example, the hole transport layer is responsible for transporting holes, the electron transport layer is responsible for transporting electrons, and the light emitting layer is responsi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D307/94C07D333/78C07D409/12C07D209/96C07D405/12C07D307/91C07F9/6568C07C209/10C07C211/61H01L51/54
Inventor 盛磊张鑫鑫高树坤王正石宇孟凡民
Owner VALIANT CO LTD
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