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Organic electroluminescent material and application thereof

An electroluminescent material and luminescent technology, applied in luminescent materials, organic chemistry, circuits, etc., can solve problems such as poor film stability, achieve good film stability and thermal stability, large steric hindrance, and start-up Effect of Brightness Voltage Reduction

Active Publication Date: 2016-03-30
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Since the birth of small molecule organic electroluminescent devices, hole transport layer materials have always been dominated by triarylamine structures, such as N,N'-diphenyl-N,N'-(1-naphthyl)-1 , 1'-biphenyl-4,4'-diamine (NPB) is one of the most widely used triarylamine hole transport materials. NPB has the advantages of fast hole transport speed and low price, but NPB The glass transition temperature Tg of the material is only 98°C, and the film stability of the material is not good.

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

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The preparation of embodiment 1 intermediate 3

[0039]

[0040] Preparation of Compound 1: In a 2L three-necked flask, add 8-quinolineboronic acid (72.6g, 0.42mol), methyl o-bromobenzoate (86.0g, 0.40mol), potassium carbonate (82.8g, 0.6mol), Pd (PPh 3 ) 4 (2.31g, 2mmol), toluene (800mL), N 2 Protect, heat up to reflux, keep warm for 2 hours, stop the reaction, cool down to 25°C, wash with water and separate the liquid, collect the organic phase, remove the solvent to obtain the crude compound 1 as a yellow viscous oil, and directly proceed to the next step without purification ( Yields are based on 100%).

[0041] Preparation of Compound 2: Add 833 mL of methyllithium solution (1.0 mol) into a 2L three-necked flask, and cool down to -78°C in a low-temperature bath under nitrogen protection. The crude product of Compound 1 is dissolved in tetrahydrofuran (400 g) and transferred to a constant temperature In the pressure funnel, add dropwise to the above-mentioned...

Embodiment 2

[0045] The preparation of embodiment 2 compound C01

[0046]

[0047] In a 100mL three-necked flask, add compound 3 (4.03g, 10mmol) prepared in Example 1, diphenylamine (3.72g, 22mmol), sodium tert-butoxide (2.88g, 30mmol), palladium acetate (0.01g, 0.04mmol) , tri-tert-butylphosphine (0.016g, 0.08mmol), xylene (50mL), N 2 Protect, heat up to reflux, keep warm for 8 hours, stop the reaction, cool down to 25°C, add 30mL of deionized water, stir for 5min, separate liquids, collect the organic phase, remove the solvent to obtain the crude product of target C01, use silica gel column layer Analysis and purification, the eluent is petroleum ether: dichloromethane=3:1 (V / V), after removing the solvent, use dichloroethane as solvent recrystallization to obtain the target object C01, off-white solid 4.5g, using chemical The vapor phase deposition system was further sublimated and purified, and the sublimation temperature was 330° C. to obtain 3.6 g of compound C01 with a yield of ...

Embodiment 3

[0049] The preparation of embodiment 3 compound C02

[0050]

[0051] Referring to Example 2, the raw materials were compound 3 and N-phenyl-1-naphthylamine prepared in Example 1 to obtain compound C02 with a yield of 65.6%. High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 50 h 37 N 3 , the theoretical value is 679.2987, and the test value is 679.2982. Elemental analysis (C 50 h 37 N 3 ), theoretical value C: 88.33, H: 5.49, N: 6.18, measured value C: 88.37, H: 5.47, N: 6.16.

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Abstract

The invention relates to an organic electroluminescent material and an application thereof. The material has a molecular structure shown in a formula (I) in the specification. The material has better thin film stability and suitable molecular energy level and can be applied in the organic electroluminescence field as a hole transport material.

Description

technical field [0001] The invention relates to an organic electroluminescence material and its application, in particular to a triarylamine small molecule organic electroluminescence material containing an azafluorene structure, and to the application of the material in the field of organic electroluminescence. Background technique [0002] The phenomenon of organic electroluminescence was first discovered by Professor Pope in 1963. He applied a bias voltage of hundreds of volts to the anthracene crystal and observed the luminescence phenomenon, but due to the high voltage and poor efficiency, it failed to arouse people's interest. Attention, until 1987, Tang et al. of Kodak Company created a double-layer film sandwich structure for the first time, and made a high-brightness green light-emitting device. Since then, the era of organic light-emitting diodes (OLEDs) has been surging. [0003] Organic light-emitting diode (OLED) has many advantages such as self-illumination, wi...

Claims

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Application Information

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IPC IPC(8): C09K11/06H01L51/54C07D221/18C07D405/14C07D409/14C07D413/14C07D417/14
CPCC09K11/06C07D221/18C07D405/14C07D409/14C07D413/14C07D417/14C09K2211/1092C09K2211/1088C09K2211/1037C09K2211/1033C09K2211/1011C09K2211/1007C09K2211/1014C09K2211/1022C09K2211/1029H10K85/636H10K85/626H10K85/633H10K85/615H10K85/631H10K85/6576H10K85/6574H10K85/657H10K85/6572
Inventor 高自良刘英瑞石宇盛磊巨成良胡葆华
Owner VALIANT CO LTD
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