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Malononitrile-substituted aryl anthracene-phenanthrene organic electroluminescent material and preparation method and application thereof

A technology of luminescent and luminescent dyes, which is applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems that it is difficult to have high exciton utilization rate and high fluorescence radiation efficiency at the same time, so as to improve device performance, external appearance and so on. The effect of good quantum efficiency and high power efficiency

Active Publication Date: 2018-09-28
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although theoretically TADF materials can achieve 100% exciton utilization efficiency, in practice, most TADF materials still have the problem of having high exciton utilization efficiency and high fluorescence radiation efficiency at the same time.

Method used

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  • Malononitrile-substituted aryl anthracene-phenanthrene organic electroluminescent material and preparation method and application thereof
  • Malononitrile-substituted aryl anthracene-phenanthrene organic electroluminescent material and preparation method and application thereof
  • Malononitrile-substituted aryl anthracene-phenanthrene organic electroluminescent material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046]

[0047] In a 250mL round bottom flask, add 2,2'-(3,6-dibromophenanthrene-9,10-dimethylene)malononitrile, 4-diphenylaminophenylboronic acid, Pd(PPh 3 ) 4 , vacuumize and blow argon gas. Add an oxygen-free mixed solvent (toluene, ethanol, saturated Na 2 CO 3solution), stirred and heated to reflux for 12 h. Sampling point plate, the reaction is complete, stop heating. Use saturated NH 4 The reaction was quenched with Cl solution and extracted three times with dichloromethane (DCM). Combine the organic phases, using anhydrous Na 2 SO 4 Dry, filter with suction, spin the filtrate to dryness, and separate by column chromatography to obtain the target product.

[0048] Elemental analysis structure (molecular formula: C 56 h 34 N 6 ): theoretical value: C 85.04; H 4.33; N 10.63, tested value: C 85.03; H 4.30; N 10.67. The relative molecular mass obtained by mass spectrometry is: 790.29.

Embodiment 2

[0050]

[0051] The preparation method of Example 2 is the same as that of Example 1, except that 4-diphenylaminophenylboronic acid is replaced with 4-(N-carbazolyl)phenylboronic acid.

[0052] Elemental analysis structure (molecular formula: C 56 h 30 N 6 ): Theoretical: C 85.48; H 3.84; N 10.68, tested: C 85.40; H 3.81; N 10.79. The relative molecular mass obtained by mass spectrometry is: 786.95.

Embodiment 3

[0054]

[0055] The preparation method of Example 3 is the same as that of Example 1, except that 4-diphenylaminophenylboronic acid is replaced with 9,9-diphenylfluorene borate.

[0056] Elemental analysis structure (molecular formula: C 70 h 40 N 4 ): theoretical value: C 89.72; H 4.30; N 5.98, tested value: C 89.71; H 4.27; N 6.02. The relative molecular mass obtained by mass spectrometry is: 936.35.

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Abstract

The invention discloses a malononitrile-substituted aryl anthracene-phenanthrene organic electroluminescent material and a preparation method and application thereof. The organic electroluminescent material uses malononitrile-substituted aryl anthracene-phenanthrene as a parent nucleus and a structural formula of the organic electroluminescent material is as shown in a formula (I). The malononitrile-substituted aryl anthracene-phenanthrene organic electroluminescent material provided by the invention is simple in preparation process; HOMO and LUMO energy level electron cloud can be effectivelyseparated; a singlet state and triplet state energy gap (delta EST) is small; triplet-state excitonic luminescence can be converted into singlet-state excitonic luminescence by RIST (Reverse InterSystem Traversing); the malononitrile-substituted aryl anthracene-phenanthrene organic electroluminescent material has the thermal activation delayed fluorescence property; when the malononitrile-substituted aryl anthracene-phenanthrene light-emitting material provided by the invention is applied to an OLED (Organic Light-Emitting Diode) light-emitting device, high device efficiency is obtained. (theformula (I) is shown in the specification).

Description

technical field [0001] The invention relates to a malononitrile substituted aryl anthraphenanthrene organic electroluminescent material and a preparation method and application thereof, belonging to the technical field of organic electroluminescent materials. Background technique [0002] In 1987, C.W.Tang et al. of Kodak Corporation of the United States reported for the first time a double-layer organic small molecule thin film device prepared by vacuum evaporation method, and the brightness of the device was greater than 1000 cd / m 2 , operating voltage below 10 V. This discovery is a breakthrough in the field of OLED, which makes people see the unlimited potential of OLED technology in the commercial market. Organic electroluminescence refers to the phenomenon that organic materials emit light under the excitation of current or electric field. Usually, devices made of small organic molecules or polymers as electroluminescent materials are called organic electroluminescent...

Claims

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Application Information

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IPC IPC(8): C07C255/42C07D209/86C07C255/34C07D219/02C07D221/20C07D279/22C07D265/38C07D241/46C07D401/14C07D413/14C07D417/14C07D405/14C07D311/80C07D409/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07C255/34C07C255/42C07D209/86C07D219/02C07D221/20C07D241/46C07D265/38C07D279/22C07D311/80C07D401/14C07D405/14C07D409/14C07D413/14C07D417/14C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088C09K2211/1092H10K85/624H10K85/626H10K85/633H10K85/615H10K85/631H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/11
Inventor 王会罗添友栾新军林智双
Owner NORTHWEST UNIV
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