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Dicarbazolyl derivative, preparation method and application of dicarbazolyl derivative, and electroluminescent device

An electroluminescent device, dicarbazole-based technology, applied in the field of dicarbazolyl derivatives and their preparation, electroluminescent devices, can solve the problems of limited application of blue phosphorescence host materials and weak electron transport ability, etc. Achieve the effect of improving the luminous efficiency of the device and reducing the efficiency roll-off

Active Publication Date: 2014-04-02
TCL CORPORATION
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide a dicarbazole-based derivative, its preparation method and application, and an electroluminescent device, aiming to solve the problems caused by the electron transport of the current dicarbazole-based phosphorescent host compound. Defects such as weak ability lead to limited application in blue phosphorescent host materials

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  • Dicarbazolyl derivative, preparation method and application of dicarbazolyl derivative, and electroluminescent device
  • Dicarbazolyl derivative, preparation method and application of dicarbazolyl derivative, and electroluminescent device
  • Dicarbazolyl derivative, preparation method and application of dicarbazolyl derivative, and electroluminescent device

Examples

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Effect test

Embodiment 1

[0047] When R= , the compound is 3,3′-diphenylphosphoryloxy-6,6′ - Bis(9-phenyl)carbazole (BCDPO), the molecular structure is as follows image 3 shown.

[0048] Its preparation method comprises the following steps:

[0049] 3,3' - Bis(9-phenyl)carbazole (1.0 mmol), N -Bromosuccinimide (NBS) (2.05 mmol), silica gel (100 g) were dissolved in chloroform (150 ml), stirred at room temperature with tin foil in the dark for 24 hours, filtered directly with a sand core funnel, evaporated Dry organic solvent to get into 3,3' - Dibromo-bis(9-phenyl)carbazole is a white solid powder in 75% yield. MS (APCI): calcd for C 36 h 22 N 2 Br 2 : 642.0, found, 643.4 (M+1) + .

[0050] In a dry round bottom flask, sequentially add 3,3' - Dibromo-bis(9-phenyl)carbazole (1.0 mmol), diphenylphosphine oxide (2.0 mmol), nickel dichloride hexahydrate (NiCl 2 ·6H 2 O) (0.3 mmol), zinc powder (6.0 mmol), 2,2′-bipyridine (0.6 mmol), N,N' -Dimethylacetamide (DMAc) (30.0 ml), stirre...

Embodiment 2

[0052] When R 1 = , the compound is 3,3′-bis(2,4-pyrimidinyl)-6,6′ - Bis(9-phenyl)carbazole (BCDNP), the molecular structure is as follows Figure 4 shown.

[0053] Its preparation method comprises the following steps:

[0054] 3,3' - Bis(9-phenyl)carbazole (1.0 mmol), N -Bromosuccinimide (NBS) (2.05 mmol), silica gel (100 g) was dissolved in chloroform (150 ml), stirred at room temperature with tin foil in the dark for 24 hours, filtered directly with a sand core funnel, evaporated Dry organic solvent to get 3,3' - Dibromo-bis(9-phenyl)carbazole is a white solid powder in 75% yield. MS (APCI): calcd for C 36 h 22 N 2 Br 2 : 642.0, found, 643.4 (M+1) + .

[0055] In a dry round bottom flask, sequentially add 3,3' - Dibromo-bis(9-phenyl)carbazole (1.0 mmol), 2,4-pyrimidineboronic acid (2.1 mmol), Pd(PPh3 ) 4 (0.08 mmol), K 2 CO 3 (2M) (8 ml) toluene (50 ml), ethanol (20 ml), under nitrogen protection conditions, stirred at 110 °C for 24 hours, after the reac...

Embodiment 3

[0057] When R= , the compound is 3,3′-dicyano-6,6′ - Bis(9-phenyl)carbazole (BCDCN); Molecular structural formula such as Figure 5 shown.

[0058] Its preparation method comprises the following steps:

[0059] 3,3' - Bis(9-phenyl)carbazole (1.0 mmol), N -Bromosuccinimide (NBS) (2.05 mmol), silica gel (100 g) was dissolved in chloroform (150 ml), stirred at room temperature with tin foil in the dark for 24 hours, filtered directly with a sand core funnel, evaporated Dry organic solvent to get 3,3' - Dibromo-bis(9-phenyl)carbazole is a white solid powder in 75% yield. MS (APCI): calcd for C 36 H 22 N 2 Br 2 : 642.0, found, 643.4 (M+1) + .

[0060] 3,3' - Dibromo-bis(9-phenyl)carbazole ( 2 ) (1.0 mmol), CuCN (3.0 mmol), anhydrous DMF (50 ml), added to a round bottom flask, heated to reflux under nitrogen atmosphere for 24 hours, cooled to room temperature, added FeCl dropwise 3 Hydrochloric acid solution, the mixture was stirred at 70°C for 30 minutes, the organi...

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Abstract

The invention discloses a dicarbazolyl derivative, a preparation method and application of the dicarbazolyl derivative, and an electroluminescent device. The general structural formula of the dicarbazolyl derivative is represented as drawing shown in the specification, wherein R is an electron withdrawing group. The adopted compound takes a dicarbazolyl group as a central structure and is bonded with various electron withdrawing groups on 3-position of any carbazolyl, so as to effectively regulate a conjugated system of a host material and regulate triplet energy levels of the host material, so that HOMO and LUMO energy levels of the host material can be better matched with energy level of a blue-light object material. In addition, electron hole transmission performance of the compound is regulated through the electron withdrawing group, so that hole and electron transmission capacity of the host material is to be balanced, and the luminous efficiency of the device is improved; the dicarbazolyl derivative is relatively low in efficiency rolling-off under a high-brightness condition, so that the dicarbazolyl derivative can be widely applied to the field of organic electroluminescence.

Description

technical field [0001] The invention relates to the field of luminescent materials, in particular to a dicarbazolyl derivative, a preparation method and application thereof, and an electroluminescent device. Background technique [0002] The application and development of dicarbazolyl-based phosphorescent host compounds in blue phosphorescent host materials are limited due to their relatively weak electron transport ability and poor matching between their HOMO / LUMO energy levels and the energy levels of adjacent active layers. As a result, there are relatively few studies and applications of dicarbazole-based phosphorescent host compounds in blue phosphorescent host materials. [0003] Therefore, the prior art still needs to be improved and developed. Contents of the invention [0004] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide a dicarbazole-based derivative, its preparation method and application, and a...

Claims

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Application Information

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IPC IPC(8): C07F9/572C07D403/14C07D209/88C09K11/06H01L51/54
Inventor 黄宏
Owner TCL CORPORATION
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