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Ruthenium complex luminescent material containing dibenzothiophene sulfone group and use thereof

An iridium complex and thiophene sulfone-based technology is applied in the field of organic electroluminescent materials to achieve the effects of improving electron injection and transport capabilities and improving luminescence properties

Active Publication Date: 2018-07-20
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still few reports of high-efficiency yellow phosphorescent iridium complexes, especially bipolar yellow phosphorescent iridium complexes containing both hole transport units and electron transport units.

Method used

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  • Ruthenium complex luminescent material containing dibenzothiophene sulfone group and use thereof
  • Ruthenium complex luminescent material containing dibenzothiophene sulfone group and use thereof
  • Ruthenium complex luminescent material containing dibenzothiophene sulfone group and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of 2-(pyridin-2-yl)-7-(9-n-butylcarbazol-3 base)dibenzothiophene sulfone:

[0033]

[0034] (1) Synthesis of dibenzothiophene sulfone:

[0035]

[0036] Add 3.7g (20.0mmol) of dibenzothiophene, 10mL of glacial acetic acid and 6mL of 30% hydrogen peroxide into a 50mL round bottom flask, heat to 90°C, react for 0.5h, then add 2mL of 30% hydrogen peroxide, and continue the reaction for 0.5h . Cool to room temperature, filter with suction, wash with plenty of water, and dry in vacuum. Chloroform was recrystallized to obtain 4.1 g of white solid with a yield of 96%. 1 H NMR (400MHz, CDCl 3 , TMS) δ (ppm): 7.96 (d, J = 8.6Hz, 2H), 7.65 (d, J = 9.8Hz, 2H), 7.39 ~ 7.33 (m, 4H).

[0037] (2) Synthesis of 2,7-dibromodibenzothiophene sulfone:

[0038]

[0039] Add 3.89g (18.0mmol) dibenzothiophene sulfone and 120mL concentrated sulfuric acid into the flask, and stir to dissolve it. Add 4.0 g of NBS in small portions, and react at room temperature for 1 hou...

Embodiment 2

[0047] Synthesis of 3-(pyridin-2-yl)-6-(9-n-butylcarbazol-3 base) dibenzothiophene sulfone:

[0048]

[0049] (1) Synthesis of 3,6-dibromodibenzothiophene:

[0050]

[0051] Add 9.2g (50.0mmol) dibenzothiophene and 100mL chloroform into a 250mL three-necked flask, add 7.7mL (150mmol) liquid bromine dropwise at 0-5°C, and react at room temperature for 40h. Add saturated NaHSO 3 The excess liquid bromine was removed by aqueous solution to obtain a pale yellow solid, which was washed with water and ethanol to a white solid. Vacuum drying afforded 11.5 g of white solid, yield 67%. 1 H NMR (400MHz, CDCl 3 , TMS) δ (ppm): 8.22 (s, 2H), 7.71~7.69 (d, J=8.4Hz, 2H), 7.58~7.56 (dd, J=10.4Hz, 2H).

[0052] (2) Synthesis of 3,6-dibromodibenzothiophene sulfone:

[0053]

[0054] 6.8g (20.0mmol) 3,6-dibromodibenzothiophene, 150mL glacial acetic acid and 120mL tetrahydrofuran, and 15mL H 2 o 2 Add it to a two-neck flask, heat to 120°C, and react for 6h. After cooling to room...

Embodiment 3

[0062] Synthesis of iridium complexes Ir-1-Cz and Ir-2-Cz:

[0063]

[0064] (1) Bis(2-(pyridin-2-yl)-7-(9-n-butylcarbazol-3yl)dibenzothiophene sulfone-N,C 2 ) (picolinic acid) iridium (Ⅲ) [Ir-1-Cz] synthesis.

[0065] Add 386.1mg (0.75mmol) of 2-(pyridin-2-yl)-7-(9-n-butylcarbazol-3yl)dibenzothiophene sulfone, 45mL of ethylene glycol monoethyl ether and 15mL of water into a 100mL In the three-neck flask, add 120.1mgIrCl rapidly under the protection of argon 3 ·3H 2 O, 100 ℃ constant temperature reaction 20h. After cooling, a yellow solid was produced, which was filtered by suction, washed with water and a little ethanol successively, and dried in vacuum to obtain a yellow powder. The product was directly used in the next reaction without further separation and purification.

[0066] In a 50 mL three-necked flask, 285.7 mg (0.082 mmol) of the reaction product of the previous step, 47.5 mg of 2-pyridinecarboxylic acid, 102 mg of sodium carbonate and 35 mL of ethylene gl...

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Abstract

The invention discloses a ruthenium complex luminescent material containing a dibenzothiophene sulfone group and a use thereof. The ruthenium complex takes a dibenzothiophene sulfone pyridine derivative as a ring metal ligand and takes picolinic acid as an auxiliary ligand; and a hole transport unit is introduced on the ring metal ligand, to balance the electron and hole transport capability of the ruthenium complex. The ruthenium complex is doped in PVK and PBD to form a light-emitting layer, and a high-efficiency polymer yellow light device is obtained; the ruthenium complex and FIrPic are mixed as a dopant, are doped into polymer PVK and OXD-7 to form a light-emitting layer. The complementary color principle is utilized to obtain an efficient polymer white light device, and the application of an OLED in flat panel display and white light lighting is promoted.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to an iridium complex luminescent material containing a dibenzothiophene sulfone group and an application thereof. Background technique [0002] Due to the advantages of low driving voltage, fast response speed, low energy consumption, wide viewing angle, and flexible display, white organic light-emitting devices (WOLED) are used as a new type of solid-state light source in flat panel display, liquid crystal display backlight and solid-state lighting. Aspects have a wide range of applications (Chem. Soc. Rev., 2011, 40, 3467; Adv. Mater., 2011, 23, 233; Adv. Mater., 2014, 26, 2459). After years of research, WOLED has achieved rapid development, and its luminous efficiency has exceeded 120lm·W -1 , far exceeding the luminous efficiency of traditional incandescent lamps (10~15lm·W -1 ), showing great application prospects (Nature, 2009, 459, 234). [0003] Among ...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342H10K50/00Y02B20/00
Inventor 梁爱辉罗明刘志谦王涵刘德旺
Owner JIANGXI NORMAL UNIV
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