Indenoanthracene derivative compound and application thereof

A technology of compounds and derivatives, applied in the field of organic electroluminescence functional materials and devices, to achieve the effect of improving luminescence stability and high thermal stability

Active Publication Date: 2019-07-23
XIAN RUILIAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because the fluorescent type uses singlet excitons to emit

Method used

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  • Indenoanthracene derivative compound and application thereof
  • Indenoanthracene derivative compound and application thereof
  • Indenoanthracene derivative compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0133]

[0134] Introduce nitrogen into a 1L three-necked flask, add 12.8g carbazole, 20g intermediate 1-5, 16.9g potassium carbonate, 0.81g 18-crown-6 ether, 400ml DMF, stir until the raw materials are completely dissolved, then add 0.58g iodide Cuprous, heated to 130°C and stirred for 10 hours, TLC monitored the complete consumption of compound 1-5, stopped the reaction, poured the reaction solution into 3 times the volume of water after cooling down to room temperature, stirred to precipitate solid, filtered, washed the filter cake with water until neutral, After the filter cake was dried, it was dissolved in toluene, passed through an insulating column, and the eluent was concentrated and recrystallized to obtain 20.8 g of white solid, namely compound 1, with a yield of 82.3%.

[0135] NMR data of compound 1: 1 H NMR (400MHz, CDCl3) δ8.08 (d, J = 7.6, 1H), 7.67-7.71 (m, 4H), 7.52-7.55 (m, 6H), 7.46 (td, J = 7.6, 4H), 7.32 -7.40 (m, 12H), 7.08 (td, J=7.2, 4H), 7.00 (td,...

Embodiment 2

[0137]

[0138] Introduce nitrogen into a 1L three-necked flask, add 11.8g sodium tert-butoxide, 16.0g 9,9-dimethylacridine, 20g intermediate 1-5, 400ml toluene, stir until the raw materials are completely dissolved, then add 69mg palladium acetate , 0.3ml tri-tert-butylphosphine toluene solution, heated to reflux and stirred for 12 hours, TLC monitored the complete consumption of compound 1-5, stopped the reaction, filtered after cooling down to 60-70°C, washed the filtrate with hot water until neutral, refluxed to remove water After passing through the insulation column, the eluate was concentrated and recrystallized to obtain 21.9 g of white solid, namely compound 3, with a yield of 78.5%.

[0139] NMR spectrum data of compound 3: 1 H NMR (400MHz, CDCl3) δ8.08(d, J=7.6,1H), 7.68(d, J=7.2,4H), 7.52(td, J=7.6,2H), 7.46(td, J=7.6, 4H), 7.32-7.40(m, 8H), 6.88(d, J=7.2, 8H), 6.83(td, J=7.2, 4H), 6.54(td, J=7.2, 4H), 1.73(s, 6H ), 1.67(s,12H).

Embodiment 3

[0141]

[0142] The synthesis procedure is the same as that of intermediate 1-4, except that intermediate 1-3 is replaced by intermediate 5-1, the amount of butyllithium is 10.3ml, the amount of diphenylphosphine chloride is 5.2g, hydrogen peroxide The amount of used was 20ml, and 17.5g of compound 8 was obtained, with a yield of 76.8%.

[0143] NMR data of compound 8: 1 H NMR (400MHz, CDCl3) δ8.13 (d, J = 7.6, 1H), 7.83 (s, 1H), 7.65-7.68 (m, 3H), 7.52-7.61 (m, 12H), 7.40-7.46 (m , 8H), 7.32-7.35 (m, 10H), 7.08 (td, J = 7.2, 4H), 7.00 (td, J = 7.2, 4H), 1.73 (s, 6H).

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Abstract

The invention discloses an indenoanthracene derivative compound and application thereof and belongs to the technical field of organic electroluminescent materials. A general molecular formula of the compound is shown as a formula (I), wherein L1, L2 and L3 are phenylene or substituted phenylene, n is any integer in a range of 0 to 3, Ar1 and Ar2 are the same or different and each of the Ar1 and the Ar2 independently represents an electron donor group; X can be a C atom, an O atom, an S atom, an N atom and a Si atom; A represents a diphenylphosphine oxide molecule or dibenzyl boron molecule derivative. The compound provided by the invention is used as a doping material and/or a main material of an OLED (Organic Light Emitting Diode), and high brightness, low voltage, high efficiency and long service life of organic electroluminescence devices can be realized; a material prepared from the compounds has relatively high thermal stability, can be used for remarkably improving the luminescent stability of luminescent devices and is widely applied to OLED luminescent devices and display devices.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent functional materials and devices, and specifically relates to an indenoanthracene derivative compound and its application. Background technique [0002] As a self-illuminating electronic component, organic light-emitting diodes (OLED: Organic Light Emission Diodes) show that the light-emitting mechanism of lighting components is a new type of optoelectronics that converts electrical energy directly into light energy with the help of organic semiconductor functional materials under the action of a DC electric field. information Technology. Its luminous color can be a single red, green, blue, yellow light or a combination of white light. The biggest feature of OLED light-emitting display technology is ultra-thin, fast response, ultra-lightweight, surface-emitting and flexible display. It can be used to manufacture monochrome or full-color displays. As a new light source technolog...

Claims

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Application Information

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IPC IPC(8): C07F9/572C07F9/64C07F9/53C07F9/6533C07F9/6547C07F9/6558C07F5/02C09K11/06H01L51/50H01L51/54
CPCC07F9/5728C07F9/64C07F9/5325C07F9/65335C07F9/6547C07F9/65586C07F5/027C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1088C09K2211/1092C09K2211/1096H10K85/623H10K85/657H10K85/6576H10K85/6572H10K85/6574H10K85/322H10K85/40H10K50/11
Inventor 孙军张宏科刘凯鹏田密杨丹丹何海晓李江楠王小伟刘骞峰高仁孝
Owner XIAN RUILIAN NEW MATERIAL CO LTD
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