Quinolyl[7,8-h]quinoline compounds and application thereof

An 8-h compound technology, applied in the field of organic compounds, can solve problems affecting device efficiency and life, poor stability, and low electron mobility, and achieve good thermal stability, thermal stability performance guarantee, and high electron mobility. Effect

Active Publication Date: 2014-03-26
KUNSHAN VISIONOX DISPLAY TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, CBP still has obvious defects: the glass transition temperature Tg is very low, only 62°C, and as a hole-type transport material, the corresponding electron transport ability of CBP is not balanced enough, which affects the efficiency and life of the device.
[0006] The traditional electron transport material is 8-trihydroxyquinoline aluminum (AlQ 3 ), but AlQ 3 Has many disadvantages: (1) Electron mobility is relatively low (about 10 -6 cm / Vs), which leads to higher voltage and thus lower power efficiency; (2) poor stability and partially decomposes at sublimation temperature; (3) has high hygroscopicity, which affects the lifetime of the device ; (4) It has color, and the color shift is caused by reabsorption and re-emission phenomenon, which affects the color purity of the device
Devices based on this hybrid electron transport layer have improved efficiency and lifetime, but increase the complexity of the device manufacturing process, which is not conducive to reducing the cost of OLEDs

Method used

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  • Quinolyl[7,8-h]quinoline compounds and application thereof
  • Quinolyl[7,8-h]quinoline compounds and application thereof
  • Quinolyl[7,8-h]quinoline compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] This embodiment is to prepare intermediate S1:

[0067]

[0068] The synthetic route is shown in the following formula:

[0069]

[0070] The preparation method is:

[0071] S1-1: Synthesis of 4,9-dichloroquinoline[7,8-h]quinoline intermediate S1-1 by the method in reference (Angew.Chem.Int.Ed.Engl., 1987,26,460.).

[0072] S1: Under nitrogen protection, 12.3g of bispinacol ester of bisboronic acid (molecular weight 254, 0.0484mol), 13.2g of 4,9-dichloroquinoline[7,8-h]quinoline (molecular weight of 299, 0.0441mol), PdCl 2 (dppf) is 1.8g (0.0022mol), anhydrous potassium acetate 13g (0.133mol), anhydrous dioxane 150ml, mixed together. Stir at 85°C for 24 hours. Cool to room temperature, filter with a sand core funnel, pour the filtrate into water with stirring, collect a white solid product, about 20.1 g in total, molecular weight 482, yield 94.5%.

Embodiment 2

[0075] This embodiment is to prepare compound M1:

[0076]

[0077] The synthetic route is shown in the following formula:

[0078]

[0079] The preparation method is:

[0080] M1-1: Under the protection of Ar gas, add 18.2g of 2,4,6-trichloropyrimidine (molecular weight 182, 0.10mol), formula S121.7g (molecular weight 482, 0.045mol), four ( Add 6.0 g (0.0052 mol) of triphenylphosphine) palladium, 600 ml of THF, 400 ml of toluene, and 60 g (0.435 mol) of potassium carbonate dissolved in 400 ml of water into the reaction flask. After repeated air exchange under reduced pressure, electric stirring was started, and the reaction was monitored by TLC (thin layer chromatography). After reflux for 5 hours, the reaction was complete. After cooling, the reaction system was divided into two layers. The organic layer was separated and evaporated to dryness to obtain a solid product, which was recrystallized with toluene to obtain 18.8 g of an intermediate with a molecular weight ...

Embodiment 3

[0084] This embodiment is to prepare compound M2:

[0085]

[0086] The synthetic route is shown in the following formula:

[0087]

[0088] The preparation method is:

[0089] M2-1: Under the protection of Ar gas, add 18.2 g of 2,4,6-trichloropyrimidine (molecular weight 182, 0.10 mol), 28.1 g of phenylboronic acid (molecular weight 122, 0.23 mol) and four Add 12.0 g (0.0104 mol) of (triphenylphosphine) palladium, 600 ml of THF, 400 ml of toluene, and 60 g (0.435 mol) of potassium carbonate in 400 ml of water to the reaction flask. After repeated air exchange under reduced pressure, electric stirring was started, and the reaction was monitored by TLC (thin layer chromatography). After reflux for 8 hours, the reaction was complete. After cooling, the reaction system was divided into two layers. The organic layer was separated and evaporated to dryness to obtain a solid product, which was recrystallized with toluene to obtain 19.9 g of an intermediate with a molecular w...

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Abstract

The invention relates to compounds disclosed a Formula (1), wherein n is 1 or 2; R1-R5 are five substituent groups on Ar in different positions, are identical or different, and are respectively independently selected from H atom or C1-C20 aliphatic straight-chain or branched-chain hydrocarbyl groups or aromatic groups; Ar is an aryl group; A is N atom or CH; and L is a single bond or is selected from C4-C10 aromatic rings or aromatic heterocyclic rings. The invention also relates to application of the compounds in organic electroluminescent devices especially as an electron transport material and / or light-emitting body material of an OLED (organic light-emitting diode).

Description

technical field [0001] The invention relates to an organic compound, in particular to a quinoline [7,8-h] quinoline compound used in an organic electroluminescent device and its application in an organic electroluminescent device. Background technique [0002] Electroluminescence (Electroluminescence, EL) refers to the phenomenon that luminescent materials are excited by current and electric field under the action of an electric field to emit light. It is a luminescence process that directly converts electrical energy into light energy. There are many solid materials that can produce electroluminescence, and those that have been studied more and can reach the level of use are mainly inorganic semiconductor materials. However, the production cost of inorganic EL devices is high, the processing is difficult, the efficiency is low, the luminous color is not easy to meet, it is difficult to realize full-color display, and it is difficult to realize large-area flat-panel display,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04H01L51/54
CPCC07D471/04C07F5/025H10K85/636H10K85/654H10K85/6572
Inventor 邱勇汤金明李银奎范洪涛段炼任雪艳
Owner KUNSHAN VISIONOX DISPLAY TECH
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