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6, 6-dimethyl-6H- benzo [cd] pyrene derivative and application thereof

A pyrene derivative, dimethyl technology, applied in the field of 6,6-dimethyl-6H-benzo[cd]pyrene derivatives, can solve the problems of low power efficiency, poor stability, affecting device efficiency and lifespan, etc. , to achieve high glass transition temperature, thermal stability performance guarantee, good thermal stability 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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  • 6, 6-dimethyl-6H- benzo [cd] pyrene derivative and application thereof
  • 6, 6-dimethyl-6H- benzo [cd] pyrene derivative and application thereof
  • 6, 6-dimethyl-6H- benzo [cd] pyrene derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] This embodiment is the precursor S11 of the synthetic intermediate S1:

[0071]

[0072] The synthetic route is shown in the following formula:

[0073]

[0074] The synthesis method is:

[0075] S11-2: Add 150ml of fuming nitric acid into a 500ml three-necked flask, cool it to about 5°C with an ice-water bath, add 22.2g of 10,10-dimethylanthrone (0.1mol) in batches under stirring, and control the feeding speed to make the reaction The temperature of the liquid is not higher than 10°C. After the addition of the reactant is completed, keep the temperature of the reaction liquid at 5°C for about 30 minutes. The reactant was poured into 400ml of ice water, stirred vigorously, and then suction filtered. The filter cake was washed with water, dried, and recrystallized with ethanol-petroleum ether mixed solvent to obtain 25 g of light yellow solid with a yield of 80%.

[0076] S11-3: Corey-Fuchs dibromoalkenylation reaction: 25g S11-2 (80mmol) and 53g carbon tetrabro...

Embodiment 2

[0083] This embodiment is the precursor S21 of the synthetic intermediate S2:

[0084]

[0085] The synthetic route is shown in the following formula:

[0086]

[0087] The synthesis method is:

[0088]S21-2: Corey-Fuchs dibromoalkenylation reaction: In a 500ml dry pressure-resistant reactor, add 22.2g (80mmol) of 10,10-dimethylanthrone, 53g of carbon tetrabromide ( 160mmol), the reaction system was evacuated three times - nitrogen circulation, added 250ml dry benzene, the mixture was stirred for 5 minutes, and 83.7g triphenylphosphine (320mmol) was added. The reaction mixture was vigorously stirred at 150° C. for 48 h, and the temperature of the system was cooled to room temperature, and an appropriate amount of CH2Cl2 was added to dissolve the reaction mixture. The crude product was separated by column chromatography (pure petroleum ether) to obtain 24.5 g of white solid S21-2, with a yield of 65%.

[0089] S21-3: Under N2 protection, add 2.6g of zinc powder (0.04mo...

Embodiment 3

[0095] This embodiment is the precursor S31 of the synthetic intermediate S3:

[0096]

[0097] The synthetic route is shown in the following formula:

[0098]

[0099] The synthesis method is:

[0100] Weigh 41.4g (97.7mmol) of S11 synthesized in Example 1, 55.1g (195.4mmol) of p-bromoiodobenzene, Pd(dba) 2 1.69g (2.93mmol), and 22.5g (234.5mmol) of NaO-t-Bu were placed in a 2000mL three-necked round-bottomed flask, and 1000mL of toluene (potassium hydroxide was dried for 3 days) was added. Warm up the bath to 90°C, add 5.9mL P(t-Bu) 3 (10%, cyclohexane solution) was slowly heated to 115°C and refluxed for 2 hours, cooled, the reaction solution was washed 3 times with an appropriate amount of water, separated, the organic phase was spin-dried, and recrystallized from ethyl acetate to obtain 33.8g of the product, with a yield of 60% .

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Abstract

The invention relates to a 6, 6-dimethyl-6H- benzo [cd] pyrene derivative, which is a class of compounds as shown in a formula (I), wherein n is 1 or 2; R1-R5 are five substituent groups at different positions on Ar, the substituent groups are identical or different from each other, and the substituent groups are respectively selected from H atoms, C1-C20 aliphatic linear chains or branch alkyls or C1-C20 aromatic groups, independently; Ar is an aromatic group; A is N atom or CH; L is a single bond, and is selected from C6-C10 aromatic ring or heteroaromatic ring. The invention also discloses an application of the compounds in organic electroluminescent devices, especially, being used as an electron transport material and / or a luminescent host material of OLED (Organic Light Emitting Diode).

Description

technical field [0001] The present invention relates to an organic compound, in particular to a 6,6-dimethyl-6H-benzo[cd]pyrene derivative used in an organic electroluminescence device, a preparation method and its application in an organic electroluminescence device applications. 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 adjust, it is difficult to realize full-color display, and it ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07D251/18C07D251/24C07D241/20C07D241/12C07D239/42C07D239/26C07F5/02H01L51/54
CPCC07D239/26C07D239/42C07D241/12C07D241/20C07D251/18C07D251/24C07D403/14C07F5/025H10K85/623H10K85/636H10K85/615H10K85/654H10K85/6572
Inventor 邱勇汤金明范洪涛段炼任雪艳
Owner KUNSHAN VISIONOX DISPLAY TECH
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