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6-trimethylphenyl-6H-6-boroheterobenzo[cd]pyrene derivatives and application thereof

A -6H-6-, trimethylbenzene-based technology, applied in the field of organic compounds, can solve the problems of high hygroscopicity, affecting device efficiency and life, low electron mobility, etc., and achieves increased film formation, good thermal stability, The effect of high electron mobility

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

[0004] 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
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.

Method used

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  • 6-trimethylphenyl-6H-6-boroheterobenzo[cd]pyrene derivatives and application thereof
  • 6-trimethylphenyl-6H-6-boroheterobenzo[cd]pyrene derivatives and application thereof
  • 6-trimethylphenyl-6H-6-boroheterobenzo[cd]pyrene derivatives and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-6

[0072] Embodiment 1-6 is the preparation embodiment of intermediate of the present invention:

Embodiment 1

[0074] This example prepares the precursor (5) 2,10-dibromo-6-trimethylphenyl-6H-6-borabenzo[cd]pyrene of formula (51) and formula (52):

[0075]

[0076] The synthetic route is as follows:

[0077]

[0078] The preparation method is:

[0079] The first step: the synthesis of intermediate I, under the protection of nitrogen, add 47.2g (0.2mol) o-dibromobenzene and 200mL anhydrous ether to a 500mL three-necked round-bottomed flask, cool to -78°C, and slowly add dropwise under magnetic stirring 80mL of n-butyllithium (0.2mol, 2.5M, the solvent is n-hexane). After maintaining the temperature for 1 h, the temperature was naturally raised to room temperature and the reaction was continued with stirring for 2 h. After cooling to -78°C again, add 50 mL of dissolved 19.2 g (0.1 mol) of MesityB(OMe) 2 ether solution, stirred for 1h. Slowly rise to room temperature, continue to react overnight, add appropriate amount of water for hydrolysis, extract 2-3 times with ethyl acetat...

Embodiment 2

[0087] This example prepares the precursor (6) 2,10-di-p-bromophenyl-6-trimethylphenyl-6H-6-borabenzo[cd]pyrene of formulas (61) and (62):

[0088]

[0089] The synthetic route is as follows:

[0090]

[0091] The preparation method is:

[0092] Weigh 50g (97.7mmol) of 2,10-dibromo-6-trimethylphenyl-6H-6-borabenzo[cd]pyrene (synthesized in Intermediate Example 1), 55.1g (195.4mmol) of p-bromoiodobenzene ), Pd(dba) 21.69g (2.93mmol), and NaO-t-Bu22.5g (234.5mmol) were placed in a 2000mL three-necked round-bottomed flask, and 1000mL toluene was added (potassium hydroxide was dried for 3 days), ventilated and ventilated Protected by inert gas, the temperature of the oil bath was raised to 90°C, and 5.9mL of P(t-Bu) was added 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, and the organic phase was spin-dried to obtain 35.7 g of the product, w...

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Abstract

The invention relates to compounds disclosed a Formula (1), wherein n is 1 or 2; R1-R5 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 present invention relates to an organic compound, in particular to a 6-trimethylphenyl-6H-6-borabenzo[cd]pyrene derivative used in an organic electroluminescent device and its application in an organic electroluminescent device application. 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 ...

Claims

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Application Information

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IPC IPC(8): C07F5/02C07F5/04C09K11/06H01L51/54
Inventor 邱勇王星李银奎段炼任雪艳
Owner KUNSHAN VISIONOX DISPLAY TECH
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