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Arylamine compound, organic light-emitting device and display device

A technology of organic light-emitting devices and aromatic amines, applied in the field of organic electroluminescent materials, can solve problems such as the difficulty in developing doped materials, and achieve the effects of improving luminous efficiency, facilitating transmission and stability, and improving transmission efficiency

Active Publication Date: 2020-09-01
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the current research status, the commercialization of heavy metal doped materials is mature, and it is difficult to develop alternative doped materials. Therefore, it is a common idea for researchers to focus on the development of phosphorescent host materials.

Method used

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  • Arylamine compound, organic light-emitting device and display device
  • Arylamine compound, organic light-emitting device and display device
  • Arylamine compound, organic light-emitting device and display device

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preparation example Construction

[0065] The present invention also provides a preparation method of the above-mentioned arylamine compound, comprising: combining the compound shown in formula (II) with Ar 1 -H and / or Ar 2 -H mixed reaction, obtain the compound shown in formula (I); Perhaps the compound shown in formula (II) is reacted with biboronic acid pinacol ester, after obtaining intermediate product, then with Ar 1 -X 3 ' and / or Ar 2 -X 4 'Mixed reaction, obtains the compound shown in formula (I).

[0066]

[0067] Among them, the Ar 1 ~ Ar 3 , L, m, n, q and a are all the same as above, and will not be repeated here; the X 1 '~X 4 ' each independently may be a halogen atom, more may be Br or I.

[0068] In the present invention, the compound represented by the formula (II) can optionally be prepared according to the following method: combine the compound represented by the formula (III) with X 5 '-Lq-(Ar 3 ) a Reaction, obtains the compound shown in formula (II).

[0069]

[0070] Whe...

Embodiment 1

[0081] The preparation method of organic compound P071 comprises the following steps:

[0082] (1)

[0083] In a 100mL round-bottomed flask, dissolve P071-1 (15mmol) into 60mL of dichloromethane, add nitric acid (30mol) and sulfuric acid (15.0mol), under a nitrogen atmosphere, the temperature is controlled at 30°C, and the reaction is stirred for 7h. Then the reaction solution was cooled to room temperature, 50 mL of methanol was added to the obtained intermediate and stirred for 1 hour, and the light yellow solid product intermediate P071-2 was obtained by standing still.

[0084] The solid product intermediate P071-2 obtained in Example 1 was analyzed by liquid chromatography-mass spectrometry, and ESI-MS (m / z) (M+) was obtained: the theoretical value was 454.9, and the test value was 454.8.

[0085] (2)

[0086] In a 100mL round-bottomed flask, dissolve the intermediate product P071-2 (12mmol) into o-dichlorobenzene (30mL), stir while heating until it is completely di...

Embodiment 2

[0102] The preparation method of organic compound P001 comprises the following steps:

[0103]

[0104] In a 100mL round bottom flask, P071-6 (15mmol), 9-H carbazole (18mmol), K 2 CO 3 (40mol), CuSO 4 .5H 2O (3.0mol) was added to dry DMF (60mL), under a nitrogen atmosphere, the temperature was controlled at 150°C, and the reaction was stirred for 5h. The obtained intermediate was filtered through a pad of diatomaceous earth, the filtrate was extracted with ethyl acetate, and then 50mL of water was washed three times, and dried with anhydrous magnesium sulfate. After filtration and evaporation, the organic phase was taken out, and the solvent was removed by rotary evaporation, and the mixed solution of ethyl acetate / petroleum ether with a volume ratio of 1:5 was used as the eluent. Silica gel column chromatography gave the solid product P001.

[0105] Elemental analysis result: C 38 h 24 N 2 , theoretical value: C 89.74, H 4.76, N 5.51; test value: C 89.75, H 4.75, N ...

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Abstract

The invention discloses an arylamine compound with a structure shown as a formula (I), an organic light-emitting device and a display device. L is selected from substituted or unsubstituted aryl; Ar1-Ar3 are respectively and independently selected from substituted or unsubstituted carbazole and derivative groups thereof, substituted or unsubstituted acridine and derivative groups thereof, and substituted or unsubstituted arylamine groups. Compared with the prior art, the arylamine compound provided by the invention takes a seven-membered aromatic heterocyclic structure as a main body, has higher stereoscopicity than other five-membered ring or six-membered ring structures, and can prevent aggregation caused by molecules passing through a plane too much, so that excitons can be prevented from being quenched, and the luminous efficiency is improved; and different electron donating groups can be connected to serve as a main body material or a hole transport-out material, the main body material is beneficial to transport and stabilization of carriers, the hole transport is beneficial to hole transport, and the transport efficiency of the device is further improved.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to an aromatic amine compound, an organic light emitting device and a display device. Background technique [0002] Organic Optoelectronic Materials (Organic Optoelectronic Materials) are organic materials with the characteristics of photon and electron generation, conversion and transmission. At present, the controllable optoelectronic properties of organic optoelectronic materials have been applied in organic light-emitting diodes (OLEDs), organic solar cells (OPVs), organic field-effect transistors (OFETs), biological / chemical / photosensors, memory devices, and even organic lasers. Different from traditional inorganic conductors and semiconductors, organic small molecules and polymers can be synthesized by different organic and polymer chemical methods, so that a large number of various organic semiconductor materials can be prepared, which is very important for...

Claims

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Application Information

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IPC IPC(8): C07D223/14C07D403/04C07D403/14C07D471/04C07D491/048C07D495/04C07D519/00C07F7/08H01L51/50H01L51/54
CPCC07D403/04C07D471/04C07D491/048C07D495/04C07D403/14C07D519/00C07F7/0816C07F7/083C07D223/14H10K85/636H10K85/615H10K85/631H10K85/657H10K85/40H10K85/6572H10K50/165
Inventor 代文朋肖文静高威张磊冉佺牛晶华
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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