Condensed ring aromatic amine compound used in organic layer of OLED device as well as synthesis method and application of condensed ring aromatic amine compound

A technology of aromatic amines and compounds, which is applied in the field of fused-ring aromatic amine compounds and their synthesis, can solve problems such as low device efficiency, interface degradation, and poor stability, and achieve stable performance, increased steric hindrance, and long life. Effect

Pending Publication Date: 2021-12-14
BOE TECH GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Molecular aggregation can lead to interface degradation, which is one of the main factors for low device efficiency or poor stability.

Method used

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  • Condensed ring aromatic amine compound used in organic layer of OLED device as well as synthesis method and application of condensed ring aromatic amine compound
  • Condensed ring aromatic amine compound used in organic layer of OLED device as well as synthesis method and application of condensed ring aromatic amine compound
  • Condensed ring aromatic amine compound used in organic layer of OLED device as well as synthesis method and application of condensed ring aromatic amine compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0094] Specifically, when the condensed ring aromatic amine compound is the general formula (2), its synthesis method includes the following steps:

[0095] N1, dibenzofuran-4-boronic acid or its derivatives, 2-bromo-4-chloro-1-iodobenzene or its derivatives and Pd(Ph 3 P) 4 Suspended in a solvent, adding potassium carbonate solution, reflux reaction to obtain the intermediate product c,

[0096]

[0097] N2, in an inert atmosphere, at -78°C, dissolve the intermediate product c in a solvent, add n-BuLi, The reaction at room temperature gives the intermediate product d,

[0098]

[0099] N3, in an inert atmosphere, the intermediate product d and amine compounds are dissolved in a solvent, and tri-tert-butylphosphine solution, Pd 2 (dba) 3 And sodium tert-butoxide, heated to reflux reaction, obtains the compound shown in formula (2);

[0100] Among them, R 1 , R 2 , X, L 1 , L 2 and L 3 The represented group is the same as in the above-mentioned formula (1) or f...

Synthetic example 1

[0132] Synthesis of intermediate product a-1

[0133] 100g (462mmol) of dibenzofuran-1-boronic acid, 138g (438mmol) of 2-bromo-4-chloro-1-iodobenzene and 10.7g (9.2mmol) of Pd(Ph3P)4 were suspended in 980ml of dioxin Add 1000ml of 2M potassium carbonate solution slowly to this suspension in alkanes, and reflux for 16h. After the reaction is completed, cool to room temperature, separate the organic phase, wash with water for 3 times and spin dry the organic solvent by rotary evaporation. The silica gel column obtained the intermediate product a-1, and the yield was 66.9g 43%;

[0134] Synthesis of intermediate product b-1

[0135] Put 35.5g (100mmol) of intermediate product a-1 into a dry reaction flask, inject 300ml of anhydrous THF into the reaction flask with a syringe, pump nitrogen for 3 times, stir at -78°C for half an hour, and pour into the reaction flask Add 50ml of n-BuLi (2M ethane solution) dropwise, and after stirring for 1 hour, add 21.8g (120mmol) benzophenone ...

Synthetic example 2

[0143] The synthesis procedure of compound 1-2 in Synthesis Example 2 is basically the same as that of compound 1-1, except that 7.9 g (22 mmol) of biphenyl-4-yl-(9,9-dimethyl-9H-fluoren-2-yl) is used Amine replaces bis-benzidine, and the obtained compound 1-2 has a quality of 10.4 g, a yield of 68%, and a molecular formula of C 58 h 41 NO, the relative molecular mass is 767.32; the structural characterization data of compound 1-2 are as follows: EA: C, 90.71; H, 5.38; N, 1.82;

[0144]1HNMR: 8.20ppm(1H); 7.98ppm(1H); 7.9-7.86ppm(2H); 7.75ppm(2H); 7.69ppm(1H); 7.55-7.54ppm(4H); 7.52ppm(1H); 7.49ppm (2H); 7.30-7.41 (8H); 7.25-7.30ppm (6H); 7.18-7.16ppm (3H); 7.10-7.08ppm (4H); 1.65ppm (6H).

[0145]

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Abstract

The invention discloses a condensed ring aromatic amine compound used in an organic layer of an OLED device. According to the invention, an SP3 hybridized carbon atom is arranged between and connected with two benzene rings in the compound, so a molecular conjugated structure can be effectively cut off, the molecular rigidity of the compound is increased, the steric hindrance of the compound is also increased, a molecule is allowed to have a high triplet state energy level and a high glass-transition temperature, the thermal stability and oxidation stability of the compound are ensured, the stability of a material is favorably improved, and the service life of the material is prolonged. Meanwhile, a five-membered heterocycle between the two benzene rings increases a molecular conjugate plane, so charge mobility is improved, the dispersion and migration of charges are easy, and the efficiency of the device is improved; due to a relatively high triplet state energy level, the compound can effectively prevent electrons from entering a light-emitting auxiliary layer, so more excitons can compositely emit light in a light-emitting layer, and the efficiency of the device is improved; and therefore, the OLED device prepared from the condensed ring aromatic amine compound is higher in efficiency, more stable in performance and longer in service life.

Description

technical field [0001] The invention relates to the field of material technology. More specifically, it relates to a fused-ring aromatic amine compound used in an organic layer of an OLED device, a synthesis method and application thereof. Background technique [0002] As we all know, OLED devices belong to injection type light emitting. Driven by voltage, the anode injects holes into the light-emitting layer, and the cathode injects electrons into the light-emitting layer. The holes and electrons meet and combine in the light-emitting layer to form excitons, and the excitons recombine and transfer energy to the light-emitting material. It shines through the process of recovery. [0003] The basic structure of an OLED device is a simple "sandwich" device. The luminescent material (luminescent layer) is spin-coated, dip-coated or vacuum thermally evaporated on a conductive glass substrate, then coated with a cathode material, and connected to a power source to form an organ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/77C07D307/91C07D307/94C07D405/12C07D409/12H01L51/54H01L51/50
CPCC07D307/77C07D405/12C07D307/91C07D307/94C07D409/12H10K85/636H10K85/6576H10K85/6574H10K85/6572H10K50/15H10K50/11
Inventor 邱丽霞孙玉倩刘杨
Owner BOE TECH GRP CO LTD
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