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Organic compound, organic light-emitting display panel and application thereof

An organic compound, an unsubstituted technology, applied in the field of organic electroluminescent materials, can solve the problems of blue phosphorescent materials instability, high cost, environmental pollution, waste of triplet excitons, etc., to suppress non-radiative transitions and improve Effect of narrowing the half peak width and improving efficiency

Pending Publication Date: 2022-05-13
SHANGHAI TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 25% of the singlet excitons and 75% of the triplet excitons are generated during the electro-excitation process. Although the first generation of traditional fluorescent materials has the advantages of low cost and simple synthesis, 75% of the triplet excitons are wasted. Theoretically only 25% internal quantum efficiency
The second-generation phosphorescent materials can convert singlet excitons into triplet excitons through the spin-orbit coupling of noble metals, and use singlet excitons and triplet excitons at the same time to theoretically achieve 100% internal quantum efficiency, but noble metals The introduction of blue phosphorescent materials has brought problems such as high cost and environmental pollution, and the instability of blue phosphorescent materials makes it difficult to commercialize
[0005] In order to achieve an efficient RISC process, molecules need to have a twisted molecular structure to obtain an effective separation of the highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO), but a highly twisted molecular structure will lead to a decrease in the strength of the oscillator, which is not conducive to the improvement of efficiency. ; At the same time, increasing the rigidity of molecules is beneficial to reduce molecular relaxation and reduce non-radiative transitions

Method used

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  • Organic compound, organic light-emitting display panel and application thereof
  • Organic compound, organic light-emitting display panel and application thereof
  • Organic compound, organic light-emitting display panel and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] This embodiment provides an organic compound M1, the structural formula of which is as follows:

[0082]

[0083] The preparation method of this organic compound comprises the following steps:

[0084] (1) Preparation of compound c-1

[0085]

[0086] At -78°C, add n-BuLi (2.20mL, 5.1mmol) to a solution of 2,5-dibromopyrimidine (a-1) (1.18g, 5mmol) in THF (20mL), and stir at -78°C 1 h, then a solution of 2-bromopyrimidine-5-carboxaldehyde (b-1) (0.95 g, 5.1 mmol) in THF (20 mL) was added dropwise, and stirred at -78°C for another 2 h. The mixture was quenched with aqueous hydrochloric acid at 0 °C and partitioned between water and DCM. The organic layer was washed with water, washed with Na 2 SO 4 Dry; add pyrimidinium chlorochromate (2.20 g, 10 mmol) to the DCM layer, and stir at room temperature for 4 h. The reaction mixture was filtered and washed with DCM. After evaporation of the solvent, purification by column chromatography gave compound c-1 (0.84 g, ...

Embodiment 2

[0095] This embodiment provides an organic compound M2, the structural formula is as follows:

[0096]

[0097] The preparation method of this organic compound comprises the following steps:

[0098] (1) Synthesis of compound d-2:

[0099]

[0100] Take 2-bromo-N-phenylaniline (e-1) (2.48g, 10mmol) in dry tetrahydrofuran (20mL) and add n-BuLi (1.6M hexane, 12.80mL, 20mmol) dropwise at -78°C. After stirring for 1 h, a solution of fluorenone (f-1) (1.98 g, 11 mmol) was added while stirring. After the reaction mixture was heated to room temperature and stirred for 3 h, it was quenched with a small amount of water, and the resulting mixture was concentrated and diluted with chloroform (50 mL). The solution was washed with water and extracted twice with chloroform. The mixture was dried over anhydrous sodium sulfate and concentrated to obtain the hydroxyl intermediate. The hydroxyl intermediate was refluxed with chloroform (40mL) and methanesulfonic acid (0.96g, 10mmol) f...

Embodiment 3

[0109] This embodiment provides an organic compound M3, the structural formula of which is as follows:

[0110]

[0111] The preparation method of this organic compound comprises the following steps:

[0112] (1) Synthesis of compound d-3:

[0113]

[0114] Take 2-bromo-N-phenylaniline (e-1) (2.48g, 10mmol) in ultra-dry tetrahydrofuran (20mL) solution, and drop n-BuLi (1.6M hexane, 12.80mL, 20mmol) at -78°C add. After stirring for 1 h, a solution of xanthone (f-2) (2.16 g, 11 mmol) was added while stirring. After the reaction mixture was heated to room temperature and stirred for 3 h, it was quenched with a small amount of water, and the resulting mixture was concentrated and diluted with chloroform (50 ml). The solution was washed with water and extracted twice with chloroform. The mixture was dried over anhydrous sodium sulfate and concentrated to obtain the hydroxyl intermediate. The hydroxyl intermediate was refluxed with chloroform (40mL) and methanesulfonic ac...

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Abstract

The invention provides an organic compound, an organic light-emitting display panel and application thereof. The organic compound has a structure as shown in a formula I. Nitrogen atoms of pyrimidine in a receptor and hydrogen atoms in a donor form intramolecular hydrogen bonds, the torsion angle between D and A is adjusted, proper HOMO and LUMO distribution is obtained, the oscillator strength is improved, meanwhile, the molecular rigidity is enhanced, and non-radiative transition of molecules is inhibited; according to the organic compound provided by the invention, carbonyl, pyrimidine and donor groups in molecules are linearly arranged due to para-position substitution, the horizontal orientation degree of the molecules is improved, the optical coupling efficiency is favorably improved, and the device efficiency is improved.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence materials, and in particular relates to an organic compound, an organic light-emitting display panel and applications thereof. Background technique [0002] Due to the advantages of self-luminescence, fast response speed, wide viewing angle, flexibility, and low power consumption, organic electroluminescent diodes have great application prospects in the fields of lighting and flat panel displays, and have attracted extensive attention. [0003] 25% of the singlet excitons and 75% of the triplet excitons are generated during the electro-excitation process. Although the first generation of traditional fluorescent materials has the advantages of low cost and simple synthesis, 75% of the triplet excitons are wasted. Theoretically only 25% internal quantum efficiency. The second-generation phosphorescent materials can convert singlet excitons into triplet excitons through the spin-...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D403/14C07D413/14C07D239/26C07D417/14C07D491/107C07D519/00C09K11/06H01L51/54H01L51/50
CPCC07D401/14C07D413/14C07D403/14C07D417/14C07D491/107C07D519/00C07D239/26C09K11/06C09K2211/1029C09K2211/1044C09K2211/1033C09K2211/1037C09K2211/1059C09K2211/1051C09K2211/1007C09K2211/1014C09K2211/1011H10K85/631H10K85/636H10K85/626H10K85/654H10K85/633H10K85/657H10K85/6572H10K50/11
Inventor 张绍丽牛晶华林亚飞华万鸣王建云
Owner SHANGHAI TIANMA MICRO ELECTRONICS CO LTD
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