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A kind of quinoline material containing benzofuran structure and its preparation method and application

A technology of benzofuran and quinoline, which is applied in the field of OLED materials, can solve the problems of poor luminous performance, high driving voltage, and low luminous efficiency, and achieve excellent performance, reduce driving pressure, and prolong working life.

Active Publication Date: 2022-03-25
烟台九目化学股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With the continuous improvement of technology level, a variety of products based on OLED technology have been industrialized, but there are still problems with poor luminous performance such as low luminous efficiency, high driving voltage, and short service life, which need to be further resolved.

Method used

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  • A kind of quinoline material containing benzofuran structure and its preparation method and application
  • A kind of quinoline material containing benzofuran structure and its preparation method and application
  • A kind of quinoline material containing benzofuran structure and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: A structural formula of compound A applied in the OLED field:

[0041]

[0042] The concrete synthetic route of compound A is:

[0043]

[0044] Preparation of Compound A-1: ​​Weigh cyanuric chloride and 2-biphenylboronic acid according to the molar ratio of 1:2.5, add catalyst palladium acetate and tricyclohexylphosphine, the molar ratio of catalyst to cyanuric chloride is 0.1:1, The solvent is toluene, and the amount of the solvent is 10 times of the weight of cyanuric chloride. The reaction is carried out at 100° C. for 4 hours. According to HPLC detection, there is no remaining 2-biphenylboronic acid, and the reaction purity is 72.2%. Compound A-1 was obtained after water washing, concentration, column dissolution and recrystallization, with a yield of 54.5% and a HPLC purity of 96.4%. 1 H NMR (400 MHz, Acetonitrile-d3): δ7.44-7.66 (8H, m), 7.96-8.08 (8H, m), 8.20 (2H, d).

[0045] Preparation of compound A: Weigh compound A-1, intermediate I a...

Embodiment 2

[0046] Embodiment 2: A structural formula of compound B applied in the OLED field:

[0047]

[0048] The specific synthetic route of compound B is:

[0049]

[0050] Preparation of compound B: Weigh intermediate I, 9-bromo-11,11-dimethylbenzofluorene and sodium carbonate according to the molar ratio of 1:1.2:2.5, add catalyst tris(dibenzylideneacetone) dipalladium ( 0) and 4,5-bisdiphenylphosphine-9,9-dimethylxanthene, the molar ratio of the catalyst to the intermediate I is 0.01:1, sodium carbonate is made into an aqueous solution with a mass fraction of 40%, and the solvent It is toluene, the amount of solvent is 10 times of the weight of intermediate I, and the reaction is incubated at 75° C. for 5 h. According to HPLC detection, 0.2% of intermediate I remains, and the reaction purity is 90.2%. Compound B was obtained after hydrolysis, water washing, column passing and recrystallization, with a yield of 88.1% and a HPLC purity of 99.2%. 1 H NMR (400MHz, CDCl3): δ1.7...

Embodiment 3

[0051] Embodiment 3: A structural formula of compound C applied in the OLED field:

[0052]

[0053] The specific synthetic route of compound C is:

[0054]

[0055] Preparation of compound C: Weigh intermediate I, 2-bromo-9,9-diphenylfluorene and sodium carbonate according to the molar ratio of 1:1.1:2.5, add catalyst tris(dibenzylideneacetone)dipalladium(0) and 4,5-bisdiphenylphosphine-9,9-dimethylxanthene, the molar ratio of catalyst to intermediate I is 0.01:1, sodium carbonate is made into an aqueous solution with a mass fraction of 30%, and the solvent is toluene , the amount of solvent was 10 times the weight of intermediate I, and the reaction was incubated at 75° C. for 8 hours. HPLC detection showed that 0.01% of intermediate I remained, and the reaction purity was 91.2%. Compound C was obtained after hydrolysis extraction, water washing, column passing and recrystallization, with a yield of 87.8% and a HPLC purity of 99.5%. 1 H NMR (400MHz, CDCl3): δ1.62(9H,...

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Abstract

The present invention relates to a quinoline material containing a benzofuran structure. The structure of the material is shown in the general formula I: in the general formula I, Ar is selected from hydrogen, halogen atoms, substituted or unsubstituted C6-60 aryl, substituted or unsubstituted 5-60-membered heteroaryl containing one or more heteroatoms, where the heteroatoms are nitrogen, oxygen or sulfur. The quinoline materials containing benzofuran structure are applied to light-emitting layer materials, electron transport layer materials and hole transport layer materials in OLED devices. The quinoline material containing benzofuran structure is used as the main material for color development. Quinoline materials containing benzofuran structure show excellent performance in OLED devices, which can reduce driving pressure, improve current luminous efficiency and prolong working life.

Description

technical field [0001] The invention relates to a quinoline material containing a benzofuran structure and a preparation method and application thereof, belonging to the technical field of OLED materials. Background technique [0002] Compared with traditional liquid crystals, OLED displays not only have the characteristics of stable performance, full color, and thin volume, but also have many advantages such as self-illumination, wide viewing angle and fast response, and flexible display. Display material will become the most favorable competitor of next generation display technology. With the continuous improvement of the technical level, a variety of products based on OLED technology have been industrialized, but there are still problems with poor luminous performance such as low luminous efficiency, high driving voltage, and short service life, which need to be further resolved. [0003] The material layers in the organic light-emitting device are all multi-layer struct...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/16C09K11/06H01L51/50H01L51/54
CPCC07D491/16C09K11/06C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1048C09K2211/1059C09K2211/1088C09K2211/1092H10K85/615H10K85/622H10K85/631H10K85/657H10K85/6574H10K85/6576H10K85/6572H10K50/12H10K50/15H10K50/16H10K50/11
Inventor 房平磊陈慕欣徐立储毅
Owner 烟台九目化学股份有限公司
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