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Imidazole spiro-containing compound and application thereof

An imidazole spiro and compound-containing technology is applied in the fields of mixtures, compositions and organic electronic devices, compounds containing imidazole spiro rings, and polymers, and can solve the problems of low performance of organic electronic components and devices, and achieve good transmission capacity. , the effect of optimizing device performance, improving efficiency and life

Active Publication Date: 2020-02-04
GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In view of the above deficiencies in the prior art, the object of the present invention is to provide a compound containing an imidazole spiro ring and its application, aiming to solve the problem of low performance of existing organic electronic components and device performance

Method used

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  • Imidazole spiro-containing compound and application thereof
  • Imidazole spiro-containing compound and application thereof
  • Imidazole spiro-containing compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0174] Example 1: Synthesis of compound (M1):

[0175]

[0176] synthetic route:

[0177]

[0178] 1) Synthesis of Intermediate M1-3: Under nitrogen atmosphere, (33.6g, 100mmol) of compound M1-1, (24.4g, 200mmol) of M1-2, (6.9g, 6mmol) tetrakis(triphenylphosphonium) ) Palladium, (6.5g, 20mmol) tetrabutylammonium bromide, (8g, 200mmol) sodium hydroxide, (40 mL) water and (250mL) toluene were added to a 500mL three-neck flask, heated at 80°C and stirred for 12 hours, After finishing the reaction, the reaction solution was rotated to evaporate most of the solvent, dissolved in dichloromethane, washed with water 3 times, and the organic solution was collected and mixed with silica gel for purification. The yield was 80%.

[0179] 2) Synthesis of intermediate M1-6: under a nitrogen atmosphere, combine (12.4g, 100mmol) of compound M1-4, (17.3g, 100mmol) of compound M1-5, (27.6g, 200mmol) of potassium carbonate and 300mL Dimethylformamide was added to a 500mL three-necked flask, heated to...

Embodiment 2

[0182] Example 2: Synthesis of Compound (M2):

[0183]

[0184] synthetic route:

[0185]

[0186] 1) Synthesis of intermediate M2-2: According to the synthesis method of compound M1-6, compound M2-1 was substituted for compound M1-4, and the yield was 85%.

[0187] 2) Synthesis of intermediate M2-4: According to the synthesis method of compound M1-7, compound M2-2 and compound M2-3 are substituted for compounds M1-6 and M1-3.

[0188] 3) Synthesis of intermediate M2-5: According to the synthesis method of compound M1, compound M2-4 is substituted for compound M1-7, and the yield of the two steps is 70%.

[0189] 4) Synthesis of Intermediate M2-6: Under nitrogen atmosphere, (21.7g, 50mmol) of compound M2-5, (12.7g, 50mmol) pinacol diborate, (9.8g, 100mmol) potassium acetate, ( 2.2g, 3mmol)Pd(ppf)Cl 2 Add 150mL of 1,4-dioxane as a solvent to a 250mL three-necked flask, heat at 110°C to react for 12 hours, after the reaction is complete, the reaction solution is cooled to room temperatur...

Embodiment 3

[0191] Example 3: Synthesis of Compound (M3):

[0192]

[0193] synthetic route:

[0194]

[0195] 1) Synthesis of intermediate M3-2: According to the synthesis method of compound M1-6, compound M3-1 was substituted for compound M1-4, and the yield was 80%.

[0196] 2) Synthesis of intermediate M3-3: According to the synthesis method of compound M1-7, compound M3-2 and compound M1-1 are substituted for compound M1-6 and M1-3.

[0197] 3) Synthesis of intermediate M3-4: According to the synthesis method of compound M1, compound M3-3 is substituted for compound M1-7, and the yield of the two steps is 65%.

[0198] 4) Synthesis of compound M3: According to the synthesis method of compound M1-3, compounds M3-4 and M3-5 were substituted for compounds M1-1 and M1-2, and the yield was 75%.

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Abstract

The invention relates to an imidazole spiro-containing compound and an application thereof. The compound has a structural general formula represented by chemical formula (1). The compound has the advantages of good stability, high luminous efficiency, long service life, and simplicity in synthesis.

Description

[0001] This application requires that it be submitted to the Chinese Patent Office on December 10, 2018, the application number is 2018115004910, and the invention title is "a class of imidazole spiro ring-containing compounds, polymers, mixtures, compositions and organic electronic devices". The priority of the application, the entire content of which is incorporated in this application by reference. Technical field [0002] The present invention relates to the field of optoelectronic materials, in particular to a compound, high polymer, mixture, composition and organic electronic device containing imidazole spiro ring. Background technique [0003] Organic semiconductor materials have the characteristics of structural diversity, relatively low manufacturing costs, and superior optoelectronic performance. They have great potential for applications in organic light-emitting diodes (OLED) and other optoelectronic devices (such as flat panel displays and lighting). [0004] In order t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/20C07D487/10C07D487/20C07D491/20C07D471/20C07D471/10C07D495/22C07D513/20C07D498/20C07F9/6561C07F5/02C09K11/06H01L51/50H01L51/54
CPCC07D495/20C07D487/10C07D487/20C07D491/20C07D471/20C07D471/10C07D495/22C07D513/20C07D498/20C07F9/6561C07F5/027C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/1059C09K2211/1048H10K85/615H10K85/657H10K85/6574H10K85/6576H10K85/322H10K85/6572H10K50/11Y02E10/549
Inventor 何锐锋吴灿洁潘君友
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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