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A kind of azaspirobifluorene derivative and preparation method thereof

A derivative, the technology of azaspiro, which is applied in the field of azaspirobifluorene derivatives and its preparation, can solve the problems of charge transport performance, poor electrothermal stability, and limited application fields, etc.

Active Publication Date: 2021-07-09
SHANGHAI UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the existing polycyclic aromatic hydrocarbon compounds still generally have poor charge transport performance and poor electrothermal stability, which limits the application field.

Method used

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  • A kind of azaspirobifluorene derivative and preparation method thereof
  • A kind of azaspirobifluorene derivative and preparation method thereof
  • A kind of azaspirobifluorene derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Embodiment one; The preparation of compound I-1

[0088]

[0089] S1, 2-Cl-nicotinic acid (a, 1.05g), phenylboronic acid (1.22g) and K 2 CO 3 (2.75g) was dissolved in 10mL of water, added to the three-necked flask, then 25mL of 1,4-dioxane was added, and finally the catalyst Pd(OAc) was added 2 / PPh 3 (0.07 / 0.35g), N 2 Reflux reaction under protection for 2 days. After the reaction was completed, salt was formed with alkali, washed with dichloromethane, separated, the aqueous phase was acidified, extracted with ethyl acetate, concentrated, and purified by silica gel column chromatography to obtain 2-phenylnicotinic acid (1.5 g);

[0090] S2, react 2-phenylnicotinic acid (b, 1.5g) and polyphosphoric acid (30g) at 200°C for about 5 hours. After the reaction is completed, adjust the pH to neutral and filter with suction, extract with ethyl acetate, Concentrate and purify by silica gel column chromatography to obtain 4-azafluorenone (1.2 g); other azafluorenones can...

Embodiment 2

[0103] Embodiment two: the preparation of compound I-23

[0104] Using 4'-aza-9,9'-spirobifluorene-4-boronic acid ester (g) and 4-bromo-(biphenyl-4-yl)benzene as raw materials, it was prepared according to the synthesis method of S6 in Example 1.

[0105] Mass spectrum: theoretical value m / e, 545.21; measured value 545.2.

Embodiment 3

[0106] Embodiment three: the preparation of compound I-33

[0107] Using 4'-aza-9,9'-spirobifluorene-4-boronic acid ester (g) and 4-bromodibenzofuran as raw materials, it was prepared according to the synthesis method of S6 in Example 1.

[0108] Mass spectrum: theoretical value m / e, 483.16; measured value 483.2.

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PUM

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Abstract

The invention discloses an azaspirobifluorene derivative, which is characterized in that the general structural formula is as follows: wherein: X 1 ,X 2 ,X 3 ,X 4 Among them, only one is a nitrogen atom, and the remaining three are carbon atoms; R is an aromatic or heteroaromatic ring containing 6-60 carbon atoms; the azaspirobifluorene derivative of the present invention can be used as a luminescent material, Including becoming a light-emitting layer alone or as a doped dye to emit light or form an exciplex with other materials to emit light, and also have carrier transport ability, the group has the ability to transport holes and the ability to transport electrons; the nitrogen of the present invention Heterospirobifluorene derivatives can form good amorphous films by vacuum evaporation or solution method (spin coating, printing, printing, etc.), and at the same time have good thermal and light stability.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials and devices, in particular to an azaspirobifluorene derivative and a preparation method thereof. Background technique [0002] Due to the potential application of polycyclic aromatic hydrocarbon compounds and heterocyclic polycyclic aromatic hydrocarbon compounds in organic light-emitting diodes (Organic Light-Emitting Diode, OLED), solar cells, field effect transistors, etc., they have attracted more and more attention in recent years. As a member of polycyclic aromatic hydrocarbon compounds, and due to its good solubility, high luminous efficiency and good thermal and morphological stability, 9,9′-spirobifluorene compounds are used as charge-emitting diodes for phosphorescent organic light-emitting diodes. Transmission materials (such as CN103108859, etc.) and main materials have achieved excellent performance. [0003] However, the existing polycyclic aromatic hydr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/20C07D405/10C07D409/10C07D401/10C09K11/06
CPCC07D221/20C07D401/10C07D405/10C07D409/10C09K11/06C09K2211/1011
Inventor 王子兴吴鹏祝俊豆德海吴跃初
Owner SHANGHAI UNIV
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