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Aza-spirobifluorene derivative and preparation method thereof

A derivative, azaspiro technology, applied in the field of azaspirobifluorene derivatives and their preparation, can solve the problems of charge transport performance, poor electrothermal stability, limited application fields and the like

Active Publication Date: 2017-06-13
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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  • Aza-spirobifluorene derivative and preparation method thereof
  • Aza-spirobifluorene derivative and preparation method thereof
  • Aza-spirobifluorene 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 aza-spirobifluorene derivative. The aza-spirobifluorene derivative is characterized by having a structural formula as shown in the specification, wherein only one of X1, X2, X3 and X4 is a nitrogen atom, and the other three are carbon atoms; and R is an aromatic or heterocyclic aromatic ring containing 6-60 carbon atoms. The aza-spirobifluorene derivative disclosed by the invention can be used as an illuminant material; the aza-spirobifluorene derivative can be independently used as an illuminating layer or doped dye for illuminating or can be formed into an exciplex with the other materials for illuminating; the aza-spirobifluorene derivative also has a carrier transporting capacity; and a group has a hole transmitting capacity and an electron transmitting capacity. The aza-spirobifluorene derivative provided by the invention can be prepared into an excellent amorphous film according to vacuum evaporation or solution methods (spin coating, printing, and the like). The aza-spirobifluorene derivative also has higher thermal stability and photo-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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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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